8 days in Boston & Ocean City Itinerary

8 days in Boston & Ocean City Itinerary

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Route & dates

8 days in Boston & Ocean City Itinerary

Start: Rochester
Fly:  3​h 45​min
1
Boston
— 4 nights
Fly + Shuttle:  7​h 15​min
2
Ocean City
— 2 nights
Shuttle + Fly:  6​h 15​min
End: Rochester

4
nights
Boston

Boston ©
Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year. New England's largest and most influential city, Boston ranks among the world's major centers of education and culture.
Explore hidden gems such as Fishing Charters & Tours and Dolphin & Whale Watching. Explore the numerous day-trip ideas around Boston: When Pigs Fly Company Store (in Kittery), Hampton Beach State Park (in Hampton) and Ogunquit Beach (in Ogunquit). There's much more to do: admire all the interesting features of Fenway Park, contemplate in the serene atmosphere at Old North Church & Historic Site, test your problem-solving skills at popular escape rooms, and walk around Charles River Esplanade.

To see photos, where to stay, and other tourist information, read our Boston trip planner .

Rochester to Boston is an approximately 4-hour flight. You can also do a combination of bus and flight; or drive. In August, daily temperatures in Boston can reach 81°F, while at night they dip to 65°F. Finish your sightseeing early on the 14th (Wed) so you can travel to Ocean City.

Things to do in Boston

Outdoors Parks Beaches

Side Trips

York Beach, When Pigs Fly Company Store, Nubble Lighthouse, Hampton Beach State Park, Dolphin & Whale Watching
Highlights from your plan
Ogunquit Beach ©
Ogunquit Beach
Dolphin & Whale Watching
Long Sands Beach ©
Long Sands Beach

2
nights
Ocean City

One of the country's favorite vacation resorts, Ocean City draws nearly 8 million visitors annually with its oceanfront boardwalk, clean beaches, and amusement parks.
You'll explore the less-touristy side of things at Stand-Up Paddleboarding and Speed Boats Tours. You'll find plenty of places to visit near Ocean City: Dewey Beach (in Dewey Beach), Dogfish Head Craft Brewery (in Milton) and Rehoboth Beach Public Beach (in Rehoboth Beach). There's lots more to do: get some thrills out on the water with a waterskiing or jet-skiing adventure, tour the pleasant surroundings at Bethany Beach Boardwalk, fly like a bird with a parasailing or paragliding tour, and have some family-friendly fun at Grand Prix Amusements.

To find traveler tips, other places to visit, ratings, and more tourist information, you can read our Ocean City trip planning site .

Traveling by combination of flight and shuttle from Boston to Ocean City takes 7.5 hours. Alternatively, you can drive; or do a combination of bus, flight, and shuttle. In August, daily temperatures in Ocean City can reach 82°F, while at night they dip to 67°F. Wrap up your sightseeing on the 17th (Sat) to allow time to travel back home.

Things to do in Ocean City

Outdoors Parks Tours

Side Trips

Dewey Beach, Dogfish Head Craft Brewery, Bethany Beach Boardwalk, Rehoboth Beach Public Beach
Highlights from your plan
Waterskiing & Jetskiing
Northside Park ©
Northside Park
Parasailing & Paragliding

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