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For those who aspire to travel as trendsetters in Jamaica, it helps to know that Port Antonio, way out on the eastern end of the island, is the destination to head for. And the address to shelter at is the Trident Hotel, whose 13 waterfront villas would not look out of place on South Beach. Nor would the crowd that hangs around its infinity pool or in its restaurant, Mike’s Supper Club, where local musicians and the occasional celeb sit down to knock out tunes on the 1917 Ferrari-red grand piano. The Trident Castle, a kind of fantasy annex, is a former private residence whose grand rooms, sea-view terraces, and dollhouse-size chapel make it ideal for destination weddings. A hard road to get there? Not for guests who avail themselves of the helicopter pad.

Surrounded by swaying palms, tropical flowers, pink sand, and sapphire waters, the 100-acre Fairmont Southampton is Bermuda’s ultimate luxury destination. The 593 rooms and suites are among the largest on the island, and feature marble baths stocked with Le Labo products and private balconies that look out onto the Atlantic Ocean, Great Sound Harbour, or the lush landscaping of the on-site Turtle Hill Golf Club. A pool, beach club, dive center, kid’s camp, and tennis courts—plus that 18-hole championship course—offer plenty to keep guests busy. If you prefer to kick back, opt for a lavender-oil massage at Willow Stream Spa, a sprawling space complete with a well-stocked health club, sauna, and steam rooms, or grab a sundowner at one of the resort’s 10 restaurants, bars, and lounges.

The nine-mile dirt road through Pike’s Peak National Forest is a properly isolated, remote, and grand driveway to Lost Valley Ranch, one of the few guest ranches in Colorado that is so close to Denver. (It is only about two hours by car from Denver International Airport, and a short drive from any other front range city.) The drive leads you through the still-recovering burn area of the 2002 Hayman Fire, then dips down into a green oasis, in a cozy corner of the Goose Creek drainage. Lost Valley is a traditional, medium-size ranch with plenty of history and a robust kids and teens program in the summer. It’s all about horseback riding in the morning and afternoon, a lazy schedule punctuated by the dining room bell and yelps of happy children and ranch dogs playing in front of the main lodge. Lost Valley Ranch books week-long, all-inclusive packages throughout the summer season; shorter stays are available in spring and fall. Rates begin at $3,020 per adult, and cheaper for children (how much cheaper depends on age), and include meals, lodging, horseback riding, evening entertainment, and children’s programming (Trap shooting, town purchases and massage therapy are extra).

Negril, or the “Capital of Casual” as it’s known in Jamaica, is everyone’s favorite getaway, from locals to the visitors who return year after year. The buzz of activity on Seven Mile Beach’s powdery white sands is tempered by the breathtaking, serene views of the West End’s cliffs towering over the Caribbean. Lots of bars, hotels, and restaurants line Seven Mile Beach, and local eateries and smaller boutique resorts are perched up on the cliffs. While there’s more hustle and bustle and throngs of tourists on this end of Jamaica, the region still offers many secluded spots and unique experiences.

One of the most fun places I dined at in Italy was Il Latini, in Florence. It’s in a large, maze-like building with aged prosciutto hanging from the ceilings, and art collaged upon the walls. Seating is at communal tables, and at times it felt like we were all at a wedding. In our case, my boyfriend and I sat with another couple from Australia, who were beginning their tour of Italy, but it’s easy to meet locals at this spot, too. The waiters and the owner are very persuasive when it comes to traditional Florentine food. I requested half of a Florentine steak, but I am sure I was given a full one—one of the largest I have ever seen served. It was cooked rare, and was extremely tender and flavorful. However, I am not much of a carnivore, and as such, my favorite part of the dinner was the fresh sage ravioli. After our meal, the waiter kept bringing shots and wine, which appeared to be on the house. There are no exact prices, and the waiter determines your meal’s cost.

After crawling through a few of the tunnels that have been somewhat expanded for tourists and seeing the displays of recovered bombs, people who were not involved in the Vietnam War (called the American War there) can get a feeling of the horror that occurred during those years. A system of 125 miles of tunnels became almost a complete underground city. The picture offered above is the delivery bomb of cluster bombs from the U.S. The Vietcong recovered many of these and other unexploded bombs and used them against South Vietnam and the U.S. It is a sad place but worth going for a better understanding of why the U.S. lost this war.

To get from point A to B on the river delta, you’ll need to board a water taxi. These polished wood boats cruise the canals day and night, dropping passengers off and picking them up at rental houses, cabin complexes and restaurants along the way. The ride, of course, is part of the fun. Board one at the harbor - and make sure you know where it’s going before you sit down, or it might be awhile before you find yourself back in civilization.

A tour of St. Nicholas Abbey is a chance to explore one of the finest so-called great houses of Barbados. Not an actual abbey, the well-preserved Jacobean plantation mansion in the northern parish of St. Peter dates from the mid-17th century and is filled with antiques. On the mahogany tree–dotted manicured grounds, visitors can also see the old steam mill and rum distillery that are still in operation; the output from the latter, and other local products, are sold in the gift shop.

The Common becomes extraordinary on winter evenings when the Christmas tree is up and soft lights seem to hold back the twilight chill, but the truth is there’s no bad time to visit the nation’s oldest public park. The former cow pasture has been a focal point for Boston’s history and culture since its inception in 1636—a site for riots and rallies from the Revolutionary War to the Vietnam War era as well as weddings, hangings, and burials. Summer splashing and winter skating at the Frog Pond are local traditions, and you can spend hours wandering from landmark to landmark (like Augustus Saint-Gaudens’s famous bas-relief Memorial to Robert Gould Shaw and the Massachusetts Fifty-Fourth Regiment, or the Soldiers and Sailors monument atop Flag Staff Hill). Or you can just laze in the sun on the park’s west-side lawn.

Occupying a prominent space between Brandenburg Gate and Potsdamer Platz, this memorial (also known as the Holocaust-Mahnmal, or Holocaust Memorial) has almost 3,000 gray oblong pillars (stelae), arranged at varying heights, that form a kind of labyrinth intended to reference the disorientation felt by Europe’s hunted Jewish population. Designed by New York architect Peter Eisenman, it opened in 2005. The effectiveness of the labyrinth is arguable; you may see groups of teenagers playing tag and picnicking on and among the blocks. However, there’s no denying the power of the site’s underground information center, which relates some of the life stories of Holocaust victims. Several other smaller but related memorials are nearby, dedicated to homosexuals, gypsies, and victims of National Socialist euthanasia killings.

Belize’s liveliest time of the year comes in September, when the entire country celebrates independence for three entire weeks leading up to Sept. 21. The major towns and cities host various events, and a countrywide calendar is published on Sept. 1, allowing you to follow along with the fun wherever you might find yourself in Belize. The most popular events are a steel pan concert called Pan Yaad, held in Belize City, and two full-blown carnival parades. Belize City Carnival, with soca and Caribbean music blaring, is held in mid-September, while Orange Walk Carnival takes place on Independence Day and celebrates Mestizo heritage. Take advantage of low-season fares to get a unique culture-filled experience in Belize in September.

The natives that guide you through Canyon De Chelly are very passionate about their historical heritage: the battles that their people have survived, the ceremonies they live by, and the dwellings that they carved out of the massive cliff sides. The Navajo people had to hide in the mountains, and for extended times they weren’t even able to come down for food or water. The Human Chain is the story of how they created a chain by climbing down each other in the night to bring up baskets of water while their enemy slept. Many survived because of that daring task.

Just outside Capitol Reef National Park, Cafe Diablo serves Southwestern fare with a local twist. From pumpkin-seed-crusted trout to rattlesnake cakes with ancho-rosemary aioli, the dishes are classics in an unexpected way. Casual and family-friendly, the restaurant offers a taste of big-city dining in a low-key atmosphere. Ask the knowledgeable staff to recommend the perfect wine or beer for your meal, or choose something from the extensive selection of tequilas.

La Specola, one of the oldest science museums in Europe, contains a collection of specimens of the natural world—some of which date back to the 16th century. It includes strange and wonderful objects ranging from tiny iridescent green beetles and multicolored butterflies to whale and rhinoceros skeletons. There’s even a hippo, preserved by taxidermy, that was once pet to the Medici family and lived in the Boboli Gardens! The extraordinary, if slightly creepy, anatomical waxes filling the last four rooms of the museum were once used to train Florentine medical students. The frescoes and elaborate pietra dura inlays that decorate the walls and ceilings detail Italian scientific achievements.

Named after the Spanish word for “pretty,” this beachfront park lives up to its moniker. Located just south of Fort Myers Beach, Bonita Beach tends to be quieter, drawing a laidback crowd and lots of families. Rather than hotels or resorts, actual homes line the shores. When you visit, head straight to the park, which functions as an undeveloped oasis on the southern tip of the beach. There are grills and tables so pack a picnic, then spend some time on the playground or sand volleyball court.