A great way to explore the islands and waters surrounding Martha’s Vineyard is to reserve a boat and captain for a day charter. Anything from a sunset cruise aboard a luxurious catamaran to a private party on a traditional schooner can be arranged. Indagare members can contact our Bookings Team for details.

Owned by Susan Chapman, this small beauty haven, on the second floor of a Victorian house in Edgartown, is a favorite pampering spot. Be sure to make a reservation—even manicures are rarely available on a walk-in basis.

This trusted rental store carries standard bikes as well as high-end specialty models. If you’re visiting during the summer, call ahead to make sure they have your kind and size in stock.

Indagare Tip: Request a bike with a basket, so you can easily store picnic food and lots of water during your excursions.

This Mass Audubon nature preserve organizes a slew of special programs perfect for children. The property boasts two miles of hiking trails through wood- and marshlands. If you’re lucky, you can even spot nesting ospreys, the island’s most magnificent birds.

The large white resin figurine sculptures of Tom Maley greet visitors in the sprawling garden that surrounds this lovely contemporary art gallery, which opened its doors in 1971. Exhibits change frequently, but look for the work of local photographer Jhenn Watts, who prints her vibrant seascapes on glass.

There is great fishing off the coast of Martha’s Vineyard. Contact our Bookings Team to be set up with a great charter captain who always seems to know where to find the best fishing.

Martha’s Vineyard’s most famous attraction, albeit kitschy, is a guaranteed home run with children. The country’s oldest carousel in use, Flying Horses is packed with tourists during the summer months. Snag the lauded brass ring and you’ll be allowed to stay on for an additional ride.

Originally a Methodist meeting ground, this gathering of pastel-colored cottages could accurately be described as a real life Candyland. Built in the “Carpenter’s Gothic” style, the gingerbread cottages are painted in hues ranging the full color spectrum, and feature unique embellishments. The cottages are now a protected historic landmark and some of the most expensive housing on the island.

You can’t miss the sister property of the Field Gallery, housed in a bright red barn off Old County Road. More than fifty artists are represented, including painters, photographers, jewelers and sculptors, so there’s a lot to see.

Housed in a quaint red barn, the Granary Gallery is the island's oldest and largest gallery. The indoor galleries, sculpture garden and courtyard boast a variety of paintings, antiques, sculptures and photographs by both national and local artists.

For active types who want a one-off aquatic adventure, Indagare can organize custom kayak tours, including sunset and full moon excursions. Members can contact our Bookings Team for details.

What started as a grass-roots film series in 2000 (screenings took place in West Tisbury’s Old Agricultural Hall) has evolved into a respected independent festival known for showing socially conscious films and documentaries. There’s also a special children’s film series. Between the children’s and grown-up films, such food as curry made with local produce, salads and sandwiches are available.

Held every other summer, the Martha’s Vineyard Book Festival is a joyous celebration of literary talent. Proceeds from this can’t-miss book festival go toward local charities. Past attendees include Lucinda Franks, Charlayne Hunter-Gault, Alan Dershowitz and Vineyard-based painter Allen Whiting.

The Vineyard institution puts on a number of cutting-edge and family-friendly plays year-round. Past years have included titles such as the Tony Award-winning play Copenhagen and Alexandre Dumas’ Three Musketeers, and their “Shakespeare for the Masses” program makes the classics fun for all ages.

The last thing you would expect at the eastern end of Chappaquiddick Island is a serene Japanese-inspired garden, but that is exactly what Mary Wakeman set out to create in the 1950s on fourteen acres near Dike Bridge. Her garden, now managed by the Trustee of Reservations, is an exquisite oasis with an iris pond and small paths that snake through a birch alley and rock garden, passing camellias, azaleas, bamboo and dwarf Japanese maple.

Indagare Tip: Mytoi is an easy fifteen-minute bike ride from the Chappy ferry dock. After you spend time in the garden, bike on to East Beach, which is open to the public.

Martha’s Vineyard’s southern shore is among the longest uninterrupted stretch of beaches north of Florida. Not all of them are open to the public, since Massachusetts is the one of only two states that allow private beaches (the other is Hawaii). Parking is always an issue during high season, so consider taking one of the shuttles offered by most hotels or the island bus service that runs often.

Some of the best public beaches on the island include Joseph A. Sylvia State Beach, which draws families thanks to its convenient location between Oak Bluffs and Edgartown and its gentle surf. South Beach, an expansive beach near the Winnetu Oceanside Resort, has a stronger surf. Those who want to escape the crowds and don’t mind a bit of a hike to get there will enjoy Long Point Beach, part of the Long Point Wildlife Refuge, which also has freshwater and saltwater ponds for more gentle swimming. Another good one that’s not too crowded is East Beach, near the Mytoi garden in Chappaquiddick.

Among the most desirable private enclaves—open only to residents, their guests and visitors booked at select hotels are: Lucy Vincent Beach in Chilmark; Lambert’s Cove in West Tisbury; and Squibnocket in Chilmark. They are only restricted until 4 p.m., so sunset picnics are an option for nonresidents as well.

Revered Vineyard native and self-taught horticulturalist Polly Hill, who passed away in 2007 at the age of 100, spent decades cultivating the multitude of plants at this arboretum. Splendid in every season, it’s particularly beautiful when the Japanese and Chinese dogwoods are in bloom (usually mid-June through July). Don’t miss Polly’s Play Pen, a fenced-off path where rare species like North Tisbury azaleas and Himalayan Daphne genkwa are found.

Indagare Tip: If you bring kids, be sure to pick up a copy of the “Polly Hill & Her Land: A Quest” brochure at the entrance; a treasure hunt in the form of a poem, it allows children to discover the arboretum.

The day spa on the ground floor of this Vineyard Haven hotel offers a number of treatments including facials, massages and body wraps (one using local Moshup mud). While the spa is not particularly luxurious, the treatments are highly recommended.