8 days in Oak Bluffs & Cape Cod Itinerary

8 days in Oak Bluffs & Cape Cod Itinerary

Created using Inspirock Massachusetts trip planner
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Oak Bluffs
— 2 nights
— 2 nights
— 3 nights
Fly to White Plains, Train to New York City


Oak Bluffs — 2 nights

Oak Bluffs is a town located on the island of Martha's Vineyard in Dukes County, Massachusetts, United States. Visit Menemsha Public Beach and Lambert's Cove Beach for some beach relaxation. Take a break from the city and head to Inkwell Beach and Oak Bluffs Town Beach. Take a break from Oak Bluffs with a short trip to Lucy Vincent Beach in Chilmark, about 32 minutes away. There's lots more to do: enjoy the sand and surf at Joseph Sylvia State Beach, see the interesting displays at Cottage Museum, take in nature's colorful creations at Mytoi, and take a tour by water with Boat Tours & Water Sports.

To see maps, where to stay, ratings, and more tourist information, you can read our Oak Bluffs online trip planner.

New York City to Oak Bluffs is an approximately 3-hour flight. You can also do a combination of car and ferry; or do a combination of train, bus, and ferry. Prepare for slightly colder weather when traveling from New York City in July: high temperatures in Oak Bluffs hover around 79°F and lows are around 63°F. Wrap up your sightseeing on the 11th (Mon) to allow time to ride a ferry to Hyannis.
Outdoors · Parks · Beaches · Tours
Side Trips

Hyannis — 2 nights

"The Capital of the Cape," Hyannis serves as Cape Cod's main transportation and commercial hub.
On the 12th (Tue), get a new perspective on things with Cap'n Kids Fishing Adventures, admire the masterpieces at Atwood Museum, then tour the pleasant surroundings at Ridgevale Beach, and finally contemplate the long history of Captain Bangs Hallet House Museum. Here are some ideas for day two: see the interesting displays at John F Kennedy Hyannis Museum, then steep yourself in history at Hoxie House, then tour the pleasant surroundings at Craigville Beach, and finally tour the pleasant surroundings at Gray's Beach.

To see maps, more things to do, reviews, and tourist information, use the Hyannis online travel route planner.

Getting from Oak Bluffs to Hyannis by ferry takes about 1.5 hours. Other options: do a combination of ferry and taxi; or do a combination of ferry and bus. In July, daily temperatures in Hyannis can reach 80°F, while at night they dip to 66°F. Finish your sightseeing early on the 13th (Wed) to allow enough time to drive to Provincetown.
Outdoors · Beaches · Parks · Tours
Side Trips

Provincetown — 3 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.
Visiting Dolphin & Whale Watching and Cape Cod Provincelands Trail will get you outdoors. Relax by the water at Race Point Beach and Head of the Meadow Beach. And it doesn't end there: kick back and relax at Long Point, take in the waterfront at MacMillan Wharf, get a sense of history and politics at Provincetown Town Hall, and learn about winemaking at Truro Vineyards of Cape Cod.

To find other places to visit, traveler tips, where to stay, and tourist information, read Provincetown trip planning tool.

Traveling by car from Hyannis to Provincetown takes 1.5 hours. Alternatively, you can take a bus. In July, daily temperatures in Provincetown can reach 79°F, while at night they dip to 64°F. Finish your sightseeing early on the 16th (Sat) to allow enough time to travel back home.
Outdoors · Parks · Beaches · Wildlife
Side Trips

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.