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Surprisingly enough, you can round the point at Point Dume and discover your own hidden nooks to spend the day. With cliffs at your back and a private beach with decent size waves in front of you, it’s not a bad place for a picnic.

In recent years, one restaurant has set the bar for cool in Cabo San Lucas. Bar Esquina, the Bahia Hotel & Beach House’s on-site bar and grill, features a chic casbah-like design aesthetic, a menu built on Mexican and Mediterranean flavors, and a commitment to organic, locally and responsibly sourced ingredients you taste in every bite. The menu is ever-evolving, but there are standouts you can always expect to find. The tuna tartare is a tiered, artistic creation, featuring tempura and an avocado-yuzu mousse. The Caesar is the signature Bar Esquina salad, here wrapped in a long, flat crouton and served with poached egg and prosciutto. Entrée selections include a generous filet mignon with potatoes au gratin and the short-rib pizza with blue cheese and arugula.

Key West doesn’t have many swimmable beaches, but this elegant 1920 oceanfront resort sits on the largest private one in town—an 1,100-square-foot strand punctuated with tall palms. While the shoreline itself is on a rocky shelf, a long dock extends out to the shallows for laps and snorkeling. Just off the beach, two large pools are set into green lawns and lush landscaping in front of the Spanish-style main building, which is on the National Register of Historic Places. The hotel’s wooden coffered ceilings, arched entryways, red-tile roofs, and other key architectural details recall the hotel’s glamorous heyday, while the clean, refreshed rooms are entirely modern, with sleek wood-framed beds, white linens and curtains, and ocean views. Children under 16 stay for free and babysitting is available for adults who want to take a break at the Spa al Mare, which has an open-air cabana right on the sand for al fresco massages and treatments.

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.

Going to dinner at Little Ochie is as fun as it is delicious. Pick your dinner—from a cooler of freshly caught fish—by species and by weight, then pick the style in which you’d like it cooked: jerk, grilled, escoveitch, and more. Pick a side of bammy, a thick round of cassava bread, to go with it. Your next decision is where to eat—head outside and choose a picnic table under one of the thatched huts carved in the shape of a fisherman’s canoe. The combination of beachy atmosphere and great fish makes this relaxed yet lively slice of Jamaica well worth the hour-long drive from Treasure Beach.

This family-owned and -managed 1,000-acre guest ranch in Lewis and Clark County is paradise for riders of all ages looking to improve technique while learning about equine psychology and Western working life. The owners, Zack and Patty Wirth, and two of their six children, all direct descendants of 1860s Montana homesteaders, breed and train quarter horses and hold wide-ranging riding rights on a neighboring ranch of 85,000 acres. Guests, a maximum 20 at a time, ride according to their interest and level; time in the saddle (or bareback) might be spent in the ring, on scenic trail rides, endurance training, or learning to rope and work with the Wirths’ 30 Corientti and Longhorn cattle.

Four cozy rooms of the same size but with different bed configurations have fireplaces and mountain views. The atmosphere is communal and convivial, the hosts dining with guests and taking note of the weather and individual interests to plan activities. Many teen visitors fulfill dreams of unlimited horse time; for non-riding family members or partners there is guided shooting, hiking, and mountain biking. There’s also technical fly-fishing on the Little Prickly Pear Creek, a spawning ground for rainbow and brown trout. For rock hounds, fossil-rich shale cliffs sit just a mile away from the barn and guest rooms.

To see everything there is to see in Oostende, I highly recommend spending an entire weekend (or longer) in the city. For a good night’s sleep, try the Mondo Hotel, located minutes from the Promenade, in a quiet corner of the city centre. Our hotel room included a mini-kitchen (although minus a fridge which we found a bit odd) and a vast bathroom with a tub and shower. We enjoyed the champagne breakfast buffet, complete with Belgian waffles, in the artsy dining room. There are 28 ‘Cosy Rooms,’ 18 ‘Superior Rooms,’ 2 suites and 14 ‘Family Rooms,’ with extra bedrooms for the kids.

Soaking tubs big enough for two and double walk-in showers provide a clue that this beachfront all-inclusive, located less than 20 minutes from the airport on a peninsula just to the southwest of St. John’s Harbour, encourages families to look elsewhere. And while only the Premium Beachfront Suites have those particular romance-inducing amenities, there are other features, such as hideaway tropical dining, that will convince honeymooners and other couples that they have stepped into their own Gauguin landscape. Hence, the most secluded rooms, each with its own plunge pool, are called the Gauguin Cottages. Even among Antigua’s 365 beaches, Galley Bay’s is a visual standout that is longer and less crowded than most. The ocean here can get too rough for swimming, but the beach seldom fails to please for sunsets. Guests with limitless energy can choose from complimentary activities such as tennis, sailing, and stand-up paddleboarding. Or they can save their energy for honeymooning.

Hopkins Bay Resort is located on the beach right near the town of Hopkins; accommodations include one-, two-, and three-bedroom beach houses. Local art and polished mahogany furniture signal that this is no cookie-cutter chain hotel. The spacious houses are perfect for families or small groups traveling together. Resort activities include dance and music performances that reflect the traditions of the local Garifuna people, descendants of Africans brought to the New World as slaves. Staff can also arrange excursions to numerous cultural and historic attractions, not only in and around Hopkins, but also to iconic sites such as Xunantunich, a Maya site, and the Blue Hole, one of the world’s most popular destinations for scuba diving.

No matter what kind of getaway you have in mind, you can find a guestroom to fit at Castle Hill Inn. Rooms in the main house vary in size and décor, but each is kitted out for romance with a fireplace, a king-sized bed, oversized tubs, and windows looking over the water and expanses of lawn. The Turret Suite, a bi-level space, has a bedroom on the first level; on the top floor, a soaking tub on a raised floor takes advantage of the 320° wrap-around windows. Below the main house, the Harbor House’s modern guestrooms feature front-porch views of Newport Bridge and the hotel’s Grace Kelly Beach. At the far end of the 40-acre property, the Beach Cottages and Beach Houses are set along the private beach, offering views that take in both the mansions along Ocean Drive and the wild Atlantic itself. The cottages, slightly smaller and closer to the beach, have peaked ceilings with rafters. The airy Beach Houses, compactly outfitted with galley kitchens, sunny decks, ceiling fans, fireplaces, and curated shelves of books, cast a kind of never-leave spell.

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.

Baja California Sur is less saturated than other Mexican seasides, but some of the beaches, like Balandra, attract a crowd. For a bit of Baha California Sur quiet, take a boat ride or a thirty-minute hike (no flip-flops, please) to Playa La Escondida. The beach is blanketed with white sand, surrounded by mountains, and bumps up against clear blue waters. Remember to bring all food, clothing, and other goodies you might need for your day as there are no shops or services.

The Peak 2 Peak Gondola that connects Whistler and Blackcomb mountains was considered a glitzy and expensive PR move when it opened in 2007. Today the 1.9-mile span, the longest unsupported span in the world, ferries hikers, bikers, and of course, skiers and snowboarders to the slopes they seek. Best of all, the Peak 2 Peak provides access to alpine wilderness usually reserved exclusively for the athletically inclined. (This is the adventure I take my 83-year-old mother on in Whistler, and she is blown away, as is her 8-year-old grandson.) Flying through the air, 1,431 feet up with hardly a support tower in sight, is a thrill. The 11-minute ride soars above snow walls, wildflower meadows, Fitzsimmons Creek, and several trails down, around, and behind the Whistler peaks.

Opened in 2003, Carlisle Bay is set on a lush, isolated section of Antigua’s south coast and has a 21st-century design that feels more contemporary than Caribbean. With muted shades of grays, whites, and greens, the hotel projects an uncluttered, understated luxury. Its most remarked-on feature, though, is the way it appeals to both couples and families by keeping the two separate. Each group has its own cluster of rooms at its own end of the beach, and never the twain have to meet, except perhaps for lunch at Ottimo, the poolside Italian restaurant. The crescent of beach is tucked into a sheltered bay, so the waves seldom do more than whisper up onto the white sand, against a backdrop of forested hills. It’s all very restful, but the long list of free non-motorized watersports and the extensive kids’ club ensures everyone has plenty to do.

The Natural History Museum houses some 35 million specimens and artifacts spanning 4.5 billion years in history. But it isn’t just what’s inside this structure that’s historic: The main building itself dates all the way back to 1913, when a Sunday school teacher—upset by the seemingly unstoppable influx of saloons, gambling locales, and other centers of vice—convinced the city to develop what’s now called Exposition Park. Fast-forward to the present, and the Natural History Museum is more than just a place to see weird animal bones and models of long-extinct Homo sapiens. The museum hosts plenty of public events throughout the year, including mini nature festivals, evening cocktail parties, and opportunities for community science. The neighboring California Science Center is a draw for the kiddos, and Exposition Park as a whole is occasionally leased out for large-scale music fests.