Here's a sample itinerary for a drive from Boston to Hilton Head Island. If you're planning a road trip to Hilton Head Island, 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.
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.
Mystic Seaport (10 mentions)
New York City (587 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?
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
Philadelphia (100 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 (158 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 (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 (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?
Pinehurst (3 answers)
Charleston (115 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
Your final destination is Hilton Head Island, South Carolina.
You can enter the exact street address of your destination, but this is optional.
Need some recommendations on somewhere to get food?
Trippy members suggest The Salty Dog Cafe, which was mentioned 2 times.
Want to research more popular restaurants in Hilton Head Island? 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 Hilton Head Island.
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!