13 days in Massachusetts Itinerary

13 days in Massachusetts Itinerary

Created using Inspirock Massachusetts itinerary planner

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Route & dates

13 days in Massachusetts Itinerary

Start: Jacksonville
bus + Fly:  8​h 15​min
1
Oak Bluffs, Martha's Vineyard
— 1 night
Drive:  2​h
2
Hyannis
— 3 nights
Drive:  1​h 15​min
3
Provincetown
— 3 nights
ferry:  1​h 30​min
4
Boston
— 5 nights
Fly + bus:  6​h 30​min
End: Jacksonville

1
night
Oak Bluffs, Martha's Vineyard

Oak Bluffs ©
Oak Bluffs is a town located on the island of Martha's Vineyard in Dukes County, Massachusetts, United States. On the 12th (Sat), admire the striking features of Trinity Park Tabernacle, visit a coastal fixture at Edgartown Lighthouse, take a stroll through Martha's Vineyard Camp meeting Association (MVCMA), then don't miss a visit to Flying Horses Carousel, then stop by Stefanie Wolf Designs, and finally take in nature's colorful creations at Mytoi.

To find other places to visit, more things to do, maps, and other tourist information, you can read our Oak Bluffs online road trip planner .

Jacksonville to Oak Bluffs is an approximately 8.5-hour combination of bus and flight. You can also do a combination of train, bus, and flight; or do a combination of bus, flight, and ferry. Prepare for little chillier weather when traveling from Jacksonville in October: high temperatures in Oak Bluffs hover around 65°F and lows are around 46°F. Finish your sightseeing early on the 12th (Sat) so you can drive to Hyannis.

Things to do in Oak Bluffs

Historic Sites Neighborhoods Shopping

Side Trip

Edgartown
Highlights from your plan
Edgartown Lighthouse ©
Edgartown Lighthouse
Trinity Park Tabernacle ©
Trinity Park Tabernacle
Mytoi ©
Mytoi

3
nights
Hyannis

Hyannis ©
"The Capital of the Cape," Hyannis serves as Cape Cod's main transportation and commercial hub.
Explore the numerous day-trip ideas around Hyannis: Shining Sea Bikeway (in Falmouth) and Plymouth (Plymouth Rock & Plimoth Plantation). There's still lots to do: examine the collection at Heritage Museums & Gardens, look for all kinds of wild species at Sandwich Fish Hatchery, engage your brain at Sandwich Glass Museum, and appreciate the history behind John F. Kennedy Memorial.

To find other places to visit, reviews, more things to do, and other tourist information, read Hyannis road trip planner.

Drive from Oak Bluffs to Hyannis in 2 hours. October in Hyannis sees daily highs of 64°F and lows of 48°F at night. Wrap up your sightseeing on the 15th (Tue) early enough to drive to Provincetown.

Things to do in Hyannis

Museums Parks Outdoors

Side Trips

Sandwich, Plymouth, Captain Bangs Hallet House Museum, Shining Sea Bikeway, Samuell Day Gallery
Highlights from your plan
John F Kennedy Hyannis Museum ©
John F Kennedy Hyannis Museum
Heritage Museums & Gardens ©
Heritage Museums & Gardens
Plimoth Plantation ©
Plimoth Plantation

3
nights
Provincetown

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.
When in Provincetown, make a side trip to see Salt Pond Visitor Center in Eastham, approximately 36 minutes away. And it doesn't end there: kick back and relax at Cape Cod National Seashore, tour the pleasant surroundings at Race Point Beach, appreciate the history behind Pilgrim Monument & Provincetown Museum, and take a leisurely stroll along MacMillan Wharf.

Ask Inspirock to suggest an itinerary and make planning a trip to Provincetown fast, fun, and easy.

Drive from Hyannis to Provincetown in 1.5 hours. Alternatively, you can take a bus. October in Provincetown sees daily highs of 63°F and lows of 49°F at night. Wrap up your sightseeing on the 18th (Fri) to allow time to ride a ferry to Boston.

Things to do in Provincetown

Outdoors Parks Beaches

Side Trips

Salt Pond Visitor Center, Truro Vineyards of Cape Cod, Cape Cod National Seashore
Highlights from your plan
Race Point Beach ©
Race Point Beach
Cape Cod National Seashore ©
Cape Cod National Seashore

5
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.
Get out of town with these interesting Boston side-trips: Marginal Way Walkway (in Ogunquit) and The House of the Seven Gables (in Salem). There's still lots to do: admire the masterpieces at Museum of Fine Arts, take in nature's colorful creations at Boston Public Garden, stroll around Boston Common, and take an in-depth tour of John F. Kennedy Presidential Museum & Library.

To find traveler tips, maps, where to stay, and other tourist information, use the Boston journey planner .

Getting from Provincetown to Boston by ferry takes about 1.5 hours. Other options: fly; or drive. In October, plan for daily highs up to 64°F, and evening lows to 50°F. Wrap up your sightseeing on the 23rd (Wed) to allow time to travel back home.

Things to do in Boston

Museums Historic Sites Parks

Side Trips

The House of the Seven Gables, Marginal Way Walkway
Highlights from your plan
Museum of Fine Arts ©
Museum of Fine Arts
Marginal Way Walkway ©
Marginal Way Walkway
Boston Public Garden ©
Boston Public Garden

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