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A Carib chief and national hero, Joseph Chatoyer led revolts against British colonists in 1772 and again in 1795. During the latter revolt, his soldiers and their French allies were planning to attack Kingstown from Dorsetshire Hill, but British soldiers marched up from the city and attacked first, killing Chatoyer. Today, he’s memorialized in a monument on that very hill, overlooking the city he fought so hard to regain.

The smallest holding in the mini-empire of Uri Jeremias, who also owns Akko’s Uri Buri restaurant and Efendi Hotel, this bright and no-frills ice cream shop sits along the old city’s western seafront. These are natural treats, made using local dairy products and no powders or stabilizers. The result is smooth and creamy, and the flavors (up to 16 available at a given time) are ones you won’t find too many other parts of the world, such as date, halva, cardamom, and rose.

Bookstore Bar & Café combines two of life’s great pleasures: books and booze. This hotel bar focuses on scotch and whiskey (over 130 varieties), though they also serve up carefully made craft cocktails; we liked the the Rum Daisy (light rum, lemon, house-made grenadine). At happy hour, you can nibble on small plates with charcuterie, cheese, or fried padron peppers, too. And if you see a book you like, they’re all for sale.

A tiny, man-made island in Clifton Harbour built with discarded conch shells, Happy Island is really just a small bar where you can tie up for a while and have a drink, a meal, and a conversation with Janti Ramage, the island’s joyful builder, owner, and operator. Just be sure to call ahead, as Ramage keeps flexible hours.

Mustique’s tiny village center is home to a handful of shops but it’s the pair of pastel, gingerbread-trimmed houses that will certainly catch your eye. Pink House specializes in elegant, hand-painted silk kaftans and sarongs from local designer Lotty B, along with beach and resort wear for women, men, and kids; jewelry and accessories; and tableware. Next door, Purple House offers less expensive kaftans, beachwear, kid toys, souvenirs, and jewelry.

On the leeward side of Union Island, remote Chatham Bay Beach—one of a dozen on the island—is a favorite anchorage for boaters, a peaceful spot for sunbathers, and a great location for snorkelers. If you’re coming by land, there’s a trail that leads right down to the beach. There’s also a bar and a couple nearby restaurants should you get hungry from all that relaxing.

A 100-foot schooner based in Bequia, The Friendship Rose takes passengers on daylong cruises to Tobago Cays for snorkeling and swimming with sea turtles, or Mustique for beaching, bar hopping, and relaxing. Excursions include breakfast, lunch, afternoon tea, and drinks throughout the day, including beer, fruit punch, and soft drinks. Whether you opt for the marine park or the private island, the entire family is sure to enjoy the experience.

The Bahamas has many attractions to choose from but if you’re looking for a memorable and exciting excursion then this experience is right for you. Arrange to be picked up either from the port or from any hotel on paradise island. The stables are about a 25 minute drive from downtown Nassau. Whether you’re a novice or an expert at horseback riding, Duke, The trainer at Happy Trails Stables, is very experienced and will teach anyone how to ride a horse the English style. Horses are assigned to you based on your riding experience. (This helps to ensure safety.) Your adventure begins at the stable where Duke will escort you and fellow riders to Coral Harbour Beach. Along your journey you will see breathtaking views of natural unused beaches while you and your horse splash around in the water to cool off. The setting is very intimate since there’s only about 6 horses available for riding. This experience will surely stick with you for a lifetime.

Muntri Mews in Penang is my kind of hotel. Formerly an old mews house, its owners have fitted it out with clean, comfortable rooms that retain the charm of their days as stables (think romantic mosquito nets and wooden beam architectural details). The hotel is small and the service is personal and friendly. Breakfast on the hotel’s patio in the heart of historic Georgetown is the perfect way to start a day of meandering through the back streets of this historic, character-filled foodie heaven.

North of Buccament Bay, a turnoff leads to Layou Petroglyph Park, where you’ll find Amerindian writings (or petroglyphs) scrawled on the side of a large boulder. The meaning of the carvings is unknown, but historians estimate that they date as far back as 300 to 600 B.C.E. Lush vegetation grows in the surrounding ridges, making for a fun area to explore. There’s also a small pool where you can take a dip to cool down.

If you weren’t sure what you were looking for, you might miss Marco Stabile’s Ora d’Aria restaurant on Via dei Georgofili. The hint of a large birdcage peeking through a tall window in an expansive and otherwise-unadorned wall is all that alerts you to the presence of greatness. White Saarinen tulip chairs are the next thing you see once you’ve decided to explore past the birdcage, and while the dining rooms, both upstairs and down, are not elaborate, they are perfectly suited to let Chef Stabile’s food be the true showpiece. Though his cuisine is not traditionally Tuscan, and nor are all of his ingredients, Stabile’s culinary creations are a delight, finally winning over the hearts of food-savvy Florence residents and every visitor who learns that a meal at Ora d’Aria is a must when in the Tuscan capital. If you’re looking to save a little while still experiencing excellence, Ora d’Aria is also open for lunch.

With just over a year in business, Green Dot Stables is still new, but owner Jacques and his wife took over a building in Corktown that isn’t. Instead, they took it from abandoned and historical to historical but fresh. The interior still retains its ode to horse racing and is kitschy appeal without being cheesy. An innovative new menu presided over by Les Molnar features more than 20 unusual and classic sliders with a “mystery meat” option that changes often. On the day I visited, the special was Lamb Tongue with Dijon Brown Butter and Fennel Relish. My favorite was the Corned Beef Slider with Wigley’s-Brinery Kraut, Pickle and Mustard Aioli. Local and imported beers anchor the drink list and their soda (or pop as it is known in the Midwest) is mixed in-house with locally made syrup. Optional sides include truffle fries, poutine, chicken and orzo salad, kale & quinoa, or classic mac ‘n’ cheese. Menus items start at an affordable $2 and it is a packed house during the lunch rush so plan accordingly or visit at odd hours to ensure fast service.

One look at this hilltop fort, perched over the Port of Kingstown, and you know the British built it to fight the locals rather than to meet any threats coming by sea—all the cannons face the island’s rugged interior, where the Caribs lived. Inside the fort, you’ll find a series of murals depicting the bloody Carib wars. Kids will love exploring the old buildings, and everyone will enjoy the views.

Between 1812 and 1815, the British ordered the construction of 300-foot-long Jasper Rock Tunnel (more commonly known as Black Point Tunnel) to provide better access from the cane field to the sugar factory to the ships for export. Slaves were responsible for the actual building, manually cutting through the mountain with shovels, picks, and sledgehammers. Now part of the Black Point Historic and Recreation Park, the tunnel also served as the site for several scenes in the first Pirates of the Caribbean movie.

In partnership with the Four Seasons Rancho Encantado, the new groundbreaking equestrian program EQUUS practices a decade-old field known as equine integrated learning. The theory is that, as our animal companions since ancient time, horses can teach us about us—participants spend quiet time moving among horses in a corral, interacting with them, and reacting to them, and, through this, learn about nonverbal communication and setting boundaries, thus gaining confidence, inspiration, and strength. At these stables in the foothills of the Sangre de Cristo Mountains, guests harness the power of the herd to gain (often very emotional) insights into themselves.