8 of the Best Stops on a Road Trip From Boston to Florida

The East Coast is home to an extensive list of big cities filled with history, culture, and cuisine. Plan out an itinerary for your next
Boston to Florida road trip with stops in almost every state along the way! Our blog provides you with the top places to grab local food, attractions to experience, and places to stay along the way! For more insider tips and information on the top sites to stop on I-95, request our free Travel Guide!  

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8 Places You Need to Stop on a Boston to Florida Road Trip

Day One


Take your first road trip stop on your way from Boston to Florida about an hour and forty-five minutes into your journey in Mystic, CT. This quaint and charming village featured in the movie “Mystic Pizza,” is a fantastic place to take a stroll on the beautiful waterfront before hopping back in your car and heading to your next destination.


Skip taking any exits in New York and New Jersey, as you’ll find yourself stuck in traffic and creating more time in the car for yourself. Stop in the City of Brotherly Love for a famous cheesesteak at Tony Luke’s before exploring Independence Hall and the Liberty Bell.  


The final day one stop on your road trip from Boston to Florida is in Delaware’s capital city, Wilmington. Spend the night at the Inn at Montchanin Village where you can relax in a serene countryside setting. If you want to see a little bit of the area before heading to your next stop, check out Brandywine Creek State Park and the ornate Nemours Estate.

Day Two


Start day two of your Boston to Florida road trip by experiencing history and cuisine in Baltimore. Taste some delicious and famous Maryland crab at Nick’s Fish House or Baltimore-style barbeque at Chap’s Pit Beef before exploring the Edgar Allan Poe House and Museum or taking a sailing tour around Baltimore’s harbor.

Washington D.C.

You can warrant a stop in D.C. by staying the night. We recommend booking a stay at The Morrison House Hotel in Alexandria, VA. If you do make this a part of your Boston to Florida road trip itinerary, take a walk on the National Mall and duck into one (or several) of the Smithsonian’s museums.

Day Three

North Carolina

There’s only one place worthy of a stop on your Boston to Florida road trip, and that is the Airborne and Special Operations Museum in Fayetteville. This unique museum provides you with an in-depth look at equipment, missions, and other aspects of the Special Forces division of the U.S. Army.

South Carolina

Your final stop on day three of your Boston to Florida road trip is our beautiful and historic Inn. Abingdon Manor is the perfect place to recuperate and prepare yourself the last stretch of your journey. Make a reservation at our elegant dining room where you can treat yourself to a prix fixe gourmet dinner. Escape the hustle and bustle of I-95 in the quaint and charming town of Latta before going to bed. You’ll wake up to a delicious breakfast that will fuel you for the final day of driving.  

Day Four


The length of your last day of driving on your Boston to Florida road trip depends on where your final destination is in the Sunshine State. If you’re going to Jacksonville-area, we recommend driving straight through Georgia to your final destination. If you’re staying further down the coast, make sure you stop in St. Augustine. The oldest city in the country has plenty of beautiful architecture and history, but the top attraction here is Castillo de San Marcos. This fort is well worth an hour or two of exploring before hitting the road.

One of the final stops on your Boston to Florida road trip should be Kennedy Space Center. You can easily spend several hours touring this museum filled with a wide variety of exhibits highlighting America’s history of space exploration. If you’re heading to Miami or the Keys, make sure you check out the South Beach Art Deco District and sample some delicious Cuban cuisine.

Plan Your Stay at Abingdon ManorAbingdon Manor exterior at night

Book your room at Abingdon Manor so you can relax and replenish yourself on your long road trip! In addition to our luxurious and comfortable rooms, you can add on one of our Special Amenities for a unique touch during your stay.

Start planning your road trip and book your stay with us today! We look forward to welcoming you to our charming and peaceful oasis!


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