"There once was a man from Nantucket" begins many a story. Call me Ishmael begins another. How will yours begin? We suggest drinks with your toes in the sand.

Put 'Em Back

The Gazebo

4 Harbor Square

Nantucket, MA 02554

The island’s unofficial meeting spot, perfect for relaxing in the breeze, day or night. Cocktails on the rocks or from the blender, featuring Gosling’s rum and the flavors of the coast. If you need to get your sugar and caffeine on, order a thick glass of their famous Mudslide.

Cisco Brewers

5 Bartlett Farm Rd

Nantucket, MA

You won’t go thirsty at the “coolest place on Planet Earth” a tri-fectanity of micro-brewing, winemaking, and artisinal vodka distilling. Tour the grounds and workshops, then hit the pub for local suds, better-than-typical food, and live music. If we need to keep listing things, you’re reading the wrong guide. Bring home a bottle or case of something you won’t find anywhere else.

The Chicken Box

16 Dave St

Nantucket, MA 02584

“There was a fine, boisterous something about everything connected with that famous old island,” said Ishmael. Especially The Chicken Box—THE spot for live music. And debauchery, rowdy crowds, spilled drinks, and ringing ears. Rally the crew early—the line gets longer than The Man From Nantucket. Or come in the off-season if relaxing is more your style.

Good Eats

The Downyflake

18 Sparks Ave

Nantucket, MA 02554

World-famous doughnuts. ‘Nuf said. The End.

Black-Eyed Susan’s

10 India St

Nantucket, MA 02554

Some say no one goes here anymore on account of the crowds. But we know the brunch is worth it. Good for cooler mornings (there’s a big griddle but no AC). Priceless when you need something buttery to melt a hangover.

Nantucket Lobster Trap

23 Washington St

Nantucket, MA 0255

The archetypal shack. Serving bugs in a variety of sizes and styles. Buck-a-shuck at the raw bar can be deadly...set a limit and stick to it. Service is hit or miss but the lobsters are the island’s best. Wash it all down with an Elbow Bender.

Provisions

3 Harbor Square

Nantucket, MA 02554

Gourmet sandwiches. You’ll have to cross an ocean channel for anything half as good. Be ready to wait if it’s close to Ferry departure time.

Good Times

Shark fishing with the island celebrity ACK SHARKS

For reals, this guy reels 'em in right off the beach. Sign a waiver, and we'll put you in touch.

Nobadeer Beach

The party beach. Rough surf, bad parking, good people, great times. Would easily win a bid to host the next Lawn Games Olympics.

Young’s Bicycle Shop

6 Broad St

Nantucket, MA 02554

Rents bikes. The best way to see the island. Also rents Jeeps—the other best way.

The Whaling Museum

13 Broad St

Nantucket, MA 02554

Once upon a time, being a nation of blubber meant something more adventurous. Revisit the days of the Pequod in this time capsule of whale bones, whalers, and whalecraft. The Island’s history in salt and blood.

did we miss anything? Hit us up in the comments....