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Dining at one of Negril’s excellent cliffside restaurants is highly recommended, and the gorgeous setting of Ivan’s Bar & Restaurant at Catcha Falling Star makes it a very nice option. The longtime favorite has one of the best views along the coast and serves lobster dinners and classic Jamaican cuisine with a bit of a modern twist. Guests are seated under an open-sided thatched roof or out under the stars at private tables on a patio near the cliff’s edge. Another favorite choice for romantic cliffside dining is the restaurant at Rockhouse Hotel. (If you want more cocktails post-dinner, walk down to LTU Pub and mingle with the locals. Casual eateries and cliff bars along West End Road include 3 Dives and Sips & Bites.)

This tiny hideaway overlooking the sea near Port Antonio originally served as a live-in recording studio for performers such as No Doubt, Alicia Keys, and Amy Winehouse. Although recording sessions still go on, Geejam is now a seven-room hotel, its guests often honeymooning couples acting out fantasies having nothing to do with rock and roll. Geejam’s cabins, especially, are very private, and guests sometimes spend days taking meals on their veranda and splashing in their outdoor Jacuzzi without being seen by anyone but the staff, who appear only when called. Of course, who wants to stay hidden forever when the Bushbar restaurant promises convivial chitchat, an occasional game of pool, and even live music? Not to mention that the hotel beach, in a cove across a road at the bottom of the property, promises four-poster sunbeds and, yes, Wi-Fi.

The 25hours brand is known for its playful take on the hotel experience, and this Zurich establishment follows suit. With an interior concocted by local designer Alfredo Häberli, the space features the usual mix of colorful, offbeat furnishings, slick design, and casual friendliness, as well as the cute touch of Häberli’s personal city tips scrawled on various surfaces.

The rooms and suites are separated into categories of silver, gold, and platinum to reflect the city’s banking-capital status. That’s as corporate as it gets, however, since the interiors are decidedly funky, with bold colors, quirky carpets and artwork, and angular work desks. The hotel also offers a restaurant, living room and business lounge (with iMac workstation and free Wi-Fi), plus an in-house kiosk that stocks everything from necessities (shampoo and toothpaste) to accessories (Freitag bags).

Equally summery and sexy, 4th & Ocean has the clothes you want to wear for a Florida weekend...from bikinis, to backpacks, to sunnies. Stocked with brands like Roxy and Billabong as well as up-and-coming designers, this store will fulfill all of your surf-style needs.

Casa Morada’s dressed-down modern coastal style reflects a love of the ocean, island plant life, and luxurious comforts. The 16-suite boutique hotel—once a 1950s roadside motel—underwent an extensive renovation in the early 2000s that transformed it into one of the Key’s sexiest spots. The Raymond Jungles–designed gardens are lush, the outdoors showers and jacuzzis are impossibly romantic, and the resort’s private island features a freshwater pool. If you can rouse yourself for anything other than relaxing by the water, try your hand at a game of bocce, snorkle around the only living coral reef in North America, go on a sunset sail, or charter a boat tour with local resident Captain Bill to visit the Mangrove Islands or Three Sisters Bird Rookery. Pro Tip: Morning yoga classes are offered every Wednesday, Saturday, and Sunday at 9, but guests can book a private session anytime.

Why we love it: A city slicker–approved beach retreat with a vibrant art collection

The Highlights:
- The secret indoor pool up a staircase from the main pool area
- Fresh-baked breads by pastry chef Simone Colla served daily in the Filosofía restaurant
- An entryway featuring a rare sculpture by KAWS and vintage armchairs hung like swings from the ceiling

The Review:
The people watching is just as entertaining as the artwork at Casa Malca, a mansion once maintained by Colombian drug lord Pablo Escobar but now owned by New York gallerist and art collector Leo Malca. Set on a Caribbean-facing swath of sand next to the Sian Ka’an Biosphere Reserve—and just a short bike ride from Tulum’s beachfront boutiques and restaurants—the hotel features 71 rooms, complete with polished concrete floors, floor-to-ceiling windows overlooking the ocean, and bold artwork from Malca’s personal collection. A black-and-white print inspired by Keith Haring covers the lobby bar, while antique baby dolls adorn the walls in one of the hotel’s three restaurants. The pool and beach areas are more sedate, with cerulean daybeds and colorful hammocks studded like jewels among the leafy palms.

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.

San Antonio’s west side is one of the city’s cultural hubs. Latin and Mexican-American influences are vibrantly displayed through public art and murals. The area around Guadalupe Street is an especially rich place to explore. You’ll find art around every corner, cultural centers, theaters, coffee shops, and bakeries. One of the best resources I came across was the San Antonio Neighborhood Tours sponsored by the City of San Antonio Office of Cultural Affairs. You can download free PDFs of the guides here: http://www.saculturaltours.com/. We did the West Side Murals Y Mas Tour. It was an awesome experience that included more than 50 unique sites.

The west-facing bay views are reason enough to stay at the Four Seasons Hotel in the center of downtown Seattle. That, and the unbeatable location: across the street from the Seattle Art Museum, and right next door to Pike Place Market. Tasteful minimalist decor; floor-to-ceiling windows that overlook Elliott Bay or neighboring towers; modern, elegant appointments in the rooms (and enormous bathtubs!); and an outdoor infinity pool that exploits the setting—all these touches add up to one of Seattle’s best hotels.

Sugar sands, shallow waters, and consistently smooth seas are just a few factors that make Captiva Beach a Southwest Florida favorite. The shelling is great here, especially after storms, but it’s the sunsets that make it famous—and why Captiva is considered one of the most romantic beaches in the state. For a swim, stroll, or sunset viewing party, it can’t be beat. Be sure to keep your eyes peeled for the dolphins that are regularly spotted offshore.

On the banks of the Macal River, at the edge of downtown San Ignacio, you’ll find a sprawling Saturday market where everything from shoes and clothing to housewares and fresh produce is for sale. Local people shop for supplies and gather to catch up on gossip at the food stalls. The market is somewhat divided between produce sellers and souvenir vendors, but as the market has grown, the separation seems to have floundered a bit. Leave enough time to wander every aisle and stall to ensure no gem is left undiscovered. Locals recommend the tacos and pupusas as the best choices for lunch, and the snow cones topped with evaporated milk for a snack. Buses also park just next to the market in a dirt lot, so transportation is not difficult if you’re coming from outside of town.

Third-generation artisan Giorgio Santamaria oversees a team of eight craftspeople who meticulously produce for his shop accessories from alligator, ostrich, and crocodile leather in a workshop tucked away down a narrow lane in the city center. The ready-made selection includes belts, wallets, key chains, bags, and luggage in a wide range of colors, and practically anything can be made to order.

Just 10 minutes from downtown Orlando, in village-like Winter Park, the Alfond Inn has a unique legacy: The boutique lodging was created to provide income for scholarship funds at neighboring Rollins College, one of Florida’s oldest liberal arts schools. If helping students isn’t reason enough to book a stay, the hotel offers lots more incentive. A skylit domed atrium in the Spanish colonial–inspired main building draws your eye to a rotating collection of artwork curated by Cornell Fine Arts Museum, and pet-friendly guest rooms are simple and cheerful. While the hotel is not a full-fledged resort, it offers guests plenty of opportunities to linger. Fire pits and rocking chairs are dotted around the property, and shaded areas for loungers enhance the rooftop pool’s already undeniable appeal. Hamilton’s Kitchen restaurant serves modern Southern cuisine paired with wines selected by an award-winning sommelier. And shops, wine bars, and independent boutiques like Rifle Paper Co. line the town’s Park Avenue, a few blocks away. You can also take a pontoon boat tour for views of many of the Mediterranean-style mansions along the waterfront. Perhaps best of all, Disney and Universal theme parks are only a half-hour drive away.

Isola has become Milan‘s hipster hangout, so you are going to want spend a lot of time here. Best way is sleeping over, and the Isola Apartments are key. Lots of light, minimal decor and all the trappings of home, the loft apartments are great for couples with kids or other kids of third wheels.

Usually, when you travel, it’s to experience a different side of yourself. The more adventurous side, the slightly less scheduled side, the sleep-in-without-guilt side. And when you stay at the Drake Hotel in Toronto, you can’t help but feel like your cooler side is making a much-needed appearance. The recently renovated property on Queen Street West features the kind of interior design that radiates style whether it’s in the kaleidoscopic lobby, the next door theater, or in two wings of suites. That’s because the hotel commissioned artists to showcase their work on plenty of open surfaces — from a black-and-white squiggle accent wall in guest rooms to personality-driven drawings in the elevator — and the results make for surroundings that are the material equivalent of black sunglasses. Paired with of-the-moment details like pink terrazzo showers and wraparound midcentury sofas, and the Drake Hotel is meant to cultivate a see-and-be-seen vibe.

But that’s not to say that the hotel sacrifices comfort for being camera-ready. The staff is kind and always available through text, the beds are soft and squarely stationed in front of a well-appointed bar and flatscreen television, and designer toiletries are filled to the brim. It’s also possible to eat throughout the day at the hotel’s delicious cafe and patio (get the French toast), and then spend the night at its second-floor bar or ground floor lounge. On weekends, even if you’re not a guest, you can stop by for regularly scheduled events including a DJ who spins old and new tunes. If you do plan on leaving the hotel to see the city, then you’re right in the midst of it, and the surrounding neighborhood can keep you readily entertained.

When you stay at the Drake Hotel, don’t be surprised if you feel relaxed, in-the-know, and decidedly cooler once you check out. These are sides of yourself the hotel may have encouraged, but feel free to hold on to them after you return home.