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Key West doesn’t have many swimmable beaches, but this elegant 1920 oceanfront resort sits on the largest private one in town—an 1,100-square-foot strand punctuated with tall palms. While the shoreline itself is on a rocky shelf, a long dock extends out to the shallows for laps and snorkeling. Just off the beach, two large pools are set into green lawns and lush landscaping in front of the Spanish-style main building, which is on the National Register of Historic Places. The hotel’s wooden coffered ceilings, arched entryways, red-tile roofs, and other key architectural details recall the hotel’s glamorous heyday, while the clean, refreshed rooms are entirely modern, with sleek wood-framed beds, white linens and curtains, and ocean views. Children under 16 stay for free and babysitting is available for adults who want to take a break at the Spa al Mare, which has an open-air cabana right on the sand for al fresco massages and treatments.

In the heart of the medina, not far from the entry to the souks and the main square, two French brothers have transformed a historic riad into an intimate, contemporary Moroccan hideaway. Opening onto two internal courtyards—one of which has a swimming pool—are seven rooms and suites, each named for a local spice (think saffron, nutmeg, and turmeric) and decorated in jewel tones like deep orange and royal purple. All have standard conveniences like hair dryers, toiletries, and air-conditioning as well as complimentary Wi-Fi.

The hotel’s public spaces are separated into a garden section, featuring trickling fountains and lots of flowers, and an oasis section, which houses the pool and a traditional steam hammam. The riad also enjoys a higher position than its neighboring buildings, resulting in particularly great views from the rooftop terrace. Here, you can take in the Atlas Mountains from the plush lounge chairs (each topped with a straw hat for extra sun protection), the fireplace, or the romantic dining tables, where you can enjoy cocktails or a candlelit dinner. Adding to its private home feel, Riad l’Orangeraie provides guests with a local cell phone to use while in town. The hotel is also available to rent out in its entirety for the ultimate house party.

If anything’s endemic to Orange County it’s surfing—there are 40 miles of coastline here, after all. It’s not hard to find passionate practitioners of the sport, but doing is one thing and teaching is very much another. For newbies or even intermediate surfers looking to get back on a board, La Vida Laguna’s approachable, confidence-boosting instructors are the surest way to success. In private and semi-private lessons, their goal is to ensure that their surf pupils—starting from age eight—stand up on a wave, of course, but they also want to create more ocean advocates in the process. Wave safety and selection plus etiquette training are part of the lessons, along with pop-up drills, positioning, and gentle pushes at Thalia Beach, which has consistently calm waves for beginners. Guides also lead stand-up paddleboard lessons, hikes, and kayak adventures (expect frequent sea life sightings), tailoring and combining experiences upon request. Appointments are necessary and can be made on the phone, online, or at the company’s historic Craftsman bungalow in downtown Laguna. Local tip: For fewer surfers in the water, book a couple lessons on weekdays during the winter season.

The Pestana Hotel Group has a knack for turning historical properties into luxe hotels; the Pousada de Lisboa is no exception. Situated on Lisbon’s grandest square, the Praça do Comércio, the 90-room property inhabits the elegant former home of the Ministry of Internal Administration. Furnishings combine clean, modern lines with ornate wall moulding and a neutral color scheme dominated by pale greens and whites. Choose one of the mezzanine rooms for views of São Jorge Castle; the high-ceilinged Suite Praça do Comércio offers sweeping vistas of the square and River Tagus from two large windows. The hotel’s RIB Beef & Wine restaurant caters to the expense account crowd, specializing in premium cuts of meat aged for 14, 28, or 60 days and served with a regional touch: Lodosa piquillo peppers. There’s also an indoor pool lined with loungers, and a spa offering a full range of treatments, including a body scrub inspired by the scents of Madeira and the Algarve.

Nearby reefs and big boulders keep Bermuda’s beaches calm and colorful for snorkelers and swimmers. Both Tobacco Bay & Church Bay offer great snorkeling conditions along beautiful shorelines. With one in the east and the other in the west, you could combine a day of snorkeling and sunrise/sunset viewing. Tobacco Bay is located on the northeastern side of the island near St. George. This small cove of calm water protects a variety of parrot, clown, and other tropical fish. Tobacco Bay has a snack bar and equipment rentals, restrooms, showers, and changing rooms. When you tire of swimming with the fishes, dry off with a short walk to the historic site of Fort St. Catherine. Its eastern location makes Tobacco Bay a prime sunrise spot. Located along the island’s western side in Southampton, Church Bay is a local favorite for snorkeling. Tucked into a small cove within cliffs of coral, the reefs are close to shore and offer lots of small hiding spaces in which to discover tropical sea life. Just watch out for the jellyfish. Youngsters will enjoy exploring the tidal pools formed by the many rocks. Forget to pack your snorkeling gear? No problem. You can rent equipment from Church Bay Beach Rentals during the summer months. Sunset seekers should not miss this beach.

Situated in the suburbs just outside Copenhagen, Charlottenlund Beach Park is a small oasis in one of Denmark’s wealthiest areas. The old fortress retains several naval artillery batteries in a space that has been converted to a park and overlooks a small, but beautiful, Danish beach. Just behind the park you can head into the park itself, which is a richly forested area that is absolutely stunning in fall. Head to the nearby Charlottenlund Palace, built by Christian the VI in 1733, as part of your stroll through the park. There’s also a lovely cafe down by the beach which is open to visitors and offers a view over the water.

Some visitors to Santa Fe are surprised to find this Gothic revival structure in the middle of all of the adobe buildings in the historic district, like a piece of medieval Paris transplanted to the Wild West. The French connection is real—the 19th-century Loretto Chapel was designed by a French architect who modeled it after La Sainte Chapelle in Paris. According to legend, though, the plans failed to include access from the chapel floor to the choir loft. So, the nuns who ran the girls’ school for which this stone structure was built began praying, and after nine days, a mysterious carpenter arrived. Neither nails nor glue nor any visible external support were used in this doubly-twisting staircase, and no one ever found out the name of the carpenter, who left without seeking payment. It must’ve been St. Joseph himself...so goes the legend of “the miraculous staircase.” The physics of the structure can be explained by architects today, but that doesn’t stop about a quarter-million visitors every year from marveling at the elegant spruce spiral. Open to the public as a privately run museum, the Loretto Chapel hasn’t been a church for decades. It can, however, be rented: a spectacular setting for a private wedding.

The Bonsecours Market is hard to miss, whether you are walking around Montréal’s historic center or looking at the skyline from the harbor. A silver dome caps the long building, which dates from 1844 and was modeled on Dublin’s Customs House. It looks more like a stately civic building than a market, and in fact it was Montréal’s city hall for a while, as well as the seat of Canada‘s parliament for one session. After serving as the central market of the city for nearly a century, it closed in 1963 and was largely abandoned until 1992, when it reopened as the home of a visitors’ center for Montréal’s 350th anniversary. Today it houses a dozen or so boutiques featuring works by local designers, as well as a few restaurants that make for good pit stops on a day of sightseeing.

What began in 1854 as a high school—then grew into a college and, later, a law school—has served as one of San Antonio’s top hotels since 1968. Located near the River Walk, not far from the city’s historic district, the leafy former campus is centered around a seven-story, Spanish colonial-style main building with 338 guest rooms. Each one mixes original touches like wood-beamed ceilings, exposed brick walls, and French doors with modern amenities like HDTVs, marble baths, and Wi-Fi (complimentary for loyalty club members). Some even look out on the River Walk, while others offer views of a verdant garden. Healthy extras like in-room fitness kits, a 24-hour gym, and a year-round heated pool help offset the indulgences served at the on-site restaurants and bars, which include the fine-dining Las Canarias (don’t miss the popular Sunday brunch.) Younger guests can look forward to game-filled backpacks and scavenger hunts, while adults will enjoy the award-winning spa and restaurant at La Mansion’s sister property, Mokara, located across the river.

The Bellini was born in Venice at Harry’s Bar, which has been hopping since 1931. Declared a National Historic Monument by the Italian government in 2001, this San Marco bar and restaurant is a cultural institution. Even though it doesn’t do the best food in Venice, and prices are ridiculously expensive, it’s worth dining here once just for the experience. Over the decades it has served a global collection of writers and artists, including Ernest Hemingway, Charlie Chaplin, and Orson Welles, and today it’s still popular with Venetian movers and shakers.

The interior decor has not changed since Giuseppe Cipriani opened Harry’s on the eve of World War II (and during the war, Harry’s was one of only a handful of restaurants in Venice that would serve Jewish patrons). The food is classic Venetian. Try the baked sea bass with artichokes for a main, and make sure to save room for dessert. Harry’s is famed for crêpes flambées and also its Cipriani chocolate cake. Reservations are imperative; when booking ask for the ground floor because dining here is all about seeing and being seen, and the second floor is considered much less cool by Venice society (although it has much better views and more dining space).

On the banks of the river Zaan, time stopped three centuries ago at Zaanse Schans. In this recreation of a Dutch village in the 17th–18th centuries, stroll down streets lined with typical green wooden houses, manicured gardens and graceful bridges. Poke into tradesmen’s workshops, historic windmills and tiny boutiques. See how wooden clogs are made and watch pewter jewelry fashioned before your eyes. Discover how artisanal Dutch cheese is crafted and purchase a wheel of Gouda or Edam to take home. Refuel with coffee and apple pie in one of numerous restaurants within the village. Explore a few museums and round off your visit with a boat trip on the river. Although several museums at Zaanse Schans charge for admission, there’s no entry fee at the popular tourist attraction created by relocating houses, windmills, storehouses and barns to form a replica of a typical Zaanse village. Alongside clusters of windmills, characteristic wooden houses and unique shops, traditional Dutch crafts are showcased and the lifestyles of people who lived in Holland long before sex, drugs and rock ‘n’ roll entered the picture are revealed.

The giant ferris wheel on the south bank of the Thames is made up of 32 futuristic glass capsules - all of which are sealed, air-conditioned and big enough to house 25 guests. Riding the attraction is effectively being stuck in a bubble, albeit one that offers 40km views in all directions (see if you can spot Windsor Castle in the farthest distance on a clear day). This is the wheel that never stops turning, and while views at the top are stunning, you won’t feel the ascent/descent: the Eye does one full rotation every 30 minutes, and turns so slowly passengers walk on and off at ground level. Curiously there is no capsule 13; since the number is thought to be bad luck, its been replaced in the lineup by the infamous no.33.

If walls could talk, you’d be stuck in conversation with the Fillmore for hours. The building was a dance hall when it opened in 1912 and a roller rink during the 1940s, and led its first concerts in 1952 with artists like James Brown and Ike & Tina Turner. But in the mid-1960s, the venue really had its moment. Concert promoter Bill Graham made the ballroom a hub for psychedelic music and brought would-be legends like the Grateful Dead, Big Brother and the Holding Company, Jefferson Airplane, and Santana to the stage. Needless to say, there’s history here. Learn it best by attending a show. The standing-room-only ballroom still brings in big-name artists—think Lorde and the 1975—at budget-friendly prices, along with a constant stream of smaller acts. There’s a full-service restaurant and a bar, and the vibrant collections of old photos, artwork, newspaper clippings, posters, and billings will school you on the club’s colorful past.

Come for the history, stay for the chowder. Bostonians have been slurping down oysters at America’s oldest continuously operating restaurant since 1826, and while you won’t find Union Oyster House on any haute dining lists, it’s well worth a stop when you’re walking the Freedom Trail or exploring the area around Faneuil Hall. Sidle up to the semicircular oyster bar right inside the front door just like Daniel Webster once did, or feast on a classic New England shore dinner in the upstairs dining room, away from the crowds. There you’ll find a plaque marking the booth where JFK liked to scarf baked beans and clam chowder—one of the restaurant’s many reminders of its long history of catering to celebrities.

Miami comes to Los Angeles at this Sydell Group hotel that took over the historic Commercial Exchange building in the center of downtown. Although it has deluxe amenities like a doorman and room service, the Freehand L.A. has a range of room types, from 167 private accommodations to 59 shared rooms with four, six, or eight bunk beds. The hotel deftly manages to combine the social culture of a hostel with innovative design by Roman + Williams, exceptional food and drinks, and stellar communal spaces where locals and travelers mingle naturally. Places to hang out include the lobby area outfitted with handcrafted furnishings, vibrant tapestries, earthy decorative elements, and murals by local artists; the lobby bar, serving tea-infused cocktails and light bites; the grab-and-go Café Integral; the plant-filled restaurant; and the rooftop pool, which is home to the award-winning Broken Shaker lounge. Providing more greenery off the lobby is a floral-filled concept store by Venice’s Flowerboy Project.