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It was raining when we arrived in Donostia-San Sebastian, but the skies cleared on our second day, and we rode the funicular railway up Mount Igueldo to take in the view back on the city, La Concha Bay, and the empty beach. The “low” travel season had just begun, and the strange little children’s amusement park on the mountaintop had shuttered up for the fall and winter, adding just the right disorienting touch of weird desolation to the Basque country panorama.

The Morada Bay Beach Cafe on the bay side of Islamorada is the perfect spot for a Keys lunch. Colorful chairs and tables dot the beach; the food is excellent and the restaurant regularly receives fantastic reviews. Try the Wagyu beef burger. It is delicious. Fresh fish and seafood are popular choices. The conch fritters and conch chowder hit the spot. The staff is very friendly, professional, and helpful. Island music or Jimmy Buffet songs waft across the beach.

From May to August, a ferry runs from the port of San Sebastián to the island that sits serenely in the middle of the Concha Bay. The island is quiet, isolated, and empty. There is a café on the island with a mysterious timetable, and a lighthouse that makes for a picturesque snapshot. Grab a loaf of bread, some cheese and ham, and settle down for a picnic and a reverse view of San Sebastián.

A belle epoque grande dame presiding over San Sebastián’s iconic La Concha Beach, the Hotel de Londres y de Inglaterra has been a palace, casino, hospital, and of course hotel since its construction in 1865. Before and after World War I, it was the kind of place where well-to-do Europeans went on seaside holidays for months at a time, enjoying direct beach access, the city’s renowned seafood, and the hotel’s elegant design. Nowadays, the society consists of a somewhat less star-studded lineup—once Toulouse-Lautrec, Archduchess Elizabeth of Austria, and Mata Hari were all guests—but the unobstructed Bahía de la Concha views, lovely rooms (all with private balconies), and pride of place at the heart of the city remain. The window-lined brasserie takes its cue from classic French bistros—it’s not hard to imagine that the well-dressed gentlemen at the next table are French aristocrats-in-exile—and its tables along the beachfront promenade are the perfect place to while away a few hours over pintxos, txakoli (a sparkling white wine from Basque Country), and people watching. If you were to spend a few months in a seaside town, this would be the way to do it.

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.

In an all-white open-air dining room that spills out onto the sand overlooking Meads Bay on Anguilla’s west end, Jacala serves just 35 guests a night. Chef Alain Laurent’s French-inspired menu includes dishes such as fennel-spiked conch chowder, snapper meunière, and a steak tartare prepared tableside upon request.

Former interior designer and gallery owner Elisabetta Capei now presides over this shop near St. Peter’s Church. It specializes in artisan handmade Swiss and Italian chocolates. Among her highlights are chocolates by Reichmuth von Reding, a little-known producer whose super-smooth, velvety-tasting bars are made with single-origin cacao beans and are conched for up to 72 hours. In the back of the shop, there’s a small counter with just eight stools for drinking Elisabetta’s hot chocolate, which she whisks herself, making just four to five liters a day.

Hemingway’s Restaurant has the best sunset views of one of the world’s most beautiful beaches, Grace Bay, from a pier-like patio. The restaurant at the Sands at Grace Bay Hotel makes blended-just-right Pina Coladas topped with an extra dollop of rum. Sip and keep watch for the resident dolphin JoJo, who has been patrolling the turquoise waters off this picture-perfect crescent of sand for more than a decade – there’s even a bell to ring if you see him, although who knows if it’s the same dolphin. After you get tipsy, order dinner. In addition to conch, the restaurant is known for steak and fresh-caught fish cooked only in olive oil. At lunch, the fish tacos are my favorite dish. There is live music twice a week.

This family-run restaurant serves up some of the best conch fritters in the Caribbean. The relaxed vibe and plastic chairs make for an unusual place for a romantic dinner, but just add a sunset and a perfectly prepared lobster, and Cow Wreck becomes the romantic setting for any BVI beach date. Also, don’t miss the chance to try their banana daiquiri!

After you’ve explored the stunning sea cliffs along Mudjin Bay, get a table on the patio of the Mudjin Bar and Grill to savor the scenery a little longer and enjoy a well-earned meal. The restaurant is part of the Dragon Cay Resort and open every day for lunch and dinner. The menu shows off local flavors such as fried local lobster and conch fritters, along with burgers and chicken wings, but it’s the view overlooking the stunning Middle Caicos coastline that steals the show. (Dinner service requires reservations.)

It’s all about the fruits of the sea at the Old Fisherman, a local favorite in the center of town. Although the decor is nautical and the dishes are named for seafaring icons, the atmosphere isn’t exactly what you’d expect on vacation. No matter, you—and the locals who pack the place at lunchtime—came for the food anyway. Among the must-try dishes are the Charlie Brouns (fried fish roe in garlic sauce), Juan Henriquez (grilled catch of the day in a mango-coconut-wine reduction), and the Jan Semeleer (conch). Pair your order with an ice-cold Balashi (the local beer) or non-alcoholic awa di lamoenchi (house-made lemonade).

Dasheene, the restaurant in the award-winning Ladera Resort, is a magical place unlike any other on the island. The open dining room, overlooking the sea, is so close to the Pitons that you feel as if you could reach out and touch the peaks. The menu, which focuses on ingredients sourced from local farms and plantations, puts a creative spin on classic St. Lucian cuisine, including plantain gratin with a coconut rum sauce, and roast conch. The restaurant is open for breakfast and lunch as well, but there’s no beating the romantic atmosphere and sunset views at dinner, which make a meal here well worth the high price.

One of the most beautiful bits of Bimini are the mangrove forests – yet this unique eco-system rarely gets the attention it deserves. Bimini’s mangroves are home to many important island species, including lobster, conch, sharks, the Bimini Boa, and the critically endangered smalltooth sawfish. This delicate system is seriously threatened by development – an important marine reserve may soon be leased out to hotel developers, who would destroy much of what little mangrove remains. Often, one first-hand experience is enough to show visitors that change is needed. You can support the health of the mangroves by choosing a low-impact tour with a local guide or kayak or paddle board adventure to explore the mangroves – local guide Strata G Smith (as well as Ebbie David and Ansil Saunders) can combine mangrove visits with charter tours (depending on tides and boat size). Photo courtesy Kathleen Fisher/Bimini Healing Arts

With its striking white facades and terra-cotta rooftops, you might mistake Cap Maison for a Mediterranean villa on the Costa Brava. However, this all-inclusive resort set on a former sugar plantation on St. Lucia’s north coast offers more than meets the eye. The pastel-hued interiors are matched by the sunny dispositions of the superb staff, who cater to every request, whether it’s finding a shady spot by the terraced pool area, booking a paddleboarding excursion off the private beach on Smuggler’s Cove, or arranging for the house yacht to take you to the neighboring island of Martinique for the day. Don’t miss the sunset views at the Cliff at Cap restaurant, where locally sourced dishes like reef conch ceviche and passion fruit soufflé are topped off with some of the resort’s house-made rum.

A 19th-century private estate just outside San Sebastián’s city center, Villa Soro was commissioned by a wealthy businessman as a wedding gift for his daughter; it was designed by the same architect who built the iconic Hotel de Londres y de Inglaterra, which towers over the La Concha waterfront at the city center. In contrast to that classic belle epoque building, the villa takes its inspiration from English architecture—complete with peaked roofs and faux-Tudor beaming—that was in vogue at the time, while the manicured gardens were designed by renowned Romantic landscape designer Pierre Ducasse.

Now an intimate, 25-room boutique hotel, Villa Soro maintains the same relaxed, cozy atmosphere one might expect to find at a friend’s estate, complete with two elegant drawing rooms outfitted with armchairs that beg to be curled up in with a book. The dark-wood-and-leather bar room (complete with a fireplace, of course) beckons visitors with vermouth and txakoli. Rooms are homey and classically elegant, spread between the main house and the restored carriage house, and they make for a romantic retreat within walking distance of the city’s sights and Michelin-starred restaurants.