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The Antigua Yacht Club is the center of so much of Antigua’s world-class sailing experience. Right in the heart of English Harbour, this prestigious yacht club has been serving the island for over 40 years. It hosts the Classic Yacht Regatta, the RORC Caribbean 600, Sailing Week, the National Sailing Academy that serves the community with free watersports education, and even the Caribbean Dingy Championships. This is the place to stock up on last-minute supplies at the shop, or grab a bite at Cloggy’s or Club Sushi. Yeah, The Antigua Yacht Club is a hub for sailors of all stripes to talk shop whether coming in or leaving for some time on the water.

Martinique’s Route Des Rhums is something of the ultimate single island rum tour. The big reason for this being there are 10 different distilleries spread across Martinique’s 425 square miles! TEN! Two of the best are Distillerie Neisson and Plantations Saint James Martinique. All of them produce what’s called rhum agricole, but all you need to know is Martinique rums are the only rums in the world that have been granted the prestigious Appellation d’Origine Contrôlée (AOC) designation. Awarded by the French government agency Institut National des Appellations d’Origine (INAO) in recognition of the finest agricultural products (wines, cheeses, butters, etc), the AOC designation is an incomparable stamp of excellence in the culinary and spirits world.

A private-island resort six minutes by boat off the coast of Antigua, Jumby Bay is one of the Caribbean’s top luxury, all-inclusive stays, and one of its most environmentally aware. A $28 million renovation in 2010, which included the addition of 28 suites and a first-ever spa, gave it all the digital-age essentials: 42-inch flat-screen TVs, iPod docking stations, Bose sound systems, free Wi-Fi. Yet its underlying spirit of environmental responsibility, highlighted by its hawksbill sea turtle preservation program and its banishment of wheeled vehicles except for golf carts and bicycles (every room comes with two bikes), continues to reign. Rosewood manages the resort, but it belongs to an association of island homeowners, some offering their properties for rent. So if, say, a 1,346-square-foot beach-view pool suite isn’t big enough, it is possible to do as celebs such as Hillary Swank, Jim Carey, and Paul McCartney have done and plop down up to $20,000 per night for a private villa or estate home. Couples can be perfectly content here, but it is especially attractive to families, who appreciate programs like the Rose Buds kids’ club.

This hotel is on our list of The 11 Best Hotels in Chicago.

Set directly across from the Art Institute of Chicago, this former members-only men’s gymnasium is now the Chicago Athletic Association, which is part of Hyatt’s Unbound Collection. Enter at street level off Michigan Avenue and walk toward the back to find a staircase that leads to the old swimming pool, now a venue for parties and pop-up concepts. Take the nearby elevator to the restaurant, Cindy’s, easily the best rooftop scene in the city, with highly Instagrammable terrace views overlooking Millennium Park, the swooping Frank Gehry–designed bandshell, and Anish Kapoor’s Cloud Gate (aka the Bean).

Park yourself in the second-floor lobby and hang with locals as they tap away on their laptops and sip lattes by the two oversize fireplaces. Walk through that expansive by Roman & Williams–designed room, where light beams in through ornate stained-glass windows, and you enter a warren of table games and darts, all festive and typically open to the public. There’s also the secret six-seat bar, the Milk Room, a relic of Prohibition, and the James Beard Award–winning Cherry Circle Room—a sexy, dark restaurant with a circulating martini cart and a meat-centric menu.

Upstairs in the 1893 landmark, 240 guest rooms reflect the building’s former life, with gym horses as foot beds, working fireplaces in some rooms, plasterwork ceilings, ornate carved wood wainscotting, and a clubby vibe. Some of the rooms are rather small, but the location is hard to beat, and the cozy, wintry ambiance makes it a popular (and fun) place to spend a weekend. And because the CAA keeps an eye on its water conservation, sources its food locally, and adheres to strict recycling standards, eco-conscious travelers can feel good sleeping here.

The Curacao Marriott is currently closed for renovations. It is slated to reopen in late 2018.

The Curacao Marriott Beach Resort may be one of the best located hotels I’ve ever been to. Situated on a private beach in Piscadera Bay, the resort feels like the height of secluded and elegant resorts. It’s also a short three-mile drive from the capital of Curacao, Willemstad; the free shuttle delivering guests to the heart of this colorful city. Whether or not you’re looking to just lounge by the pool or get out and explore the island, the Marriott makes it easy to do it all.

Deemed the second-smallest Catholic church in the world by the Guinness Book of World Records in 1983, St. Francis by the Sea clocks in at just 1,008 square feet, with room for just 42 people at Sunday mass. While it’s certainly diminutive, it more than makes up for its size in charm. In addition to hosting regular services, the church is home to the National “Sick Call” Set Museum, which features kits from as far back as the 1880s that were used to perform last rites. In the choir loft, visitors can peruse everything from crucifixes and bowls for holy water to devotional items like statues, then head downstairs to ogle the church’s beautiful stained-glass windows and wood-beamed ceilings. Though St. Francis doesn’t hold regular hours, guests are welcome following Sunday mass or during larger Laguna Beach tours.

Since its dedication in 1959, this Byzantine-Romanesque shrine to the Virgin Mary has welcomed over one million visitors a year, among them Pope John Paul II, Pope Benedict XVI, and Mother Teresa. At more than 77,500 square feet, it is the largest Catholic church in the Western Hemisphere and the eighth-largest church in the world. Walking through the basilica, 70 ornate chapels, oratories, and sacred images like the Our Lady of Guadalupe Chapel flank the sides of the upper church and crypt, and the shrine’s gorgeous ceiling bears one of the largest and most intricate mosaic renderings of Jesus. Named “Christ in Majesty” (some have humorously nicknamed it “The Scary Christ” due to his stern look), it’s made up of over three million tiles.

The mother church of the Diocese of the Windward Islands, St. George’s Cathedral (also known as Kingstown Anglican Church) was built in 1820 on the site of an earlier church that was destroyed by a hurricane in the late 1700s. It’s the biggest church on the island and features a number of unique adornments, from a gilded wood chandelier to a brass lectern and a circular mahogany pulpit. It’s also home to a stained-glass window gifted by Queen Victoria. As the story goes, the queen initially commissioned the window for St. Paul’s Cathedral in honor of her first grandson but was horrified by the angel’s red robe and immediately sent the window abroad to St. Vincent.

Ferries between St. Vincent and Bequia run frequently, all day and evening. The one-way trip takes about an hour, and the fare is about $10 each way or $17 round-trip. En route, passengers have breathtaking views in all directions, including volcanic St. Vincent and Kingstown Harbour, Young Island, Mustique and Canouan in the distance, and Bequia’s lovely Port Elizabeth. Once on Bequia, take an island tour, have lunch, go for a swim, or explore Port Elizabeth before heading back to St. Vincent at sunset. If you’re traveling in the other direction, spend the day on St. Vincent walking around historic Kingstown, touring the Botanical Gardens, or hiking the Vermont Nature Trail.

Casa Morada’s dressed-down modern coastal style reflects a love of the ocean, island plant life, and luxurious comforts. The 16-suite boutique hotel—once a 1950s roadside motel—underwent an extensive renovation in the early 2000s that transformed it into one of the Key’s sexiest spots. The Raymond Jungles–designed gardens are lush, the outdoors showers and jacuzzis are impossibly romantic, and the resort’s private island features a freshwater pool. If you can rouse yourself for anything other than relaxing by the water, try your hand at a game of bocce, snorkle around the only living coral reef in North America, go on a sunset sail, or charter a boat tour with local resident Captain Bill to visit the Mangrove Islands or Three Sisters Bird Rookery. Pro Tip: Morning yoga classes are offered every Wednesday, Saturday, and Sunday at 9, but guests can book a private session anytime.

Once summer has arrived in all her glory, city folk yearn to escape the concrete jungle. The cheap and chic solution for locals is to pack a picnic and head for a beach day on the Toronto Islands, just a short ferry ride away. Of the three primary islands, all of which are connected by paths and bridges, Centre Island boasts the highest number of visitors; people head straight to its main strip to get to the beach and the amusement park. Ward’s Island offers more charm: In addition to the sandy shore, there are small summer cottages and gardens. Those intent on exercise can rent bicycles or paddleboats.

Wherever your travels may take you around the world whenever you ever see anyone sporting this distinct hook bracelet, you’ll know they possess a special place in their heart occupied by the island of St. Croix. There are many, many imitations and evolutions of the Crucian hook bracelet (some better than others), but this is the original and, in my opinion, only truly authentic version. Pick one up and Sonya’s, wear it wherever you go and you’ll be surprised how many new friends you make.

At Lizard Island, luxurious amenities meet an ecologically diverse island paradise. The sole resort on the island, the exclusive spot features 40 rooms as well as 24 private beaches, all but guaranteeing your own pristine sliver of paradise. Accommodations range from posh villas set apart from one another (including the two-bedroom, cliff-top villa, with its 26-foot pool and endless views of the Coral Sea), to garden-view rooms with private terraces and pathways leading directly to Anchor Bay beach. Furnishings follow a tranquil white-and-gray color scheme, while amenities include LCD smart TVs and Apple docking stations. Guests also receive their own motorized dinghy, standup paddleboards, clear-view sea kayaks, and snorkeling gear for exploring Giant Clam gardens and the schools of brightly colored fish in the surrounding waters. The more adventurous can even arrange for private deep-sea dives to locations accessed exclusively by the Lizard Island Marine & Dive team, ensuring you’ll have the coral reefs all to yourself.

Esperanza is located on the southern side of Vieques island with a laid-back vibe reminiscent of Key West. This small town has an main street that runs parallel to the ocean called “El Malecón” that is dotted with friendly guest houses, funky bars and even gourmet restaurants. It makes a great base for exploring the island’s treasures: it’s walking distance to Playa Esperanza and Sun Bay and only a 10-20 minute drive to the secluded beaches in the wildlife refuge.

Dining in a beach chair—or at least a chair by the beach—is an essential part of the experience at Spice Mill Restaurant, which looks directly across the water to St. Kitts’ sister island of Nevis. The menu here journeys across the global culinary landscape, but the fish and produce are sourced as locally as possible—including from the restaurant’s own gardens. Expect fine dining with your toes in the sand.