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Deep within Grand Cayman, one finds another restaurant on the water. Be careful not to sit too close to the edge on the deck, however, the breeze might blow you right off. Inside the restaurant is a different story. All the tables and chairs are close together, making your dining experience intimate yet open to that of your neighbor and you can’t help smiling at those sitting next to you. Written on a savvy chalkboard one finds the specials of the day, of which you will find rarities like chicken liver pate and ceviche. The food is fantastic and the drinks are phenomenal. I personally recommend anything with mango in it. Once you’re good and full it almost feels necessary to sit and talk with the wait staff before leaving. The close knit environment makes it all the more friendly. Calypso Grill is definitely one of my favorite restaurants in Grand Cayman and I definitely recommend it to seafood lovers or just food lovers in general.

Located down on the harbor and hidden inside the chic Reykjavik Hotel Marina, this vintage-cool bar is run by master mixologists who create dapper cocktails from fresh, local ingredients and house-made syrups. Behind the handsome wooden bar there are also several types of beer (including Icelandic brews) on tap, a bunch of wines, and a wide choice of liquor—including ten different types of rum. The food menu is pretty good too, with steaks, fish, lamb, and vegetarian options.

Located in the charming harbor town of Portpatrick, Campbell’s is the perfect combination of welcoming informality and smart professionalism—with views of pleasure crafts and fishing boats, to boot. The best dishes highlight the fruits of the sea, whether it’s grilled langoustines or poached halibut, but also worth trying are the Thai green curry, the surf-and-turf with Galloway beef, and desserts like chocolate marquise and crème brûlée. Most ingredients come from the nearby coastline and surrounding farms, and bread is made daily on the premises. There’s also a decent wine list for pairing with your meal. Designed to mimic the seaside, the dining room is done up in shades of green, blue, and gold, with fresh flowers, candles, elegant glassware, and rustic cutlery lending the restaurant a homey yet elegant feel.

Take a 70-minute guided train tour of Ålesund that includes spectacular views from Mount Aksla and Borgund Fjord near Ålesund’s harbor. Other sites include the Molja Lighthouse (Norway’s oldest lighthouse, built in 1858), the Color Line Stadium, the historic Ålesund Church and a trip across the Hellebroa Bridge that connects the islands of Nørvøya (which includes the city center of Ålesund) and Aspøya. Tours are offered in English (as well as Dutch, French, German, Italian, Norwegian, Russian and Spanish) and include free Wi-Fi.

The past two decades have seen the dozens of islands scattered across Boston Harbor transformed from barely noticed dots on the horizon to one of the city’s most popular attractions. The Boston Harbor Island National Recreation Area, established in 1996, has propelled them into prominence, with ferries carrying day-trippers and overnight campers from downtown Boston, Hingham, and Hull to eight of the islands (19 more are accessible by private boat or charter excursions). Most visitors head to Georges Island, home of the Civil War–era Fort Warren, or the beaches and hiking trails of Spectacle Island, the one closest to downtown Boston. (Don’t skip the concession stands here: The food is from James Beard Award–winning Boston chef Barbara Lynch.) You can also camp on Peddocks, Grape, and Bumpkin islands, or take a tour to Little Brewster Island to witness the 300-year-old Boston Light, the nation’s oldest lighthouse.

You can easily spend an entire day exploring the various attractions at this vast ocean-themed casino resort, which sits just over Nassau’s harbor bridge on Paradise Island. Purchasing a day pass to the property lets you access, for instance, its gigantic aquarium and marine habitat; shallow-water swims with sea creatures at Dolphin Cay; and a 57-hectare (141-acre) water park, which includes wave pools, swimming areas and—most famously—a six-story waterslide that plunges you into a lagoon seemingly filled with sharks (actually a glass-bottomed pool where sharks swim underneath).

Located on Sullivan’s Island, Fort Moultrie was a key defensive position in controlling Charleston Harbor during the Revolutionary War. In June 1776, the Royal Navy of Britain attacked what was then called Fort Sullivan, firing cannonballs directly into its walls. Colonel William Moultrie and his patriot regime were able to hold the British off, however, since the walls were constructed from the soft trunks of the island’s palmetto tree and could absorb the cannonballs rather than break apart. Eventually renamed for Moultrie, the fort was rebuilt in 1798, then “modernized” in 1870 to include two massive cannons that still stand today. Dive deep into the history at the National Park Service’s museum before touring the armaments and taking in the unparalleled views of Charleston Harbor and the Atlantic Ocean.

Chef Drew Hedlund combines classic and contemporary Southern fare here in a retired 1940s naval building on the east side of the Charleston peninsula. Long used for storage by the South Carolina Port Authority, today it’s home to one of the city’s most popular waterfront restaurants, with incomparable views of the harbor. Some highlights of the menu include crispy whole flounder with apricot glaze, Charleston shrimp and grits, crab cakes, Lowcountry boil and lump crab bruschetta.

Montevideo’s Ciudad Vieja, or Old Town, is located on a peninsula separating the Río de la Plata from the harbor. It has the orderly grid typical of many Spanish cities in the New World. Until 1829, the Ciudad Vieja was walled though today only one gate (the Puerta de la Ciudadela) remains of those defenses. This section of Montevideo is home to many of the city’s most famous historic buildings, including the cathedral and the Cabildo, which today houses the city’s archives.

The edges of the iceberg (technically, bergy bits) are a great place for animal sightings. Harbor seals ride the floes, basking in the sun; orca whales prowl just around the ice barrier, waiting for an unwary seal to come out to where the whales’ sonar can reach. Humpbacks feed off krill upwellings, and bald eagles are as common as sparrows. Those who are very lucky (and who have good spotting scopes) can see mountain goats on occasion. They’re a wonder in the wild: How does a goat get up 3,200 meters of rock?

Located in the heart of Bridgehampton, Topping Rose House occupies a grand old Greek Revival mansion, built back in 1842 for a local judge. The luxurious property features 22 guestrooms, including a number of cottages, with elegant décor like four-poster beds and glass doors that open onto verdant grounds. Also on site is a Jean-Georges Vongerichten restaurant, complete with a seasonal menu that incorporates ingredients from the property’s one-acre farm. Unusual for a small Hamptons hotel, Topping Rose offers a wide selection of amenities, including a lovely outdoor pool, a fitness center, yoga classes, and a spa with a range of massage and beauty treatments.

Rugged Monhegan, aka the Artists’ Island, lies about a dozen miles out to sea, and is reachable only by passenger ferries. About 60 hardy souls live here year-round, most making a living from the sea. If you get a sense of déjà vu when visiting Monhegan, it’s likely because so many of the island’s icons and vistas have been painted by American masters, including Robert Henri, Rockwell Kent, Jamie Wyeth, George Bellows, Edward Hopper, James Fitzgerald, Andrew Wyeth, Alice Kent Stoddard, Reuben Tam, and William Kienbusch. Artists and art lovers come in summer; bird-watchers flock here in spring and fall. Hiking trails access remote rocky beaches and craggy headlands. Go for the experience, the art, and the hiking, and don’t miss the museum at the lighthouse.

Cerro Ancón, or Ancón Hill, is a patriotic symbol for all Panamanians. While the Stars and Stripes waved atop the hill throughout the period of United States control of the canal, now the proud promontory displays Panama’s colors. There’s just one footpath that leads to the top. In addition to its historical significance, it’s worth scaling the peak to visit the surrounding jungle and catch a glimpse of the area’s wildlife, all of which makes the park an oasis amid big-city bustle. Cerro Ancón’s second-generation, restored forest is home to more than 260 plant and 70 animal species. Once you hit the summit, every vantage point offers views of the Casco Viejo, the modern metropolis, the harbor, and densely populated downtown districts.

A UNESCO World Heritage site, this 1,700-year-old palace sits on the Adriatic seafront, serving as the focal point of Split. It was built by the Roman emperor Diocletian as a seaside retirement home and has served as a refuge for many a conqueror over the centuries. Today, some 2,000 locals reside within the compound’s thick walls, making it a lively urban quarter. Getting lost in the labyrinth of surrounding streets is the best way to explore downtown Split—as you meander around, you’ll stumble across lively cafés and shops tucked into millennia-old buildings. Be sure to check out the Peristil, an imperial square framed by two colonnades, where Diocletian used to address the public. Towering above the square is Split’s major landmark—a 187-foot-tall belfry that you can climb for panoramic views of town.

One of the best places to feel the local side of Reykjavik life, the Kolaportid Flea Market is set in a spacious industrial warehouse close to the city’s old harbor. Open at weekends only, you can find anything from wool jumpers and vintage fashion garments to fermented fish and licorice, plus plenty of second-hand books and decorative knickknacks. Best to go early to avoid the crowds (it opens at 11 a.m.)—and best to have cash on you since many of the market’s vendors don’t accept credit cards.