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My best friend from college grew up spending her summers on Martha’s Vineyard with her father, relishing in lobster rolls and clambakes, and watching everyone from celebrities to salty New Englanders merely relax. To honor her father’s memory, we rented a house and vacationed on this woodsy, 23-mile stretch of isle each summer that’s home to the communities of Edgartown, Chappaquiddick, Katama, West Tisbury, Oak Bluffs, Vineyard Haven, Chilmark, Menemsha, and Aquinnah. We prefer to fly direct to Boston or Providence and hop over to the island via a short, low-flying trip on Cape Air, versus a choppy ride on the ferry boats. Tear this out for your next trip:

Stay
Harbor View Hotel & Resort: Views of a lighthouse and a wraparound porch (complete with rocking chairs) make for a perfect summer respite. The NYC-based design firm Hart|Howerton is presiding over a six-year hotel renovation, with beachy decor in place and guest cottages to come.131 N. Water St., Edgartown, 508.627.7000; harbor-view.com.
Winnetu Oceanside Resort: Eleven acres house studio rooms, suites and private cottages on Edgartown’s South Beach. Tennis, basketball, putting greens and heated pools cater to the more adventurous type. 31 Dunes Road, Edgartown, 508.310.1733; winnetu.com.
Harborside Realty: If you’re looking for more privacy, scour Harborside Realty’s enormous rental-home database for the perfect dwelling, and remember to seek out private beach access. 256 Edgartown Road, Edgartown, 800.537.3721; harborsiderealtymv.com.

Dine
Atria: Chef Christian Thornton fills his menu with locally grown fare, such as poached island lobster with mascarpone gnocchi and seared foie gras, at one of the finest dining establishments on the island. 137 Main St., Edgartown, 508.627.5850; atriamv.com.
Larsen's Fish Market: The Larsen family has steamed lobsters to order, serving them with oysters, steamers, littlenecks clams, mussels and chowder since 1969. Place a to-go dinner order for sunset-watching at Menemsha beach. 56 Basin Road, Menemsha, 508.645.2680.
The Black Dog Tavern: Famous for its iconic T-shirts, but even more famous for its Sunday brunch — I can’t leave the island without delving into a Scooby Snack of English muffins, sliced tomatoes, poached eggs and white cheddar. 21 Beach St., Vineyard Haven, 508.693.9223; theblackdog.com.
PJ’s Café and Catering: It took us four years to discover PJ’s, a hush-hush favorite for gourmet sandwiches. While not the most attractive shop, it’s packed with locals and provides a nice break from our daily $50-per-person lunch tab. Order the Scissor. 258 Upper Main St., Edgartown, 508.627.4558.

Shop
Midnight Farm: A mishmash of all things delightful for your home, closet and body. Find everything from bedding from India to vermeil cuffs by Chan Luu and CDs by Carly Simon (she’s an owner). 18 Water-Cromwell Lane, Vineyard Haven, 508.693.1997; midnightfarm.net.
Katydid: The best selection of Roberta Roller Rabbit beach tunics, sarongs and blankets on the island. 38 Main St., Edgartown, 508.627.1232.
The Field Gallery: Three galleries of contemporary art plus a sculpture garden, photography and jewelry by local and national artists. 1050 State Road, West Tisbury, 508.693.5595; fieldgallery.com.

Don’t Miss
Renting a Bike: Book a hybrid bicycle weeks in advance of your trip — you’ll be surprised how much of your vacation will be spent behind handlebars. Edgartown Bike Rentals, 1 Main St., Edgartown, 800.627.2763; edgartownbikerentals.com.
Biplane Flights at Katama Airfield: Strap on a leather flight cap and goggles, and climb into daredevil pilot Mike Creato’s vintage biplane. Take off on a grass runway, fly over Meg Ryan’s estate and happily scream over his aviation tricks — think barrel rolls and flips over the ocean — if you pay extra for those. We always do. Katama Airfield, Edgartown, 508.627.7677; biplanemv.com.