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On Puerto Rico, horses roam the farms, the mountains, the town centers—and also the beaches. A couples’ horse ride at sunset is a perfect way to kiss the day good-bye. With Tropical Trail Rides, in the northwestern municipality of Isabela, you can take a two-hour ride through the forest and by the beach as the sun sinks down toward the water. Make sure you take the opportunity to break for a hike or a swim along the way. On the north side of the island in Manatí, Kerry’s Horses designs personalized sunset rides by the beach or through nature reserves.

You may not expect to find the world’s best frozen pina colada at a joint hidden behind a gas station and underneath a condo unit, but that’s where to order the drink—lovingly dubbed the “Erik Estrada” and mixed with coconut milk and spices with a dash of Angostura bitters—and that’s how co-owner T.J. Lynch rolls. He took the hidden-gem aesthetic from his New York bar, Mother’s Ruin, and translated to the laid-back vibe of Folly Beach. In addition to the island’s best cocktails, Lowlife’s loyal following saddle up at the indoor/outdoor bar for the Old Bay-dusted local shrimp roll, the bold, rich tuna poke, and the Duke’s mayo-doused, addictive double cheeseburger.

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.

Ferries between St. Vincent and Bequia run frequently, all day and evening. The one-way trip takes about an hour, and the fare is about $10 each way or $17 round-trip. En route, passengers have breathtaking views in all directions, including volcanic St. Vincent and Kingstown Harbour, Young Island, Mustique and Canouan in the distance, and Bequia’s lovely Port Elizabeth. Once on Bequia, take an island tour, have lunch, go for a swim, or explore Port Elizabeth before heading back to St. Vincent at sunset. If you’re traveling in the other direction, spend the day on St. Vincent walking around historic Kingstown, touring the Botanical Gardens, or hiking the Vermont Nature Trail.

With more than 400 shipwrecks and its fair share of coral reefs, St. Kitts is a favorite of the scuba set. To try your hand at the hobby, consider staying at Bird Rock Beach Hotel, which houses one of the island’s most popular dive operators. Here, guests can charter a boat to nearby Devil’s Cave and swim among barracuda, lobsters, and nurse sharks, then retire to one of 46 tropical-hued rooms overlooking the sea. Less adventurous travelers can visit the on-site dolphin park, sunbathe on the private beach, or simply sip rum punches from the pool’s swim-up bar. Hotel staff is also happy to arrange off-site activities like catamaran cruises, rainforest treks, and volcano crater tours.

Updated in 2017, the rooms and public areas in this attractive, airy resort have an island-themed decor. Rooms now come equipped with marble bathroom vanities, Smart LED Samsung televisions, and Starbucks Coffee. But the star attraction remains a prime, crowd-free position on Grand Cayman’s Seven Mile Beach, famous for clear water and powder-fine white sand. Resort sun loungers are spread far apart to give guests a sense of privacy. A day camp with fun activities and a healthy meals program for kids (ages 4-to-12) means parents get guiltless downtime (or scuba diving and other water sports). Shopping and alternative dining are within walking distance.

Opulent is the word that may occur to you as you stroll into this split-level steakhouse. The art deco-inspired main dining room features oak pillars, camel-colored banquettes, and a jaw-dropping six-tiered brass and crystal chandelier. Upstairs, diners sit on a teak terrace with views of the San Diego skyline. A meal here often includes a show: Many dishes from caesar salad to Tournedos Rossini are prepared and served tableside from custom-made carts. The star of the menu is the Creekstone Farms Beef which has been dry-aged in a glass-enclosed meat locker for more than 25 days. Dry-aged duck and lamb, vegan tartares, and vegetable side dishes like leeks roasted over coals, or broccoli with salty bagna cauda round out the menu. Executive Chef Jason McCleod earned two Michelin stars working at Ria at the Elysian in Chicago. While Born & Raised is a high-end venue, the service is friendly and laid back with suit-clad servers sporting sneakers.

An understated, private landing stage for gondolas and water taxis on a side canal of the lagoon marks the entrance to the lovely Baglioni Hotel Luna in San Marco. Steeped in history, the palazzo, with lagoon-facing windows and charming Juliet balconettes, dates to the 12^th century and is said to have given refuge to the Crusade-era Knights Templar. Interiors are more in keeping with noble 18^th-century fashions. There’s a sleek marble lobby, sparkling crystal chandeliers, antique furnishings, and a healthy showing of brocade fabrics. The standout room is the pristinely preserved Salone Marco Polo, filled with18^th-century frescoes painted by pupils of influential Venetian painter and printmaker Giambattista Tiepolo.

Conveniently located just steps from bustling and culture-packed St. Mark’s Square, this hotel, with its award-winning restaurant, relaxed lounge, and rooms full of delightful period details, makes for an elegant home base in Venice.

Hotel Solamar is all about providing warm SoCal hospitality. Mingle in the lobby during the daily happy hour, and rent a free designer bike for beachside cruising. You can even turn your room into your ideal retreat, thanks to an eight-option pillow “menu” and in-room spa services. Wellness-minded travelers should take advantage of the available yoga mats and tune into yoga, Pilates, and core-strengthening exercise programs on TV. Pets are also given special attention with free amenities that include welcome treats and beds.

The chic downtown hotel is design-focused without being stuffy, creating a laid-back vibe throughout the property. Oversized chairs, sleek mahogany furniture, and plush stitched walls adorn the rooms. Sunny days aren’t hard to come by in San Diego, so don’t miss the fourth-floor terrace with its memorable skyline views. You can also take a dip in the heated Shore Pool or catch some rays on one of the lounge chairs.

“What are all those people doing?” This is probably the most common reaction upon stumbling onto the botellón. People of all ages (but tending towards under 40) gather in a public space, toting plastic bags bearing substantial weight. They contain bocadillos (sandwiches) wrapped in foil and litros (liter-sized plastic soft drink bottles) whose contents have been replaced at least in part by hard liquor. In San Sebastián, the seats lining the port are the most popular spot for the botellón. In a botellón there are (almost) no rules...just have something to drink and a friend, or two, or ten. And let the night begin.

Rekondo is a little hidden treasure of a restaurant, started by an aficionado of wine. A real aficionado. His varied collection means the restaurant has a wine list of hundreds of pages. These are wines critics dream about, at prices that are a fraction of the cost in other parts of the world. They are so well-priced, in fact, that the restaurant only allows bottles to be taken off the premises if they are opened. On the outskirts of town, it is rarely completely booked and has a spacious terrace that is absolutely perfect for having a bottle of wine at sunset.

During the day, the Piazza San Marco in Venice is an overwhelming flurry of activity, but once the sun sets, you’d be surprised at just how much a sense of ease and languor settles in. Life simply slows down as the crowds depart. Stop by Caffè Florian for a memorable evening. Opened in 1720, this is Italy‘s oldest cafe, and features ornate frescoed and gilded salons, as well as an outdoor seating area for great people-watching. Sip a drink and enjoy Caffè Florian’s live orchestra and singers as you sit under the beautiful night sky, with an illuminated St. Mark’s Basilica in the background. Looking around at my family, I could see total contentment reflected on each of their faces—the most magical and relaxing night of my trip. While not inexpensive, this evening was worth every Euro to me—a night that I will remember fondly for the rest of my life.

In an otherwise flat and forlorn section of desert between Tucson and San Diego, exit 67 on I-8 is a sweet pit stop: Dateland! A grove of date palms was planted beside the railroad tracks here in the 1920s. Today, it’s more than just a typical refueling station—it’s a true road-trip oasis for your sweet tooth. Sample the variety of caramel ovals, and then get a milkshake! The date shakes are definitely “local-" if not “world"-famous, and prickly pear cactus fruit is also a flavor option. Look for the palms on the horizon about an hour east of Yuma; it’s not a mirage.

You’ve made it to the splendid isolation of Ulleung-do island’s north shore...Now, where to sleep? “Chusan Ilga Pension” is one of the island’s best choices: above the waves, on a clifftop beneath a volcanic peak, with a granite Buddha overlooking the greenery to the west and a fishing village just down the steep road to the east... This is rustic comfort: the floors are heated in the traditional Korean manner, the timbers are exposed, but the double-paned windows can either shut out the roar of the sea or let in the salty breeze, as you wish. Downstairs is a restaurant that serves the local seafood and mountain vegetables. There are several buildings on this clifftop, but the one with the restaurant offers three rooms with balconies almost directly above the sea; ask for one of these. To get here: take the coastal road from the port where you disembark from the ferry. You can’t get lost--there’s only one coastal road. Go counterclockwise around the island. Once you reach the north side, look out for the Elephant Rock in the sea and Songotsan peak on your right. Soon you’ll see a sign for Seongbulsa Temple, pointing up an almost immpossibly steep road. Start climbing and after the first bend, Chusan Ilga will be on your right. (The website is in Korean only, but the central tourist office in Seoul can phone for you; you’ll have to wire money through a Korean bank to confirm your room.)

The laid-back restaurant Carbon Caribbean Cuisine takes you on a culinary journey around the Caribbean. You can order typical dishes from Cuba, Jamaica, Puerto Rico, and, of course, the Dominican Republic. Popular with locals, Carbon offers a glimpse of island life beyond the beaches and resorts.