5-Day Ultimate Martha's Vineyard Adventure Itinerary

Day 1: Arrival & Relaxation

Oak Bluffs, USA

8:00AM

Breakfast at Linda Jean's

Start your day with a hearty breakfast at Linda Jean's, known for their delicious pancakes and omelets.
Head to Linda Jean's, located at the heart of Oak Bluffs.
USD15, 1.5 hours

10:00AM

Visit the Flying Horses Carousel

Experience the charm of the oldest carousel in the United States in Oak Bluffs.
From breakfast, walk 10 minutes towards the Oak Bluffs harbor.
USD3, 1 hour

12:00PM

Lunch at The Wharf

Enjoy casual waterfront dining with burgers and seafood at The Wharf.
It's a short 5-minute walk from the carousel.
USD20, 1.5 hours

2:00PM

Explore Oak Bluffs Campground

Stroll through this historical area filled with colorful cottages and beautiful gardens.
Walk 15 minutes from lunch to the Campground.
Free, 2 hours

4:30PM

Relax at Inkwell Beach

Unwind at the beautiful Inkwell Beach, perfect for swimming or sunbathing.
It's a short 10-minute walk from the campground.
Free, 2 hours

7:00PM

Dinner at Atria

Indulge in fine dining at Atria, known for its farm-to-table approach and seasonal menu.
It's a 15-minute drive from the beach.
USD50, 2 hours
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Day 2: Exploring Edgartown

Edgartown, USA

8:00AM

Breakfast at The Deli

Savor fresh pastries and coffee made with local ingredients.
Drive 20 minutes from Oak Bluffs to Edgartown.
USD10, 1 hour

9:30AM

Visit the Edgartown Lighthouse

Take a photo at the iconic Edgartown Lighthouse located on the coast.
A 10-minute walk from the deli.
Free, 1 hour

11:00AM

Walk through the Historic District

Explore the charming streets lined with historic whaling captain's homes.
Stroll around the nearby streets.
Free, 1.5 hours

12:30PM

Lunch at The Seafood Shack

Enjoy casual seafood dining with beach views at The Seafood Shack.
Drive 5 minutes to the restaurant.
USD25, 1.5 hours

2:00PM

Take a Bike Ride to South Beach

Rent a bike and ride to South Beach for sun and surf.
A 10-minute bike ride from lunch.
USD20 (bike rental), 3 hours

5:30PM

Dinner at The Port Hunter

End your day with cocktails and local cuisine in a casual atmosphere.
Head back into Edgartown and it will be a 15-minute drive to the restaurant.
USD40, 2 hours
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Day 3: Cultural Exploration in Vineyard Haven

Vineyard Haven, USA

8:00AM

Breakfast at Black Dog Bakery

Start with a delightful breakfast at the famous Black Dog Bakery.
Drive 10 minutes to Vineyard Haven.
USD12, 1 hour

9:30AM

Visit the Martha's Vineyard Museum

Learn about the island's history and culture in this small yet comprehensive museum.
A 5-minute walk from the bakery.
USD10, 1.5 hours

11:00AM

Stroll on the Vineyard Haven Harbor

Enjoy scenic views while walking along the beautiful harbor.
Just a 10-minute walk from the museum.
Free, 1 hour

12:00PM

Lunch at The Italian Bakery

Taste authentic Italian food and pastries at this local favorite.
Walk 10 minutes to reach the bakery.
USD20, 1.5 hours

2:00PM

Explore the Gingerbread Cottages

Discover the unique Victorian houses that showcase Martha’s Vineyard’s charm.
Drive 15 minutes to Oak Bluffs to see the cottages.
Free, 2 hours

4:30PM

Dinner at The Black Dog Tavern

Relish a delicious meal with views of the harbor.
Return to Vineyard Haven for dinner, a 15-minute drive.
USD35, 2 hours
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Day 4: Adventure in Aquinnah

Aquinnah, USA

8:00AM

Breakfast at Aquinnah Shop

Start off with fresh bagels and coffee right in Aquinnah.
Drive 30 minutes to Aquinnah from Vineyard Haven.
USD15, 1 hour

9:30AM

Visit the Aquinnah Cliffs

Marvel at the stunning coastal cliffs and vibrant colors of the clay.
The cliffs are a short drive from the bakery.
Free, 2 hours

12:00PM

Lunch at The Outermost Inn

Enjoy a seasonal menu with fresh ingredients sourced locally.
A 10-minute drive from the cliffs.
USD30, 1.5 hours

1:30PM

Visit the Gay Head Lighthouse

Explore this iconic lighthouse and discover its history.
A 5-minute drive from lunch.
USD5, 1 hour

3:00PM

Explore Moshup Beach

Relax on the stunning Moshup Beach with its breathtaking views.
It's only a 10-minute drive from the lighthouse.
Free, 2 hours

6:00PM

Dinner at The Red Cat Kitchen

Finish the day with locally sourced dishes and friendly service.
Drive back to Aquinnah and dine at The Red Cat Kitchen.
USD35, 2 hours
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Day 5: Relax in Chilmark

Chilmark, USA

8:00AM

Breakfast at Chilmark General Store

Enjoy a famous breakfast sandwich paired with local coffee.
Drive 15 minutes from Aquinnah to Chilmark.
USD12, 1 hour

9:30AM

Visit Menemsha Beach

Spend the morning relaxing at this picturesque beach famous for sunsets.
A short 10-minute drive.
Free, 2 hours

12:00PM

Lunch at The Beach Plum Inn

Dine al fresco with seaside views and delicious selections.
Just a 5-minute drive from the beach.
USD30, 1.5 hours

1:30PM

Explore the Aquinnah and Chilmark Shores

Take a scenic walk at the beautiful nearby shoreline.
Drive to the shore access points, about 15 minutes.
Free, 2 hours

4:00PM

Visit the Chilmark Flea Market

Browse local crafts, food, and unique finds at this vibrant market.
A short drive back into Chilmark.
Free, 1.5 hours

6:00PM

Dinner at The Yard

Enjoy farm-to-table fresh fare with local atmosphere.
It's located in Chilmark, a quick drive.
USD40, 2 hours
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