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It’s fun to imagine that Xcalak, a sleepy coastal village south of Mahahual on Mexico’s Costa Maya, is what the entire Caribbean coast of Mexico looked like before the creation of the Cancún megaresort in the 70s. No Spring breakers, no cruise ships, no thumping beachside clubs, no big hotels. Just white sand and palapas, palm trees and pelicans, hammocks and fishing boats. Just you in secluded relaxation away from it all. Several clean and basic hotels are located on the old coast road and fresh, cheap seafood is abundant at local favorite Toby’s. Dive and snorkel trips can be arranged at XTC Dive Center (www.xtcdivecenter.com), located about 300m north of town.

Dating to 1521, the Cathedral of San Juan Bautista isn’t just one of the oldest buildings in San Juan—it’s the second-oldest cathedral in all of the Americas. Go inside to see the tomb of Spanish explorer Ponce de León, who founded the first settlement on Puerto Rico and in 1509 was named the island’s first governor. The remains of St. Pio, a Roman martyr, can also be seen in the cathedral—the saint’s mummy has been displayed here in a glass box since 1862.

A recent addition to the Puerto Rican capital’s culinary scene are food hall–style spots where diners can choose among multiple kiosks, or stalls, each featuring a distinct kind of cuisine. Lote 23 is one such spot, located in the working-class neighborhood of Santurce. More than a dozen food entrepreneurs have fare on offer here, from pizza and tacos to bao and burgers. If you just need something to cool yourself off in the tropical heat, there are popsicles and cocktails, too. The alfresco eating area has plenty of picnic tables where you can sit and enjoy whatever you’ve ordered.

A shared love for southern Italian comfort food and a chance encounter in the supermarket drew chefs Antonio d’Alaimo and Ciro Genova into this gastronomic venture. The Italian duo, known to everyone as Ciro and Tony, personally welcome every guest to their small dining room. The menu features, among other things, veal marsala, snapper in wine sauce with fresh tomato and laurel, and tortellini Alessandro (pasta stuffed with chopped ham and cream). A wide-ranging wine list and tempting dessert menu help round out the evening.

Every once in a while, the sun shines bright in San Francisco and every city residents flocks to the nearest park or beach to soak up the sun and day drink. Baker Beach, in the confines of SF, seems worlds away from city life. The view of the Golden Gate Bridge is spectacular, and the diverse group of Baker Beach visitors is a testament to what a hodge podge San Francisco truly is. Parking can be a pain in the butt; take the 29 bus and save yourself the hassle.

Before Columbus arrived in the West Indies, indigenous tribes had lived on Puerto Rico for at least 2,000 years. The Igneri were the oldest recorded inhabitants, followed by the Taino, and artifacts from both peoples have been found at the Tibes Indigenous Ceremonial Center, a settlement just outside of Ponce that flourished from roughly 400 C.E. to 1000 C.E. Many of the artifacts are on display at the on-site museum, and a replica Taino village shows how native Puerto Ricans lived in the pre-colonial era.

After falling in love with Salvador Dali at his museum in Figueres, we caught one of three buses out to the cliffside town of Cadaques where you can get to know Dali a bit more intimately by touring his house. Full of odds and ends, including mini cages where he kept crickets and a polar bear draped in jewels, his house also includes spectacular views (including this one) of the serene Port Lligat. Tips: You must book tickets in advance to tour his house, and double-check the bus schedules because there are only three buses per day that go from Figueres - Cadaques and back.

Situated on the second floor of the Langham Hotel, this restaurant is open around the clock—and after tasting the team’s handiwork, we’re all the more thankful. Seasonal American cuisine is the specialty here, a focus that chef Ricardo Jarquin honors in plates like the Charred-Tar (a steak tartare twist with tenderloin, A1-sauce aioli, fried quail eggs, and truffle oil), watermelon salad (a summer favorite that includes shrimp, jicama, and cucumbers), and grilled Nigerian prawns (with lemon butter and herbs). Whatever you do, save room for dessert; pastry chef Scott Green has a knack for sweets that look as good as they taste. Case in point: the lemon pavlova, with lemon cream, coconut dacquoise, and lemon croutons.

In the shadow of El Yunque, The St. Regis Bahia Beach Resort is situated on 486 acres of former coconut plantation and native maritime forest. There are still plenty of palms here, but now the flora also includes all manner of tropical flowers and trees, positioned around numerous trails for walking, running, and biking. Families love the resort for its many amenities, from four tennis courts and a Robert Trent Jones Jr.-branded golf course to a luxurious spa and state-of-the-art fitness center. A new partnership with Aquavento Water Sports provides equipment for everything from kayaking and paddle-boarding to fishing and sailing on nearby lakes, while the Soul of Bahia program gives guests the opportunity to volunteer with a rescue organization for local cats and dogs or help maintain a turtle sanctuary during hatching season. Still, the most popular activity might just be lounging at the pool or on the two-mile-long golden beach.

Part of a $60 million renovation following Hurricane Maria, the hotel now features a design by celebrated Puerto Rican designer Nono Maldonado and San Francisco-based firm Hirsch Bedner Associates. The plantation-style dark woods and warm browns have been swapped out for more modern, sea-inspired colors, and the 139 rooms have a chic, residential feel, with sprawling bathrooms, private terraces, and glass bar cabinets that can be stocked to your personal tastes by a 24-hour butler. Occupying a two-story building overlooking the ocean, the Casa Grande lobby is the place to go to experience the hotel’s daily Champagne sabering ritual, enjoy live music from a Steinway piano, admire the mural over the St. Regis Bar, or enjoy Greek-inspired fare at the hotel’s signature restaurant, Paros. The poolside restaurant and beach shack have also been redone to ensure uninterrupted views over the water.

Old San Juan may look, at first glance, like a few other charming cities built during the height of Spanish colonialism—Havana or Santo Domingo, for example—but what sets it apart is the extent to which its architectural infrastructure from that era remains visible. It’s the only city that has its original colonial wall almost entirely intact, and both of its principal forts are in excellent condition, remain accessible to the public, and offer panoramic views of the Atlantic Ocean (so bring your camera). Both El Morro and Fuerte San Cristobal are run by the National Park Service; guided tours will leave you with greater knowledge about the era, as well as the forts’ construction and their role in Puerto Rican history. (There are other, smaller forts in and around the capital, next to the Caribe Hilton, and in Luís Muñoz Rivera Park, plus Fort San Juan de la Crúz in the nearby town of Cataño.)

Get down and dirty on an unforgettable spelunking experience at the Venado Caves, 45 minutes from La Fortuna. The caves were formed some 15 to 20 million years ago by tectonic shifting and erosion from underground streams. In them, you’ll see stalagmites and stalactites galore, and get the chance to check out colorful frogs and fascinating marine fossils and learn about the bat communities hanging right over your head. The experience is real (and really humid)—so wise adventurers bring insect repellent, knee pads, and an extra change of clothes. Waterproof your camera, too.

This white tablecloth, fine dining restaurant in the country’s capital. Headed by Chef Alejandra Girón, who trained at Institut Paul Bocuse in France, the menu is informed by her stint in that country, as well as stages and jobs at renowned restaurants in Spain and Australia. Dishes include rabbit, veal, and tongue entrées, and a wine list that’s fairly extensive for this region.

A Hawaiian fantasyland on Oahu’s more remote leeward coast, about 40 minutes from Waikiki, Aulani is so seductive—for all ages—that many guests are loath to leave the property at all. And who can blame them? The beach is an idyllic cove (albeit a man-made one) stocked with kayaks, boogie boards, and everything else little beach bums could want. Then there are the three pools, including one for adults only and one filled with tropical fish for snorkelers-in-training, two impressive waterslides, and the biggest crowd-pleaser of them all, a 900-foot-long lazy river where guests, big and small, splash around on inner tubes as they meander around a faux-rock grotto. Goofy, Minnie, Mickey, and the rest—all in their vacation outfits—make occasional cameos at the breakfast buffet or by (sometimes, in) the pool. But while Aulani is most assuredly every kid’s dream, it is not every parent’s nightmare. The resort decor is more traditionally Hawaiian than obnoxiously Magic Kingdom; the lobby is built to recall an old canoe house, on a grand scale, and is covered in murals, painted by local artists, depicting island life. Hawaiian storytellers gather around a fire pit at night, and rooms have warm woods, with a single subtle reference to the Mouse King—a wooden carving of Mickey with a surfboard and ukulele that doubles as a desk lamp. Perhaps best of all, the Aulani has an outstanding, supervised kids’ club that’s free to guests ages 3 to 12. Babysitters are available for kids as young as six weeks old.

Old San Juan offers historically and culturally significant experiences including a walk through 500-year-old forts, visits to UNESCO sites, historic churches, museums, the second oldest cathedral in the Americas and Ponce de Leon’s mansion. Cobblestone streets and pastel buildings are perfect for exploration during the day and variety of restaurants and shops make for a complementary evening.

This itinerary trades busy beaches for cloud forests, quiet rivers, and rural communities.