The moment the ferry pulls away from the harbor in Woods Hole, I release the breath I haven’t realized I’ve been holding. That’s the effect Martha’s Vineyard has on me. It’s a small thing, but it’s the signal that I’ll be on the island soon, a world away from the stress-filled streets of Boston, where I live and work.

I’ve been going to Martha’s Vineyard for 20-plus years, first as a young tourist on the back of a moped (the one and only time doing that), later spending summer vacations there with my family and introducing my daughter to the joys of swimming in the ocean, and then finally discovering the secret pleasures of visiting in the off-season, now my favorite time to go.

The Vineyard, which is seven miles off the Cape’s coast and encompasses about 100 square miles, is made up of six different towns, each quite distinct from the other, each with its own compelling charms.

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Girls playing on Fuller Beach

When the ferry arrives, you’ll either be in Oak Bluffs, the island’s main tourist hub, or in Vineyard Haven, home to the island’s year-round ferry port. Edgartown is famous for its historic 18th-century whaling captains’ houses. Further afield are the towns of Aquinnah, with its picture-perfect clay cliffs and the Gay Head Lighthouse, Chilmark, made up of quiet fishing villages and my favorite lobster roll in the world, and, West Tisbury with its acres of rolling farmland.

A three-car ferry can also quickly zip you over to the island of Chappaquiddick, located just 527 feet off the Vineyard’s eastern coast, where you’ll encounter awesome birdwatching and secluded beaches.

Since my day job involves a lot of traveling, which takes me to unfamiliar places on a regular basis, when I’m enjoying time off I revel in familiar and cherished spots, to the point of being upset with menu updates at a longtime favorite restaurant—unreasonable, I know! But, most of the island’s charms remain unchanging, hopefully for years to come.

Since my day job involves a lot of traveling, which takes me to unfamiliar places on a regular basis, when I’m enjoying time off I revel in familiar and cherished spots.

A hike through the Mass Audubon Felix Neck Wildlife Sanctuary is always a delight. I’ll always root for one lucky child to grab the brass ring at the Flying Horses Carousel in Oak Bluffs. I will forever find the Mytoi Japanese Garden on Chappaquiddick a relaxing place to wander through. And the challenging waves at South Beach are always a thrill.

For me, food is an integral part of any trip and a single dish can evoke a cherished moment in time as easily as a photograph. While restaurants and bars certainly do come and go on the island—it’s a tough business, after all—there are a few that have managed to stick around since I’ve been visiting.

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Menemsha at sunset

The Black Dog Tavern is an institution. On a cold winter’s day, there’s nothing better than sitting by the fire with a bowl of chowder and a beer. The Newes From America Pub, also open year-round, is another island mainstay; its cozy pub vibe feels like a warm embrace.

Other favorites include Giordano’s, where the cheesy garlic bread is to die for, Offshore Ale Co., where the potato pizza is a revelation, and for sheer fun, Sharky’s Cantina, please order the Escorpion Bowl for two to go with its Mexican comfort food.

Finally, you must try the best, and my favorite, lobster roll in the world, at Larsen’s Fish Market in Chilmark. They pick the lobster in front of you, pile it onto a hot dog bun and slather it with hot butter.

This is what memories are made of.

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Gliding across Casco Bay