The Ultimate 3-Day Itinerary for Martha’s Vineyard
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Martha’s Vineyard is a charming New England island getaway that offers breathtaking beaches, quaint fishing villages, historic lighthouses, and farm-to-table dining experiences. Whether you’re visiting for a long weekend or planning a quick escape, this 3-day Martha’s Vineyard itinerary will help you make the most of your trip.
Day 1: Arrival & Exploring Edgartown
Morning – Ferry Ride & First Impressions
Start your adventure with a scenic ferry ride from Woods Hole, MA to Vineyard Haven or Oak Bluffs. Book your ferry tickets in advance—especially during peak summer months.
Once you arrive, pick up a rental bike or car for easy island exploration.
Late Morning – Stroll Through Edgartown
Head straight to Edgartown, one of the island’s most picturesque towns. Wander the cobblestone streets lined with white-clapboard captain’s houses and boutique shops. Don’t miss the Edgartown Lighthouse, perfect for panoramic coastal views and Instagram-worthy photos.
Lunch – Seafood by the Harbor
Grab lunch at Seafood Shanty or Larsen’s Fish Market for fresh lobster rolls, oysters, and chowder.
Afternoon – South Beach Relaxation
Spend the rest of your afternoon at South Beach, a favorite for sunbathing, swimming, and long walks along the shore.
Evening – Dinner & Sunset
Book a table at Alchemy Bistro & Bar or Atlantic Fish & Chop House for a delicious dinner, then head to Menemsha Beach for one of the island’s legendary sunsets.
Day 2: Oak Bluffs & Vineyard Haven Charm
Morning – Oak Bluffs Exploration
Begin your day in Oak Bluffs, famous for its colorful Gingerbread Cottages in the Martha’s Vineyard Camp Meeting Association. Stroll through the whimsical neighborhood and soak in the Victorian charm.
Late Morning – Flying Horses Carousel
Take a ride on the historic Flying Horses Carousel, the oldest operating platform carousel in the country.
Lunch – Casual Eats
Try Back Door Donuts for their famous apple fritters, then enjoy a casual lunch at Nancy’s Restaurant, known for its waterfront views.
Afternoon – Vineyard Haven Shopping
Head to Vineyard Haven for boutique shopping, art galleries, and a visit to Bunch of Grapes Bookstore.
Evening – Seafood Feast
Have dinner at Garde East, offering a refined take on island seafood with stunning harbor views.
Day 3: Up-Island Adventure
Morning – Aquinnah Cliffs
Drive or bike to the Aquinnah Cliffs for some of the island’s most dramatic scenery. The colorful clay cliffs and Gay Head Lighthouse are a must-see.
Late Morning – Chilmark & Farmers Markets
Stop in Chilmark for farm-fresh produce at the Chilmark Flea Market or West Tisbury Farmers Market (seasonal).
Lunch – Menemsha Seafood
Enjoy a picnic lunch from Menemsha Fish Market right on the docks.
Afternoon – Outdoor Activities
Spend your afternoon kayaking, paddleboarding, or hiking one of the many island trails, such as Menemsha Hills Reservation.
Evening – Farewell Dinner
End your trip with a sunset dinner at State Road Restaurant, known for its farm-to-table cuisine.
Tips for Your Martha’s Vineyard Trip
Best Time to Visit: Late spring to early fall offers the warmest weather and most activities.
Getting Around: Renting a bike or car is highly recommended for full island access.
Accommodations: Book early during peak summer months, as hotels and B&Bs fill quickly.
Final Thoughts
This 3-day Martha’s Vineyard itinerary offers the perfect blend of relaxation, exploration, and indulgence. Whether it’s your first visit or your fifth, the island’s coastal beauty and small-town charm will leave you wanting more.