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Comprised of just 10 suites with distinctly different designs, Palácio Belmonte feels more like a dream vacation home than a hotel. The vibe is spot on, given the backstory: A Frenchman traveled to Lisbon looking for a vacation home in the Portuguese capital. He first saw the building from a taxi and thought to himself, “It has nine windows, just like my home in France. I’ll buy it.” It wasn’t until after purchasing the property that he actually set foot inside and saw just how enormous it was—far too large for him and his family. Thus, he set about remodeling the building (which was originally owned by a noble family in the 1400s) with the notion of converting it into a space for visitors.

Though there are plenty of surf shops to be found around Laguna and Dana Point, none is more important to the community than Hobie. Way back in 1950, Hobie Alter started shaping surfboards in his family’s Laguna Beach summer home. In 1954, he opened Southern California’s first surf shop in Dana Point, where his brand became synonymous with innovation and craftsmanship. Some 70 years later, his surfboards remain a favorite of top athletes like Phil Edwards, Joey Cabell, and Corky Carroll and continue to inspire surfers all over the world. Stop into the shop, which now stands just two blocks from the original location, to pick up a board of your own, plus apparel, accessories, and everything else you need for hanging ten.

With a nickname like the “Cave State,” Missouri certainly isn’t short on impressive caverns. Of the more than 6,000 across the state, however, Meramac Caverns is the largest—and stays open year-round for tours. Said to have been a hideout for the outlaw Jesse James in the 1870s, the seven-level, 4.6-mile-long natural wonder was purchased by Lester Dill in 1933 and opened as a tourist attraction in 1935. Today, visitors can take guided tram tours past the cave’s complex mineral formations, stopping at a “wine room” (named for its grape-like botryoids and accessed by a long stairwell). While exploring, keep your eyes peeled for the resident tricolored bats that call Meramac home.

Nestled on the beach in the small town of Savaneta, Aruba Ocean Villas is home to the island’s only over-water bungalows, the most camera-ready of which is the Isla Alistaire. A favorite of Instagram influencers, it offers gorgeous sunset views and a hammock strung over a cut-out in the broad wooden deck so guests can sway over the water. Should you not have the budget for an over-water room, there are also a variety of waterfront and bungalow-style accommodations available, some with direct access to the sand. Additional amenities at the hotel include a popular seafood restaurant, spa services, and complimentary use of watersports equipment like snorkels and paddleboards. If you’re staying for more than three nights, be sure to ask the concierge for a private photographic island tour.

Located just a few minutes’ stroll from the Rialto Bridge, Al Volto is Venice’s oldest wine bar and home to an impressive 1,000-bottle collection. The list includes Italian and international wines, but not all are offered at the same time—the wine list rotates daily. If you aren’t sure what to order, the staff is very knowledgable. Beyond the attraction of the wine, the atmosphere is jovial and the vibe is cozy with wood-paneled walls and every bit of the ceiling plastered with wine labels. If you’re hungry, the adjoining restaurant cooks up delicious traditional Venetian lagoon fare. The homemade pastas are excellent—keep it simple and try the spaghetti with clams and olive oil.

A UNESCO World Heritage site, this hotel was the home of Hispaniola’s first governor, Nicolás de Ovando, and one of the first colonial structures built at the top of cobbled Calle Las Damas (the first paved street in the Americas). Built in 1502 and connected in 1974 during a reconstruction ordered by then President Joaquín Balaguer, the three stone buildings retain their original coffered ceilings, massive arches, tile floors, and brick and stone walls. In addition to 92 rooms and suites, including a dozen Imperial Club rooms overlooking the Ozama River and Don Diego Harbor (Room 4015 has a particularly stunning view and gorgeous bathroom), you’ll find a lovely reading nook, gourmet restaurant, lobby mojito bar, and tranquil garden, which features herbs and fruit trees used by the hotel kitchen.

The mother church of the Diocese of the Windward Islands, St. George’s Cathedral (also known as Kingstown Anglican Church) was built in 1820 on the site of an earlier church that was destroyed by a hurricane in the late 1700s. It’s the biggest church on the island and features a number of unique adornments, from a gilded wood chandelier to a brass lectern and a circular mahogany pulpit. It’s also home to a stained-glass window gifted by Queen Victoria. As the story goes, the queen initially commissioned the window for St. Paul’s Cathedral in honor of her first grandson but was horrified by the angel’s red robe and immediately sent the window abroad to St. Vincent.

Sunny as it is, Cabo has never been known for its beaches because of its rough surf. Not so at adults-only ME, however, which sits on the area’s only swimmable stretch of shoreline, in view of the famous El Arco rock formation. While the 162 rooms are the picture of tranquility (deep soaking tubs, private balconies), the hotel itself boasts a party atmosphere—a house DJ spins by the pool, and bottle service is available in the cabanas on the pool terrace. Thankfully, there’s also a spa specializing in traditional Aztec and Mayan-inspired treatments (don’t miss the temazcal cleansing ritual), so you can rejuvenate before returning home.

An Aboriginal territory turned shipping port between the Rocks district and King Street Wharf has been transformed into a harborfront reserve, modeled after what the headland may have looked like before Europeans arrived. It’s a great area for a walk or a picnic as well as for special events. And the surrounding area is home to dozens of new bars and restaurants. The seafood-centric Cirrus is run by the award-winning Bentley Restaurant team, and 12-Micron celebrates Australian produce through a menu organized around the elements. Early birds flock to cult favorites Micro by Coffee Alchemy and Bourke Street Bakery, while the after-work crowd unwinds at Sydney’s first vermouth bar, Banksii; the tropical rooftop Untied; and Smoke bar, on the top level of Barangaroo House.

Surprisingly, great cocktails and an ocean breeze can be hard to find in San Diego, which makes JRDN at the Tower23 Hotel somewhat of an anomaly. It may be a scene—there are bouncers at the door, and the 70-foot-long wave wall would be more at home in Miami—but the wind-protected patio is practically on the boardwalk, offering great views of Crystal Pier and surfers catching waves. On warm evenings, drinks like the cava-based Raspberry Sparkler and the spicy chili-mango margarita make the experience even sweeter. JRDN’s happy hour (Mondays–Fridays, 4 p.m.–6 p.m.) offers discounted beer, wine and sake and coincides with the sunset for much of the year, making it a prime time to score a seat outside.

Situated in three high-rise towers on the Golden Mile along Eagle Beach, the Blue Aruba complex is home to luxury condominiums as well as a full-service resort. Expect enormous windows with stunning ocean views and modern furnishings in apartment-style configurations that top out at more than 2,000 square feet; most come with fully equipped kitchens, and ground-floor residences have private patios and Jacuzzis. All the resort touches are here, including private beach facilities, two infinity pools, a spa and fitness center, and even a high-end restaurant that offers eight-course dinners. But golf lovers have an excellent reason to venture off-resort: The nearby Tierra del Sol Resort combines tee times on an 18-hole championship golf course designed by Robert Trent Jones II with sublime seaside panoramas.

Changuu Island, also known as Prison Island, is about a 30-minute boat ride from Stone Town. The water around the island is crystal-clear and cerulean blue, which makes snorkeling here hard to resist, but a visit also lets you gain an understanding of a grim period of Zanzibar history. In 1860, the small island was used as a prison for disobedient slaves. By 1893, construction of an actual prison complex was completed, but instead of housing prisoners, it was used to quarantine yellow fever cases. Nowadays, the island is home to some endangered Aldabra giant tortoises, given to the island in 1919 by the British governor of the Seychelles. Some of those original tortoises are supposedly still alive here to this day!

A classic New England bed and breakfast with a boutique hotel vibe, the Union Street Inn is housed in an impeccably maintained 1770 whaling captain’s home just off Main Street in downtown Nantucket. A short walk from the Hy-Line ferry and harbor, the inn has a convenient location in town (including parking, a huge perk on the island) and can also outfit guests with beach gear for a day on the sand. A quintessential gray-shingled exterior contrasts with the bright blue chinoiserie patterns and crisp white Frette and Matouk linens in the inn’s 12 immaculate rooms. Union Street’s cherry on top is the made-to-order gourmet breakfast, which might feature fresh peach cinnamon rolls or homemade carrot cake, depending on the season.

This small, family-run wine shop in the Oltrarno district has been a gathering place for Florentines since 1947. Now run by the founder’s grandson and his family, it remains a place where neighborhood denizens come to buy wine to take home or to have a chat over a glass. Inside the shop, floor-to-ceiling shelves display bottles from a variety of Italian regions and vintages, with options in every price range. Glasses of red or white wine, dispensed from taps, can be enjoyed at the narrow bar. Or linger a little longer: Ask for a seat at one of the sidewalk tables, then order a glass of Chianti and a snack of chicken liver pâté (made from Nonna’s recipe) served on grilled Tuscan bread.

Hit the Fondouk Kaat Smen, otherwise known as the honey souk, to taste your way through as many as 17 different wild honeys for sale. Varieties range from familiar orange blossom and lavender to more unusual treats like caper and carob. If jujube is available, note that it’s favored for its anti-inflammatory and antioxidant properties, is considered to be particularly good for the liver and is locally consumed more as a medicine than something to spread on toast. People travel from afar to take this honey home, so the proprietor, Mr. Hicham, is used to packing it for air travel. Pop around the corner to the spice shop on Rue Bouhaj to stock up on freshly ground spices, too, like lemon-scented cumin, rich red paprika, ground ginger, sweet and earthy turmeric, and heady cinnamon.