Year-round neighborhood hangouts hold an invaluable place; they keep many of us sane and slaked throughout the coldest months. But sometimes it’s nice to go where not everybody knows your name and kick back in a classy joint with a glass of wine or a favorite drink. Here are five places on Martha’s Vineyard where you can do that. They trend toward expensive and outdoors, so let’s raise a glass to getting what you pay for and enjoying the fresh air while you still can. But don’t delay; many of them close for the season by the end of October.

20byNine (Oak Bluffs)

If whiskey and people watching are your things, this is your place. It’s named for the dimensions of the Island in nautical miles and boasts a great – but small – outdoor patio that overlooks Kennebec Avenue. Noteworthy details include homemade syrups and monster ice cubes that don’t water down your drink. Plus, there’s a great selection of gourmet small plates. If you just hit the lottery and want to celebrate with the rarest commercially available bourbon, try a shot of Pappy Van Winkle’s Family Reserve 23-Year. It’ll only set you back the first $275 of that lottery check.

16 Kennebec Avenue, 508-338-2065,

Détente (Edgartown)

Weave your way through Nevin Square in Edgartown and you will find this cozy restaurant with a small front bar that is a perfect spot to make peace and relax. The superb staff seems to blend into the background until just the moment they are needed. The bar menu, like the restaurant, features lots of local fish and produce. There is also a variety of cheeses from around the world.

15 Winter Street, 508-627-8810,

l’étoile (Edgartown)

The cozy little back bar at l’étoile is one of the nicest spaces on the Island to enjoy a fine cocktail. Personally, I think the best way to ruin good gin is to throw salty olives in it, but I make an exception for the Bleu Sapphire Martini, which comes with big fat olives stuffed with creamy bleu cheese. The signature drink, called a Startini, has citrus vodka, Cointreau, lime juice, pomegranate purée, and a Prosecco floater. A fantastic bar menu and snack mix are a big plus.

22 North Water Street, 508-627-5187,

Outermost Inn (Aquinnah)

If a spectacular sunset is on your to-do list, consider skipping the Menemsha mayhem and heading instead to the Backyard Bar. Sit at the rustic bar, porch tables, or lawn recliners and take in the view of the rolling hills and Vineyard Sound. It’s as reminiscent of Tuscany as it is Martha’s Vineyard. The setting screams for a bottle of wine, and the establishment has an extensive collection by the bottle and by the glass. Most nights it’s only open to those with a dinner reservation, so call ahead to inquire about availability.

81 Lighthouse Road, 508-645-3511,

The Sweet Life (Oak Bluffs)

The tiny bar at the back of the Sweet Life patio is a lively mix of interesting visitors and in-the-know locals. Bartenders are pros and will often come up with a special craft cocktail, which is usually a hit. A former bartender became a friend for life when he garnished my Hendrick’s martini with a fresh slice of cucumber. Hendrick’s Gin fans will know what I mean. The bar menu is outstanding.

63 Circuit Avenue, 508-696-0200,