A road trip from Boston to Miami can lead you to incredible destinations along the U.S. east coast. Solid driving will take around 23 hours to reach Florida, covering about 1491 miles (2399 kilometres). Depending on your route and chosen stops, you could pass through 12 states, including Massachusetts as your starting point and Florida to complete your journey. Giving up a day or two on your road trip from Boson to Miami gives you a flavour for each place and may even entice you to return.
Yes, you can fly, but why not take some time to explore by road? Not only will you discover new destinations, but your road trip will be a more enjoyable experience. Begin your road trip in Boston by exploring the city you depart from before heading on your epic road trip with fresh eyes. You may discover something you didn’t know about or find new favourite locations. Here are 20 places to explore on a Boston to Miami road trip that you should not miss.
Boston To Miami
20 Places To Explore On A Boston To Miami Road Trip
1- Boston, MA
Start your road trip in the Massachusetts state capital, a city packed with history, culture and plenty of things to do both during the day and in Boston at night.
The museums in Boston are some of the best in the country and they offer insights into the city’s rich history.
If you’ve been to Boston before, avoid the touristy destinations and head to The Boston Athenaeum.
This building is one of the oldest libraries in the USA and is packed with incredible books in an intellectual and beautiful setting.
If it is your first time in Boston, take some time to explore the city on foot and tick off the popular Boston landmarks.
Book a historical walking tour or wander around and get lost in one of the city’s beautiful parks.
The food in Boston is amazing, so make sure you try some local dishes there. Order a lobster roll to truly get a flavour for this New England city.
Recommended tour: Haunted Boston’s Historic Streets Walking Guided Tour.
Also read: Where to stay in Boston.
2- Hartford, CT
Like Boston, Hartford is Connecticut’s capital city and is jam-packed with history.
Hartford is a literary lover’s dream, as both Mark Twain and Harriet Beecher Stowe resided in the city.
Their histories are woven into the city with plenty of museums about their lives, bookshops and sites open to follow in the authors’ footsteps.
Head to the houses dedicated to each author to feel inspired.
If literature hasn’t drawn you to Hartford, take the time to explore the city’s fascinating history.
From its Old State House with impressive red bricks and greek columns to its historical society museum housed in a Colonial Revival mansion, there is plenty to uncover.
Driving from Boston to Hartford covers 100 miles (160.93 kilometres) and takes approximately 1.35 hours.
Recommended: Hartford Scavenger Hunt
3- New Haven, CT
Head towards the coastal city of New Haven, which lies on Long Island Sound and has some beautiful stretches of coastline and some of the best beaches in Connecticut to relax on.
New Haven is home to one of the most well-known landmarks in Connecticut, Yale University, an Ivy League university on impressive grounds.
If Yale draws you in, explore some of the school’s museums with stunning works of art and intriguing historical artefacts.
Complete your educational foray into New Haven by stopping by the Beinecke Rare Book and Manuscript Library.
This library houses some of the rarest books in existence, including a range of ancient manuscripts.
Driving from Hartford to New Haven covers 39 miles (62.76 kilometres) and takes approximately 40 minutes.
Recommended tour: New Haven’s Ghost Walk.
4- New York City, NY
Give up a few days on your road trip to explore New York City.
This almost definitely will not be enough time in the Big Apple, but it will give you a flavour of the city and potentially entice you to book a New York City trip in the future.
Explore the quirky vibes of the Meatpacking District or the chic stores along 5th Avenue.
If you stay longer than a day, try to catch a Broadway or Off-Broadway show or join a Broadway walking tour to get the inside scoop about the most popular shows.
Visit two of the best museums in the state, the Natural History Museum and Moma (skip the line and book your tickets here) or head through Central Park for some fresh air and tranquillity in the centre of the hustle and bustle.
Driving from New Haven to New York City covers 84 miles (135.18 kilometres) and takes approximately 1.5 hours.
Recommended tour: New York in One Day Guided Sightseeing Tour.
5- Philadelphia, PA
Enter your fourth state with a stop in Philadelphia, the largest city in Pennsylvania and another old city in the USA packed with history.
There’s lots to see during the day and more than enough distractions to keep you busy in Philadelphia at night.
Visit Independence Hall, where the Declaration of Independence was signed and see the Liberty Bell while you are there.
No visit to Philadelphia would be complete without trying a Philly cheese steak sandwich. These hoagie rolls packed with steak and cheese are available across the city, with many sellers touting that their cheesesteaks are the best.
Don’t forget to snap a photo with the Rocky statue before hitting the road again.
Driving from New York City to Philadelphia covers 95 miles (152.88 kilometres) and takes approximately two hours.
Recommended tour: Philadelphia Hop-On Hop-Off City Tour.
Also read: Where to stay in Philadelphia.
6- Baltimore, MD
Take a break in Baltimore as you drive through Maryland, a historical seaport town perfect for breathing in the salty air and enjoying a bite to eat.
Head to the 200-year-old Lexington Market to stock up on snacks or grab lunch from one of the vendors.
Try a box of hot and tasty crab cakes or seek comfort in the form of chicken and waffles.
While in Baltimore, check out the Fort McHenry National Monument and Historic Shrine.
This fort, built in the shape of a five-pointed star, was the inspiration behind The Star Spangled Banner.
Driving from Philadelphia to Baltimore covers 101 miles (162.54 kilometres) and takes approximately 1 hour and 45 minutes.
Recommended tour: Signature Spirit of Baltimore Dinner Cruise with Buffet.
7- Chesapeake and Ohio Canal National Historical Park, MD
Break up your journey with a natural escape at the Chesapeake and Ohio Canal National Historical Park.
The entire national park covers 184.5 miles (296.92 kilometres) of canals and waterways between Maryland and Washington D.C.
Take a break here and stroll along the canals.
There is a designated bicycle trail stretching the full route if you feel more energetic.
There are plenty of locations within the national historical park to stop and marvel at the canal, and to get a drink and bite to eat.
If you plan on staying longer than a day here, there are several campsites maintained by the National Park Service available.
Driving from Baltimore to Chesapeake and Ohio Canal National Historical Park covers 94 miles (151.27 kilometres) and takes approximately 1 hour and 45 minutes.
8- Washington D.C.
Take a day or so to explore the capital of the United States.
Washington D.C. never fails to impress with its imposing neoclassical architecture, rich political history and different types of impressive museums.
Of all the landmarks in Washington DC, be sure to visit the Lincoln Memorial at the end of the National Mall.
The breathtaking memorial has a large statue of the 16th president of the USA looking back out towards the waters of the Mall.
Continue your political journey by visiting the Library of Congress, the State Capitol, and the White House.
If you are hungry, grab a chilli half-smoke. This humble beef and pork blend hot dog is spiced with a secret blend of herbs and spices and is best served smothered with ketchup and mustard.
Driving from Chesapeake and Ohio Canal National Historical Park to Washington D.C. covers 83 miles (133.57 kilometres) and takes approximately two hours.
Recommended tour: Washington DC in One Day Guided Sightseeing Tour.
9- Williamsburg, VA
Williamsburg is a must-visit on your Boston to Miami road trip.
This small Virginian city was a crucial part of the American Revolution and forms a historical triangle with Jamestown and Yorktown.
When in Williamsburg, visit the heart of the city, Colonial Williamsburg.
This historical centre is a living museum that transports visitors back to the American Revolution.
There are actors portraying inhabitants and workers, and the buildings are reconstructed to reflect life at the time.
Dine in a historical location before departing the city. Kings Arms Tavern has been open since 1722. Head here for a cosy dinner immersed in American history.
Driving from Washington D.C. to Williamsburg covers 153 miles (246.23 kilometres) and takes approximately 2.5 hours.
Recommended tour: Colonial Williamsburg Admission.
10- Richmond National Battlefield Park, VA
A short drive from Williamsburg is another key historical location and must-visit stop for history buffs on your Boston to Miami road trip.
Richmond National Battlefield Park was the site of many bloody battles during the American Civil War.
When Virginia seceded from the Union, Richmond became the capital of the Confederacy.
The city of Richmond was home to weapons factories and hospitals.
Today, the park has protected close to 3000 acres (1214 ha) of historical importance during the Civil War, with buildings such as an ironworks and the largest hospital camp.
Driving from Williamsburg to Richmond National Battlefield Park covers 40 miles (64.37 kilometres) and takes approximately 50 minutes.
11- Raleigh, NC
As you enter North Carolina, stop in the state’s capital Raleigh.
Raleigh oozes Southern charm and is mixed with modern touches.
Visit the North Carolina Museum of Art, which has both indoor and outdoor exhibits.
The art on display at the museum features prominent pieces from the USA and beyond.
Pose for a photograph with the giant globe outside the North Carolina Museum of Natural Sciences before stepping inside to explore its immersive exhibitions on the wonders of nature.
Before continuing your journey try some of Raleigh’s traditional Southern dishes, such as BBQ, chicken and waffles, and shrimp and grits: all are popular and wholesome dishes in the city.
Driving from Richmond National Battlefield Park to Raleigh covers 180 miles (289.68 kilometres) and takes approximately 2 hours and 45 minutes.
Recommended tour: Carolina Hurricanes NHL Game Ticket at PNC Arena.
12- Lake Norman, NC
Staying in North Carolina, head towards Lake Norman for a relaxing stop on your road trip.
Lake Norman is a man-made lake and is the largest in the state.
The lake is ideal for staying for a night or two and getting out into nature.
There are numerous hiking trails around the lake.
Visit Jetton park for its gentle 1.5-mile (2.41 kilometre) hiking trail and to relax on its sandy beach.
If you’re looking for a more energetic experience, stop at Latta Nature Preserve, which has 18 miles (28.97 kilometres) of hiking trails.
Or get out onto the lake by paddling in a canoe from the preserve’s custom canoe launch access areas.
Driving from Raleigh to Lake Norman covers 158 miles (254.27 kilometres) and takes approximately 2.5 hours.
13- Charlotte, NC
Charlotte is a great place to spend a day stretching your legs while on a Boston to Miami road trip.
Spend the night here after unwinding at Lake Norman.
NASCAR fans should head to the Charlotte Motor Speedway to catch a race.
If plants appeal to you more than cars, pay a visit to the Daniel Stowe Botanical Garden.
This garden is packed with plants from across the globe in its seven themed gardens.
For a bite to eat, call into 7th Street Public Market, where you’ll find a myriad of delectable dishes on offer.
Grab a coffee as you enter and peruse the stalls before settling on something to try.
Driving from Raleigh to Charlotte covers 40 miles (64.37 kilometres) and takes approximately 50 minutes.
Recommended tour: Charlotte’s Historical City Tour.
14- Myrtle Beach, SC
Myrtle Beach is a popular vacation spot in South Carolina because of its 60 miles of beaches that makes it a great destination to relax and unwind.
Spend some time on the beach sunbathing, swimming or playing frisbee.
There are plenty of water sports at Myrtle Beach, including surfing and para-sailing.
Explore the boardwalk and be sure to board the SkyWheel.
This giant wheel has great views from your gondola over the city and out towards the ocean.
Visit at sunset for the best views and photo opportunities.
Myrtle Beach is a great family-friendly destination with plenty of activities for kids, including pirate-themed mini golf courses, water parks and quirky interactive museums.
Driving from Charlotte to Myrtle Beach covers 175 miles (281.64 kilometres) and takes approximately 3 hours and 40 minutes.
Recommended tour: Guided Myrtle Beach Kayak Tour.
15- Charleston, SC
Call into Charleston as your last stop in South Carolina. This port city is vibrant and perfectly blends historical and modern architecture.
The city was founded in 1670 and still sports its cobbled streets and elegant pastel houses in the French Quarter.
Explore Charleston on a walking tour with a knowledgeable local guide who will share the city’s history and highlight hidden gems off the tourist trail.
If you don’t fancy walking, hop on a horse-drawn carriage for a more elegant way to see the sights of the historic district.
Driving from Myrtle Beach to Charleston covers 98 miles (157.71 kilometres) and takes approximately 2 hours and 10 minutes.
Recommended tour: Charleston’s Old South Carriage Historic Horse & Carriage Tour.
16- Savannah National Wildlife Refuge
Kick off your time in Georgia by visiting the Savannah National Wildlife Refuge, which opened in 1927 as a sanctuary for migratory birds.
The sanctuary spans more than 30,000 acres (12,140 ha) of diverse habitats, such as hardwood forests and freshwater marshes fed by the tides.
Expect to see a range of birds in the sanctuary year-round, including great blue herons and snowy egrets.
You may also catch a glimpse of river otters and armadillos.
There are plenty of trails to explore throughout the refuge, and seasonal activities such as Earth-caching and wildlife watching are offered.
Driving from Charleston to Savannah National Wildlife Refuge covers 105 miles (168.98 kilometres) and takes approximately 2 hours and 10 minutes.
17- Savannah, GA
After spending some time exploring the Savannah National Wildlife Refuge, head into the city itself.
One of the best tours to discover the city is on a trolley tour.
These hop-on, hop-off tours are ideal for getting your bearings and to find some great places to visit and explore further.
The city has many historical buildings to explore, and there are plenty of guided walking tours to help you uncover the area’s secrets.
Spend some time in the beauty of Forsyth Park with its elegant fountain and 300-year-old oak trees. Before you leave, head to Wormhole State Historic Site.
The oak-lined avenue leading up to the plantation is a great place to photograph.
Driving from Savannah National Wildlife Refuge to Savannah covers 11.5 miles (18.5 kilometres) and takes approximately 20 minutes.
Recommended tour: Savannah Hop-On Hop-Off Trolley Tour.
18- Jacksonville, FL
As you enter your final road trip state on your Boston to Miami journey, spend some time in Jacksonville, where you will find stretches of coastline and beaches to explore and a rich cultural scene.
Jacksonville Zoo and Gardens is a great destination for visitors of all ages.
Learn about its 2000-plus animals and how the zoo works to conserve rare and endangered species.
Immerse yourself in history that should not be forgotten at the Kingsley Plantation and follow in the footsteps of the slaves who lived at the plantation through a guided ranger tour.
Round off your day in Jacksonville by visiting St Johns Town Centre to shop and grab a bite to eat.
Driving from Savannah to Jacksonville covers 139 miles (223.69 kilometres) and takes approximately 2 hours.
Recommended tour: Electric Bike Guided Tour in Jacksonville Art and Architecture.
19- Orlando, FL
No road trip to Florida would be complete without a stop in Orlando.
Regardless of who your travel companions are, Orlando and its myriad of theme parks are perfect to spend a couple of days having fun and making memories.
Visit Walt Disney World Resort and its rides, water parks and Disney-themed restaurants.
Remember to pick up some Mickey Mouse ears as a souvenir and try some of their must-eat dishes in the shape of the iconic rodent’s head.
Fans of Harry Potter should head to Universal Orlando Resort. Once here, stroll along Diagon Alley and explore its magical stores, or take a dip in the pools in Volcano Bay.
Driving from Jacksonville to Orlando covers 141 miles (226.91 kilometres) and takes approximately 2 hours and 10 minutes.
Recommended tour: Go City Orlando Explorer Pass – Choose 2, 3, 4 or 5 Attractions.
20- Miami, FL
End your epic road trip from Boston in Miami, famous for its lush palm trees, pristine beaches and art-deco vibe.
Spend some time on South Beach, the best beach in the city.
Art-deco houses and plenty of bars and restaurants back the beach.
If the art deco style appeals to you, visit the historic district dedicated to this architectural design style. There are more than 800 buildings preserved in this style to admire.
Little Havana is a cultural capital for Cuban Americans and offers some of the best Cuban food.
Driving from Orlando to Miami covers 237 miles (381.42 kilometres) and takes approximately 3 hours and 40 minutes.
Recommended tour: Little Havana Food and Walking Tour.
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