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Though it lacks a beach, this family-owned and professional diver–managed resort on the rocky coast just south of George Town has direct ladder access into the Caribbean. Grand Cayman’s two famous underwater sites, Eden’s Rock and Devil’s Grotto, are just a short swim away, and boat trips offer the option of two daily dives (including night dives). Images by some of the world’s most respected underwater photographers decorate many of the tiled and comfortable smoke-free rooms, some of which have kitchens and private balconies or terraces. The vibe is laid-back; post dive, guests sit by the pool or swap stories at the palapa bar, which has the island’s best sunset vista. Managers Anne Briggs and Lisa Evans, the granddaughters of Sunset House’s founders, make sure everything runs smoothly and ensure visitors explore the best of Grand Cayman both on shore and underwater.

By law, every beach in Antigua is public. But at this all-inclusive resort surrounded by 140 acres of undeveloped land on the island’s west coast, guests feel “their” beach belongs almost exclusively to them. The hotel is a 35-minute drive from the airport, and it’s accessed by an unpaved road. Seclusion is a big part of the appeal at this adults-only (except in July and August) hideaway. Its 27 minimalist but spacious cottage suites begin on the beach and are scattered up a hillside that overlooks a picture-perfect bay. All the cottages have outdoor showers, king-size beds with mosquito netting, and at least a partial view of the sea. Expect to see a lot of honeymooners and other romantically inclined couples here, but don’t expect to see much of them, except at meal times, when the foodie-approved mix of European, American, and Caribbean dishes draws out even the most recently married.

Barefoot Bar is a place that’s known for just that: bare feet. Located on the shores of the Caribbean Sea, Barefoot is a Placencia staple where locals and visitors mingle, drink, and eat great Belizean food. The bar is known for the lobster grilled cheese—a huge grilled cheese sandwich stuffed with catch-of-the-day lobster. Buy two: one to eat now, and another to bring home for later. Barefoot also makes perfectly crispy salbutes, which are a great tacolike light lunch to go with your $3 drink special.

The moment you walk into Buba’s, you feel like family. It’s easy to understand why when you consider that surrounding this blink-and-you’ll-miss-it hillside restaurant are Buba’s house, Buba’s sister’s house, and Buba’s Brother’s house across the street. Buba’s own two daughters, nephews, cousins, and other miscellaneous family either host, help in the kitchen, play dj, man the bar, or simply greet visitors from their porches with welcoming, West Indian waves. This homegrown approach extends beyond hospitality to deliciously impact the food as well. Nearly every fruit, vegetable, and herb used in the dishes at Buba’s are all grown on the sloping overgrown gardens surrounding the restaurant. The result is a quintessential island restaurant with no real set menu. Instead, expect the freshest ingredients of the day lovingly coaxed into a collection of authentic Caribbean fare like rice and peas, stew chicken, steamed veggies, salad, and more.

This open-air bar and restaurant is right at the ferry dock in the heart of Cruz Bay. It’s a great spot to have lunch between island adventures, or just to grab a drink and enjoy some people-watching along the dock. The menu lists barbecue ribs, fish tacos and Caribbean-style roti, as well as a variety of sandwiches and salads.

I’m not sure exactly how Rainbow Beach got its name, though I wouldn’t be surprised if it actually had a lot to do with rain. The island’s most popular beach bar, especially on Sundays, is centrally located on St. Croix’s West Coast, some of the island’s tallest peaks and dense rainforest just a few miles behind it. Prevailing weather patterns, particularly during the summer months, make brief afternoon showers a fairly regular occurrence here. That doesn’t stop the party, though. Live bands play on and everyone keeps dancing. When you’re already wet from the sea and feeling the vibes, a little rain doesn’t hurt one bit.

Around since the 18th century, the Avila Beach Hotel is Curaçao’s longest operating hotel. The property’s signature Pen restaurant got its name from the English and Dutch governors who once used the hotel as a country residence, while its classic Schooner Bar has been a beach fixture since the 1950s. A variety of room types all have bright, modern décor and private balconies or patios. Some even have kitchenettes or fully outfitted apartments, which are perfect for families. For a distinctly Caribbean experience, book one of the Ocean Front Blues rooms, housed in an all-wood building on the pier with unbeatable water views.

The resort features two beaches (one of which is exclusive to guests staying in suites), an infinity pool, and a fitness center with a sauna, steam room, and outdoor Jacuzzi. About a 20-minute walk from Willemstad’s UNESCO World Heritage buildings, it also offers a shuttle to town—a very welcome amenity on hot days. Check the resort schedule for weekly happy hours, live music, classical concerts, and arts events, and be sure to look for the vintage Rolls Royce inside the gift shop.

Built between 1914 and 1916 on an octagonal base, this stone, double-lens lighthouse is Aruba’s marquee landmark. Standing tall at 98 feet, it’s the highest structure on the island and offers the best views in its respective area. It gets its name from the SS California, a British steamship that sank in nearby waters in 1891 and now functions as a fantastic dive site. Adjacent to the lighthouse, visitors will find a beloved Italian restaurant and the California White Sand Dunes, a hot spot for dune surfing.

One of the best spots in the Caribbean for surfing is Barbados. And if you’re not one of the best surfers in the world (like me), one of the best breaks on the island to catch some waves has got to be Freights Bay. The added bonus is that most late afternoon sessions end with a spectacular flourish as the sun sets smack in the middle of the bay.

Many Caribbean islands (Anguilla included) are made primarily of limestone. Over many thousands of years, caves often form in this type of rock speckling the islands with tons of little caves to explore. On Anguilla there are plenty to explore, but the hike to the Iguana Cave is particularly pleasant. It starts on the quiet and isolated sands of Katouche Bay Beach just past the Masara Resort. It’s pretty much due West of the capital of The Valley and very easy to find. The only awkward part is the very steep road that descends the last mile toward the shore. There you should find a gap in the sea grape trees. Staying on this path will take you past a salt pond, through a forest crawling with hermit crabs, up an old stone staircase, through a grove of cactus, past the occasional red-footed tortoise, and finally to the cave. Going at an easy pace, the hike clocks in at around 45 minutes up and 45 minutes back. For the most part, it’s pleasant and I highly recommend it as a way to break up a bounty of beautiful beach days.

Wagyu katsu sando (beef cutlet sandwiches) have been around for a long time, but under the able hands of Hisato Hamada, the dish is hip and cool. The sleek, Instagram-friendly, stand-and-eat shop is in the trendy Nakameguro area along the Meguro River. Diners select a cut of marbled beef, ranging in price from 2,000 to 20,000 yen ($19–$190), which is then breaded, deep-fried, and served as a sandwich. Truffle fries and salads round out the menu. Drinks include an impressive selection of craft beers, wine, and champagne.

Continue west beyond Boulder’s iconic Pearl Street walking mall, and you’ll find yourself surrounded by incredible restaurants. New to the block is Bartaco, a fun, hip South American–inspired eatery that always seems to be hopping; while there might be a wait for a table, keep an eye on the first-come, first-served bar seating. Choose from unique taco flavors like glazed pork belly with arbol chili sauce or tamarind-glazed duck, and sides like a spicy cucumber salad or fresh pineapple with lime—and make sure to save room for the fresh, hot churros. The Kitchen, self-described as an American bistro, is one of the fancier, albeit relaxed, eateries, offering brunch, lunch, and dinner that have been sourced as much as possible from local farmers. For delicious pub food, jump into the classic West End Tavern. Burgers, beers, ribs, BBQ, and more make this a place to satisfy everybody.

This Playa del Carmen restaurant takes its name from a traditional Mexican dish known as aguachile: chili-marinated shrimp with lime juice, onion, and sometimes other ingredients that lend it a strong, spicy-citrus flavor. With its open-air setting and laid-back, beachy style, plus a location a few blocks from bustling 5th Avenue, Los Aguachiles is in fact more local hangout than tourist joint. There’s an extensive menu of other casual Mexican seafood, most notably delicious tacos and tostadas (crispy tortillas piled high with traditional ingredients), as well as mezcal cocktails and chamochela (michelada-style beer mixed with sauces, then rimmed with chili powder and decorated with a shrimp).

Some friends had been hiking in Austria in May and had to cut the trip short because of an unexpected blizzard. After all day hiking in the snow and not prepared for it, we came to a hut that was open to guests run by a woman named Helga. Helga didn’t speak a word of English, but she served us some delicious Mittenwald beer, that tasted like the best in the world. So a few days later, we decided we had to go to the source of this magical elixir, the town of Mittenwald in Bavaria. We went to the brewery and met the proprietors of the restaurant associated with the brewery, Postkeller, where we thought we would have a couple of tastes. Instead, it turned into an all-day affair. We tested the many different varieties of Mittenwald, and our hosts cooked up a roast for us, and we had a great evening of laughs with them.

Offering a bit of the South Pacific in the Caribbean, the Van der Valk Kontiki Beach Resort features thatched-roof cottages set amid gardens and green, saltwater pools. The deep, wood-paneled rooms have direct paths to the pools as well as the Cabana and Mood Beach clubs. For an extra $20 per night, you can even book a full-service room, which includes a lounging bed at the beach (reserve it a day in advance to ensure you get a spot), a minibar with drinks and snacks, and nightly turndown service. The beach clubs serve the standard international fare and host weekly theme nights like a Friday fresh fish market with live music. A range of additional dining and nightlife options exists along Mambo Beach Boulevard, adjacent to the resort, and the aquarium is a short walk away. While Kontiki does not have a full-service spa, guests can book massages and manicures right on the beach.