7 days in Nantucket, Martha's Vineyard & Provincetown Itinerary

7 days in Nantucket, Martha's Vineyard & Provincetown Itinerary

Created using Inspirock Massachusetts travel route maker
Make it your trip
— 2 nights
Oak Bluffs
— 2 nights
Ferry to Hyannis, MA, Taxi to Provincetown
— 2 nights
Ferry to World Trade Center Pier, Boston, MA, Fly to San Diego


Nantucket — 2 nights

Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Start off your visit on the 16th (Sun): look for gifts at The Hub, then enjoy the sea views from Brant Point Lighthouse, and then make a trip to St Paul's Episcopal Church. Keep things going the next day: take an in-depth tour of Nantucket Shipwreck & Lifesaving Museum, enjoy the sea views from Sankaty Head Lighthouse, and then enjoy the sand and surf at Jetties Beach.

For traveler tips, other places to visit, ratings, and more tourist information, read our Nantucket travel route planning site.

San Diego to Nantucket is an approximately 9.5-hour flight. You can also do a combination of car and ferry; or do a combination of bus and ferry. Traveling from San Diego to Nantucket, you'll lose 3 hours due to the time zone difference. Prepare for little chillier weather when traveling from San Diego in October: high temperatures in Nantucket hover around 64°F and lows are around 51°F. Wrap up your sightseeing on the 18th (Tue) early enough to ride a ferry to Oak Bluffs.
Museums · Beaches · Parks · Outdoors

Oak Bluffs — 2 nights

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 19th (Wed): wander the streets of Martha's Vineyard Camp meeting Association (MVCMA), make a trip to Flying Horses Carousel, then stroll around Ocean Park, and finally kick back and relax at Katama Beach/ South Beach.

Find out how to plan Oak Bluffs trip without stress by asking Inspirock to help create an itinerary.

Traveling by ferry from Nantucket to Oak Bluffs takes 2 hours. Traveling from Nantucket in October, expect a bit cooler with lows of 46°F in Oak Bluffs. Finish your sightseeing early on the 20th (Thu) to allow enough time to travel to Provincetown.
Parks · Beaches · Neighborhoods · Outdoors
Side Trip

Provincetown — 2 nights

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.
Venture out of the city with trips to Nauset Beach (in Orleans) and Coast Guard Beach (in Eastham). The adventure continues: appreciate the history behind Pilgrim Monument & Provincetown Museum, take a tour by water with Boat Tours & Water Sports, kick back and relax at Marconi Beach, and tour the pleasant surroundings at Race Point Beach.

For reviews, traveler tips, more things to do, and tourist information, read Provincetown trip planner.

Traveling by combination of ferry and taxi from Oak Bluffs to Provincetown takes 3 hours. Alternatively, you can do a combination of ferry and car; or do a combination of ferry and bus. In October in Provincetown, expect temperatures between 63°F during the day and 49°F at night. Wrap up your sightseeing on the 22nd (Sat) to allow time to travel back home.
Outdoors · Beaches · Parks · Museums
Side Trips

Martha's Vineyard travel guide

Beaches · Lighthouses · Landmarks
Martha's Vineyard is an island located south of Cape Cod in Massachusetts that is known for being an affluent summer colony. It includes the smaller Chappaquiddick Island which is usually connected to the Vineyard, though storms and hurricanes have been known to separate the two. The last such separation of the islands was in 2007 and the two islands are again connected as of April 2, 2015.It is the 58th largest island in the United States, with a land area of 100sqmi, and the third largest on the East Coast of the United States, after Long Island and Mount Desert Island. The island constitutes the bulk of Dukes County, Massachusetts, which also includes the Elizabeth Islands and the island of Nomans Land.The Vineyard was home to one of the earliest known deaf communities in the United States; consequently, a special sign language developed on the island called Martha's Vineyard Sign Language (MVSL).The 2010 census reported a year-round population of 16,535 residents, although the summer population can swell to more than 100,000 people. About 56% of the Vineyard's 14,621 homes are seasonally occupied.