Here's a sample itinerary for a drive from Boston to Sarasota. If you're planning a road trip to Sarasota, you can research locations to stop along the way. Traveling with a dog or cat? View pet-friendly stops between Boston and Sarasota. Find the best hotels, restaurants, and attractions based on the most talked about places recommended by Trippy members.
Your starting point is Boston, Massachusetts.
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.
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!
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
hotels around Philadelphia:
Loews Hotel Philadelphia
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.
Washington, DC (165 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
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?
Richmond (9 answers)
Carytown (4 mentions)
Virginia Museum of Fine Arts (2 mentions)
restaurants around Richmond:
Buz and Ned’s Real Barbecue
questions about Richmond:
What is there to do in Richmond?
What is your favorite restaurant in Richmond?
Nightlife in Richmond & hotels?
Pinehurst (3 answers)
Charleston (117 answers)
King Street (8 mentions)
Boone Hall Plantation (6 mentions)
The Battery (6 mentions)
Folly Beach (5 mentions)
Waterfront Park (5 mentions)
restaurants around Charleston:
Slightly North of Broad
Bowen's Island Restaurant
questions about Charleston:
Two day trip - what are the must sees, eats, and drinks?
Best oceanfront place to stay closest to Charleston SC
Dinner with family in Charleston tonight...
Afternoon in Charleston
Newbie in Charleston, How to Spend an Afternoon
Savannah (93 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
Ocala (4 answers)
Your final destination is Sarasota, Florida.
You can enter the exact street address of your destination, but this is optional.
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 Sarasota.
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 Boston well, please help your fellow travelers and answer their questions about Boston!