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Family-Friendly Road Trip in Oak Bluffs, MA

Viewed by 124 travelers

Day 1: Exploring Oak Bluffs

Oak Bluffs, MA

8:00AM

Breakfast at Linda Jean's Restaurant

Start your day with a delicious breakfast at Linda Jean's Restaurant, known for their hearty and tasty meals.
Head to Linda Jean's Restaurant located in downtown Oak Bluffs.
$15 per person, 1 hour

10:00AM

Explore Oak Bluffs Campground

Take a leisurely walk through the iconic Oak Bluffs Campground, known for its colorful gingerbread cottages and historic charm.
Walk or drive to Oak Bluffs Campground.
Free, 1-2 hours

12:00PM

Lunch at Nancy's Restaurant

Enjoy a waterfront lunch at Nancy's Restaurant, offering fresh seafood and stunning views of the harbor.
Head to Nancy's Restaurant by the Oak Bluffs Harbor.
$20-$30 per person, 1 hour

2:00PM

Visit Flying Horses Carousel

Ride the historic Flying Horses Carousel, a beloved attraction for both kids and adults, located in the heart of Oak Bluffs.
Walk to Flying Horses Carousel on Circuit Avenue.
$5 per person, 30 minutes

4:00PM

Relax at Inkwell Beach

Unwind at the beautiful Inkwell Beach, a popular spot for families to swim and sunbathe.
Drive to Inkwell Beach for relaxation.
Free, 2 hours

6:00PM

Dinner at Offshore Ale Company

End your day with a delicious dinner at Offshore Ale Company, a local brewery and restaurant known for its craft beers and tasty menu.
Head to Offshore Ale Company for dinner.
$25-$40 per person, 1-2 hours
Find Hotels in Oak Bluffs

Day 2: Visiting Edgartown

Edgartown, MA

9:00AM

Breakfast at Among the Flowers Cafe

Start your day with a cozy breakfast at Among the Flowers Cafe, offering delicious pastries and coffee.
Head to Among the Flowers Cafe in Edgartown.
$10-$15 per person, 1 hour

10:00AM

Explore Edgartown Harbor

Take a stroll along the picturesque Edgartown Harbor, admiring the historic waterfront and charming sailboats.
Walk to Edgartown Harbor from the cafe.
Free, 1-2 hours

12:00PM

Lunch at The Seafood Shanty

Enjoy a seafood lunch with a view at The Seafood Shanty, known for its fresh catches and waterfront dining experience.
Head to The Seafood Shanty for lunch.
$20-$30 per person, 1 hour

2:00PM

Tour the Edgartown Lighthouse

Visit the iconic Edgartown Lighthouse for a tour and panoramic views of the island and Atlantic Ocean.
Drive or walk to the Edgartown Lighthouse.
$5 per person, 1 hour

4:00PM

Shop on Main Street

Explore the quaint shops and boutiques on Edgartown's Main Street, perfect for picking up souvenirs and gifts.
Stroll along Main Street for shopping.
Variable, 1-2 hours

6:00PM

Dinner at The Port Hunter

Indulge in a delicious dinner at The Port Hunter, known for its creative cocktails and modern American cuisine.
Head to The Port Hunter for dinner.
$30-$50 per person, 1-2 hours
Find Hotels in Edgartown

Day 3: Experiencing Martha's Vineyard

Martha's Vineyard, MA

8:00AM

Breakfast at Artcliff Diner

Enjoy a classic breakfast at Artcliff Diner, a beloved local diner known for its comfort food and friendly atmosphere.
Head to Artcliff Diner on Martha's Vineyard.
$10-$20 per person, 1 hour

10:00AM

Visit Menemsha Beach

Spend your morning relaxing at Menemsha Beach, a pristine spot for swimming and enjoying the scenic beauty of the island.
Drive to Menemsha Beach for some beach time.
Free, 2-3 hours

1:00PM

Lunch at Larsen's Fish Market

Feast on fresh seafood for lunch at Larsen's Fish Market, a local favorite for lobster rolls and clam chowder.
Head to Larsen's Fish Market for a seafood lunch.
$15-$25 per person, 1 hour

3:00PM

Explore Aquinnah Cliffs

Discover the stunning Aquinnah Cliffs, famous for their vibrant clay cliffs and breathtaking views of the ocean.
Drive to Aquinnah Cliffs for sightseeing.
Parking fee, 1-2 hours

5:00PM

Family Fun at Island Cove Adventures

Enjoy mini-golf, go-karts, and other family-friendly activities at Island Cove Adventures to end the day with some fun.
Drive to Island Cove Adventures for family entertainment.
$15-$20 per person, 1-2 hours

7:00PM

Dinner at The Ritz Cafe

Conclude your Martha's Vineyard experience with a casual dinner at The Ritz Cafe, a laid-back spot with a diverse menu.
Head to The Ritz Cafe for dinner.
$20-$30 per person, 1-2 hours
Find Hotels in Martha's Vineyard
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