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Housed in side-by-side 19th-century townhouses amid the gas streetlights and cobblestoned streets of Boston‘s Beacon Hill, the high-end Beacon Hill Hotel retains a distinctly European feel. The original owners and neighborhood residents Peter and Cecilia Rait bought the properties with the intent of opening a hotel and bistro. Nowadays, the property is managed by Saunders Hotel Group, but the who’s-who clientele hasn’t changed. Since the hotel opened in 2000, the intimate property has hosted innumerable A-listers seeking a lower profile, including Todd English.

Each of the 13 rooms has plantation shutters, pedestal sinks, flat-panel TVs with DirecTV, and windows that actually open for fresh air. The second-floor common area invites guests to meet and mingle. Plus, the hotel has a private, residential-feeling roof terrace overlooking Charles Street, perfect for morning coffee or afternoon reading.

On the still-bucolic site of a former coconut plantation just west of Montego Bay, Round Hill is another of the legendary hotels created in the early 1950s to accommodate wealthy Brits and Americans who were discovering the pleasures of a Jamaican winter. Since then, it has evolved into a thoroughly modern resort that manages to retain its original, exclusive, clublike spirit. In the beginning, Round Hill consisted of a group of shareholders (British playwright Noel Coward was one) who rented out their private villas when they were absent. That’s how it still works, although the celebrity shareholder most mentioned these days is designer Ralph Lauren, who rents neither of his two villas. Along with 27 other villas, which can be divided into 86 suites, there’s the Pineapple House, a seafront block of 36 rooms, all decorated, predominantly white on white, by Lauren. The ambience is quiet luxury, the service is relatively formal (the doorman wears white), and the children among the guests are treated as the heirs and future holiday decision makers that they are. Almost every villa has a story, whether it has to do with Coward, the Kennedys, or How Stella Got Her Groove Back. And Montego Bay, whose city lights can be seen only from the highest villa (#28), is still another world away.

Atenas (whose name means Athens, as in Greece‘s capitol) is actually a quaint agricultural town in the province of Alajuela, about a 45 minute drive west of San Jose. With a population of only 27,000 people, and surrounded by coffee plantations and mountains, this is the absolute perfect place to experience Costa Rica as it truly is. The village has cute shops, some eateries, and stores that will carry any items you may need during your stay. The town square is adorable, and the various restaurants (all very casual) have excellent food based on local fresh catches and fresh-from-the-farm fruits and vegetables. The particular view above is from a lookout point on a private gated property. However, there are three housing developments in the area, and various owners rent out their places for very reasonable rates, and plenty have a view like this. Another fast fact about Atenas: it’s claimed to have one of the best climates in the world according to National Geographic, and you will come to know the phrase ‘El Mejor Clima del Mundo’ because it is proclaimed everywhere - and it’s true.

You won’t find a better pool than the one that awaits at this 357-room family-friendly resort situated on the powdery sands of Palm Beach. With cascading waterfalls, a swim-up bar and grill, two outdoor Jacuzzis, and a two-story waterslide, the 8,000-square-foot stunner is every kid’s dream. If more adult-centric diversions are on your wish list, the concierge can arrange catamaran-sailing excursions, deep-sea fishing trips, and snorkeling and scuba-diving expeditions off nearby shores, as well as spa treatments that utilize local ingredients like red mud, seaweed, and aloe vera. The resort’s 10 dining options provide plenty of atmosphere for winding down after a jam-packed day: sample seafood specialties like scallops a la plancha in a setting inspired by the island’s plantation ruins, or watch the sun set over the water, rum punch in hand, from your perfect perch at the pier bar.

Originally a private summer home, Casa Bonita is now a beautiful 12-room resort run by the third generation of the Schiffino family. Located on the Dominican Republic’s southwestern coast near the town of Barahona, the property was constructed from felled trees and thatch, giving it a luxuriously rustic vibe. Inspired by nature, rooms feature white linens, palm wood accents, and wicker furnishings; some have private balconies overlooking the jungle, others have infinity pools with ocean views, and the two-bedroom Villa Bonita includes a terrace with a grill.

The resort’s farm-to-table restaurant uses produce from the local community and on-site Pat’s Organic Garden, while the spa incorporates traditional Dominican ingredients like coffee, chocolate, and coconut into each of its indulgent treatments. Also available to guests are activities like water sports, tennis, yoga, horseback riding, mountain biking, and a zip-line canopy tour through the jungle. Should you want to venture off property, the UNESCO-designated Jaragua-Bahoruco-Enriquillo Biosphere Reserve is just next door. There are also coffee plantations, lakes, and caves with ancient tribal art nearby.

Located on the Samaná Peninsula, 300 feet above Playa Cosón and the Atlantic Ocean, this 18th-century, plantation-style home impresses with Victorian trim and wraparound terraces perfect for sipping cocktails in the shade. Inside, antiques from Asia, Europe, and Turkey; rugs from Istanbul; and details like Brazilian hardwood floors and French doors add further charm. The six guestrooms, all housed on the second floor, feature four-poster beds, mahogany soaking tubs, and private terraces—rooms 5 and 6 have the best ocean views.

Breakfast and dinner are served on vintage china in the main house, while lunch takes place a seven-minute shuttle ride away at the Beach Club. This is where you’ll also find the inn’s pristine beach, a nearly 90-foot stretch of sand that’s mostly empty, great for swimming, and considered one of the country’s best places for kiteboarding. When you’re not lounging here, visit the town of Las Terrenas (just 10 minutes away) or try to spot the humpback whales that migrate from as far off as Greenland and Iceland to mate and calve in the warm waters surrounding the Samaná Peninsula (every January through March).

Renowned Costa Rican architect Ronald Zürcher looked to his country’s colonial past when designing this hacienda-style property—witness its central courtyard, arched doorways, and terra-cotta roofs. Set amid a 30-acre coffee plantation just outside the capital city of San Jose, the hotel’s 308 traditional accommodations follow suit with dark wood furnishings, but a modern aesthetic pervades renovated guest rooms with streamlined furniture, intricately patterned bathroom tiles, and expansive views that extend from green lawns to forested mountains and urban skyline; some include small balconies that overlook the hotel’s two pools. On-site dining options include gourmet takes on Costa Rican fare at Hacienda Kitchen, Peruvian specialties at La Isabela, and fresh-made sushi at La Castilla, as well as a sports bar and café. The open-air great room invites reading and quiet conversations, but if you’re up for something a little more energetic, there are tennis courts, a driving range, a fitness center, and invigorating coffee scrubs at the spa.

The perfect souvenir for the food-loving traveler? Slim bars of chocolate wrapped in paper patterned with groovy midcentury designs. Or a pale blue box tied with a satin ribbon, holding a treasure of pralines, caramels, and squares of dark chocolate. Vestri is a family-run establishment that has been turning out delicious chocolate creations for more than 30 years. The clan owns its own cocoa plantation in the Dominican Republic, which ensures the quality and ethical sourcing of its products. The shop also sells modern confections like white chocolate with salt and sesame, as well as sweets based on ancient Florentine recipes. Take decadence to the next level and indulge in a scoop of creamy gelato affogato, drowned in hot chocolate, while you shop.

This gem right off Bourbon Street is close to the action but far enough (and insulated enough) to make you feel like you can get away from the frenetic pace of the city’s most famous avenue at a moment’s notice. Guest rooms are well-appointed and comfy, with plantation-shuttered windows, plush beds and sleek bathrooms. Plus, every guest gets a voucher for a welcome drink in the hotel’s smoke-free bar, the Bourbon O. Be sure to catch live music there on Friday nights, as well as bartender Cheryl Charming, whom a local magazine named Mixologist of the Year in 2014. Back at the hotel, the Roux on Orleans restaurant can satisfy breakfast, lunch and dinner desires, and a heated saltwater pool makes lazing about in a lounge chair all day very, very easy. But if you want to be the ultimage envy of Bourbon Street revelers, make sure to reserve a balcony suite; it features a porch overlooking all the boozy revelry below and lets you party above the action.

This 12-cottage luxury hotel, 3,100 feet up in the Blue Mountains, is Jamaica without the beaches. It is the Jamaica of misty mornings, cool, cuddle-worthy evenings, and a musical heritage recognized worldwide. First as a private estate belonging to music producer Chris Blackwell and then as part of his Island Outpost collection of hotels, Strawberry Hill has been a creative refuge for performers including Bob Marley, the Rolling Stones, and Willy Nelson. After Hurricane Gilbert destroyed the estate’s great house in 1988, Blackwell commissioned Jamaican architect Ann Hodges, who specializes in historic reconstructions, to build the cottages, a restaurant, and a pool, which were opened in 1994. Yet despite the rock and roll history, and the hanging with like-minded souls up in the mountain mists, what guests seem to remember most is the far-below views of Kingston, especially at night, when the lights glow and sparkle from what must certainly be another world.

For a taste of Miami by way of St. Lucia, look no further than Sugar Beach. Set on a white-sand crescent between the Piton mountains—within a 100-acre former sugar plantation studded with shady palm trees—the resort’s white-on-white cottages have all the amenities worthy of a five-star retreat, from sumptuous Egyptian cotton linens to butler service and access to a private chef. (No wonder Gwyneth Paltrow and Matt Damon have stayed here.) But don’t linger too long in your room. The coral reefs in the bay are home to triggerfish, turtles, and exotic sponges that can be viewed on an instructor-led dive or snorkel trip, and whale-watching, waterfall hikes through the rain forest, and adventure tours on ATVs await. If you have more leisurely pursuits in mind, the tree-house spa offers treatments using locally sourced ingredients for the ultimate in relaxation.

In the native Hawaiian language, the word “Lahaina” literally translates as “cruel, merciless sun.” Given the name, it should come as little surprise that not only is Lahaina the hottest place on the island, but it can be five degrees warmer than neighboring Ka’anapali, just three miles down the road. When walking around town, one of the best ways to beat the heat is to cool off with a syrupy shave ice. This sweet treat has become synonymous with Hawaii, and its origins date to Japanese plantation workers who would combat the heat by shaving ice off of blocks. Today, no visit to Maui is complete without enjoying a refreshing shave ice, and the best shave ice on the west side of the island can be found at Local Boys West. Conveniently situated across from the Banyan Tree, Local Boys is an island favorite for all of the free add-ons which accompany each serving. In addition to the soft, melt-in-your-mouth ice flakes that can be flavored with multiple syrups, Local Boys includes ice cream on the bottom and Kauaʽi Cream on top, completely free of charge. For those traveling with kids, you can even top the treat with gummy bears for exactly the same price. While waiting in line for your syrupy treat, take a moment to watch the surf films or shop for locally-made merchandise. This store was opened by a man and his young son who humbly sold snacks on the street, and it’s grown into arguably the best place in Lahaina to enjoy the island flavor.

Lanai, a sleepy, 140-square-mile former pineapple plantation, is suddenly in the spotlight. Following the island’s purchase by tech billionaire Larry Ellison in 2012, the bay-facing Four Seasons Resort Lanai underwent a multimillion-dollar overhaul that reduced the number of guest rooms from 286 to 213. The rooms shook off their dated look with mahogany floors and walls clad in slate and teak. Guests can dine at outposts of Nobu and Los Angeles–based Malibu Farm, take private flight lessons and horseback-riding excursions, or book one of the resort’s wellness-focused retreats.

Located just two miles north of Port Elizabeth, on an 18th-century sugar plantation and working sea salt farm that overlooks Spring Bay, Firefly Bequia has all the sophistication of its sister accommodations on tony Mustique. Scattered along the hillside to maximize ocean views, the four suites and one two-bedroom cottage are outfitted with king-size four-poster beds, indoor-outdoor showers, and rattan ceiling fans that recall the island’s colonial past. Though it’s a five-minute walk to the beach, you’ll spot the remnants of the plantation’s original sugar mill, a croquet lawn and swimming pool, and the hotel’s resident goats along the way. Upon your return, a cocktail in the stone bar, where green bananas hang like chandeliers, is just the thing to ease you into a star-filled night.

The Estate Whim Plantation Museum, billed as the only sugar plantation museum in the Virgin Islands, is set on magnificently landscaped grounds occupying 12 acres of what was formerly a 150-acre property. The restored early-18th-century buildings include a great house, fully restored windmill, and sugar-factory ruins that are open to visitors and can be toured alone or with a docent. Sugarcane still grows in one of the plantation gardens.