Here's a sample itinerary for a drive from Naples to Boston. If you're planning a road trip to Boston, you can research locations to stop along the way. Traveling with a dog or cat? View pet-friendly stops between Naples and Boston. Find the best hotels, restaurants, and attractions based on the most talked about places recommended by Trippy members.
Your starting point is Naples, Florida.
You can enter an exact street address if you want to get precise directions, but this is optional.
Since there are only 2 travelers, we assume you're driving 1 car. You can adjust the number of people traveling at the top. We assume a maximum of 4 passengers per car, but you can change the number of cars to fit your situation.
Tampa (56 answers)
International Plaza and Bay Street (6 mentions)
Busch Gardens Tampa (5 mentions)
Bayshore Blvd (4 mentions)
Tampa Riverwalk (4 mentions)
South Howard Ave (3 mentions)
restaurants around Tampa:
Piquant Hyde Park
Bern's Steak House
questions about Tampa:
Best new restaurants in Tampa?
Popular areas in Tampa for shopping?
Beaches around Tampa
Best free things to do in Tampa?
Weekend ideas for a first timer in Tampa
Jacksonville (19 answers)
questions about Jacksonville:
What's the best neighborhood in Jacksonville for a first time visitor?
Savannah (92 answers)
Forsyth Park (9 mentions)
Bonaventure Cemetery (5 mentions)
Savannah's Historic District (3 mentions)
The Pirates House Savannah GA (3 mentions)
River Street (3 mentions)
restaurants around Savannah:
Mrs. Wilkes Dining Room
Crystal Beer Parlor
The Olde Pink House
Gryphon Tea Room
questions about Savannah:
What is your favorite under rated attraction in Savannah?
Leisurely trip to Savannah
What are fun things to do in Savannah on a budget?
Little Ones in Savannah
Great restaurants in Savannah
Myrtle Beach (43 answers)
Broadway At the Beach (2 mentions)
questions about Myrtle Beach:
What is your favorite restaurant in Myrtle Beach?
Things to do, see, and eat in Myrtle Beach
Romantic beach-front hotel
Looking for nice place to stay oceanfront w/ lazy river & on site cooking
I only have 4 days -- what should I do?
Raleigh (13 answers)
North Carolina Museum of Art (2 mentions)
restaurants around Raleigh:
hotels around Raleigh:
The Umstead Hotel & Spa
questions about Raleigh:
What is your favorite restaurant in Raleigh?
Best Non-Chain Restaurants for Families
What's the best neighborhood in Raleigh for a first time visitor?
Washington, DC (159 answers)
National Mall (30 mentions)
National Air and Space Museum (29 mentions)
Washington Monument (25 mentions)
Museum of Natural History (23 mentions)
Lincoln Memorial (22 mentions)
restaurants around Washington, DC:
National Gallery of Art
hotels around Washington, DC:
JW Marriott Hotel
Hotel Palomar Washington DC
Hotel Monaco Alexandria
W Washington DC
questions about Washington, DC:
Best hotel near museums
Fun free things to do in D.C.?
Getting from Union Station to National Mall?
How to make the most of three days in DC
Best of the Smithsonian?
Philadelphia (102 answers)
Philadelphia Museum of Art (16 mentions)
The Liberty Bell (12 mentions)
Eastern State Penitentiary (8 mentions)
Spruce Street Harbor Park (8 mentions)
Independence Mall (7 mentions)
restaurants around Philadelphia:
Reading Terminal Market
Pat's King of Steaks
questions about Philadelphia:
What is there to do in Philly besides eat cheese steaks?
Pat's or Geno's: Which has the better cheesesteak?
What is your favorite restaurant in Philadelphia?
Anybody know of great gems in the city I can dine at during my stay?
Eating out on a budget.
Your final destination is Boston, Massachusetts.
You can enter the exact street address of your destination, but this is optional.
Are you going straight to a hotel, or looking for a vacation rental or Airbnb?
The best resource on neighborhoods, areas, and hotels is the Trippy page on where to stay in Boston.
You can also see most people recommend as the best amount of time to visit. Find out how many days in Boston to stay.
If you're looking for a quick answer, you can check out The Westin Copley Place, which was mentioned 4 times on Trippy.
Here are some more hotels people talk about:
Want to research more popular hotels in Boston? Click the blue button below.
Need some recommendations on somewhere to get food?
Trippy members suggest Mike's Pastry, which was mentioned 15 times.
Here are some more restaurants people talk about:
Want to research more popular restaurants in Boston? Click the blue button below.
This section could be endless, so rather than trying to suggest every local activity or attraction, we'll leave it open-ended.
These are some of the places people talk about on Trippy:
Of course, Trippy is the perfect place to ask questions because there's an entire community of travelers talking to each other and sharing tips and advice. Trippy is where you can get answers personalized for your tastes, budgets, trip dates & more!
Click the button below to explore more questions and answers related to Boston.
Yes, even this step is optional, because if you're on vacation who wants the trip to end? It's okay, you can start planning your next trip!
Don't forget about exploring your own hometown with a staycation. You can also find some cool day trips or get away for a weekend. Maybe try typing in a faraway location like London, Hong Kong, or Sydney, and get inspired for your dream trip around the world.
And if you know Naples well, please help your fellow travelers and answer their questions about Naples!