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 Knoxville. 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 (57 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
Valdosta (4 answers)
Atlanta (111 answers)
Georgia Aquarium (29 mentions)
World of Coca-Cola (20 mentions)
Piedmont Park (16 mentions)
Midtown Atlanta (14 mentions)
High Museum of Art (11 mentions)
restaurants around Atlanta:
Mary Mac's Tea Room
Antico Pizza Napoletana
Empire State South
JCT Kitchen & Bar
questions about Atlanta:
Good Restaurants Unique to Atlanta?
Great, reasonable places to eat.
Tourist spots worth seeing in Atlanta?
Authentic Southern Food!
Best family activities in Atlanta?
Knoxville (12 answers)
questions about Knoxville:
New Years in Knoxville reccomendations
Charlottesville (14 answers)
Monticello (2 mentions)
questions about Charlottesville:
Any recommendations for hikes, good food and wine for a long-weekend trip?
Trip with husband
Harrisburg (15 answers)
questions about Harrisburg:
What are the 5 best sights to see in Harrisburg PA
New York City (589 answers)
Central Park (149 mentions)
High Line Park (110 mentions)
The Metropolitan Museum of Art (85 mentions)
Statue of Liberty (69 mentions)
Times Square (59 mentions)
restaurants around New York City:
questions about New York City:
Where do the cool kids stay in NYC these days?
Is it a good idea to visit NYC in December?
free or cheap things to do in NYC
What is your favorite restaurant in New York City?
48 Hours in NYC - I NEED to know the best Pizza spots!
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!