MileHacker Logo
Marthas Vineyard Itineraries

Marthas Vineyard Itineraries

Marthas Vineyard Massachusetts, USA Travel Guide

-Hour Layover Highlights

If you possess a very short visit, focus on the easily accessible towns.

Morning: Arrive in Vineyard Haven by ferry. Rent a bicycle near the terminal. Bike along the scenic Beach Road path to Oak Bluffs. See the iconic Gingerbread Cottages and take a ride on the Flying Horses Carousel.

Afternoon & Evening

  • Afternoon: Enjoy relaxing on the beach at State Beach, known for its tranquil waters.
  • Have a casual lunch in Oak Bluffs before continuing your day.
  • Evening: Take VTA bus or bike to Edgartown. Stroll old streets, see Edgartown Lighthouse.

Weekend & Week-Long Itineraries

A weekend or a week provides good opportunity to see the island'the key attractions and diverse offerings.

Weekend Getaway 2-3 Days

A two-day trip visit lets you experience a good taste of the island.

Sample Weekend Plan

  • Day 1: Arrive Vineyard Haven, explore shops, Martha''s Vineyard Museum, dinner.
  • Day 2: Morning in Oak Bluffs (Gingerbread Cottages, Flying Horses); afternoon at State Beach; Edgartown for shopping, lighthouse, fine dining.
  • Day 3: Up-island exploration (Aquinnah Cliffs, Gay Head Lighthouse, Menemsha seafood lunch), depart.
  • Get more weekend ideas on GetYourGuide.
This itinerary provides a mix of the urban area exploration, beach relaxation, and scenic views.

One-Week Comprehensive Experience

A week allows for an exploration of the island's diverse offerings.

Full Week Itinerary

  • Days 1-3: Explore Vineyard Haven, Oak Bluffs (Gingerbread Cottages, beaches), and historic Edgartown (South Beach, lighthouse).
  • Day 4: Up-island scenic drive (West Tisbury, Menemsha seafood, Aquinnah Cliffs).
  • Day 5: Outdoor Adventure (biking, kayaking, paddleboarding, fishing charter).

Two-Week In-Depth Exploration

A two-week stay allows for a truly immersive experience.

Extended Island Journey

  • Combine the one-week itinerary with more beach days plus detailed activity days.
  • Dedicate full days to art galleries, hiking trails, or conservation areas.
  • Consider a multi-day extension to Nantucket or Cape Cod.
  • Engage with local community events and farmers markets.

Long-Term Stay Recommendations

True Local Living

  • Book a vacation rental for cost efficiency, space, and a true "local living" experience.
  • Explore all towns and their hidden gems, including lesser-known trails and conservation areas.
  • Consider an off-season stay for an unique perspective, tranquility, and connection with the year-round community.
  • Immerse yourself in the island's rhythms and local culture.

Day 6 & 7 for One-Week Itinerary

The final days of a week-long stay are for choice and departure.

Day 6: Choice Day

Select your adventure: take a day trip to Nantucket, explore an outdoors preserve like Felix Neck, or revisit a favorite beach.

Day 7: Departure

Enjoy a leisurely breakfast, perhaps some last-minute souvenir shopping, and then depart away from the island.

GetYourGuide Options

Discover and book additional activities for your stay on GetYourGuide.

Itinerary Note

Plan your multi-day extensions with the same attention to detail as your main Martha's Vineyard trip, especially about ferry and accommodation bookings. Explore activities on GetYourGuide.

Interest-Based Routes for Martha's Vineyard

Tailor your Martha''s Grape farm adventure to your passions with these interest-specific itineraries.

Historical and Heritage Focus

Explore the rich past and preserved heritage of the island.

Historical Sites

  • Edgartown Walking Tour: Historic homes, Old Whaling Church, Vincent A Museum in a house.
  • African American Heritage Trail: Explore locations commemorating significant figures and events.
  • Aquinnah Cliffs and Gay Head Lighthouse: Learn about the Wampanoag Tribe's history.
  • Oak Bluffs Camp Ground: Stroll through the iconic Gingerbread Cottages.
Consider a led historical walks tour for an exploration of the island's past.

Food and Culinary Experiences

Indulge in the island's fresh flavors and local dining scene.

Culinary Highlights

  • West Tisbury Farmers Market: Sample local produce, baked goods, and artisanal products.
  • Menemsha Seafood Feast: Enjoy fresh seafood from local shacks right on the dock.
  • Fine Dining in Edgartown: Upscale culinary time at renowned restaurants.
  • Oak Bluffs Eateries: Explore diverse casual eateries and dessert spots on Circuit Avenue.

Adventure and Outdoor Activities

Embrace the island's beautiful nature with various outdoor pursuits.

Active Island Exploration

  • Biking the Island: Cycle the extensive network of paved bike paths, connecting towns and scenic vistas.
  • Hiking: Explore trails in Manuel F. Correllus State Forest, Menemsha Hills, or Cedar Tree Neck Sanctuary.
  • Water Sports: Try kayaking or paddleboarding in a calm pond, or go surfcasting or charter fishing.
  • Beach Hopping: Visit different shores to experience their unique characteristics.
Explore and book outdoor activities on GetYourGuide.

Family-Friendly Itinerary

Activities tailored for families with children of all ages.

Fun for All Ages

  • Oak Bluffs Fun: Ride the Flying Horses Carousel, explore Gingerbread Cottages, visit Island Alpaca Company.
  • Beach Day: Enjoy calm, shallow waters of State Beach or Inkwell Beach.
  • Lighthouse Visits: Explore the Edgartown Lighthouse and Gay Head Lighthouse.
  • Martha''s Grape farm Agricultural Fair (August): Classic family entertainment.

Art and Architecture Emphasis

Discover the artistic and architectural treasures of Martha's Vineyard.

Artistic Exploration

  • Gingerbread Cottages (Oak Bluffs): Marvel at the unique Victorian architecture.
  • Edgartown's Historic Architecture: Stroll through streets, admiring whaling captains' homes.
  • Featherstone Center for the Arts: Visit galleries, check for workshops or events.
  • Martha's Vineyard Glassworks: See glass art and demonstrations.

Spiritual and Wellness Journey

Find tranquility and rejuvenation on the peaceful island.

Path to Serenity

  • Quiet Beach Walks: Seek out remote beaches in the off-season for peaceful reflection.
  • Yoga Classes: Attend classes at one of the island's yoga studios.
  • Spa Treatments: Indulge in a relaxing spa treatment at a hotel or independent practitioner.
  • Nature Meditation: Find serene spots in conservation lands or at Polly Hill Arboretum.

Explore Your Interests

GetYourGuide offers diverse tours and activities to suit every interest, from historical walks to culinary adventures. Plan your perfect trip by filtering based on your passions.

Budget-Based Plans for Martha's Vineyard

Martha''s Grape farm has experiences for every budget. Plan smartly to make your trip affordable or indulgent.

Backpacker's Guide

Experience the island on a minimal budget with smart choices.

Budget Travel Tips

  • Accommodation: Stay at Martha's Vineyard Family Campground or in budget motels during shoulder/low season.
  • Transportation: Rely on the VTA bus system and rent bicycles. Avoid bringing a car on the ferry.
  • Meals: Cook your own using groceries; focus on casual eateries and BYOB restaurants.
  • Activities: Prioritize free activities like public beaches, hiking trails, walking through towns.
Travel in the shoulder or low season for significantly cheaper prices.

Mid-Range Traveler's Itinerary

Balance comfort and experience without overspending.

Balanced Travel Approach

  • Accommodation: Choose B&Bs or mid-range hotels. Consider a vacation rental for a group to share costs.
  • Transportation: Use a mix of VTA buses, bike rentals, and occasional taxis or ride-hailingshares.
  • Meals: Enjoy a mix of casual and sit-down restaurants. Try a few signature dishes with seafood.
  • Activities: Include some paid attractions like museums, a boat tour, or a lighthouse climb.

Luxury Experience Plan

Indulge in the finest Martha's Vineyard has to offer.

Premium Stays & Transport

  • Accommodation: Luxury hotels (Harbor View Hotel, Charlotte Inn) or high-end private hires.
  • Transportation: Private car service, luxury car rental, or extensive use of taxis/rideshares.
  • Consider hiring a private boat for an exclusive experience.

Exclusive Dining & Activities

  • Meals: Enjoy fine dining, possibly including private chefs or exclusive culinary events.
  • Activities: Book private guided tours, spa treatments, and exclusive island experiences.
  • Access to bespoke services and unique island adventures.

Value-Focused Recommendations

Maximize your experience while keeping spending in check.

Smart Savings

  • Timing: Travel during May, early June, September, or October for lower prices and fewer crowds.
  • Advance Booking: Book all accommodations, ferries, and rentals well ahead to secure the top deals.
  • Mix Activities: Combine free activities (beaches, walks) with select paid experiences aligning with interests.
  • Picnic Lunches: Pack picnic lunches for beach days or treks to save on dining costs.

Explore More Options

Discover a wide range of activities and tours to match your budget and preferences.

Diverse Activities

  • Utilize GetYourGuide to filter activities by price point and interest.
  • Look for free walking tours or self-guided audio tours.
  • Seek out local events or festivals that offer free entry.
  • Explore lesser-known spots that are often free and less crowded.

Budgeting Strategy

GetYourGuide offers a range of options, from budget-friendly tours to high-end activities, suitable for any traveler's financial plan.

Seasonal Specialties for Martha's Vineyard Visits

Each season on Martha's Vineyard has its unique charm and a distinct set of experiences.

Summer Highlights June-August

The island buzzes with energy, including all businesses open.

Summer Experience

  • Perfect for classic beach vacations, family fun, and social gatherings.
  • nightlife and many dining options are available.
  • Expect higher crowds and peak prices for accommodations and activities.
  • Events: Martha''s Grape farm Agricultural Fair (August), African American Film Festival (August).
Book accommodations and ferries far in advance for summer travel.

Winter Highlights November-April

Experience tranquility and the quiet, year-round community spirit.

Winter Charm

  • Highlights: Tranquility, dramatic stormy seascapes, cozy indoor activities (museums, local pubs).
  • Focus: Ideal for peaceful retreats, reading, connecting with nature in solitude.
  • Discounts: Significant on accommodations and other services.
  • Less Crowds: Enjoy attractions and natural beauty with fewer people.

Off-Season Exploration Strategies

Embrace the quiet and unique aspects of Martha's Vineyard outside of peak summer.

Embrace the Quiet

  • The off-season (fall, winter, spring) lets you experience the island's the beauty of nature without summer crowds.
  • Focus on nature walks, cozy dining by a fireplace, and browsing shops at a leisurely pace.
  • Enjoy the island as locals do, often finding a more authentic and relaxed atmosphere.

Confirm Open Businesses

  • Many seasonal businesses close during the off-season.
  • Always confirm which restaurants, shops, and attractions are open before you go to.
  • Check ferry schedules, which could be reduced.

Festival or Event-Centered Visits

Plan your trip around specific events that interest you.

Event Planning

  • Plan Around Events: If a specific festival or event interests you, plan your visit around it.
  • Book Early: Popular events draw crowds, so book accommodations and ferries far in advance.
  • Examples: Martha's Vineyard Food & Wine Festival (October).
  • Check island event calendars for up-to-date information.

Other Seasonal Considerations

Be aware of these details for any seasonal visit.

Additional Notes

  • Weather: Summers are warm and humid; the cold season is cold, windy, and may have snow.
  • Insects: Mosquitos and ticks are prevalent in warmer months, take precautions.
  • Packing: Layers are advisable for all seasons due to changeable coastal weather.
  • Current Guidelines: Stay informed on any local health or travel advisories.

Important Seasonal Advice

Always Verify

Before planning your off-season trip, always verify operating hours for particular sights, restaurants, and accommodations.

Flexible Travel

Be prepared for potential ferry delays or cancellations due to weather, particularly in winter. Keep your schedule flexible.

Seasonal Planning

GetYourGuide has seasonal things to do. Check listings for availability throughout the year to tailor your visit to Martha's Vineyard to the season's unique charm.