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One of the best spots in the Caribbean for surfing is Barbados. And if you’re not one of the best surfers in the world (like me), one of the best breaks on the island to catch some waves has got to be Freights Bay. The added bonus is that most late afternoon sessions end with a spectacular flourish as the sun sets smack in the middle of the bay.

I was on a cruise in Italy when I heard about this place. I’d mentioned that I was heading to Portland, and a fellow cruiser, a native of the town, had told me that if they had one recommendation it would be the ice cream at Salt and Straw.

What she didn’t tell me was that the flavors are not your usual vanilla, chocolate, and raspberry ripple. In fact, the first thing I tasted at Salt and Straw was their new “Bollywood” recipe, which included carrot custard and cardamom, which sounds almost sensible when you considered that some of their most popular flavors include prosciutto and goat cheese.

There was a huge line, even on a Friday mid-afternoon, but it was worth it for the almond brittle with salted ganache, not to mention the apple pie with real chunks of cheddar cheese. They’re doing their best to “Keep Portland Weird” here...and it tastes good.

A trip to the original Magic Kingdom Park in Orlando is a theme park rite of passage. This is the mouse’s original outpost. And if you hit only one theme park among Orlando’s vast amusement offerings, you won’t go wrong here. Home to such iconic attractions as the original Cinderella’s Castle, the Space Mountain roller coaster ride, the nightly parade down Main Street, It’s a Small World kids’ ride, Big Thunder Mountain Railroad, and much, much more, you can easily occupy two days taking it all in. And while many of the rides and character meet and greets (every princess and her cousin is in attendance here) are clearly oriented toward younger visitors, there’s enough to keep adults smiling, too. Favorite tamer rides for younger kids include Adventure Land’s Pirates of the Caribbean and the Jungle Cruise. And if you’ve still got some staying power after a whole day of rides and shows, stick around for the park’s nightly grand finale—a fireworks display on par with anything you’d see in a big city on the Fourth of July.

Nestled within Positano’s hillside tangle of pastel residences and stepped alleys, Le Sirenuse is a legendary boutique hotel that feels more like a private home. Run by the Sersale family since its opening in 1951, the crimson-hued house is filled with antiques, potted plants, and oil paintings that lend it a friendly atmosphere devoid of any snootiness. White-walled guest rooms are accented with Vietri floor tiles and heirloom walnut furniture, while marble bathrooms have whirlpool tubs and Eau d’Italie toiletries, the hotel’s bespoke line. Dining is excellent: The Michelin-starred La Sponda restaurant is as tasty as it is charming, illuminated in the evening entirely by candlelight. There’s also a champagne and oyster bar that commands dazzling views from a panoramic terrace; the vistas are no less stunning from the pool deck, where potted lemon trees scent the air. The hotel also has a top-notch spa, plus fun perks such as free daily excursions on its vintage wooden boat.

Located on the north coast of Isla Robinson Crusoe, Cumberland Bay sits in the shadow of the volcanic peaks that form the spine of the island. Along the bay is the island’s only settlement, San Juan Bautista, a quiet town of fishermen living in modest homes. Below the sea here is an artifact of a moment when the island played a brief part on the global stage. The German SMS Dresden was launched in 1908 and took part in the Battle of the Falkland Islands in December 1914, during World War I. The ship then sought a safe harbor on Isla Robinson Crusoe, as Chile was neutral in the war. British ships, ignoring Chile’s neutrality, attacked the Dresden and its captain intentionally sunk the ship. It remains to this day resting on the bottom of Cumberland Bay.

This mirador, or viewpoint, is worth the climb for its unparalleled 360-degree views of the entire city, the Mediterranean Sea, and the rolling green hills of Collserola. Located some 900 feet above sea level, the hilltop was considered a strategic spot for defending Barcelona from bombings during the Spanish Civil War; anti-aircraft batteries and gunner bunkers were built here for this purpose. After the war, there was a desperate lack of housing, and the abandoned military structures were incorporated into a shantytown. Remarkably, people lived here until 1990, when the city took it over and turned it into a heritage site, complete with illuminating photographs and signage detailing the history of this unique place.

Surrounded by 40 pristine sand- and grass-topped acres, endless water views, and the sound of crashing waves, Bekal Fort—the largest fort in Kerala—feels like it rose up from the sea. In fact, it was built some three centuries ago as a defense post, lingering evidence of which includes the old ammunition storage areas and the cannon windows lining the outer walls. Today, visitors can wander around the complex, climbing up the observation tower, strolling around parts of the original walls, venturing out to the waterside walkways, and picnicking on the main lawns. (Along with the history and scenic beauty, the filming of some hit movies here has made the fort even more popular with domestic tourists.) After exploring the site, head down to the beach for some sea air and views of the fort from a different vantage point.

With its leafy side streets, must-browse boutiques, and burgeoning food scene, Gueliz is quickly resembling pockets of Paris, particularly as more and more bistro-inspired places open their doors. Le Petit Cornichon is like a breath of spring with its splashy Majorelle blue and daffodil yellow color palette, floor-to-ceiling windows that look out onto the street, and animated atmosphere. Toward the end of the week, you’ll find half of Marrakech here indulging in a laid-back lunch before heading down to the beach at Essaouira for the weekend, but it’s a lovely place for a prix fixe lunch any old time and a good value to boot: two courses for $17, three for $21. Settle in to peruse an excellent wine list before tucking into dishes such as sea bass ceviche with grapefruit and pink peppercorns, tarragon chicken, and a sliver of wickedly rich chocolate tart.

The isolated, car-free island of Käringön is a 40-minute ferry ride from Orust, and has less than 100 full-time residents who stay year round, even through the long winter. But it’s a different story in the summer. In the 19th century, the middle classes in Sweden became enamored with the benefits of fresh sea air and started flocking to the small islands along the coast. Today about a thousand visitors arrive daily by ferry or private boat to enjoy the island’s relaxed vibe. Come for a lunch of fresh-caught seafood at Petersons Krog or watch children on the pier trying to catch the little crabs crawling through the seaweed down below. In the cold weather, visitors can take a lobster fishing tour or sample fresh oysters at the Käringö oyster bar, which also has a hot tub that seats six.

Just southwest of Astoria, Fort Clatsop replicates the encampment built by Lewis and Clark’s Corps of Discovery soon after they reached the Pacific. From December 1805 to March 1806, they hunted and gathered food, distilled salt, traded with the local tribes and documented their surroundings. The center includes the log fort (staffed by costumed rangers), an exhibit hall, a gift shop and films, plus trailheads for the Fort to Sea Trail and the Netul River Trail.

Housed on a 1,100-foot stretch of beachfront, Grace Bay Club is as stylishly current as it was in 1993, when it became the first luxury hotel to open on the then nearly empty sands of Grace Bay. From its original 21 rooms, the upscale property has grown to 82 suites, each of which features ocean views, a private veranda or patio, and chic interiors by renowned designer Thom Felicia. Guests can also look forward to superior service, including a personal concierge available day or night via a provided cell phone.

When hunger strikes, there’s the oceanfront Infiniti Restaurant & Raw Bar, which boasts sea-to-table fare and the longest bar in the Caribbean, as well as several other family-friendly venues, including The Grill. If it’s pampering you seek, make time to visit the spacious Anani Spa, where you’ll find six treatment rooms, including one just for couples. A spa tent is also available for beachfront massages.

Old San Juan offers historically and culturally significant experiences including a walk through 500-year-old forts, visits to UNESCO sites, historic churches, museums, the second oldest cathedral in the Americas and Ponce de Leon’s mansion. Cobblestone streets and pastel buildings are perfect for exploration during the day and variety of restaurants and shops make for a complementary evening.

Built in the 1930s as a private villa, this boutique hotel was renovated in 2012, but still makes guests feel as if they’re staying in someone’s home. Perched on a steep hillside across the bay from the Old Town, it features stone terraces, vine-covered pergolas, and colorful gardens, all of which offer breathtaking vistas of the Adriatic and Dubrovnik’s signature tiled roofs. The 13 rooms—all but one with sea views—have high ceilings and arched windows lined with white shutters to soften the afternoon sun, while modern bathrooms come stocked with plush bathrobes and decadent Bulgari amenities. When not enjoying their daily delivery of fresh fruit or cookies, guests can head to the bathing platform at the bottom of the stone stairs, the outdoor pool at the neighboring Grand Villa Argentina, or the spa at the Hotel Excelsior.

A rocky, reptilianlike spine runs through the center of Hong Kong Island, and there are some 30 miles of hiking trails spreading over it like arteries, offering visitors exercise along with excellent sightseeing. One of the most popular sections is the three-mile Dragon’s Back trek that follows the undulating ridge on the southern end of Hong Kong Island, between Wan Cham Shan and Shek O Peak. The walk isn’t strenuous, but the views may take your breath away. All along the way, soak up panoramas of the island and the sea. The entrance to the hike is on Shek O Road near To Tei Wan village, and the trek should take about 4-5 hours.

Although Chile’s central coastline boasts a string of attractive beaches along with towns filled with visitors seeking relief from the heat, the truth is the water is freezing cold year-round due to the Humboldt Current that brings Antarctic water up the coast. You’ve got to go pretty far north to find temperate seas. Bahía Inglesa is a stretch of coastline where the turquoise waters are tranquil, the sand is white, and there are dozens of beaches—some are along waveless bays (perfect for children), and others are great for scuba diving, kayaking, and kitesurfing. The area has restaurants for all tastes, and while there are lots of lodgings, in summer crowds flock in, so reserve as early as possible.