A trip to Cape Cod, Nantucket, and Martha’s Vineyard is the perfect destination for your next girls trip! We chose to do a single day on all three versus spending our entire trip on one. I recommend this approach for any first-timers out there!
Here’s a rundown of our trip itinerary!
Day 1 – Welcome
- Arrive, Car Rental Pickup, and Hit the Road!
- Lunch at The Black Whale (highly recommend; refreshing margaritas, delicious lobster roll and great outdoor dining)
- Wine sampling at Cape Cod Winery (recommend; beautiful outdoor space)
- Drinks at East End Tap (recommend; fun dive bar!)
- Dinner at Sienna in Mashpee (do not recommend; the food wasn’t great yet we enjoyed dining on the outdoor patio)
Day 2 – Nantucket
- HyLine Fast Ferry from Hyannis to Nantucket
- Rented bike at Young’s BIke Shop to explore the island on two wheels! Please note: the streets downtown aren’t straight and contain uneven cobblestone making cycling on them tough. We walked most of our exploring in central downtown but used the bikes to go everywhere else!
- Explored many sights from Elin Hilderbrand books around the island
- Lunch at The Galley Beach (cautiously recommend; The Galley is the most expensive restaurant on the island. We splurged for a lunch here as it is a favorite spot in Elin’s books)
- Relaxed at Jetties beach
- Happy Hour at Cisco Brewers (highly recommend; super cool outdoor venue with a brewery, winery, mix
- Sushi Dinner at Bar Yosi (recommend; small, intimate space on the pier)
- Drinks at The Chicken Box (cautiously recommend; we visited because it is a favorite spot in Elin’s books and had to check it out! It is a true dive bar on the outside of town)
Day 3 – Cape Cod
- Drove up the Cape to Provincetown, the most northern point!
- Walked up and down Commercial Street, the main street
- Lunch at Cafe Heaven (highly recommend; delicious food!)
- Relaxed and soaked up the sun at Marconi Beach. The Ocean. Aww.
- Private Sunset Cruise with Cape Sailing Charters (highly recommend; the highlight of the trip)
Day 4 – Martha Vineyard
- Ferry from East Falmouth to Edgartown
- Walked and shopped around Edgartown which was my overall favorite town of the trip
- Rented bikes from Edgertown Bicycles (recommend; located next to the bike trail for easy access)
- Rode up to Oak Bluffs stopped at the bridge where the movie “Jaws” was filmed. Yes, we saw people jumping off the bridge!
- Walked around downtown Oak Bluffs and had a dockside lunch
- Walked through the Gingerbread Cottage homes
- Took the ferry (with bikes!) to Chappaquiddick Island and cycled across Dike Bridge
We had great weather and even better company! I recommend taking time to connect with your girlfriends every chance you get!
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