5 days in Cape Cod, Martha's Vineyard & Nantucket Itinerary

5 days in Cape Cod, Martha's Vineyard & Nantucket Itinerary

Created using Inspirock Massachusetts travel planner

Make it your trip
— 2 nights
Taxi to Hyannis, MA, Ferry to Oak Bluffs
Oak Bluffs
— 2 nights
— 1 day



Capital of Cape Cod

"The Capital of the Cape," Hyannis serves as Cape Cod's main transportation and commercial hub.
On the 20th (Wed), get curious at Sandwich Glass Museum, then visit a coastal fixture at Edgartown Lighthouse, and then examine the collection at Heritage Museums & Gardens.

To find maps, reviews, and more tourist information, read our Hyannis trip itinerary website.

Philadelphia to Hyannis is an approximately 6.5-hour car ride. You can also fly; or do a combination of train and flight; or drive. Prepare for a bit cooler weather when traveling from Philadelphia in October: high temperatures in Hyannis hover around 64°F and lows are around 48°F. Cap off your sightseeing on the 20th (Wed) early enough to go by car to Provincetown.

Things to do in Hyannis

Museums · Childrens Museums · Historic Sites

Side Trips


— 2 nights

Birthplace of American Liberty

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.
On the 21st (Thu), kick back and relax at Race Point Beach, get up close to creatures of the deep with a dolphin and whale watching tour, see the interesting displays at Pilgrim Monument & Provincetown Museum, then admire the striking features of Trinity Park Tabernacle, then browse the collection at Provincetown Library, and finally make a trip to Commercial Street. On the next day, kick back and relax at Katama Beach/ South Beach.

To see traveler tips, ratings, and tourist information, you can read our Provincetown travel website.

You can drive from Hyannis to Provincetown in 1.5 hours. Other options are to drive; or take a bus. In October in Provincetown, expect temperatures between 63°F during the day and 49°F at night. Finish up your sightseeing early on the 22nd (Fri) so you can travel to Oak Bluffs.

Things to do in Provincetown

Outdoors · Tours · Wildlife · Beaches

Side Trips

Oak Bluffs

— 2 nights
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 23rd (Sat): make a trip to Flying Horses Carousel.

To find traveler tips, where to stay, maps, and tourist information, go to the Oak Bluffs tour app.

Do a combination of taxi and ferry from Provincetown to Oak Bluffs in 3 hours. Alternatively, you can do a combination of car and ferry; or do a combination of bus and ferry. In October, daytime highs in Oak Bluffs are 65°F, while nighttime lows are 46°F. Finish up your sightseeing early on the 24th (Sun) so you can catch the ferry to Nantucket.
Highlights from your trip


— 1 day
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Start off your visit on the 24th (Sun): see the interesting displays at Whaling Museum, then don't miss a visit to Brant Point Lighthouse, and then sample the tasty concoctions at Cisco Brewers.

To see photos, more things to do, other places to visit, and other tourist information, go to the Nantucket online driving holiday planner.

Getting from Oak Bluffs to Nantucket by ferry takes about 2 hours. In October, plan for daily highs up to 64°F, and evening lows to 51°F. Finish your sightseeing early on the 24th (Sun) to allow enough time to fly back home.

Things to do in Nantucket

Breweries & Distilleries · Wineries · Museums · Historic Sites

Cape Cod travel guide

Beaches · Dolphin & Whale Watching · Specialty Museums
Located on the southern shore of Massachusetts, Cape Cod contains some 15 towns and two islands. The arm-shaped peninsula is a popular holiday destination throughout the year because of its historical attractions, art galleries, award-winning restaurants, and a scenic coastline dotted by sandy beaches. Start your sightseeing in Provincetown, located at the very tip of the cape and famous for being the site of the first Pilgrims' landing in 1620. From there you can hit up all of the Cape's other small towns, renowned for their comfortable bed and breakfasts and distinctive cuisine of fresh fish and oyster dishes. This maritime community features more than a dozen lighthouses. Part of experiencing the Cape means a trip to its two islands--which showcase several lighthouses and numerous restaurants.

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.