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Henry VIII has been an island favorite for 40 years. Not surprisingly, given its namesake, the restaurant serves some typical English dishes — bangers and mash, fish and chips — but the menu also includes some of the island’s best sushi. The food comes with ocean views that are especially spectacular at sunset. “This is my local place,” Mike says. “It’s just a two-minute drive from my house. They take good care of their guests. On Saturday nights, a DJ plays old-school music and every day there’s an awesome cross section of people here: locals, visitors, and expats. It’s a good place to dance the night away, and the sushi is off the hook.”

A miniature volcanic archipelago made up of seven idyllic islands, only two of which are inhabited, Îles des Saintes (commonly known as Les Saintes) is one of Guadeloupe’s crown jewels. This reef-hugged set of isles offers French sophistication mixed with a funky, laid-back Caribbean lifestyle. Take a day-trip via daily ferry to Terre-de-Haut, the archipelago’s main island, and enjoy the white-sand beaches, sailing, and snorkeling in the bay or head up to Fort Napoleon on foot or by rental scooter for panoramic views. Make sure to dine at one of the French and Creole bistros along the water, and to try a local tourment d’amour—a crusty-edged, soft-centered tart flavored with guava, pineapple, or coconut.

One month in Jamaica could mean four weeks of endless adventures, from beaches to museums and parties to festivals. Travel from lively Negril to lush Portland via Jamaica’s scenic north coast and fishing villages, before kicking back on the calm black sands of the south. The great thing about spending a whole month in Jamaica is that you have plenty of time to lounge on the beaches and to explore inland, so you get the best of all worlds.

Historians place the arrival of the first humans in the Hawaiian Islands on the southern side of the Big Island of Hawaii. From the Island’s South Point mooring places and petroglyphs on the volcanic lava fields, to churches and gathering places dotted throughout the historical ahupuaa (a region of land from the uplands to the sea), the Big Island is a showcase for the history of humankind in the Hawaiian islands.

At just 278 square miles, Singapore (aka Lion City) is tiny, but you’ll never run out of fun things to do. From the Singapore Zoo and its nocturnal animals to the spectacular Singapore Botanic Gardens and Gardens by the Bay, nature is always on show. But it’s well worth heading inside to the temples, churches, mosques, and museums to learn about the country’s diverse history.

There is so much to fall in love with in Providenciales, the only touristy island in the Turks and Caicos, but there are certain experiences you just must do. The Turks and Caicos are a true paradise, and Providenciales (Provo, to locals) is home to one of the world’s most stunning shorelines, the 12-mile Grace Bay Beach. Other top experiences in the Turks and Caicos include DIY snorkeling, an island fish fry, or taking a homeless “potcake” dog to the beach.

Cristina Hoyos, probably the most famous flamenco dancer of all time (her image from the 1960s is often used to represent the iconic flamenco dancer, with a slicked-back raven-black chignon and a fiercely passionate demeanor), founded this museum full of interactive exhibits. It also features a popular nightly flamenco performance. Even if you can’t make the live performance, video displays tell the story of the history and various styles of this noisy, sensual and compelling art form.

Okay, some of these restaurants are technically still in Charleston, but what they have in common is food that merits a trip outside the well-trodden tourist area. Get there however you can, but don’t miss the extraordinary things—soul food, Chinese food, barbecue, French-accented local, whatever!—being cooked up in these remarkable South Carolina kitchens.

Toast your vacation at one of Maui’s many bars, which range from dives to rooftop lounges to thatched huts serving Champagne. Soak up the sun at Hula Grill or Leilani’s on Kāʻanapali Beach, then retire to spots like the island’s oldest bar, the Pioneer Inn, or Monkeypod Kitchen, which serves cocktails by the legendary Peter Merriman, a leader of Hawaii Regional Cuisine. End the night with dancing into the wee hours at local favorite South Shore Tiki Lounge.

Given its long history—including time before records or even writing—Scotland has a wealth of fascinating sites to visit. Spread across the country, from the Borders in the south to the Shetland Islands (which are closer to Norway than to most of Britain), these must-see attractions range from standing stones and prehistoric settlements to ancient abbeys, medieval battlegrounds, and Jacobite monuments.

Croatia’s sixth-largest island—once known as Melaina Korkyra (Black Korkyra) because its vast oak forests reminded Greek settlers of Corfu—is covered in pine trees, olive groves, and vineyards. Korčula Old Town is the island’s treasured highlight and a UNESCO World Heritage Site candidate. Its stone architecture and historic ambiance reflect almost four centuries of Venetian rule, with towered gates, lion statues, magnificent palazzos, and elaborate stonework peppering the charming streets. Venturing out of the Old Town, you will encounter historic villages, picturesque bays, waterfront promenades, and welcoming locals. Korčula is one of the last places on earth where knightly games like the Moreška dances are still regularly performed and where medieval fraternities still keep up their centuries-old traditions. The island truly is a treasure trove of history, nature and serenity.

While in Cape Town, be sure to take the red bus route and head to Camps Bay Beach. Camps Bay is a beautiful spot to enjoy dinner and watch the sunset for a perfect way to end the day. Many restaurants have outdoor seating facing the beach so you can enjoy a bottle of delicious South African wine while admiring the last rays of sun in the afternoon. Camps Bay has really cool rock formations and the views of the Twelve Apostles mountain chain.

For a different stay in Cape Town, seek out boutique hotels and bed and breakfasts with exceptional hospitality. Along the coastline, you’ll find boutique lodges that feature uninterrupted views of the Atlantic Ocean. You can be sure that by the end of your stay at these hotels, the staff will know you on a first name basis.

Jamaica’s best beaches are as varied as the island is beautiful. Many of these beaches are famous and grace the glossy pages of brochures, whereas others require more work, rewarding travelers willing to search for that quiet, postcard-perfect stretch of sand. Here are our favorites, popular ones as well as insider finds, spread all across Jamaica, from the white sand of the west coast to the tranquil black shores of the south and the secluded coves of the east.

If you’re looking for accommodations that are more geared toward longer-term or family stays, check out Pan Pacific Mountainside. All 121 rooms include fully equipped kitchens—perfect for longer visits when you’ll need to cook the occasional meal for yourself. Suite sizes range from studios to two bedrooms, meaning there’s plenty of space to bring along the kids or travel in groups.