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Boston to Hilton Head Island drive

2 travelers   /   driving   /   3 days



Boston to Hilton Head Island road trip planner

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.

customize this trip
 Day 1

9:00 am  start in Boston
drive for about 1.5 hours

10:41 am  Mystic Seaport
stay for about 1 hour and leave at 11:41 am
drive for about 2.5 hours

2:05 pm  New York City
stay for about 4 hours and leave at 6:05 pm
drive for about 1.5 hours

7:48 pm  Philadelphia
stay overnight at Loews Hotel Philadelphia
leave the next day around 9:00 am

day 1 driving ≈ 6 hours
find more stops

 Day 2

9:00 am  leave from Loews Hotel Philadelphia
drive for about 2.5 hours

11:25 am  Washington, DC
eat at National Gallery of Art
stay for about 3.5 hours and leave at 2:55 pm
drive for about 2 hours

4:41 pm  Richmond
stay for about 1 hour and leave at 5:41 pm
drive for about 2.5 hours

8:12 pm  Raleigh
stay overnight at The Umstead Hotel & Spa
leave the next day around 9:00 am

day 2 driving ≈ 6.5 hours
find more stops

 Day 3

9:00 am  leave from The Umstead Hotel & Spa
drive for about 1 hour

10:11 am  Pinehurst
stay for about 1 hour and leave at 11:11 am
drive for about 3.5 hours

2:54 pm  Charleston
stay for about 2.5 hours and leave at 5:24 pm
drive for about 2 hours

7:17 pm  arrive in Hilton Head Island
eat at The Salty Dog Cafe

day 3 driving ≈ 7 hours
find more stops

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  Alternate route
Enter a city to drive through on the way from Boston to Hilton Head Island.
Via:  
 




Where does my trip begin?

Your starting point is Boston, Massachusetts.

You can enter an exact street address if you want to get precise directions, but this is optional.




How many cars do we need?

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.




Where should I stop along the way?

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:
        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
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
        Jim's Steaks
        Pat's King of Steaks
        Geno's Steaks
        Zahav
    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
        Mitsitam Cafe
        Founding Farmers
        Rose's Luxury
        Pavilion Café
    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:
        The Pit
        Poole's
        Bida Manda
    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:
        Husk
        Hominy Grill
        FIG
        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




Where does my trip end?

Your final destination is Hilton Head Island, South Carolina.

You can enter the exact street address of your destination, but this is optional.




Where's the best place to eat in Hilton Head Island?

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.






What are some things to do in Hilton Head Island?

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:

Hilton Head Island  (3 mentions)

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 Hilton Head Island. Click on any question to see answers from the community!

 Bo Nash from Arlington (Texas) asked:
Best historical locations/tours on Hilton Head Island?  (5 answers)

 Brooke Coleman from Chandler (Oklahoma), Oklahoma asked:
Girlfriend getaway in Hilton Head  (1 answer)

 Gail Smith from asked:
road numbers  (1 answer)

Click the button below to explore more questions and answers related to Hilton Head Island.






Do I really have to go back home?

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 Hilton Head Island 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 Hilton Head Island. Or get a full Boston to Hilton Head Island 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!






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At a Glance
without making any stops
total driving distance is 1,013 miles
driving time of 15 hours, 20 minutes
Hilton Head Island is the same time as Boston
195 Boston travel answers
587 New York City travel answers
100 Philadelphia travel answers
158 Washington, DC travel answers
8 Richmond travel answers
13 Raleigh travel answers
3 Pinehurst travel answers
115 Charleston travel answers
25 Hilton Head Island travel answers





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