Apr 01, 2019

As savvy gay travelers know, it’s never too early to start planning your summer gaycation. This year, skip hectic big cities and head to New England's dreamiest small towns, some of which boast oceanfront downtown districts or stunning mountain views. We’ve got our favorites picked out, along with details on where to eat, what to do, and which gay-friendly hotels should be on your list.

Nantucket, Massachusetts

When summertime rolls around, there’s nothing like escaping the daily grind and heading to a tiny island lined with sandy beaches. In this case, we don’t mean those found in Hawaii or the Caribbean—why venture so far away when New England has a pristine, super-chic option in the Atlantic between Boston and New York?

Nantucket’s irresistible charm and glorious summer weather are two major draws to this remote island retreat, but there’s also the fact that it’s easy to get around without a car. Since the only way to reach Nantucket is by ferry or plane, most visitors don’t bother with vehicles (aside from the occasional moped). If you're lucky enough to travel with someone who is game to pedal along with you, why not explore the island in the most quintessential summer dream way and rent a bicycle built for two?

If it is your first visit to the Faraway Isle, we suggest strolling the delightful cobblestone streets lined with whaling captain's homes and buildings dating as far back as the late 17th century. For you history buffs, put the Whaling Museum on your bucket list and be sure to climb to the top of the circular stairs. From this vantage point, the world is your oyster! You'll also have a bird's-eye view of the exquisite town below along with its unique, locally owned shops, resplendent art galleries, and lively bistros. One of Natucket's unique virtues is that they do not allow corporate chains on the island, making for interesting and authentic retail and hospitality options.

Photo Credit: Bobak Ha'Eri - Wikimedia Commons

To fully experience Nantucket's magic, we recommend staying at 21 Broad, located right in the heart of the downtown village. 21 Broad boasts a superb combo of historic authenticity with contemporary chic. Each morning, indulge in a thoughtfully curated small-plate breakfast and assorted bites to sample. Now you are nourished and ready to tour the rest of the island, where you will find hidden treasures everywhere, including the Old Mill windmill, the cranberry bogs, and the Brant Point Lighthouse. At the end of your day, wind down in the impeccably designed lounge of 21 Broad where you can listen to music on the turntable (vinyl, of course - we told you 21 Broad was authentic and chic)! Next, take a private Vitamin C shower for the smoothest skin you'll ever have and tuck yourself into your luxurious, comfy bed. Sweet New England Summer Dreams!

Nantucket Gay Travel Tips from Our Friends at 21 Broad

Perfect hangouts for gay weekend getaways:

“Sip hand-crafted beers at Cisco Brewery or sample fare from our local food trucks. Enjoy live music at the Chicken Box, and be sure to hit Jetties Beach and its lively Sand Bar restaurant, where you can watch boats coming into harbor. For amazing sushi, we recommend Lola 41.”

Top choice for a mouthwatering meal:

“The Proprietors Table offers sharable seasonal dishes so you can sample lots of different items on the menu.”

Best bar for socializing on gay-friendly vacations:

“Club Car has amazing cocktails and an extensive bourbon and whiskey collection. There’s a piano in the corner of the bar and with everyone singing along, it's a great time.”

Read our full gay travel guide to Nantucket and see more LGBT travel tips from our friends at 21 Broad.