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Oak Bluffs

3 day itinerary for Oak Bluffs

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Hotel and airfare for two. September 8-11, 2025

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Itinerary

Oak Bluffs is such a charming destination on Martha's Vineyard, and I’m excited to help you plan a delightful 3-day itinerary for your trip from September 8-11, 2025. Let’s dive in!

## Day 1: Arrival and Exploring Oak Bluffs

Morning: Arrival

  • Flight: Arrive at Martha's Vineyard Airport (MVY). Depending on where you're flying from, you might have a layover, but it’s a small airport, so it should be a smooth experience.
  • Hotel Check-in: Consider staying at the charming Mansion House Inn or the cozy Oak Bluffs Inn. Both offer great amenities and are centrally located.

Afternoon: Stroll Around Oak Bluffs

  • After settling in, take a leisurely stroll around Oak Bluffs Harbor. The views are stunning, and you can enjoy the colorful gingerbread cottages that the town is famous for.
  • Lunch: Grab a bite at Linda Jean's Restaurant for some classic New England fare. Their clam chowder is a must-try!

Evening: Sunset and Dinner

  • Head to Inkwell Beach for a beautiful sunset. It’s a perfect spot to relax and take in the scenery.
  • Dinner: Enjoy a lovely dinner at The Red Cat Kitchen, known for its fresh, local ingredients and delicious seafood dishes.

## Day 2: Adventure and Culture

Morning: Biking and Beaches

  • Rent bikes from a local shop and explore the scenic bike paths. You can ride to State Beach or even venture to Edgartown if you’re feeling adventurous.
  • Brunch: Stop at The Art Cliff Diner for a hearty brunch. Their pancakes are legendary!

Afternoon: Visit the Tabernacle and Shops

  • After brunch, visit the Oak Bluffs Campground and check out the Tabernacle, a beautiful structure with a rich history.
  • Spend some time exploring the local shops and boutiques. Don’t forget to pick up some unique souvenirs!

Evening: Dinner and Entertainment

  • Dinner: Head to The Lookout Tavern for a casual dinner with a view. Their lobster rolls are fantastic!
  • If you’re up for it, check out any local events or live music happening in town. The Martha's Vineyard Playhouse often has performances, so see if there’s something that piques your interest!

## Day 3: Day Trip and Relaxation

Morning: ## Day Trip to Aquinnah

  • After breakfast, take a short drive or bike ride to Aquinnah to see the stunning Gay Head Cliffs. The views are breathtaking, and you can visit the lighthouse.
  • Lunch: Pack a picnic or grab a bite at The Aquinnah Shop for some local snacks.

Afternoon: Beach Time

  • Spend the afternoon at Moshup Beach. It’s a beautiful spot to relax, swim, or just soak up the sun. Bring a good book and enjoy the peaceful atmosphere.

Evening: Farewell Dinner

  • Head back to Oak Bluffs for your final dinner. Treat yourselves to a special meal at The Wharf, where you can enjoy fresh seafood and a lovely view of the harbor.
  • After dinner, take a stroll along the harbor and enjoy the twinkling lights reflecting on the water. It’s a perfect way to end your trip!

Departure ## Day: September 11

  • Enjoy a leisurely breakfast at your hotel or a local café before checking out.
  • Depending on your flight time, you might have a little time for some last-minute shopping or a quick visit to the beach.

Tips:

  • Make sure to book your hotel and flights early, as September can still be a popular time on the Vineyard.
  • Consider renting a car or using local transportation to get around the island easily.
  • Don’t forget your camera! The scenery is absolutely Instagram-worthy.

I hope this itinerary helps you have a fantastic time in Oak Bluffs! If you have any other questions or need more suggestions, feel free to ask. Safe travels! 🌊🌅

Places of interest

Martha's Vineyard Airport (MVY) Oak Bluffs

Martha's Vineyard Airport (MVY)

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Mansion House Inn Oak Bluffs

Mansion House Inn

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Oak Bluffs Inn Oak Bluffs

Oak Bluffs Inn

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Oak Bluffs Harbor Oak Bluffs

Oak Bluffs Harbor

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Linda Jean's Restaurant Oak Bluffs

Linda Jean's Restaurant

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Inkwell Beach Oak Bluffs

Inkwell Beach

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The Red Cat Kitchen Oak Bluffs

The Red Cat Kitchen

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State Beach Oak Bluffs

State Beach

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Edgartown Oak Bluffs

Edgartown

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The Art Cliff Diner Oak Bluffs

The Art Cliff Diner

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Oak Bluffs Campground Oak Bluffs

Oak Bluffs Campground

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Tabernacle Oak Bluffs

Tabernacle

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The Lookout Tavern Oak Bluffs

The Lookout Tavern

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Martha's Vineyard Playhouse Oak Bluffs

Martha's Vineyard Playhouse

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Aquinnah Oak Bluffs

Aquinnah

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Gay Head Cliffs Oak Bluffs

Gay Head Cliffs

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The Aquinnah Shop Oak Bluffs

The Aquinnah Shop

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Moshup Beach Oak Bluffs

Moshup Beach

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The Wharf Oak Bluffs

The Wharf

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