Going on an East Coast road trip is an unforgettable adventure through American history, culture, and scenery.
This 10-day itinerary takes you from New England charm to Southern warmth in a logical route down the coast.
The pace balances famous cities with relaxing nature stops.
Each day below includes key activities, approximate drive times, and practical tips.
Grab some snacks, cue up your favorite playlist, and let’s hit the road!
Day 1: Boston, MA
Walk the Freedom Trail
Begin your journey in historic Boston.
Start the morning by walking the Freedom Trail – a 2.5-mile red-brick path connecting 16 important sites from the American Revolution
This easy walking route leads you past landmarks like Boston Common, Paul Revere’s House, and Old North Church.
It’s a fun, interactive history lesson for all ages (look for the red line on the sidewalk!).
Travel Tip: Wear comfortable shoes and bring a bottle of water; you’ll be doing a lot of walking.
Lunch at Quincy Market
In the afternoon, head to Quincy Market at Faneuil Hall for lunch.
You can sample New England clam chowder or a lobster roll among the many food stalls.
The market’s street performers and souvenir shops add a lively atmosphere.
Afternoon Harborwalk or Duck Tour
After lunch, consider a stroll along the Harborwalk to see boats and maybe catch a glimpse of the USS Constitution (“Old Ironsides”) across the water.
If time permits, a Duck Tour – an amphibious vehicle city tour – is a hit with kids and offers a quirky overview of Boston.
Dinner in the North End
Wrap up the day with dinner in the North End, Boston’s Little Italy.
Enjoy some family-friendly pasta or pizza, and don’t miss a cannoli from the famous Mike’s Pastry for dessert.
In the evening, relax at your hotel or take a leisurely walk by the Charles River.
Travel Tip: Parking in downtown Boston is tricky. If you have a car, use a parking garage or your hotel’s parking and explore the city on foot or via the T (Boston’s subway).
Tomorrow, an early start will help beat traffic on the way to New York City.
Day 2: New York City, NY
Drive from Boston to NYC
Say goodbye to Boston and hit the road for New York City.
The drive is about 215 miles (346 km) and typically 4 hours via I-90 and I-95.
Leave early to avoid the morning rush hour leaving Boston.
On the way, you can stretch your legs in Mystic, Connecticut – a quaint seaside town.
It’s a great lunch stop; try a slice at the famous Mystic Pizza (the movie Mystic Pizza was filmed here) or simply enjoy the cute downtown and harbor views.
After your break, continue southwest through Connecticut and into the bustle of NYC.
Explore Central Park & 5th Avenue
Arrive in New York City by early afternoon.
Check into your hotel and prepare to take on the Big Apple!
With only a day here, focus on a few iconic experiences.
Start at Central Park – wander the paths, say hi to the ducks at the pond, and let kids run on the lawns or playgrounds.
The skyline views from the park are fantastic.
From Central Park, you can walk down 5th Avenue to see bustling city life and pass famous stores (even if you’re just window shopping).
Go Up for City Views
By late afternoon, make your way to Midtown.
A top recommendation is to go up to an observation deck for panoramic city views.
The Empire State Building is a classic choice, but Top of the Rock at Rockefeller Center or the new SUMMIT One Vanderbilt also offer amazing 360° vistas.
Viewing Manhattan from above is memorable for everyone.
Travel Tip: Book observation deck tickets in advance for late afternoon to catch daylight and sunset if possible.
Experience Times Square at Night
In the evening, experience the neon glow of Times Square.
The billboards and big screens are dazzling after dark – a sight kids and adults alike will marvel at.
Grab a quick bite for dinner: New York pizza slices or hot dogs from a cart for a true NYC street food experience.
If you still have energy, an after-dinner walk to Rockefeller Center to see it lit up (and perhaps the Rockefeller Plaza if it’s winter ice-skating season) is worthwhile.
Otherwise, unwind – you’ve had a full New York day.
Rest up, because tomorrow morning you’ll continue southward.
Day 3: Philadelphia, PA
Drive from NYC to Philly
This morning, depart New York City and drive south to Philadelphia.
The distance is about 95 miles and usually a 1.5–2 hour drive via the New Jersey Turnpike (I-95).
Plan to leave after rush hour (around 9–10 AM) to avoid NYC commuter traffic.
As you drive through New Jersey, you might catch glimpses of the skylines of Newark and Philadelphia in the distance.
Visit Independence Hall & the Liberty Bell
Arrive in Philadelphia before lunchtime. Philly is the birthplace of American independence, so head straight to the historic district.
Start at Independence National Historical Park.
Here you can visit Independence Hall, where the Declaration of Independence (1776) and U.S. Constitution (1787) were debated and signed.
Timed entry tickets are required (free from the Visitor Center), but even seeing the exterior and the nearby Liberty Bell Center is inspiring.
Check out the Liberty Bell itself – the iconic cracked bell that symbolizes American freedom – through the glass window if lines are long.
Travel Tip: If you want to tour Independence Hall, stop by the Visitor Center first to pick up free tickets with a scheduled tour time to plan the rest of your day around it.
Lunch at Reading Terminal or Pat’s/Geno’s
By midday, grab an authentic Philly cheesesteak for lunch.
Two famous rival spots, Pat’s and Geno’s, are in South Philly (if you want the classic experience), or you can try the closer Reading Terminal Market which has diverse food options under one roof.
Reading Terminal is a fun stop to taste local treats (donuts at Beiler’s or ice cream at Bassetts) and the bustling market scene is an experience in itself.
Climb the Rocky Steps
In the afternoon, consider a quick visit to Philadelphia Museum of Art – not for the art (unless that’s your interest), but to run up the “Rocky” steps in front of it!
It’s a short drive or rideshare from the historic center.
At the top of the stairs, pump your fists like Rocky Balboa and enjoy a great view down Benjamin Franklin Parkway to City Hall.
Another family-friendly option is the Franklin Institute Science Museum, if you have more time and the weather is bad – but on a nice day, staying outdoors might be preferable.
Drive to Washington, D.C.
By late afternoon, it’s time to get back on the road. Washington, D.C. is your next major stop.
The drive from Philadelphia to D.C. is roughly 140 miles and can take about 2.5 to 3 hours.
You’ll pass through Delaware and Maryland, and around the major city of Baltimore on the way.
Travel Tip: Plan a rest stop near Delaware or Maryland House service plazas on I-95 to break up the drive and avoid peak traffic hours around Baltimore and D.C. if possible.
Aim to reach Washington, D.C. in the evening.
After checking into your D.C. hotel, you might be tired from the travel, but here’s a bonus tip: a quick night tour of the National Mall by car or on foot can be magical.
Many monuments are beautifully illuminated at night, and it’s much quieter.
Even a drive by the glowing U.S. Capitol and Washington Monument, or a short walk up to the Lincoln Memorial steps, can be a serene way to preview D.C. without the daytime crowds.
Otherwise, get a good night’s sleep so you can explore the capital in the morning.
Day 4: Washington, D.C.
Morning Monuments
Welcome to the nation’s capital! A full day in Washington, D.C. offers plenty to see without rushing.
Start your day at the National Mall, the expansive green park lined with Smithsonian museums and monuments.
Early morning is a great time to visit the Lincoln Memorial at the west end of the Mall – the giant statue of Lincoln and the view across the reflecting pool to the Washington Monument is inspiring.
From there, walk toward the Washington Monument, passing by war memorials like the Vietnam Veterans Memorial (the reflective black wall of names) or the World War II Memorial.
This walk is a meaningful journey through American history, and kids often find the huge monument and wide-open spaces fun to explore (plenty of room to run a bit).
Smithsonian Museum Visits
By late morning, head to a Smithsonian Museum of your choice.
All the Smithsonian museums have free admission, which is a nice break for the budget.
For families, two favorites are the Smithsonian National Air and Space Museum (rockets, planes, and interactive exhibits, including the Wright brothers’ plane and moon rocks) and the Smithsonian National Museum of Natural History (dinosaur fossils, a giant whale model, mummies, and more).
Both are on the National Mall and typically require at least 1-2 hours to do them justice.
Travel Tip: Security lines can be a bit long at peak times – consider going right when the museum opens or later in the afternoon.
Also, note that the Air and Space Museum currently requires timed-entry passes (free, but reserve online) due to renovations, so plan ahead if that’s on your must-do list.
Lunch Options
For lunch, you can eat at a museum café or pack a picnic to enjoy on the Mall’s grassy areas.
Alternatively, venture to the nearby Penn Quarter or Chinatown neighborhoods for many quick dining options.
In the afternoon, continue exploring: perhaps visit another museum (the National Museum of American History has the Star-Spangled Banner flag and Kermit the Frog, among other treasures) or take a tour of the U.S. Capitol building if you’ve arranged passes in advance.
You might also stop by the White House for a photo from outside the gates on Pennsylvania Avenue – the north side (Lafayette Square area) has a pedestrian plaza where you can snap a picture of the President’s residence.
Afternoon Activities
If everyone’s energy is holding up, consider a quick trip to Georgetown in the late afternoon.
This historic neighborhood has charming old houses, the C&O Canal, and plenty of cafes and shops.
It’s a nice place to grab an early dinner or cupcake (Georgetown Cupcake is famous from TV, and there’s also an excellent ice cream shop, Thomas Sweet).
However, it’s a bit off the Mall (you’d need to drive or take a rideshare/cab, about 10-15 minutes from downtown).
So this is optional if you prefer a change of scenery.
Evening Highlights
Spend the evening in D.C. at a relaxed pace.
You could return to the National Mall to see any monuments you missed (the Jefferson Memorial across the Tidal Basin is lovely at sunset).
Or simply relax – maybe enjoy your hotel’s pool if there’s one, which the kids might appreciate after several days of city walking.
Travel Tip: Washington’s Metro subway is a convenient way to get around if you want to avoid driving in city traffic.
Day passes are available, and major sites are metro-accessible (Smithsonian station drops you right at the Mall).
Using the Metro or DC Circulator bus can save you the hassle of finding parking near the Mall, which can be limited.
Tomorrow, you’ll transition from big cities to some colonial charm and beach scenery in Virginia.
Day 5: Williamsburg & Virginia Beach, VA
Drive from D.C. to Williamsburg
Leave D.C. in the morning and drive south toward Virginia.
Today’s journey will take you into the heart of early American history and then to the Atlantic coast.
First stop: Colonial Williamsburg.
The drive from Washington, D.C. to Williamsburg, VA is about 150 miles and roughly 2.5 hours via I-95 and I-64 (barring traffic).
To avoid D.C. morning rush hour, consider departing after 9 AM.
Explore Colonial Williamsburg
Arrive in Williamsburg around midday.
Colonial Williamsburg is a living history museum – a entire 18th-century town restored and recreated.
Park at the Visitor Center and take the shuttle or walk into the historic area.
As you enter Duke of Gloucester Street, you truly step back in time.
You’ll see costumed interpreters in colonial garb going about their “daily life” – blacksmiths hammering iron, farmers tending crops, and townsfolk discussing the news of 1775.
This isn’t a typical museum; it’s the world’s largest living history museum, an immersive experience where you can see, hear, and touch the 18th century.
Spend a few hours exploring the colonial capital.
Highlights for general visitors include the Governor’s Palace (tour the opulent home of Virginia’s royal governor), the Capitol building, and tradespeople’s shops (weavers, silversmiths, bookbinders, etc.).
Kids often love the shoemaker and blacksmith shops – the artisans are friendly and explain their crafts.
You can even try some colonial games like hoop rolling on the lawn.
Travel Tip: Many buildings are open to the public for free roaming, but certain sites and all guided tours require tickets.
If you want the full experience (including entry to the Palace, courthouse reenactments, etc.), it’s worth purchasing a day pass.
However, even without a pass, you can walk the streets and soak up the atmosphere freely, which is enjoyable on its own.
Lunch in Merchants Square or a Tavern
For lunch in Williamsburg, there are tavern restaurants in the historic area (like King’s Arms Tavern) serving colonial-inspired fare.
These can be a bit pricey, but it’s a unique experience to eat Brunswick stew or turkey pie by candlelight in a colonial tavern.
Alternatively, grab a quick sandwich from a bakery in Merchants Square (adjacent to the historic area).
Merchants Square also has modern shops and is a nice place to pick up a souvenir or two.
Optional Detour: Virginia Beach
In the afternoon, as you wrap up your Williamsburg visit, you have a choice: continue straight toward North Carolina or take a detour to Virginia Beach for the evening.
If you’re craving some ocean breeze and relaxation, Virginia Beach is only about an hour east of Williamsburg (60 miles via I-64 E).
You could drive there for a quick beach fix before heading south.
If you prefer to push closer to North Carolina tonight, you might skip Virginia Beach.
But let’s assume you choose a bit of beach time for diversity!
Drive east to Virginia Beach, arriving by late afternoon.
Head to the oceanfront where a long sandy beach and a famous boardwalk await.
Take a pleasant walk on the 3-mile boardwalk along the Atlantic Ocean – you might see surfers in the waves and people biking or rollerblading on the path.
There’s a fun bronze statue of King Neptune (a 34-foot-tall Neptune holding a trident) along the boardwalk that makes for a great photo op.
Let the kids splash in the water or play in the sand to unwind after days of city exploration.
Downtime Tip: This is a well-earned relaxed evening. No major schedule, just enjoy the sea air and maybe catch a seaside sunset.
Dinner by the Sea
For dinner, Virginia Beach has countless seafood restaurants.
Eating fresh fish or Chesapeake Bay blue crabs with an ocean view is a treat.
A casual option is to find an outdoor deck restaurant – many are family-friendly.
Try some crab cakes or shrimp – you’re in the Mid-Atlantic, after all.
Overnight Options
Tonight, you’ll stay somewhere around this area.
You could overnight in Virginia Beach to enjoy the resort town vibe, or drive a bit further to position yourself for tomorrow’s journey.
Many travelers choose to stay in Norfolk or Chesapeake, VA (about 30 minutes from Virginia Beach) to be closer to the route toward North Carolina.
Either way, tomorrow morning you’ll head for North Carolina’s Outer Banks.
Travel Tip: If you have time and interest, driving the 17-mile Chesapeake Bay Bridge-Tunnel is a unique experience not far from Virginia Beach.
It’s a bridge-tunnel that crosses the mouth of Chesapeake Bay – an engineering marvel with two tunnel sections going under the ocean.
This would be a detour northward, though, so only do it if you’re very curious and have extra time.
Otherwise, rest up for Outer Banks adventure ahead!
Day 6: Outer Banks, NC
Drive to the Outer Banks
Get ready for a day of sun, sand, and Carolina scenery.
From the Norfolk/Virginia Beach area, drive south toward the Outer Banks of North Carolina.
The Outer Banks (OBX) are a string of narrow barrier islands along the Atlantic coast known for their beautiful beaches and historic lighthouses.
The drive from Virginia Beach to the central Outer Banks (Kitty Hawk/Nags Head area) is about 1.5–2 hours (approximately 80–90 miles).
You’ll cross into North Carolina and take Highway 158 over the Wright Memorial Bridge onto the islands.
Morning at Wright Brothers Memorial
By mid-morning, you’ll arrive in Kitty Hawk/Kill Devil Hills, the northern part of OBX.
This is the perfect place to dive into some aviation history.
Wright Brothers National Memorial in Kill Devil Hills commemorates where Wilbur and Orville Wright achieved the first successful powered airplane flight in 1903.
Visit the memorial on top of the big hill and see the reconstructed camp buildings and launch rail on the field where those first flights took place.
There’s a visitors center with a replica of the Wright Flyer and engaging exhibits that explain how the brothers made aviation history here.
Standing at the very spot of the first flight (marked by a stone) is pretty awe-inspiring – it’s a big field, and you can follow the markers showing how far each of the four flights went (the longest was 852 feet).
Kids can run on the field, which gives a sense of how short that first 12-second flight was.
Travel Tip: Climb Big Kill Devil Hill up to the monument for a panoramic view of the Outer Banks – you can see both the ocean and the sound from up there, and it’s often breezy and cooler on the hill.
Sand Dunes at Jockey’s Ridge
After getting your fill of history, it’s time for pure beach fun and nature.
A short drive south brings you to Jockey’s Ridge State Park in Nags Head – home to the tallest natural sand dunes on the East Coast.
It’s essentially a mini desert by the sea, with huge sand hills that are popular for flying kites and even hang gliding.
Hike (or rather, trudge!) up the soft sandy slopes – it’s a bit of a workout, but the views at the top are worth it.
The endless dunes make you feel like you’re in the Sahara, and you can see both the Atlantic Ocean and Roanoke Sound from the summit on a clear day.
It’s a great spot to let kids roll or slide down the sand.
You’ll often see colorful kites in the sky; there’s a kite store (Kitty Hawk Kites) across the street that even offers kite-flying lessons.
In fact, giant kite festivals are held here – don’t be surprised if you see giant animal-shaped kites dancing in the wind.
Feel free to join the fun and fly a kite yourself (you can buy an inexpensive one locally).
Pro tip: the sand can be hot on summer afternoons – bring sandals and sunscreen, and maybe plan this for the morning or late afternoon in the hotter months.
Lunch in Nags Head
By lunchtime, you might be hungry. Nearby in Nags Head and Kill Devil Hills are plenty of casual beach eateries.
Grab some Carolina BBQ or a basket of fish and chips at a local grill.
Seafood is obviously a good bet – perhaps try a fried shrimp platter or fresh fish tacos.
Many spots are very laid-back, and some offer outdoor seating which is nice if you’re sandy or have kids who don’t want to sit still too long.
Scenic Lighthouse Stops
In the afternoon, continue south along NC Highway 12 (the Beach Road) to see more of the Outer Banks scenery.
You’ll pass through the Cape Hatteras National Seashore, with dunes on your left and the shimmering sound on your right. Consider a stop at Bodie Island Lighthouse (pronounced “Body”) which is just south of Nags Head.
It’s a classic black-and-white striped lighthouse amid marshlands.
In summer, you can climb its 200+ steps to the top for a small fee, but even a look from the grounds and a stroll on the boardwalk through the marsh is pleasant.
Further south, if you’re up for a longer drive, the Cape Hatteras Lighthouse in Buxton is the crown jewel of OBX lighthouses.
It’s the tallest brick lighthouse in the United States, famous for its black-and-white spiral pattern.
Reaching Cape Hatteras Light is about a 1.5-hour drive one-way from Nags Head, so it’s only recommended if you have extra time or really love lighthouses.
But if you do go, the drive is beautiful, and the lighthouse area has a nice museum and beach access.
(You can also see where the lighthouse was moved 2,900 feet inland in 1999 to save it from the encroaching sea – a fascinating bit of preservation history!)
Even if you don’t go all the way to Hatteras, there’s plenty to enjoy around Nags Head.
The beaches here are wide and inviting – you might spend the remainder of the afternoon swimming or beachcombing.
Public beach accesses are common, and many have parking and showers.
Beach Time and Sunset Views
As the sun starts to lower, treat yourself to a classic OBX experience: sunset over the sound.
Because the Outer Banks are narrow, you can easily drive to the sound side (Roanoke Sound or Pamlico Sound) to watch the sunset over the water.
One great spot is the soundside dock at Jockey’s Ridge State Park – seeing the sun sink while silhouetting the dunes is gorgeous.
Or find a waterfront restaurant on the sound side (in Nags Head or Roanoke Island) and have dinner with a view.
Dinner and Overnight
For dinner, how about some Carolina coastal cuisine? Try a steamer pot of crab legs, corn, and potatoes, or savor locally caught tuna or mahi.
The vibe in OBX restaurants is beachy and relaxed; many are family-run and very welcoming.
After dinner, indulge in a scoop of ice cream from a local creamery – a perfect way to cap off a beach day.
Tonight, sleep in the Outer Banks.
There are many accommodation options from beach hotels to rental cottages.
Staying in Nags Head or Kill Devil Hills keeps you central.
Falling asleep to the sound of ocean waves (if you’re oceanfront) is heavenly.
Travel Tip: The Outer Banks can get busy in summer, so book accommodations ahead.
Also, note that OBX is spread out – having a car is essential to get between attractions, but everything is a short drive and quite scenic.
You’ve had a mix of history and beach relaxation today – tomorrow will be a longer drive as you continue south to Charleston, so get a good rest.
Day 7: Travel Day to Charleston, SC
Morning Departure from OBX
Today is mostly a travel day as you make your way from North Carolina to South Carolina’s Lowcountry.
The distance from Nags Head, NC (central Outer Banks) to Charleston, SC is around 450 miles, so you’ll want an early start and plan some stops to break up the drive.
It’s a long haul, but we’ll make it interesting!
In the morning, bid farewell to the Outer Banks.
As you drive inland, take US-64 or US-158 westward from the OBX to reconnect with I-95 South on the mainland.
An optional but worthwhile detour: if you’re up early and have an extra hour, swing by Roanoke Island (just before returning to the mainland) to see the site of the “Lost Colony” at Fort Raleigh or the adorable coastal town of Manteo.
Even a quick stop by the Roanoke Marshes Lighthouse on Manteo’s waterfront could be nice.
Otherwise, continue on.
Midday Stop Ideas
Once on I-95 South, you’ll cruise through the forests and fields of North Carolina.
Consider a lunch stop around Wilmington, NC, roughly halfway to Charleston (it’s a bit off I-95, but a charming city if you need a break).
If you detour to Wilmington (adds time), you could have lunch on the Riverwalk overlooking the Cape Fear River and even glimpse the Battleship North Carolina moored there.
A quicker pit stop is Fayetteville, NC or Florence, SC right along I-95, which have plenty of roadside restaurants and gas stations.
Roadside Diversions
As you cross into South Carolina, you might notice the landscape starting to change to more marshes and live oaks.
A quirky road trip landmark to break the monotony: South of the Border, just south of the NC/SC border on I-95.
It’s a retro roadside attraction/rest stop with a sombrero tower and neon signs – very kitschy but kids might find it amusing to stretch legs here.
There are restrooms, eateries, and souvenir shops full of goofy trinkets.
Even if you just snap a photo with one of the giant fiberglass animal statues, it’s a fun little diversion.
Arrive in Charleston by Evening
Continue on I-95 then take I-26 East toward Charleston.
The last hour or so, you’ll drive through South Carolina’s Lowcountry – expect flat land with salt marshes and waterways as you approach the coast.
Arrive in Charleston, South Carolina by late afternoon or early evening.
Congrats, the long drive is done!
Now it’s time to enjoy one of America’s most beautiful and historic cities.
After checking in to your Charleston lodging, spend the remainder of the day relaxing.
You’ve earned a slower evening. One great way to unwind is to take a leisurely walk in Charleston’s historic French Quarter or along The Battery (the waterfront promenade).
The city’s streets are filled with antebellum charm – think cobblestone lanes, gas lanterns flickering, and rows of rainbow-colored historic homes.
Speaking of which, stroll by Rainbow Row on East Bay Street – a series of 13 pastel-painted historic houses that are an iconic Charleston sight.
As the evening sets in, the city’s charm only grows with warm glows in the windows and the scent of jasmine in the air (if it’s spring/summer).
Dinner in the Historic District
For dinner, Charleston is a foodie heaven.
You might be craving a sit-down meal after the road food.
Treat yourself to some famous Southern cuisine here.
How about shrimp and grits or a Lowcountry boil? Many restaurants in the historic district cater to families while still offering top-notch fare.
If you’re not too tired, you could even take a carriage ride – in the evening, horse-drawn carriages still clip-clop through the streets offering narrated tours.
It’s a relaxing way to learn a bit about the city without walking, and the guides often throw in entertaining stories.
Charleston has a rich 300-year history and is America’s most beautifully preserved architectural and historical treasure – you’ll fully explore it tomorrow.
Tonight, get some rest at your Charleston hotel or B&B (perhaps in a historic building for added ambiance!).
Travel Tip: Charleston’s historic district hotels have limited parking, so check if your hotel offers it. If not, there are city garages. Once parked, it’s easy to explore the city on foot or by pedicab.
Day 8: Charleston, SC
Morning Walk through Historic Charleston
Charleston will likely steal your heart with its Southern hospitality and postcard-perfect streets.
Start your day with a hearty Southern breakfast – maybe biscuits and gravy or chicken and waffles at a local café.
Then set out to explore Charleston’s Historic District.
The city is essentially a living museum of antebellum architecture.
Begin at the Battery and White Point Garden at the tip of the peninsula.
This park has old cannons and statues, and offers views of Charleston Harbor where the Ashley and Cooper Rivers meet the Atlantic.
Stroll East Battery Street to admire the grand historic mansions facing the water.
Many have plaques with names and dates – you’ll see some that are over 200 years old, painted in beautiful pastel hues with wraparound piazzas (porches).
It’s hard not to imagine ladies with parasols and gentlemen in seersucker suits lounging on those balconies catching the breeze.
Charleston’s preservation efforts mean these streets look much like they did centuries ago, truly a “living museum” vibe.
French Quarter & Churches
Next, walk up to Rainbow Row (if you didn’t last night) in the morning light for photos.
The colors really pop – pink, peach, green, blue – it’s one of the most photographed spots in Charleston.
From Rainbow Row, wander into the French Quarter along Chalmers Street or Church Street.
Chalmers is one of the last cobblestone streets, which gives you a literal feel of history under your feet (watch your step!).
On Church Street, you’ll pass the Dock Street Theatre (America’s first theater building) and the towering steeple of St.
Philip’s Church – one of many, many church steeples in the city’s skyline (Charleston’s nickname is “The Holy City” due to its abundance of historic churches).
Optional Tours
By late morning, consider a guided tour to deepen your understanding of Charleston.
A popular choice is a historic carriage tour (if not done already) or a walking tour led by a local guide.
They’ll share fascinating stories – from pirate tales to Civil War history – as you trot or walk through quaint backstreets you might otherwise miss.
For a DIY approach, the Old Exchange and Provost Dungeon is an interesting site to tour; it’s a colonial-era building where George Washington once danced and where American Patriots were imprisoned by the British below ground.
Another must-see is the City Market on Meeting Street – a historic market complex where local vendors sell sweetgrass baskets (a traditional Gullah craft), artwork, and other souvenirs.
It’s touristy but fun, and the long open-air “sheds” of the market have been the city’s marketplace for over 200 years.
Southern Lunch
Come lunchtime, you’re in for a treat. Charleston’s food scene is stellar.
You could sample Lowcountry cuisine at a place like Hymans Seafood or Fleet Landing (for waterfront dining).
Must-tries include she-crab soup (a creamy crab soup), fried green tomatoes, or the classic shrimp and grits.
If you prefer something light, there are also sandwich shops and cafes in the market area.
Afternoon Excursions
In the afternoon, delve into history or nature – your choice.
For history, you might take a ferry ride to Fort Sumter National Monument out in Charleston Harbor, where the first shots of the Civil War were fired in 1861.
The boat ride (departing from Liberty Square near the Aquarium or from Patriots Point) is breezy and scenic, and visiting the fort ruins with a park ranger talk can be quite engaging if you’re a history buff.
The entire excursion takes about 2-3 hours.
Alternatively, visit a historic plantation just outside the city: Boone Hall (famous oak avenue and gardens) or Magnolia Plantation (known for beautiful gardens and a petting zoo) are both about a 20-minute drive away.
Boone Hall has that iconic avenue of moss-draped oak trees you might recognize from films.
It’s a picturesque and educational trip, with insights into the antebellum South, including the enslaved people’s history on the plantation (Boone Hall has original slave cabins with exhibits).
Keep in mind, though, fitting a plantation visit might make for a busy day – it could be saved for Day 9 morning if you want a slower pace today.
Evening Ideas
If you’d rather stay downtown and are craving some downtime, take a break at Waterfront Park.
Grab a bench or swing seat by the famous Pineapple Fountain and watch sailboats in the harbor.
Kids often enjoy splashing their hands in the Pineapple Fountain or running through the splash pad fountain nearby (have a towel handy if they do!).
The park is also lovely for just sitting under the palmetto trees and soaking in the atmosphere.
You’ll likely see locals fishing off the pier or families out for a stroll.
As evening approaches, consider an early dinner in Charleston (perhaps trying another Southern classic like “chicken bog” or a fresh catch of the day).
Charleston has everything from barbecue joints to fine dining, so you can find whatever suits your mood.
Travel Tip: Charleston’s popularity means restaurants can be crowded – making a reservation for dinner (or using a call-ahead list) is wise, especially on weekends.
For a spooky twist tonight, how about a ghost tour? Charleston is very proud of its ghost lore given how old the city is.
Walking ghost tours at night are popular – a guide will lead you by lantern through graveyards and old alleys, telling eerie tales.
It’s usually more fun than frightening and can captivate older kids/teens and adults alike with stories of pirates and haunted houses.
If ghost stories aren’t your thing, an evening walk through the King Street boutique district or the quiet residential South of Broad area is equally pleasant.
The architecture looks different in the soft gaslight at night, and you’ll catch the scent of night-blooming jasmine or gardenias in the summer months – truly delightful.
Spend a second night in Charleston, enjoying the comfort and charm.
Tomorrow you’ll head to Savannah, which, luckily, is not too far – meaning you can enjoy a relaxed morning here if you like.
Day 9: Savannah, GA
Drive to Savannah
Bid adieu to Charleston and set course for Savannah, Georgia.
The drive is mercifully short today – about 108 miles, roughly 2 hours via US-17 and I-95.
For a scenic option, you can take the coastal highway US-17 part of the way through the Lowcountry wetlands and small towns (like Beaufort, SC, which is a charming historic town in its own right if you want to stop).
Otherwise, the faster route is I-26 W out of Charleston connecting to I-95 S toward Georgia.
If you’re a morning person, you might depart Charleston early.
But given the short distance, you could also enjoy a leisurely Charleston breakfast (maybe some fresh benne seed wafers or pralines for the road from a local candy shop) and leave mid-morning.
Either way, you should arrive in Savannah by late morning or around midday.
Savannah’s vibe is quaint, artsy, and a bit slower-paced than Charleston’s, but equally steeped in history.
The city is famous for its historic squares – small park-like oases dotted in a grid throughout downtown (22 out of the original 24 squares remain today).
Driving in, you’ll notice the Spanish moss draping elegantly from giant live oak trees, giving the city a dreamy Southern Gothic look.
Fun Fact: Savannah’s well-preserved city plan dates back to 1733 and those tree-filled squares are a defining feature – they were designed by founder James Oglethorpe as communal gathering spots and have helped Savannah retain its historic charm.
Morning in Forsyth Park
Start your Savannah exploration at the Historic District’s riverfront or Forsyth Park, depending on your hotel location.
A good first stop is Forsyth Park, the largest park in the historic downtown.
There you’ll find the famous Forsyth Fountain, a beautiful white cast-iron fountain (built in 1858) that’s one of Savannah’s most recognizable landmarks.
It makes a great photo backdrop (often dyed green on St. Patrick’s Day!).
The park is lined with oaks and often you’ll see artists painting or families picnicking.
Let the kids run around the playground or simply relax on a bench beneath the moss.
Walk Through Savannah’s Squares
From Forsyth Park, you can walk north through the heart of the Historic District along Bull Street, which will take you through a series of picturesque squares: Monterey Square (home to the Mercer-Williams House of Midnight in the Garden of Good and Evil fame), Madison Square, Chippewa Square (where the “Forest Gump bench” scene was filmed – though the bench is now in a museum), and others.
Each square has its own character, statue or monument, and surrounding architectural gems.
It’s like a treasure hunt discovering each one.
Travel Tip: Savannah is a very walkable city, but wear comfy shoes – the brick sidewalks and cobblestones can be uneven.
Also, summer heat can be intense; fortunately, those mossy oaks provide lots of shade and there are plenty of cafes to duck into for a cold drink.
Lunch on River Street
Make your way to Savannah’s River Street by early afternoon.
River Street runs along the Savannah River and is paved with old cobblestones (actually ballast stones from ancient ships).
This area was once the bustling cotton warehouse district; now those old brick buildings are shops, galleries, and restaurants.
It’s a bit touristy but fun.
Watch the giant cargo ships glide by – surprisingly close – as Savannah is a busy port.
Pop into River Street Sweets for free samples of fresh pralines (a local candy made of pecans, butter, and sugar) – they are delicious when warm.
For lunch, you have lots of choices: perhaps try a bowl of Savannah’s famous she-crab soup or a crab cake sandwich at a riverside restaurant.
If you’re craving something casual, grab a hot dog or sandwich from a street vendor and sit on a bench overlooking the river.
Afternoon Activities
After lunch, you might enjoy a short sightseeing cruise on a Savannah riverboat (they offer hour-long cruises in paddlewheel-style boats, with views of the skyline and narration about the port’s history).
If boats aren’t your thing, a trolley tour is a popular land option to see more of the city with minimal effort.
Old Town Trolley or Old Savannah Tours have hop-on, hop-off trolleys that loop around all the key sites with informative guides narrating.
This can be helpful to cover ground and learn tidbits of history (like tales of General Oglethorpe or Juliette Gordon Low, who founded the Girl Scouts here).
Be sure to visit a house museum or two if time allows – they offer a peek into the elegant lifestyle of Savannah’s past.
The Mercer-Williams House (if you know the book/movie Midnight in the Garden of Good and Evil, this is that house), or the Davenport House (a meticulously restored 1820s home), or Juliette Gordon Low Birthplace (the childhood home of the Girl Scouts founder) are all interesting options.
Guides in period costume often lead the tours, and it’s fascinating to see the antique furnishings and hear stories of the families who lived there.
Savannah’s unique Flannery O’Connor Childhood Home might interest literature buffs, and the Cathedral of St. John the Baptist is a must-see for architecture fans – its twin spires and ornate interior are stunning (and it’s free to enter when services aren’t occurring).
It’s often called the “Sistine of the South” for its beautiful murals and stained glass.
Sweet Treats & Sunset
By late afternoon, you might be ready for a sweet treat or pick-me-up.
Leopold’s Ice Cream on Broughton Street is legendary – they’ve been scooping homemade ice cream for over a century.
The line can be out the door, but their classic flavors like Tutti Frutti are worth it.
Alternatively, stop by a bakery for a cupcake or an iced coffee at one of Savannah’s many charming coffeehouses (perhaps Coffee Fox or Gallery Espresso).
As dusk falls, Savannah’s squares take on a romantic glow.
The streetlights and the hanging Spanish moss create a slightly mysterious atmosphere. It’s the perfect time for – you guessed it – a ghost tour if you’re up for more haunts.
Savannah proudly claims to be one of America’s most haunted cities.
Whether you believe in ghosts or not, the stories on these tours are entertaining and you’ll get to enter or stand by some eerie old mansions or cemeteries like Colonial Park Cemetery (dating back to 1750).
Even if you skip a formal tour, an evening walk through the historic district (in well-populated areas) is pleasant.
Safety Tip: Savannah is generally safe in tourist areas, but some parts of downtown get quiet at night; stick to main streets or tour groups if out late.
Dinner & Evening Vibes
For dinner, indulge in Savannah’s food scene.
Perhaps dine under the oaks in a square at The Olde Pink House (a famous pink colonial mansion-turned-restaurant) for upscale Southern fare – think pecan-crusted chicken or praline-glazed pork tenderloin.
Or go casual at a place like Crystal Beer Parlor for burgers and local craft brews.
Seafood lovers might try Alligator Soul or Sorry Charlie’s Oyster Bar for fresh oysters, shrimp and grits, or Lowcountry boil (a mix of shrimp, sausage, corn, and potatoes).
One more quirky Savannah attraction for after dinner:
River Street at night often has live music and even occasional fireworks on weekends over the river.
If it’s a weekend, you might catch street performers or music coming from the open-air bars.
It’s a lively yet laid-back scene – feel free to grab a “to-go cup” (Savannah allows carrying alcoholic drinks in plastic cups in the historic district) and stroll, if that’s your style.
Or get a scoop of gelato and enjoy the cooler night air.
Tonight, sleep tight in Savannah. Many lodgings here are historic inns or modern hotels tucked into old buildings.
Enjoy the Southern hospitality – a lot of places may offer sweet tea or lemonade in the lobby for guests.
Tomorrow, you’ll make the final drive to Florida to cap off your East Coast road trip.
Day 10: St. Augustine, FL
Drive to the Nation’s Oldest City
Your final day brings you to Florida’s northeast coast and the nation’s oldest city.
From Savannah, drive about 180 miles south to St. Augustine, Florida.
It’s roughly a 2.5-hour drive down I-95, passing the marshes of coastal Georgia and crossing into the Sunshine State.
If you have time in the morning, you could stop at Jekyll Island or St. Simons Island (just off I-95 in Georgia) for a quick beach walk or to see Driftwood Beach’s gnarled tree skeletons – a beautiful sight.
Otherwise, continue straight on. Drive Time: ~2.5 hours (Savannah to St. Augustine).
Arrive in St. Augustine around late morning or midday.
St. Augustine was founded in 1565 by Spanish explorers and is the oldest continuously inhabited European-established settlement in the continental U.S.
The city’s Spanish colonial heritage sets it apart from the English-settled places you’ve seen so far.
You’ll notice the architecture has a Mediterranean flair – red tile roofs, stucco walls, and central courtyards.
Explore Castillo de San Marcos
Begin at the Castillo de San Marcos, the star-shaped stone fortress on the waterfront.
Built in the 17th century (completed 1695) by the Spanish, it’s the oldest masonry fort in the continental US.
Park nearby (the lot fills up in peak times, but there’s overflow parking down the street) and head inside the fort (entry fee for adults, kids free).
Walking the ramparts is really neat – you can see the old cannons lined up overlooking Matanzas Bay, and the view of the water is fantastic.
Park rangers or volunteers often do cannon-firing demonstrations here with real cannons (minus the cannonballs, of course!).
The thick coquina stone walls (made of compressed seashells) have withstood attacks for centuries – the fort was never taken by force.
You can explore the many rooms inside which once housed soldiers and supplies; exhibits explain the fort’s history under Spanish, then British, then American control.
Kids might enjoy the feeling of walking through a real-life castle of sorts, with its drawbridges and moat (now dry).
Fun Fact: The coquina walls absorbed cannon fire rather than shattered – which helped the fort survive sieges.
Wander Historic St. George Street
After touring the Castillo, wander across the street to St. Augustine’s historic old town.
St. George Street is the main pedestrian lane through the colonial quarter – it’s lined with charming shops, cafes, and historic buildings.
You’ll find everything from boutiques to an old-fashioned ice cream shop and the oldest wooden schoolhouse in the USA (a tiny, weathered wood building you can peep inside).
The atmosphere is lively but with a centuries-old ambiance. Street musicians often play Spanish guitar or other tunes, adding to the vibe.
For lunch, you have plenty of options here: Spanish cuisine at Columbia Restaurant (a famous spot serving paella, Cuban sandwiches, and their beloved 1905 Salad), casual tacos or pizza at one of the small eateries, or fresh catch seafood at a tavern.
Given it’s your last day, maybe try something Spanish-inspired in honor of the city – the Columbia’s menu has been a staple for decades and is great for families (they have a beautiful tiled dining room and fountain).
Afternoon Attractions
In the afternoon, delve deeper into the sights.
A must-see is Flagler College – formerly the Ponce de Leon Hotel built in 1888 by Henry Flagler.
The campus (you can take a guided tour) is an architectural masterpiece of the Gilded Age, with ornate carvings, stained glass by Tiffany, and a grand courtyard.
Across the street, the Lightner Museum (former Alcazar Hotel) has interesting collections (from Victorian oddities to art) and a pretty indoor courtyard with a koi pond – even if you don’t tour the museum, it’s lovely to walk into the lobby and peek at what was once the world’s largest indoor swimming pool (now drained and used for events).
Kids (and adults) might enjoy the quirky St. Augustine Pirate & Treasure Museum, which has artifacts like real pirate treasure and interactive displays about pirates – very fitting for a city that saw its share of privateers in the 1600s.
Another fun stop is the Fountain of Youth Archaeological Park, especially if you like history legends – it’s the site associated with Ponce de Leon’s search for the Fountain of Youth.
You can actually drink from the spring there (spoiler: it tastes like minerals, but why not try a sip for longevity?).
The park also has peacocks roaming around and a reconstructed Timucua Native American village area with demonstrations.
If you’re interested in old churches, check out the Cathedral Basilica of St. Augustine, the oldest church in Florida, with its lovely Spanish-style facade and painted ceiling.
It’s right on Cathedral Street off the plaza.
Speaking of the Plaza de la Constitución, this central square downtown has a historic market and monuments (including one of the oldest public monuments in the country, an obelisk from 1812). It’s a nice resting spot under the oaks.
Optional Beach Time
For some late afternoon relaxation, consider driving over the Bridge of Lions (the white bridge you likely saw from the fort, guarded by marble lion statues) to Anastasia Island.
Here you can visit St. Augustine Beach or Anastasia State Park to enjoy the ocean one more time.
The beach here is wide and usually less crowded than further south Florida beaches.
Even an hour of playing in the sand or wading in the waves can be a refreshing break in a history-heavy day.
Plus, Florida’s sun will likely be shining – a dip in the Atlantic might be tempting if it’s warm.
As the sun sets on your final day, head back into the old city for an evening ghost tour (yes, St. Augustine has ghost tours too – sensing a theme on the East Coast?).
The Old City’s cobbled streets and overhanging balconies certainly set the stage for ghost legends from its 450-year history.
The old Spanish Military Hospital and the city gates are known “haunted” spots often featured on tours.
Final Dinner & Reflection
Otherwise, enjoy a farewell dinner.
There’s something poetic about ending in a city that blends the flavors of Spain, Cuba, and the American South.
You might try a dish like Minorcan clam chowder (a local spicy red chowder) or devour some Florida key lime pie for dessert.
If you haven’t yet, raise a glass of sangria or sweet tea to toast the journey you’ve just completed.
Finish the night with a quiet walk along Avenida Menendez (the bayfront road by the fort) to see the Castillo lit up, and perhaps catch the moonlight on the bay.
The sea breeze here is gentle and the city often has a guitarist playing in the distance or the clip-clop of a horse carriage as backdrop.
It’s a serene way to reflect on the miles traveled and memories made.
Wrapping Up Your Trip
Congratulations – in 10 days, you’ve experienced a broad swath of the East Coast’s wonders: from revolutionary Boston and bustling New York, through the founding of a nation in Philly and D.C., to the coastal beauty of the Outer Banks and the Southern charm of Charleston and Savannah, ending in the historic warmth of St. Augustine.
This road trip packed in cities, nature, iconic landmarks, and cultural highs just as promised.
It’s been a well-paced adventure mixing busy sightseeing with moments of relaxation under oak trees or by ocean waves.
As you wrap up your East Coast road trip, you can either extend your stay in Florida, head to nearby Orlando or Miami for a completely different Florida experience, or simply cherish the journey’s end and head home.
No matter what, the diverse experiences of these 10 days will stay with you – each day a story to tell and a chapter in your travel memories.
Travel Tip: Before driving off tomorrow (or dropping off your rental car), double-check for any souvenirs or snacks tucked away – you’ve collected quite a few mementos along the way!
