A Retiree’s Guide to Martha’s Vineyard: What to Do, See, and Discover

Discovering historic Martha’s Vineyard should be on every retiree’s travel bucket list. This charming New England island, known for its breathtaking coastal views, rich history, and relaxed pace, is the perfect getaway for retirees looking to explore, unwind, and enjoy a mix of adventure and tranquility.

Contrary to what some may believe, getting to Martha’s Vineyard is easier than you think. You can simply walk onto the ferry in Woods Hole, Massachusetts, and in just 45 minutes, you’ll find yourself stepping off onto an Island paradise. Whether you’re a retiree seeking laid-back leisure or one who thrives on active exploration, Martha’s Vineyard offers something for everyone.

Here’s your ultimate guide to experiencing Martha’s Vineyard as a retiree, covering everything from where to stay and what to do, to must-visit sites and hidden gems that will make your trip unforgettable.

Where to Stay: Cozy Inns & Boutique Hotels

One of the best ways to enjoy Martha’s Vineyard is to book a charming bed and breakfast or boutique inn that offers a welcoming, home-like atmosphere. Unlike large hotels, these accommodations provide personalized service, locally inspired decor, and cozy common areas where you can relax after a day of exploring.

Here are some of the best places to stay:

• Hob Knob Luxury Boutique Hotel, Edgartown – A luxury boutique hotel with a cozy New England charm, complete with afternoon tea and bike rentals. 
• Nobnocket Boutique Inn, Vineyard Haven – Known for its modern, stylish design, this inn provides a peaceful retreat within walking distance of shops and restaurants.
• Menemsha Inn and Cottages, Menemsha – A tranquil retreat with stunning views of the Vineyard Sound and charming cottages perfect for a peaceful escape.
• The Sydney Hotel, Edgartown – A boutique hotel in the heart of Edgartown offering elegant accommodations and modern amenities.
• The Richard Hotel, Edgartown – A stylish and sophisticated inn providing a luxurious and comfortable stay.
• Summercamp Hotel, Oak Bluffs - an upscale rustic hotel in the heart of Oak Bluffs overlooking the harbor. 

While it’s possible to explore the Island in a single day, we recommend staying at least a weekend to truly immerse yourself in everything Martha’s Vineyard has to offer.

Relaxing & Leisurely Activities for Retirees

For those seeking a slower pace, Martha’s Vineyard is a dream destination with plenty of opportunities to unwind, reflect, and soak in the Island’s beauty.

Take an Island Tour

A great way to get an overview of the Island’s history, culture, and stunning landscapes is by taking a guided Island tour. Some excellent tour companies include:

• HomeGrown Tours MV – A small, family-owned business offering private and customizable tours to ensure you see the best of Martha’s Vineyard at your own pace.
• Experience MV Tours – Known for its friendly and knowledgeable guides, this company provides scenic and historical tours tailored to visitor interests.
• Greetings from Martha's Vineyard Tours – Offers a mix of standard and custom tours, ensuring you get the perfect experience based on what you want to explore.
• The African-American Heritage Trail of MV - A self-guided journey through over 30 historic sites honoring the Island’s rich Black history

Indulge in a Spa Day

Nothing says relaxation like a massage or wellness treatment. The Island has several spas that offer services like:

• Reflexology
• Full-body massages
• Hot stone pedicures
• Acupuncture

Whether you choose to book a treatment at your hotel spa or visit a dedicated wellness center, you’ll leave feeling rejuvenated.

Some of the best spas on the Island include:

• Mansion House Spa

• Sea Spa Salon

• Revive by Sarka

Visit the Martha’s Vineyard Museum

The Martha's Vineyard Museum is a must-visit if you love history and culture. Located in Vineyard Haven, this museum offers a deep dive into the Island’s rich heritage, featuring exhibits on maritime history, indigenous Wampanoag culture, and the evolution of Vineyard life over the centuries.

The museum’s collection includes historic artifacts, artwork, and photographs that bring the Island’s past to life. Visitors can explore exhibits detailing the whaling industry, early colonial life, and famous residents who have left their mark on the Island. Interactive displays and rotating exhibits ensure there is always something new to discover, making it a great stop for history buffs.

Browse Local Bookstores

Book lovers will feel right at home on the Island. Spend time browsing Edgartown Books or Bunch of Grapes Bookstore in Vineyard Haven. Both offer a carefully curated selection of books, including works by local authors. Grab a new read, then head to a café or the beach for some peaceful reading time.

Explore the Island’s Farms and Farm Stands

Martha’s Vineyard has a rich agricultural scene, and exploring the Island’s local farms and farm stands is a fantastic way to experience fresh, locally grown produce and artisanal products. Some farms allow visitors to tour their grounds, meet the farmers, and even participate in seasonal activities like berry picking or pumpkin harvesting.

• Morning Glory Farm (Edgartown): This family–run farm is a must–visit. It offers fresh vegetables, baked goods, and local honey.
• The Grey Barn and Farm (Chilmark): This farm is a treat for food lovers, Known for its award-winning cheeses and organic produce.
• North Tabor Farm (Chilmark) – Offers fresh microgreens, vegetables, and farm-raised meats.
• Island Grown Initiative – A nonprofit organization that promotes sustainable farming and offers educational experiences for visitors.

Picking up fresh produce from these farms and enjoying a picnic by the beach is one of the simplest yet most rewarding experiences on Island.

Explore Art Galleries on Martha’s Vineyard

Martha’s Vineyard is home to a thriving art scene with several galleries showcasing local and regional talent. Here are a few not-to-miss spots:

• The Granary Gallery  (West Tisbury) – One of the Island’s oldest and most beloved galleries, featuring works by local and national artists.
• The Field Gallery (West Tisbury): This gallery, known for its whimsical sculptures and vibrant paintings, offers a unique, open-air experience.
• Old Sculpin Gallery/MVAA (Edgartown) – A historic gallery displaying works of local artists in various mediums, from paintings to photography.
• 51art Gallery (Vineyard Haven) - Newly located in the heart of Vineyard Haven, a wonderful gallery featuring local and national artists. 
• Miner Family Gallery (Vineyard Haven) - a year-round gallery known for painting, sculpture work and other various forms of contemporary art. 

These galleries offer a great way to immerse yourself in the creative spirit of Martha’s Vineyard and take home a piece of the Island’s artistic heritage.

Outdoor Adventures for Active Retirees

If you prefer a more active itinerary, Martha’s Vineyard offers plenty of outdoor adventures to keep you engaged.

Kayak with Island Spirit Kayak

Experience the beauty of Martha’s Vineyard from the water with Island Spirit Kayak. Whether you're a beginner or an experienced kayaker, this outfitter offers guided tours that include sunset paddles, moonlit tours, and even paddleboarding. Kayaking is a fantastic way to enjoy the Island’s natural surroundings while getting some gentle exercise in the process.

Golfing on Martha’s Vineyard

Golf enthusiasts will love the scenic and well-maintained courses available on Martha’s Vineyard. Whether you're looking for a casual round or a more challenging game, the Island has fantastic options:

• Farm Neck Golf Club (Oak Bluffs) – A beautiful semi-private course with stunning water views.
• Edgartown Golf Club (Edgartown) – A classic New England course known for its welcoming atmosphere.
• Mink Meadows Golf Club (Vineyard Haven) – A serene and picturesque course with rolling greens.

Walking Trails & Nature Preserves

For those who love exploring on foot, Martha’s Vineyard has miles of scenic walking trails and nature preserves. Felix Neck Wildlife Sanctuary, Menemsha Hills, and Long Point Wildlife Refuge offer breathtaking views and a chance to connect with the Island’s natural beauty.

Whether you're drawn to the Island’s peaceful charm or its natural beauty, Martha’s Vineyard offers something for every retiree looking to escape the hustle and bustle of everyday life. With its welcoming accommodations, rich history, and diverse array of activities, the Island is the perfect destination for relaxation or exploration. From leisurely spa days and scenic tours to outdoor adventures and cultural experiences, your time on Martha’s Vineyard will be a rejuvenating and unforgettable getaway. So, pack your bags, take the ferry, and let Martha’s Vineyard reveal its many treasures to you.