Here's a sample itinerary for a drive from Boston to Orlando. If you're planning a road trip to Orlando, you can research locations to stop along the way. Find the best restaurants, hotels, and attractions based on the most talked about places recommended by Trippy members.
Day 1, 9:00 am: start in Boston
drive for about 3.5 hours
Day 1, 12:40 pm: New York City
eat at Katz's Delicatessen
stay for about 4 hours and leave at 4:40 pm
drive for about 4 hours
Day 1, 8:26 pm: Washington, DC
stay overnight at JW Marriott Hotel
leave the next day around 10:00 am
Day 2, 10:00 am: leave from JW Marriott Hotel
drive for about 2 hours
Day 2, 11:46 am: Richmond
eat at Buz and Ned’s Real Barbecue
stay for about 1 hour and leave at 12:46 pm
drive for about 2.5 hours
Day 2, 3:17 pm: Raleigh
stay for about 1 hour and leave at 4:17 pm
drive for about 3.5 hours
Day 2, 7:39 pm: Pawleys Island
stay overnight and leave the next day around 9:00 am
Day 3, 9:00 am: leave from Pawleys Island
drive for about 3 hours
Day 3, 12:09 pm: Savannah
eat at Mrs. Wilkes Dining Room
stay for about 2 hours and leave at 2:09 pm
drive for about 2 hours
Day 3, 4:08 pm: Jacksonville
stay for about 1 hour and leave at 5:08 pm
drive for about 2 hours
Day 3, 7:13 pm: arrive in Orlando
eat at Cafe Tu Tu Tango
stay at Universal's Cabana Bay Beach Resort
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 (575 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:
Katz's Delicatessen
Shake Shack
Lombardi's Pizza
Balthazar Restaurant
Eataly
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?
What is your favorite restaurant in New York City?
48 Hours in NYC - I NEED to know the best Pizza spots!
free or cheap things to do in NYC
Washington, DC (145 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
Mitsitam Cafe
Founding Farmers
Rose's Luxury
Pavilion Café
hotels around Washington, DC:
JW Marriott Hotel
Hotel Palomar Washington DC
The Willard
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?
Richmond (8 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?
Raleigh (12 answers)
North Carolina Museum of Art (2 mentions)
restaurants around Raleigh:
The Pit
Poole's
Bida Manda
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?
Pawleys Island (2 mentions)
Savannah (84 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
Clary's Cafe
questions about Savannah:
What is your favorite under rated attraction in Savannah?
Leisurely trip to Savannah
Things to do and where to stay
What are fun things to do in Savannah on a budget?
Little Ones in Savannah
Jacksonville (21 answers)
questions about Jacksonville:
What's the best neighborhood in Jacksonville for a first time visitor?
Your final destination is Orlando, Florida.
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 Orlando.
If you're looking for a quick answer, you can check out Universal's Cabana Bay Beach Resort, which was mentioned 2 times on Trippy.
Here are some more hotels people talk about:
Want to research more popular hotels in Orlando? Click the blue button below.
Need some recommendations on somewhere to get food?
Trippy members suggest Cafe Tu Tu Tango, which was mentioned 5 times.
Here are some more restaurants people talk about:
Want to research more popular restaurants in Orlando? 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!
For example, here are some questions people have asked about Orlando. Click on any question to see answers from the community!
Kimmy Lee from Los Angeles asked:
How many days for Disney + universal? (13 answers)
miss M from Los Angeles asked:
What to do during one day in Orlando that's not Disney World (10 answers)
Colby Danforth from Providence asked:
Top golf courses in Orlando? (9 answers)
Andreas Rossi from Manhattan asked:
Fine dining for client meeting in Orlando (8 answers)
Alexander Wise from Fort Walton Beach asked:
What's the best time of year to visit theme parks? (7 answers)
Click the button below to explore more questions and answers related to Orlando.
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!
Want to plan the trip back? Get the reverse directions for a Orlando to Boston drive, or go to the main page to plan a new road trip.
You can also compare the travel time if you're flying or driving by calculating the distance from Boston to Orlando. Or get a full Boston to Orlando flight plan.
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!
