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

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

Created using Inspirock Massachusetts trip planner

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Make it your trip
Drive
1
Hyannis
Drive
2
Provincetown
— 2 nights
Taxi to Hyannis, MA, Ferry to Oak Bluffs
3
Oak Bluffs
— 2 nights
Ferry
4
Nantucket
— 1 day
Fly to New York JFK, Train to Philadelphia

S M T W T F S
2
3
4
5
6
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Hyannis

Capital of Cape Cod

"The Capital of the Cape," Hyannis serves as Cape Cod's main transportation and commercial hub.
Start off your visit on the 4th (Tue): explore the world behind art at Sandwich Glass Museum and then see the interesting displays at Heritage Museums & Gardens.

To see reviews, traveler tips, other places to visit, and other tourist information, use the Hyannis online trip builder.

Philadelphia to Hyannis is an approximately 6.5-hour car ride. You can also do a combination of train and flight; or fly; or drive. Expect a bit cooler temperatures when traveling from Philadelphia in May; daily highs in Hyannis reach 65°F and lows reach 49°F. Cap off your sightseeing on the 4th (Tue) early enough to go by car to Provincetown.

Things to do in Hyannis

Museums · Childrens Museums

Side Trip

Provincetown

— 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.
Kick off your visit on the 5th (Wed): enjoy the sand and surf at Race Point Beach, examine the collection at Pilgrim Monument & Provincetown Museum, then browse the collection at Provincetown Library, and finally make a trip to Commercial Street. On the next day, look for all kinds of wild species at Wildlife Areas.

To find other places to visit, maps, traveler tips, and other tourist information, read our Provincetown driving holiday planner.

Traveling by car from Hyannis to Provincetown takes 1.5 hours. Alternatively, you can drive; or take a bus. In May in Provincetown, expect temperatures between 63°F during the day and 48°F at night. Finish up your sightseeing early on the 6th (Thu) so you can travel to Oak Bluffs.

Things to do in Provincetown

Outdoors · Tours · Wildlife · Beaches

Oak Bluffs

— 2 nights
Oak Bluffs is a town located on the island of Martha's Vineyard in Dukes County, Massachusetts, United States. On the 7th (Fri), kick back and relax at Katama Beach/ South Beach, then visit a coastal fixture at Edgartown Lighthouse, then steep yourself in history at Trinity Park Tabernacle, and finally make a trip to Flying Horses Carousel.

To find ratings, where to stay, maps, and more tourist information, read our Oak Bluffs route planner.

You can 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 May in Oak Bluffs, expect temperatures between 65°F during the day and 47°F at night. Cap off your sightseeing on the 8th (Sat) early enough to catch the ferry to Nantucket.

Things to do in Oak Bluffs

Beaches · Parks · Outdoors · Historic Sites

Side Trip

Nantucket

— 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 8th (Sat): examine the collection at Whaling Museum, then enjoy the sea views from Brant Point Lighthouse, and then learn about winemaking at Cisco Brewers.

To find other places to visit, maps, where to stay, and other tourist information, refer to the Nantucket online driving holiday planner.

Traveling by ferry from Oak Bluffs to Nantucket takes 2 hours. In May in Nantucket, expect temperatures between 62°F during the day and 49°F at night. Finish your sightseeing early on the 8th (Sat) to allow enough time to travel back home.

Things to do in Nantucket

Breweries & Distilleries · Museums · Wineries · Historic Sites

Cape Cod travel guide

4.4
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

4.4
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.

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