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The Coronado Bridge links San Diego to Coronado Island—and the present to the past. In the span of just 2.12 miles, you’ll travel from the digital age to a century when “electrified” hotels were practically unheard of. When the Hotel Del Coronado debuted in 1888, its electric lights and telephones made a sensation—as did its resplendence. In 1892, a young guest named Noel proclaimed in a letter to her family back east that “the red and the white between the bluest sky and the bluest water is like a beautiful dream in a fairy story.” Legions of A-listers have checked in ever since, as a who’s who of vintage portraits attests. But while a stay here is delightfully nostalgic—featuring bike rentals, beachside cabanas, and evening clambakes—the 757-room hotel doesn’t live entirely in the past. Take advantage of its upscale spa, spin classes on the beach, and restaurants serving updated takes on coastal cuisine along with creative cocktails. In the historic Victorian Building Suites, you’ll find modern coastal-chic interiors, streaming TVs, and, of course, Wi-Fi. The Beach Village Suites include additional modern luxuries—like a Sub-Zero fridge and dedicated concierge to help you fill it.

Lincoln Road is a pedestrians-only boulevard in the heart of South Beach and one of the most popular places to visit in the area. Lined with shops and restaurants in historic Art Deco buildings and shaded by tall trees and fountains, Lincoln Road Mall has some of the best people-watching in Miami. Every restaurant has outdoor seating, and there are street performers and a farmers’ market that showcases the local community, farms, and purveyors. Visitors come from all around the world, so grab a cortadito and take it all in.

Known as the “Jewel in the Crown” of the Southern Grenadines, Tobago Cays Marine Park comprises five picture-perfect, uninhabited islands surrounded by a clear lagoon. Here, you’ll find sea turtle nesting sites and feeding areas, small systems of mangroves, and the most well-developed coral reef complexes in St. Vincent. Swim with the resident turtles, snorkel around the almost 2.5-mile-long Horseshoe Reef, or simply relax on a magnificent white-sand beach—each island has at least one.

The peak called Monserrate towers over central Bogotá and lends its name to the church that tops it. Perched more than 10,000 feet above sea level, the sanctuary—dedicated to the Passion of Christ—has beautiful gardens showcasing marvelous highland vegetation, and the city views from here are spectacular (sunsets are especially recommended). Ascend Monserrate by cable car, via railway, or on foot (this last is only for the fittest and those already acclimated to the altitude). That beautiful white house on the mountainside is Casa Santa Clara restaurant, a better-than-expected, special-occasion-suitable venue at which to try traditional Bogotá favorites like ajiaco, a thick potato-and-chicken soup.

On the Dominican Republic’s northern coast, near the tip of the Samaná Peninsula, this unpopulated Atlantic beach stretches three miles from Cape Samaná to the cliffs of Cape Cabrón. To get here, you’ll need to take a four-wheel-drive vehicle or a boat charter from the small fishing village of Las Galeras, but once you arrive, you’ll find a nearly empty stretch of sand. The west end of the beach features calm waters ideal for swimming and snorkeling, while the east end has great waves for surfing. You’ll also find spots to rent kayaks, snorkeling gear, chairs, and umbrellas, as well as a few food vendors serving rice, beans, and seafood cooked over an open-hearth fire. This is the place to go when you want to get away from the crowds.

A landmark since the 1920s, this glamorous resort at Monaco’s easternmost border with France still evokes the glory days of Monte Carlo, when high-society scenesters were frequent guests. The rooms, airy and bright after a makeover by designer India Mahdavi, have an elevated Deco-meets-nautical vibe with porthole windows, Mediterranean stripes—in turquoise, white, brick red, and beige—tailored furnishings, and artsy line drawings on the walls that recall Matisse and Cocteau. The superb, all-organic restaurant Elsa (named after Elsa Maxwell, the American columnist and hostess who was instrumental in attracting the beau monde to the hotel) is another throwback, while the Olympic-size heated seawater pool—open to guests and Beach Club members who swan around on weekends with their children in tow—remains a draw now as it was then.

While Tamarindo in Costa Rica is no longer a sleepy beach town known only to a lucky few, we can still settle ourselves onto the sand and feel like we have the vast skyline to ourselves. Staying in Playa Langosta, the beach just south of Tamarindo, provides a welcoming relief from clusters of tourists while keeping us close enough for sunsets like this! Extra bonus: Have a friend or loved one in one hand and a cocktail in the other.

Catch a glimpse of what Hawaii looked like before European contact. An unmissable destination for culture buffs, this sacred area stretches along the lava flats of the Big Island’s western coast. Behind a massive wall stands an ancient pu’uhonua (place of refuge)—where defeated enemies and those who violated the kapu (laws) could seek pardon. The park also shelters the Royal Grounds, a residential and ceremonial epicenter, and the 1871 Trail that takes in the shoreline. Tip: This is a religious site, so be respectful and don’t smoke, picnic, play sports, take wedding photos, or carry beach equipment (including towels) here. Just north of the boat launch outside of the park you can find Two Step, a phenomenal scuba and snorkeling spot.

From a members-only beach club in the 1960s, The Dunmore has evolved into a 16-room boutique stay whose spirit and decor evoke that era. Local interior designer Amanda Lindroth oversaw a major renovation when the hotel’s current owners bought the property in 2010. Wicker and rattan furniture, patterned prints, and spaces that are as much outdoors as indoors create a look that is somewhere between late British colonial and timeless Bahamian. Although the landmark sits on Harbour Island’s Pink Sands Beach, a pool with an airy pavilion adds to The Dunmore’s reputation as a place of amiable gathering. After a day of sunfilled fun, head to the on-site restaurant, where chef Cindy Hutson, one of the region’s rising culinary stars, prepares modern twists on island delicacies—think grouper curry with lychee and grilled pineapple and banana fritters with rum caramel.

Cozy and comfortable, it’s hard to leave Pangas. The hours fly by here, where the Las Baulas estuary meets the Pacific, at wooden tables, right on the sand; or beneath marvelous, sparkle-lit trees in a setting that’s practically one with the surrounding nature. A tropical fusion menu makes the most of local bounty, featuring innumerable fruits, grass-fed beef, and locally caught seafood; fresh-prepared cocktails intensify the vibe. Surf-racks and showers available to those coming off the waves; reservations suggested.

Just steps from the beach, Sapphire offers outdoor dining year-round on its cozy patio. Run by executive chef Azmin Gahreman for more than a decade, the restaurant is certainly a Laguna institution, but one that’s constantly evolving to stay fresh. Though Sapphire is worth a visit for every meal, it really shines at brunch, when such indulgent dishes as buttermilk pancakes, fried chicken and cheddar biscuits, and eggs Benedict with roasted jalapeño hollandaise are on the menu. Pair your breakfast with bottomless mimosas in flavors like orange, mango, and grapefruit and you’ll have the makings of a perfect morning.

Mercury Lounge is one of the best places to be seen in this see and be seen city. Abide by the dress code or risk being turned away—but if you make it in, revel in the views of the Gulf and the Burj Al Arab, the sophisticated crowd, and the delicious (pricey) drinks.

The beef is local and grass-fed, the french fries and french toast are good, the people are nice, and it’s got views of a little bay. We ate one meal here, then another, and another. Sometimes when you find a good thing, you stick with it. Especially when you’re traveling with a 5-year-old.

The Miami outpost of a hotel brand well known for its Los Angeles and New York properties, The Standard Spa, Miami Beach is less a hotel in the traditional sense, and more a spa with guest rooms set amid tropical gardens. The concept extends to the hotel’s atmosphere, which is downright staid compared to the party scene of so many Miami Beach hotels. A nearly all-white color scheme and extra-comfortable linens, pillows, and robes give rooms—small by local standards—a calm, comfortable air. Extra attention has been invested in the hotel’s common areas, with lots of Danish and 1950s-inspired furniture and spaces arranged in such a way that some spots offer solitude while others focus on bringing people together. There’s a reason many guests have called The Standard a playground for adults: a co-ed hamam, gardens with hammocks and swing chairs, and a hydrotherapy circuit (including bayside infinity and icy plunge pools) are just a few of the on-site attractions.

The start of the path is quite easy to find in Friar’s Bay. Just walk North past Kali’s Beach Bar and past Friar’s Bay Beach Bar until you see a path marked by orange arrows. It should lead up a hill. (There appears to be another path that goes around the rocks lower down, but I wouldn’t recommend taking that one.) Once you crest the hill, the still somewhat clearly marked path opens wide in all directions. You get a clear view of the ocean on your left and grassy hills on your right. Cross through a fence. Walk past some old ruined condos. Meet up with a road. Wait, a road? I could have driven here? Yeah, well… the walk is pleasant and you’re at Happy Bay before you know it. And talk about “happy”! This secluded bay is often almost devoid of the throngs which plague some St. Martin beaches like Orient Bay. Here, there are practically no facilities (though they have been talking for a long time about adding some) so it just doesn’t attract crowds! It’s not as expansive as my favorite beach on St. Maarten (Long Bay) though… Anyway, once you take your pick of the many excellent spots to spend the day on this beach, it’s just a matter of deciding how much you’re going to take off. ;-)