14 days in Boston & Oak Bluffs Itinerary

14 days in Boston & Oak Bluffs Itinerary

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Route & dates

14 days in Boston & Oak Bluffs Itinerary

Start: Boston
1
Boston
— 10 nights
Drive:  2​h 30​min
2
Oak Bluffs
— 3 nights
Drive:  2​h 30​min
End: Boston

10
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.
Eschew the tourist crowds and head to Dolphin & Whale Watching and Ogunquit Beach. Explore the numerous day-trip ideas around Boston: Tributary Brewing (in Kittery), Marginal Way Walkway (in Ogunquit) and Provincetown (Race Point Beach, Pilgrim Monument & Provincetown Museum, & more). There's lots more to do: admire all the interesting features of Fenway Park, visit a coastal fixture at Cape Neddick Nubble Lighthouse, take in the spiritual surroundings of Old North Church & Historic Site, and take an in-depth tour of Plimoth Plantation.

To see more things to do, reviews, traveler tips, and tourist information, read Boston travel route planner .

If you are flying in from Canada, the closest major airports are General Edward Lawrence Logan International Airport, Portsmouth International at Pease Airport and Bradley International Airport. Expect a daytime high around 20°C in October, and nighttime lows around 11°C. Finish your sightseeing early on the 18th (Fri) to allow enough time to travel to Oak Bluffs.

Things to do in Boston

Historic Sites Museums Parks

Side Trips

Provincetown, Newport, Ogunquit, Salem, Harvard University
Highlights from your plan
Fenway Park ©
Fenway Park
Old North Church & Historic Site ©
Old North Church & Historic Site
Cape Neddick Nubble Lighthouse ©
Cape Neddick Nubble Lighthouse

3
nights
Oak Bluffs

Oak Bluffs ©
Oak Bluffs is a town located on the island of Martha's Vineyard in Dukes County, Massachusetts, United States. Start off your visit on the 19th (Sat): identify plant and animal life at Felix Neck Wildlife Sanctuary, then browse the collection at Edgartown Public Library, then don't miss a visit to Flying Horses Carousel, and finally admire the landmark architecture of Trinity Park Tabernacle. On the next day, stop by Ben and Bill's Chocolate Emporium, take in nature's colorful creations at Polly Hill Arboretum, visit a coastal fixture at Edgartown Lighthouse, then make a trip to Katama Airfield, and finally take in the dramatic natural features at Aquinnah Cliffs.

To see where to stay, ratings, and tourist information, read our Oak Bluffs travel planner.

You can do a combination of car and ferry from Boston to Oak Bluffs in 2.5 hours. Alternatively, you can fly; or do a combination of bus and ferry. October in Oak Bluffs sees daily highs of 21°C and lows of 9°C at night. Wrap up your sightseeing by early afternoon on the 21st (Mon) to allow enough time to travel back home.

Things to do in Oak Bluffs

Parks Historic Sites Wildlife

Side Trips

Edgartown, Aquinnah Cliffs, Polly Hill Arboretum
Highlights from your plan
Aquinnah Cliffs ©
Aquinnah Cliffs
Edgartown Lighthouse ©
Edgartown Lighthouse
Trinity Park Tabernacle ©
Trinity Park Tabernacle

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