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Hidden out past quaint Five Islands Village, Hawksbill resort is seamlessly sprinkled over 37 acres of Caribbean gardens right on the water. Sure, Antigua is known for its 365 beaches so it shouldn’t be a surprise when a resort has more then one beach, but Hawksbill has, an impressive, four secluded strips of sugar-white sand easily accessible to guests with a fifth accessible to truly intrepid sun worshipers. Besides the sheer quantity, Hawksbill also sports a one-of-a-kind beach for Antigua. Beyond the southern point of the the 99 non-smoking guest rooms, down a little path, through a white fence, and around the bend is Eden Beach — Antigua’s one and only extremely concealed clothing-optional shore. It’s here, a matter of meters into the Caribbean Sea, that you’ll find majestic Hawksbill Rock (so named for its uncanny resemblance to a hawk’s profile) from which the property gets its name.

Islands of the Caribbean with historically strong ties to Great Britain aren’t exactly known for letting it all hang out but just to the south of Galley Bay Resort and Spa, is Antigua’s one-and-only clothing-optional stretch of sand: Eden Beach. Intrepid (or maybe a little fool-hardy) travelers can borrow bikes from Galley Bay to make the trip, but be warned: there are several steep hills standing between you and taking it all off, but, as I found out on my last visit, that just makes the payoff that much sweeter! The beach is much larger than you might expect with lots of private nooks. There’s even an exotic mini-islet within swimming distance from shore. The place is positively picturesque. But you’ll have to show some restraint. There’s a strict “no cameras allowed” policy out of respect for your fellow nude neighbors.

Tucked among the pristine rain forests of Kauai’s remote North Shore, Princeville Resort’s lush 9,000 acres feel like they’re straight out of South Pacific. In fact, the classic musical used neighboring Mount Makana as a stand-in for Bali Hai. The peak’s verdant slopes are visible from many of the property’s 251 rooms, which are clad in ocean- and floral-inspired hues and outfitted with custom wood furnishings and marble baths, but the real draws lie elsewhere on the property: in the private snorkeling beach and massive infinity pool overlooking the cerulean waters of Hanalei Bay, an 11,000-square-foot spa that specializes in traditional Hawaiian clay treatments, and a world-class golf course designed by Robert Trent Jones, Jr.

Too often us intrepid experiential travelers can get caught up in the whole effort of trying to do it all. “I must explore this off-the-map place!” “I have to try this exotic dish!” It’s easy to forget that sometimes the best way to get to know a place is to simply stroll aimlessly. Luckily, Barbados makes it an attractive prospect.

A few minutes north of Tulum, Xcacel (pronounced “ish-kah-sel”) is one of the region’s more unspoiled coastal areas. The beach has long been a local favorite, especially on Sundays, and in-the-know tourists are showing up now, too. Natural vegetation lines the shore and while there are no restaurants or beach clubs, there is a building with restrooms and showers. The best snorkeling is along the coral reef at the north end, and a small, swimmable cenote lies nearby. Sea turtles lay eggs here, in spring and summer, so take care not to trample nests; local conservation projects collect modest entrance fees to support their efforts.

One of three atolls in Belize, Lighthouse Reef Atoll is blessed with a handful of the most prized natural sights along the Belize Barrier Reef. The Great Blue Hole attracts divers eager to add a notch to their diving belt by exploring an underwater cavern more than 400 feet deep. On shore, Half Moon Caye Natural Monument, the country’s first protected site, is a turtle-nesting beach dotted with towering palm trees and no permanent inhabitants save for hermit crabs. Last but not least, you can view a thriving red-footed booby sanctuary, the only one in the Western Hemisphere aside from the Galápagos. It’s no wonder Lighthouse Reef is a popular day-tripper choice, whether you dive, snorkel, or simply love nature.

Le Chat has an awesome view, it’s just perfect to finish the day or to have a long lunch. You can enjoy the view over the 25th April Bridge and the Tagus River to the other shore and maybe you will see a cruise ship leaving Lisbon and heading towards the ocean. This glass cube of a joint—near the National Museum of Ancient Art—offers seats inside and outside on a terrace. Even in winter the terrace is appealing, with heat lamps and blankets provided. Rather than ordering a full meal, share some appetizers like sweet potato chips, sautéed shrimp, and a traditional Portuguese dish, Peixinhos da Horta (batter-fried green beans), while enjoying the fresh air and expansive views.

Sugar Ridge is much about the view. One of those rare Caribbean hotels that doesn’t sit at the edge of the sand, this boutique luxury resort, ranging up a hillside on Antigua’s west coast, not only overlooks palm-lined beaches and the marina at Jolly Harbour but also looks out across the greens and blues of the Caribbean toward St. Kitts, Nevis, and Redonda. The rooms, in clusters of four, two upstairs, two down, are Caribbean modern, with a focus on the four-poster, netting-draped, king-size beds. There are two restaurants, two pools, an Aveda Spa, and a fitness center so large it’s almost as if they were expecting a sports team to show up. And beach lovers fear not. A complimentary shuttle will have you down to the shore in minutes.

First built in 1967, the Surf Lodge has been a destination for surfers, artists, and musicians for decades. Today’s Surf Lodge has kept that bohemian spirit, creating a breezy boutique for savoring Montauk’s simple pleasures: sunsets, fishing, surfing, sunbathing, and music. Every summer season, live concerts attract music lovers. Hammocks on private balconies, cozy lounge furniture in the sand, and a spacious waterfront deck set the scene for relaxation. The Restaurant serves fresh seafood plucked from Montauk’s shores, while the bar serves healthy juices by day and potent cocktails by night. At the heart of the Montauk community, this local landmark is the perfect base for a trip to the serene sibling of the Hamptons.

Once summer has arrived in all her glory, city folk yearn to escape the concrete jungle. The cheap and chic solution for locals is to pack a picnic and head for a beach day on the Toronto Islands, just a short ferry ride away. Of the three primary islands, all of which are connected by paths and bridges, Centre Island boasts the highest number of visitors; people head straight to its main strip to get to the beach and the amusement park. Ward’s Island offers more charm: In addition to the sandy shore, there are small summer cottages and gardens. Those intent on exercise can rent bicycles or paddleboats.

About a 30-minute drive west of downtown Tampa, this popular beach on the Gulf of Mexico is built up with mid-range and luxury hotels, shops, and restaurants. But all that matters when you’re down on the shore is the sugar-fine sand and beautiful, crystal clear water for swimming. The Clearwater pier has really come into its own in recent years, drawing crowds by the hundreds for nightly sunset celebrations that attract buskers and vendors selling crafts. Visit the marina to book fishing trips or dolphin-spotting tours, or head out on a pirate ship into the bay for another way to enjoy the sunset.

Among vacationers who’ve been coming to Grand Cayman forever, there’s a whole faction that essentially camps out at Rum Point all day every day, and you’ll understand why as soon as you see the place. Tucked away, super low-key, and graced with a ridiculously photogenic pier—its perfectly weathered planks cutting a striking figure against the tranquil, turquoise surroundings—this beach is the ultimate spot for settling into a lounger or hammock between water-sports outings. Rum Point’s namesake booze—which used to wash ashore by the barrel, according to legend—is available in all manner of cocktails here, of course. But order at least one mudslide at its spiritual birthplace: the beach’s beloved Wreck Bar.

If you love art in all its many forms, the Museum of Fine Arts (MFA) in Boston is a ‘must-see’ destination. They have a great collection of Impressionism and Asian art works, from Monet and Van Gogh, to Chinese furniture and Japanese paintings, as well as the Egyptian collections. In addition, their newly opened west wing contains many stunning pieces of American art. Besides the arts, there is a cafe, a restaurant, gift shops of course, and a mini cinema for special shows. To get there: The MFA has its own subway stop called, what else, the MFA. If you drive, there are parking garage options as well. You can easily spend half a day here—or more!

The one-hour drive from Cabo San Lucas to Todos Santos is dotted with tempting detours. Chief among them is Playa Cerritos, one of the few Pacific-side beaches safe for swimming. Of course, it’s not the swimming conditions that attract legions of surfers each year, but the wonderful swells and breaks, which invariably make for an excellent outing on the waves. You can rent a board or sign up for lessons at Mario Surf School, and otherwise there’s plenty to support a day at the beach. Grab a bite at the Cerritos Beach Club, pick up a trinket or two from one of the local artisans, and treat yourself to a shoreline horseback ride or an oceanfront massage.

Situated off the eastern shore of Long Island, The Chequit is old school in an elegant way. The hotel occupies a big white building, surrounded by grassy lawns, impeccably maintained hedgerows, and towering deciduous trees, and features bright, homey rooms, complete with large windows that let in plenty of natural light. While all the rooms have been refurbished, those in the main house retain much of their original architecture, lending them a certain vintage charm. The Chequit operates on a bed-and-breakfast model, and guests can either take their morning meal in the lobby or opt to have a lighter option sent straight to their room. While the target audience here is weekenders seeking an escape from New York City, the hotel is also a popular spot for weddings and retreats, with two meeting rooms and full catering services available from on-site Red Maple Restaurant.