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  • Basseterre, St Kitts & Nevis
    A combination of train and bus, this three-hour tour weaves a fascinating route past some of the island’s most historic sights. Constructed from 1912 to 1926, the rail system originally carried sugar from St. Kitts’ estates to the factory in Basseterre, but today serves as a fun tourist attraction. Visitors ride in double-decker cars—the lower is air-conditioned, the upper open-air—past black-sand beaches, old plantations, and sugarcane fields, and then up a portion of Mount Liamuiga.

  • 11546 Andy Rosse Lane, Captiva, FL 33924, USA
    The quintessential Florida sunset moment plays out night after night at this waterfront pub and restaurant in Captiva. Open since the 1970s, the British-style spot draws tourists and locals alike with sweeping views of the Gulf of Mexico and more than 16 different beers. To eat, there are seafood classics like clam chowder, fried calamari, and oysters Rockefeller. Go right before sunset and gather with everyone on the sand to catch the elusive green flash before settling in for your meal.
  • 76 Pitts Bay Rd, Hamilton HM 08, Bermuda
    As a rule, Bermuda’s sense of sophistication includes a certain level of old-school formality. With the opening of this namesake eatery from the internationally renowned and somewhat hipster chef Marcus Samuelsson, the island’s approach to haute cuisine has taken a chic turn. Housed in the Hamilton Princess hotel with its landmark pink facade, the restaurant boasts a vibe that’s contemporary and airy with an emphasis on the turquoise sea. All tables have excellent views of Hamilton’s harbor, and the menu is—as might be expected—seafood-heavy, with dishes like Oysters with Black Rum Mignonette and grilled salmon. The local catch of the day and island-grown onions, along with other dishes, are prepared on a wood-fired grill that’s visible from the dining space.
  • Charlotte Amalie West, St Thomas 00802, USVI
    Those looking for some island spirits may be surprised to find that the liquid concoctions at this historic outpost are body products, not liquor. Invented in 1838, the signature blend of bay leaf oils and island-made rum hydrates and nourishes skin. The unisex bars and tonics are infused with various spices, including lime, cinnamon or orange blossom.

  • Pape'ete, French Polynesia
    You can drive the 71-mile circular road around Tahiti Nui in a day, either by renting a car for a day or by joining a guided tour (your hotel will have info for either). Either way, the loop road takes you along the wild and rocky east coast, where you will see spectacular black sand beaches, many hosting excellent surf breaks. By contrast, the island’s west coast is tamer and features peaceful lagoons for swimming and even a few white sand beaches, like popular Maui Beach. Extend the drive by continuing into Tahiti Iti, the smaller section of the island at the south end, and forming a figure eight loop to return to Papeete.
  • 200 Ednam Dr, Charlottesville, VA 22903, USA
    A bucolic resort in the Virginia Piedmont, the Boar’s Head Resort is as deeply rooted in Virginia as its owner and neighbor, the University of Virginia. The land has hosted travelers since 1759, with the original Birdwood mansion dating to 1830. A short drive from downtown Charlottesville, Boar’s Head has plenty to keep a visitor occupied without even leaving the property, including an 18-hole golf course, a full-service spa, a fitness center with squash and tennis courts, and three swimming pools. The resort has 175 rooms spread over 573 acres; suites feature a seating area and balcony or patio, and some have fireplaces. Dining options range from healthy café fare (necessary fuel for all those tennis matches), to a grill overlooking the golf green, to an elegant meal in the restored Old Mill Room. The Blue Ridge mountains are renowned for their fall foliage, but visit in summer for fewer crowds (and UVA students) and the English-inspired grounds and gardens in full bloom. Be sure to ask for details on arranging a hot-air balloon ride over the countryside to appreciate all of historic Virginia.
  • Limón Province, Costa Rica
    It’s diminutive, to be sure, but “Little Grape Island” has a big claim to historical fame: Christopher Columbus landed here in 1502, anchoring his ships for repairs. Since then, a lot has happened (and been rumored to have happened) on this now-uninhabited island. It even once served as a quarantine site during a leprosy outbreak. Today, it’s an easy and interesting day trip for beach lounging, surfing and hiking. Take a boat over to the quiet spot and play modern-day explorer, keeping an eye out for colorful bird and fish species.
  • Käringön, 474 74 Käringön, Sweden
    The isolated, car-free island of Käringön is a 40-minute ferry ride from Orust, and has less than 100 full-time residents who stay year round, even through the long winter. But it’s a different story in the summer. In the 19th century, the middle classes in Sweden became enamored with the benefits of fresh sea air and started flocking to the small islands along the coast. Today about a thousand visitors arrive daily by ferry or private boat to enjoy the island’s relaxed vibe. Come for a lunch of fresh-caught seafood at Petersons Krog or watch children on the pier trying to catch the little crabs crawling through the seaweed down below. In the cold weather, visitors can take a lobster fishing tour or sample fresh oysters at the Käringö oyster bar, which also has a hot tub that seats six.
  • 74-2 Cruz Bay Town, St John, VI 00830
    The sleepy town of Cruz Bay, nicknamed Love City, is the main settlement on St. John, and the hub where most visitors arrive after a ferry ride from St. Thomas. The island draws everyone from salty sailors to A-list celebrities, and Cruz Bay is where they all gather in the afternoon to drink Cruzan rum at beachfront bars while deconstructing their day spent hiking, scuba diving or lounging on beaches around the island.

  • Via Alloro, 4, 90133 Palermo PA, Italy
    See some of Sicily’s most prized artworks at the Regional Gallery of Sicily, housed in the Palazzo Abatellis, in Palermo’s Kalsa neighborhood. The palace’s Catalonian Gothic–style architecture, which dates from the 1490s, is worth a visit in its own right. Among the prominent works in the collection are the Virgin Annunciate by Renaissance artist Antonello da Messina and a sculpture of the head of Eleonora of Aragon by Francesco Laurana.
  • Banjar Dukuh, Desa Kelating, Kerambitan, Kelating, Kec. Tabanan, Kabupaten Tabanan, Bali 82161, Indonesia
    Terraced like the surrounding rice paddies, Soori Bali occupies an undeveloped stretch of fertile coastline roughly 25 minutes from Tabanan, a town northwest of Denpasar known for traditional farming and artisan crafts. The resort’s modern design plays on the shapes, colors, and landscapes of the surrounding area and incorporates local stone. (At the recommendation of the surrounding village’s elder, the property also constructed 10 stone temples onsite within the property.) Outdoor spaces feature bright green trees and grasses along with infinity pools, while high ceilings, cool colors, and marble floors inside create a tranquil escape from the heat. The property’s spacious rooms and wood-slat shades give off an art-gallery vibe, and the reading-room lounge displays the works of the hotel’s artists in residence. Food is another big focus here, both at the resort’s three restaurants and in tours that explore rice cultivation, exotic ingredients found at the Kerambitan market, and the spices, cacao, and coffee from nearby Jatiluwih.
  • 4100 Wailea Alanui Dr, Wailea, HI 96753, USA
    Of all the accommodations in Maui’s tony Wailea resort community, the 22-acre, waterfront Fairmont Kea Lani may be the most family-friendly of the bunch thanks in large part to its all-suite-and-villa setup. The property’s 450 guest rooms are some of the biggest on the island—the smallest suites start at a generous 860 square feet, while the two- and three-bedroom beachfront villas weigh in at 1,800 square feet and up. All cater to families, with separate sleeping and living areas, entertainment systems, furnished outdoor space (for lounging and dining), sleeper sofas, and some type of kitchen facilities, while villas encourage group gatherings with plunge pools and BBQ grills. Both adults and kids will love the deep-soaking tubs, too. Elsewhere, three indoor and three outdoor pools provide space for fun when kids’ club activities (among them volcano building, hula lessons, and tide pool excursions) aren’t on the agenda. Grown-ups can also amuse themselves with activities like outrigger canoe journeys, cultural programs, tee times at three nearby championship golf courses, and locally inspired treatments at the Willow Stream Spa, which offers dedicated fitness and wellness programs. Fuel your adventures at the five on-site restaurants, including the seafood-focused Nick’s Fishmarket Maui (with its 2,000-bottle-strong wine cellar) and the award-winning Kō, where the flavors are inspired by Hawaii, the Philippines, Korea, and beyond.
  • Round Top Dr, Honolulu, HI 96822, USA
    My favorite part about living in Hawaii is the view from where I live. I am tremendously blessed to have the spectacular ‘perch’ that I do looking over Diamondhead, Waikiki, Honolulu, and past the airport to Ko’olina. If you are looking to see such a spectacular view of Southern Oahu, drive up Round Top Drive to Pu’u Ualaka’a State Park for sunset. You will find a large grassy area to share a picnic or lay back and watch the clouds roll by. Or you can stand up a bit higher at the lookout and identify all the places and roads you have been while in Honolulu. If hiking is more your style, there are plenty of trails up on this scenic route as well. Or, perhaps, you will just enjoy the curly queues and hairpins of the the Tantalus-Round Top Drive loop. No matter what you do, it is a refreshing reprieve from the busy scene in Waikiki!
  • One of Dalmatia’s most underrated cities, Šibenik is finally being recognized as an exciting coastal destination. Its medieval heart is a stone maze of steep alleyways dotted with charming squares and hidden cul-de-sacs, not to mention a pretty harbor and a seafront promenade lined with cafés. Crowning it all is the Cathedral of St. James, an architectural masterpiece incorporating style elements of both the Gothic and the Renaissance. The cathedral is said to be the world’s largest church built entirely of stone—most of which was quarried in the nearby Adriatic islands. Of particular note in this UNESCO World Heritage site: the frieze of 71 heads on the cathedral’s outer wall, which depicts 15th-century citizens of Šibenik with many different moods and personalities.
  • Frigate Bay, St Kitts & Nevis
    A narrow strip of land divides the northern Atlantic and southern Caribbean sides of Frigate Bay, making it easy to walk from one section to the other. Many visitors do just that, as hotels like the St. Kitts Marriott Resort and Sugar Bay Club are on the north side, while the beach bars of The Strip sit on the south side. The sand and scenery around the resorts is better, but the nightlife on South Frigate Bay is among the island’s best.