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High above English Harbour in Nelson’s Dockyard National Park sits the Blockhouse, a brick ruin. On a perch overlooking the southeastern coast of Antigua, the circa-1787 site encompasses an officer’s quarters and those of servants, as well as stables. An ammunition-storage space, a catchment and a cistern have been restored in recent years.

If the horse races at Cagnes sur Mer aren’t hands-on enough for you, get up on that horse yourself. Les 3 Fers, an equestrian club in St. Raphaël, offers a trip that takes riders of all levels along the sea cliffs, as well as one on the beach. For more advanced riders, Les Ferrières follows a trail to an archaeological ruin through a forest, and longer trips lead riders through the Vars region of the Alps.

Originally a sweet shop, Sénéquier first gained fame in the 1800s for its soft nougat. Then its candied fruits became the rage. The St. Tropez shop has since turned into a chic café by a Parisian restaurateur and now attracts yacht owners and affluent locals who come down to the waterfront from the hills above town, all of them happy to pay a pretty price for a king crab salad or the perfect sole meunière. More modest locals know the place as a good spot for a cool rosé on a hot afternoon as they watch the world go by.

You’ll recognize this setting as one that appears in some of the most iconic Amalfi Coast photos. The villa’s riotous beds of pansies and garden walls covered with vibrant bougainvillea are as jaw-dropping in real life. One section of the gardens dates back to the 13th century, but only traces of the medieval part remains. Most of the space is dedicated to a Romantic era–style garden that was designed by Francis Nevile Reid, a wealthy Scottish expat who owned and restored the villa in the late-19th century. In addition to touring the gardens, a small museum on the grounds with a cloister and tower is worth visiting. From June through September every year, the Ravello Festival is held here.

Centuries-old catacombs decorated with human bones pepper the crypts at this Franciscan monastery dating to 1774. Decked out in impressive Spanish Baroque architecture, the canary-yellow church and monastery also house a remarkable library with some 25,000 antique texts (some predating the Spanish Conquest) and are flush with romantic courtyards and cloisters. Don’t forget to look up: A magnificent Moorish-style cupola, carved of Nicaraguan cedar in 1625, oversees the main staircase.

Generally speaking, shopping isn’t a big draw on St. Vincent, but if you’re searching for the perfect souvenir, you can’t do better than Nzimbu Browne’s famous banana art. Besides tourism, banana production is a driving force behind St. Vincent’s economy. By using the industry’s waste products—the banana leaves—Browne creates sustainable art with a strong sense of place. His works depict local scenes, brought to life with snippets of dried, multicolored leaves. If you’re not into art, he also makes goat-skin drums and tie-dye clothing. His studio is located on McKie’s Hill in Kingstown, but he often sets up shop in front of the Cobblestone Inn on Upper Bay Street.

Boat-building as an industry has existed on Bequia as far back as the 1800s. At one point, the island was even known as the “boat-building capital of the West Indies,” having produced the largest wooden vessel in the region. While construction has slowed over time, it still occurs—albeit on a much smaller scale—at places like Sargeant Brothers Model Boat Shop, just up the road from the ferry landing in Port Elizabeth, where Benson Phillips and other craftsmen make and sell their models. Handcrafted using hand planes, chisels, and carving knives, their boats are incredibly detailed and realistic. Choose from whale boats, sailboats, power boats, and wooden schooners, or commission Phillips to build a custom model of your own yacht. The simplest models take about a week to make, but there are always a few boats available for immediate sale, ranging in price from around $250 all the way up to $7,000.

Around since 1765, the St. Vincent Botanical Gardens claims to be the oldest of its kind in the Western Hemisphere. Tour the gardens with an informative guide, who will point out all the native and exotic plants growing here, including a breadfruit tree descended from the one Captain Bligh brought to St. Vincent in 1793. In the aviary, you’ll also be able to catch a glimpse of the colorful St. Vincent parrot—the island’s national bird.

Set on St. Lucia’s westerly Anse Cochon beach, Ti Kaye is a secluded, adults-only oasis that feels worlds away from the rest of the island. Each of the 33 cliffside, gingerbread-style houses feature outdoor showers and verandas with double-wide hammocks, and some even include plunge pools. Since there are no TVs, the focus remains squarely on the picturesque beach, home to a PADI diving center, crashing waves, and breathtaking sunsets. The same is true in the resort’s two open-air restaurants (don’t miss the banana pancakes at the beachfront grill) and treetop spa. Rum connoisseurs can schedule a tasting in Ti Kaye’s wine cave, but if you crave a rowdier scene after all the relaxation, know that it’s a 20-minute drive to the nearest fishing village—you’ll want to make the trek on Friday nights though, when Anse La Raye hosts its weekly street parties.

Chef Chuck Hughes’ first flagship restaurant remains one of the best good-time spots in Old Montreal, featuring a blackboard menu full of seasonal dishes and insane cocktails. The Caesar is a must-try and comes with a salad’s worth of vegetables and a whole snow-crab leg sticking out of a monster mug. After feasting on lobster salad, short ribs with cauliflower mash, or pan-fried sea scallops with carrot butter, hang out in this dimly lit joint and watch the night turn into a party, with the drinks flowing and the music thumping louder and louder as the cooks and waiters from nearby restaurants file in after their shifts.

To me, no other place in Montréal represents the city better than Place d’Armes. After all, it is the second oldest public site in the city, and its center is home to a statue of Paul de Chomedey, the founder of Montréal. And the varied architectural styles surround the square in a way that clearly demonstrates just how old and historic Montréal is. A blend of Gothic Revival, classic Art Deco, and ultra-modern sleek skyscrapers illustrates the major periods of Montréal’s development. It’s definitely a great place to start or end an Old Montreal exploratory tour, or to stop and people watch!

Perched high above the sea on the east coast of St. Kitts is Brimstone Hill, a massive stone fortress built by African slaves for the British during the 17th and 18th centuries. Now a UNESCO World Heritage Site, the military stronghold, which took 100 years to complete, is considered one of the best-preserved fortifications in the region. From the top, you can see six neighboring islands on a clear day.

Independence Square lies at the busy center of St. Kitts’ capital city, Basseterre. Known as Pall Mall Square prior to the island’s independence in 1983, it’s always been the center of commerce—albeit a darker business in years past. A careful look at the surrounding historic buildings reveals places where slaves were held prior to being auctioned off in the square. Today, however, an ornate fountain stands at the center of the park, and the grassy areas play host to parties and public gatherings.

Château de Montaigne is worth a detour, especially if you need a little break from the wine tastings, that Bordeaux is so known for. The 14th century castle is nestled deep in the countryside near Bergerac and Saint-Émilion and was once the residence of Michel de Montaigne, one of France’s most important, early philosophers. If you haven’t heard of him, he is the one you may (or may not) thank for making essays popular as a literary genre.

After arriving on the tiny island of Iona near Mull in 563, Irish pilgrim Saint Columba proceeded to establish a Christian church and monastery, creating a vibrant religious community that lives on to this day. The monastery survived until the 12th century despite repeated Viking raids, and around 1200, the sons of Somerled founded a Benedictine abbey on the site. Though monastic life ended on Iona with the Protestant Reformation of 1560, pilgrimages to St Columba’s Shrine continued for many years. Today, it’s believed that the Book of Kells, along with several other great works of art, was created here.

Visit this most sacred of Scottish sights to see the four iconic high crosses, then tour the abbey church, with its 13th- to 16th-century architecture. You can also stop by St Columba’s Shrine, the longest-standing structure in the abbey, dating to the 9th or 10th century; climb Tòrr an Aba, a hill above the abbey where Saint Columba is said to have had a writing hut; or walk through Reilig Odhráin, the graveyard where ancient Scottish kings were laid to rest. While you’re exploring, keep an eye out for the vallum—a boundary ditch and bank of earth that serves as the only evidence of Columba’s original monastery.