10 days in Provincetown & Oak Bluffs Itinerary

10 days in Provincetown & Oak Bluffs Itinerary

Created using Inspirock Massachusetts attractions planner
Make it your trip
Drive
1
Provincetown
— 6 nights
Drive to Woods Hole, Ferry to Oak Bluffs
2
Oak Bluffs
— 3 nights
Drive

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Provincetown — 6 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.
Cafe Mews has been added to your itinerary. Get out of town with these interesting Provincetown side-trips: Orleans (Addison Art Gallery & Nauset Beach), Chatham (Kate Gould Park & Atwood Museum) and Eastham (Salt Pond Visitor Center & Eastham Historical Society). And it doesn't end there: don't miss a visit to Commercial Street, stroll through Long Point, kick back and relax at Herring Cove Beach, and do a tasting at Truro Vineyards of Cape Cod.

To find where to stay, more things to do, maps, and tourist information, use the Provincetown visit planning site.

Dracut to Provincetown is an approximately 3-hour car ride. You can also drive. When traveling from Dracut in May, plan for slightly colder days and about the same nights in Provincetown: temperatures range from 63°F by day to 48°F at night. You'll have a few hours on the 20th (Thu) to wrap things up before traveling to Oak Bluffs.
Parks · Outdoors · Beaches · Museums
Side Trips

Oak Bluffs — 3 nights

Oak Bluffs is a town located on the island of Martha's Vineyard in Dukes County, Massachusetts, United States. Your day by day itinerary now includes The Ritz Cafe, Ben and Bill's Chocolate Emporium and Oak Bluffs Marina. When in Oak Bluffs, make a side trip to see Chappaquiddick in Edgartown, approximately Edgartown away. There's still lots to do: enjoy the sea views from Edgartown Lighthouse, enjoy the sand and surf at Lighthouse Beach, don't miss a visit to Edgartown Books, and take in nature's colorful creations at Mytoi.

For reviews, other places to visit, ratings, and tourist information, read our Oak Bluffs trip itinerary planning tool.

Traveling by combination of taxi and ferry from Provincetown to Oak Bluffs takes 3 hours. Alternatively, you can do a combination of car and ferry; or do a combination of bus and ferry. In May, plan for daily highs up to 65°F, and evening lows to 47°F. On the 23rd (Sun), you'll have the morning to explore before heading back home.
Parks · Nature · Beaches · Nightlife
Side Trip