18 days in Oak Bluffs, Cape Cod & Boston Itinerary

18 days in Oak Bluffs, Cape Cod & Boston Itinerary

Created using Inspirock Massachusetts holiday planner

Plan created by another user. Make it yours
1
Oak Bluffs
— 1 night
2
Hyannis
— 4 nights
3
Provincetown
— 5 nights
4
Boston
— 7 nights

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1
night
Oak Bluffs

Oak Bluffs ©
Oak Bluffs is a town located on the island of Martha's Vineyard in Dukes County, Massachusetts, United States. Kick off your visit on the 29th (Sat): enjoy the sea views from Edgartown Lighthouse, then stroll through Katama Beach/ South Beach, and then examine the collection at Cottage Museum. On the 30th (Sun), you'll have a packed day of sightseeing: stroll through Joseph Sylvia State Beach, kick back and relax at Oak Bluffs Town Beach, and then visit Martha's Vineyard Camp meeting Association (MVCMA).

For other places to visit, maps, reviews, and tourist information, you can read our Oak Bluffs trip itinerary planner.

San Francisco to Oak Bluffs is an approximately 10-hour flight. You can also do a combination of car and ferry; or do a combination of subway, train, bus, and ferry. The time zone difference when traveling from San Francisco to Oak Bluffs is 3 hours. In June in Oak Bluffs, expect temperatures between 73°F during the day and 54°F at night. Finish your sightseeing early on the 30th (Sun) to allow enough time to ride a ferry to Hyannis.

Things to do in Oak Bluffs

Outdoors · Parks · Beaches

Side Trip

Edgartown
Highlights from your plan
Katama Beach/ South Beach ©
Katama Beach/ South Beach
Edgartown Lighthouse ©
Edgartown Lighthouse

4
nights
Hyannis

Hyannis ©
"The Capital of the Cape," Hyannis serves as Cape Cod's main transportation and commercial hub.
Popular historic sites such as Edward Gorey House and Captain Bangs Hallet House Museum are in your itinerary. Get outdoors at Monomoy National Wildlife Refuge and Kalmus Beach. Explore the numerous day-trip ideas around Hyannis: Brewster (Crosby Landing Beach & Nickerson State Park). There's lots more to do: see the interesting displays at Whydah Pirate Museum, get a new perspective on nature at Cape Cod Museum of Natural History, have some family-friendly fun at Putter's Paradise, and kick back and relax at Craigville Beach.

To see maps, more things to do, other places to visit, and more tourist information, read our Hyannis trip builder site.

Traveling by ferry from Oak Bluffs to Hyannis takes 1.5 hours. Alternatively, you can do a combination of ferry and taxi. In June in Hyannis, expect temperatures between 73°F during the day and 58°F at night. Finish up your sightseeing early on the 4th (Thu) so you can go by car to Provincetown.

Things to do in Hyannis

Parks · Outdoors · Beaches

Side Trips

West Yarmouth, Yarmouth Port, Brewster, Monomoy National Wildlife Refuge, Mayflower Beach
Highlights from your plan
Monomoy National Wildlife Refuge ©
Monomoy National Wildlife Refuge
Mayflower Beach ©
Mayflower Beach
Craigville Beach ©
Craigville Beach

5
nights
Provincetown

A small resort town with a year-round population of just 3,000, Provincetown draws nearly 60,000 annual visitors with its scenic beaches, art colonies, galleries, theaters, and shops.
Bring the kids along to Dolphin & Whale Watching and Herring Cove Beach. Discover out-of-the-way places like Race Point Beach and Nauset Lighthouse. Venture out of the city with trips to Eastham (Nauset Light Beach, Salt Pond Visitor Center, &more). There's still lots to do: stroll through Cape Cod Provincelands Trail, get a new perspective on nature at Sea Space Marine Discovery Center, get to know the fascinating history of Wellfleet Bay Wildlife Sanctuary, and take in the waterfront at MacMillan Wharf.

To see maps, reviews, more things to do, and tourist information, read Provincetown online holiday planner.

You can drive from Hyannis to Provincetown in 1.5 hours. Alternatively, you can take a bus. In July in Provincetown, expect temperatures between 79°F during the day and 64°F at night. Finish your sightseeing early on the 9th (Tue) to allow enough time to ride a ferry to Boston.

Things to do in Provincetown

Outdoors · Parks · Beaches

Side Trips

Eastham, Wellfleet, Truro
Highlights from your plan
Dolphin & Whale Watching
Wellfleet Bay Wildlife Sanctuary ©
Wellfleet Bay Wildlife Sanctuary
Cape Cod Provincelands Trail ©
Cape Cod Provincelands Trail

7
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.
Visiting Ogunquit Beach and Halibut Point State Park will get you outdoors. You'll get in some beach time at Hampton Beach State Park and Short Sands Beach. Change things up with these side-trips from Boston: Marginal Way Walkway (in Ogunquit), Tributary Brewing (in Kittery) and Strawbery Banke Museum (in Portsmouth). There's still lots to do: appreciate the extensive heritage of Freedom Trail, steep yourself in history at Granary Burying Ground, stroll through Long Sands Beach, and pause for some serene contemplation at Old North Church & Historic Site.

To find reviews, more things to do, maps, and other tourist information, read our Boston trip planning app.

Ride a ferry from Provincetown to Boston in 2.5 hours. Alternatively, you can fly; or drive. In July in Boston, expect temperatures between 83°F during the day and 67°F at night. Finish your sightseeing early on the 16th (Tue) to allow enough time to travel back home.

Things to do in Boston

Parks · Outdoors · Historic Sites

Side Trips

York, Ogunquit, Stoneface Brewing, The House of the Seven Gables, Hampton Beach State Park
Highlights from your plan
Ogunquit Beach ©
Ogunquit Beach
Hampton Beach State Park ©
Hampton Beach State Park
Long Sands Beach ©
Long Sands Beach

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