The serene and captivating island nestled seven miles off the coast of Massachusetts is famously known as Martha’s Vineyard. It beckons coastline-loving travelers seeking an indulgent and tranquil escape from the chaos of daily life and into luxury destinations. This picturesque haven is famed for its pristine beaches, rolling hills and charming buildings with preserved natural beauty. Martha’s Vineyard embraces diversity in people, art and experiences, and welcomes every traveler. Travelers can bask in the tranquil shorelines, delectable cuisine and the tapestry of culture, history and small-town luxury living.
Best time to travel: April to May and September to October (shoulder seasons), June to August (peak season)
Time zone: Eastern Standard Time (EST)
Noteworthy: Vineyard Artisans Festivals (year-round), African American Film Festival (August), Martha’s Vineyard Book Festival (August), Martha’s Vineyard International Film Festival (September), Martha’s Vineyard Food & Wine Festival (October)
Best for: Nature Enthusiasts, History Lovers, Art and Culture, Food & Wine Tour, Couples Trips
Play: Things To Do In Martha’s Vineyard
African American Heritage Trail of Martha’s Vineyard
The African American heritage trail is an enriching experience for those who want to explore the location’s profound stories. Through descriptive plaques in over 30 dedicated sites, this trail highlights the unrecognized contributions of African descendants. By supporting this excursion, travelers contribute to the research and dissemination of Martha’s Vineyard’s African American history.
This immersive journey is possible because of the collaboration between Carrie Camillo Tankardn and Elaine Cawley Weintraub. They recognize the importance of introducing this history to schools in the vineyard.
Venture Scavenger Hunt
Embark on the Venture Scavenger Hunt around the island for an unforgettable experience. It starts at a beloved local spot and ends with memories that’ll last a lifetime. This creative and nontraditional quest takes visitors on a journey through carefully curated locations in town. Guests can either walk or drive around town solving clues and doing wacky challenges. The hunt seamlessly transitions between indoor and outdoor settings.
Guests send photos to the remote host who will provide assistance along the way as needed. With 300 city hunts and custom-designed experiences available, this experience is perfect for everyone.
Caleen’s Day Spa
Caleen’s Day Spa is a Black women-owned center of relaxation. The day spa offers a wide range of services, including manicures, pedicures, waxing, massages, facial treatments and more. Every instrument that the staff uses is disinfected using hospital-grade procedures and individually packaged. That ensures the utmost health and hygiene standards.
This local salon takes pride in its selection of products that are locally made. These products include the salon’s soaks, scrubs, oils and butters. They also use Zoya Nail Lacquers, which is a salon-quality polish line free from harmful chemicals.
Martha’s Vineyard Playhouse
For the traveler that needs a theatrical experience on the itinerary, the Martha’s Vineyard Playhouse is worth a visit. Located in downtown Vineyard Haven, the theatre opened in 1833. With year-round operations, visitors can enjoy a diverse selection of contemporary and classic plays.
The Playhouse takes a strong stance against racism and discrimination. It commits to diversity, equity, inclusion and social justice by supporting local artists from marginalized groups. Every visit contributes to their vision of expanding the campus. They want to provide housing for actors and create vibrant indoor/outdoor spaces for workshops, rehearsals and children’s programs. Donations help secure the theater’s operations through endowment and ensure a lasting legacy of artistic excellence.
Gourmet: Best Restaurants in Martha’s Vineyard
Winston’s Kitchen embodies the passion and expertise of a husband and wife team. Located in the Oak Bluffs area, Winston and Lisa Christie run this Black-owned restaurant with over 30 years of experience. They are committed to serving generous portions of homestyle food with the freshest ingredients at an affordable price. From breakfast sandwiches to vegan options, their menu changes daily and has a diverse range of delicious dishes. Some of the dishes include Winston’s Jamaican specialties, like jerk chicken and curry chicken.
Biscuits is a Black family-owned restaurant that has served customers memorable breakfast and lunch menu items for over 20 years. The menu showcases the finest seasonal ingredients, which creates simple and satisfying dishes for everyone. From classic favorites to unique creations, everyone will leave happy and full.
The Waterside Market in Vineyard Haven is a market and café that serves breakfast, salads and chef-created sandwiches. The market has a long-standing reputation. It is a delightful community hub where people gather for freshly made food, fantastic views and a welcoming ambiance.
The passionate individuals who run Waterside Market don’t only love the market itself. They also are happy and eager to help visitors enjoy the island gem they get to call home. This market also has convenient online ordering and curbside pickup. It is the perfect stop to grab good food to go on a busy day of beach fun.
Soul of Sonoma
Soul of Sonoma is a Black-women-owned food and wine hotspot. Founded by a family of Black bi-coastal wine lovers, the restaurant offers curated wine pairings, chef-inspired menus and picturesque views. Traveling wine enthusiasts will be delighted to sample wines from award-winning black- and women-owned wineries. They will also have the opportunity to dine al fresco in the lush English Garden.
To add to the charm, the restaurant owners host an annual Wine Festival. They provide an intimate and luxurious picnic-style wine-tasting experience. The family aims to create awareness around premium black-owned wineries.
Vineyard Caribbean Cuisine
Vineyard Caribbean Cuisine is a Black-owned takeout restaurant that prides itself on serving Jamaican dishes. Executive Chef Newton Waite hails from Jamaica and brings his roots, expertise and passion to every plate. With over 27 years of experience, Waite cultivated a menu of delicious Jamaican classics and tantalizing appetizers. To complete the savory meal, indulge in something sweet, like the vanilla rum cake or the fruit cake.
This island-themed modern eatery is the perfect spot to grab a refreshing smoothie or light lunch during the day. Lilikoi Cafe is a vibrant cafe that stands out for its high-end single-origin coffee and espresso. Their full service Poke Bar offers a variety of fresh seafood proteins for customizable island-inspired lunchtime bowls. The Acai and Smoothie Bar serves fruity refreshments with tropical toppings that complement the tropical ambiance.
Stay: Best Places to Stay In Martha’s Vineyard
Oaks Bluff Inn
The views from the Oaks Bluff Inn are captivating and the historical significance is fascinating. This Black-owned establishment seamlessly blends classic Victorian elegance with a refreshing modern coastal charm. It is located near the town center, Circuit Avenue’s renowned restaurants, The Harbor and the beautiful beaches.
The beautiful rooms and Erik’s famous breakfast heightens the allure of Oaks Bluff Inn. It is a local gem that has been visited by cultural icons, such as Spike Lee, Wynton Marsalis, Woody Harrelson and more.
Inkwell Beach House
The black-owned Inkwell Beach House has 150-year-old Victorian rooms. Each room exudes a distinct and whimsical character that complements Oak Bluffs’ unique vineyard cottage chic vibe. This 12-room guest house offers a variety of accommodations.
Every space boasts its own en-suite bathroom for comfort and convenience. The rooms are spread across the first, second and third floors. To start the day right, the hosts serve a complimentary continental breakfast. The breakfast includes freshly baked pastries, cereal and a variety of hot drinks.
Dog-friendly Studio Close to Beach
For travelers seeking a delightful beach getaway with their pup, this dog-friendly studio is close to the beach. Nestled within the charming Island Inn community, this cozy condo offers a range of amenities. It has easy access to the beach, tennis courts and a refreshing shared pool.
This stay provides all the comforts of home, such as WiFi, cable TV, a well-equipped kitchenette and ample parking space. With dog-friendly accommodations, this studio will make for a memorable and fun vacation for two.
The Inn at Shearer Cottage
The Inn at Shearer Cottage has been a historic Martha’s Vineyard institution for over a century. This black-owned establishment modernized its facilities, breathing new life into its outdoor landscapes. The landscapes cater to various special occasions.
With the renovations complete, the inn is reopening this summer, which offers guests a refreshed and expanded experience. The Inn at Shearer Cottage is perfect for enjoying rich history, modern amenities and beautiful surroundings.
Get Away: Getting To and Around Martha’s Vineyard
Since many high-profile visitors enjoy a private vacation at the island, the area has its own airport: Martha’s Vineyard Airport. There are direct flights to the airport for those flying out of certain cities. Some of those cities include Boston, New York City, New Jersey and Nantucket.
For those living in cities where no direct flight is available, there is an option to take a connecting flight from a nearby airport in Massachusetts.
Because you can’t drive directly to the island, travelers can drive a car by ferry services. The most common departure points that offer ferry service to Martha’s Vineyard are Woods Hole, Falmouth or Hyannis.
It’s best to make a reservation to transfer from car to ferry, especially during peak travel seasons or weekends. The ferry ride to Martha’s Vineyard usually takes about an hour, depending on the departure point.
By Public Transit
There is public transit available to help visitors get around the island. The Vineyard Transit Authority operates a network of buses that serve various towns and destinations on Martha’s Vineyard. The public transit system offers different routes and services, including fixed-route buses, shuttle buses and paratransit services. The public transit system is an affordable and convenient way for travelers to explore the area and reach anything on their itinerary.
Explore Martha’s Vineyard on Foot
Martha’s Vineyard is best explored with a planned route and a map or guidebook. Travelers can start in Vineyard Haven or Oak Bluffs to enjoy the coastal views. They also can visit the Martha’s Vineyard Camp Meeting Association for its gingerbread cottages or can walk down the charming streets of Edgartown and Aquinnah. In those charming streets, visitor will find local gems for dining, shopping and relaxing.