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Most people who visit Florence know that walking to Piazzale Michelangelo is a must. However, fewer people know that walking a little higher to the old church of San Miniato al Monte is an even better experience. Amble down the Arno River to Viale G. Poggi, up the green pathways to Piazzale Michelangelo, then continue on until you reach the busy square with a bronze cast of Michelangelo’s David at its center. This church facing the square is one of the oldest in the area, a beautiful 12th-century example of Romanesque architecture. Note, especially, the mosaics on the facade and, inside, above the altar; the floor decorations are also worth a look. There is also a small shop next to the church, run by monks. Take in the views from the outside, stroll the grounds, and see the old cemetery. Entrance to the church is free, and if you’re lucky, you might even hear the monks singing.

Amsterdam’s State Museum reopened in 2013 after a decade of renovations, and it is oh so worth a visit! Weave your way through the museum’s vast assemblage of historic art (there are over 8,000 pieces!) to check out works from Dutch masters such as Rembrandt, Van Dyck, and Vermeer in person. The collection’s best-known and most prominently displayed piece is Rembrandt’s Night Watch, but visitors can find everything from sculptures to artifacts from both the Netherlands and Dutch-colonial territories around the world. Opt for the multimedia tour for a special surprise.

Hands down the best place to stay in Mexico City’s Centro Histórico is the aptly named Downtown. Located inside a restored 17th-century casona (mansion), the hotel shares its property with a select group of Mexican businesses, including a chocolate boutique and a mezcal bar, as well as restaurants, cafes, and fashion and jewelry ateliers. Appropriately, rooms evoke a bygone era, with low lighting, brick ceilings, and tile floors somewhat reminiscent of a monastery. Amenities are spare but select (C.O. Bigelow toiletries, for starters), and service is unobtrusive but attentive. After a day spent exploring the city, head to the rooftop pool and bar, where you can sunbathe on a bright yellow chaise lounge or sit under an oversized umbrella while waiting for your cocktail to arrive.

Among the neighborhood’s art-minded hotels, the Gladstone is the most interactive, with shows, classes, and ongoing events. The 37 rooms, all designed by local artists, have breathed new life into the 128-year-old icon, which filmmaker Christina Zeidler took over in 2003 and revitalized in 2005. The Victorian landmark, named for its avenue (in turn named after four-time Canadian Prime Minister William Gladstone), has been a gathering spot for over a century. And it was home to legendary Toronto characters like cowboy Hank Young, who became a fixture at the hotel as a country singer in 1961 and manned the hand-operated elevator from 2005 to 2009, and Peter Styles, former host of Karaoke Night, with applause sign in hand. The legend of Hank lives on in a framed photo in the stairwell en route to the second floor.

The Gladstone continues to push the boundaries of community and culture with creative events like its educational workshop series, Get School’d, and its annual alternative design event, Come Up to My Room (CUTMR), which runs alongside the city’s Interior Design Show. Begin your stay in this architectural gem with a drink at the Café or Melody Bar (that is, if you’re not first thrust into Fameless Karaoke Night).

The Glenn Miller Orchestra introduced America to the Chattanooga Choo Choo and Track 29 in the 1940s, but the train and its home at Terminal Station date all the way back to 1909. In 1973, the original Pullman train cars were converted into luxury hotel rooms, transporting guests to a past era of travel—albeit with modern amenities like high-speed internet, refrigerators, and coffeemakers. Spend the night at the hotel, or simply explore the former terminal complex, which now features multiple restaurants, bars, retail outlets, a comedy club, and a beautiful rose garden. At Gate 11 Distillery, you can even sample artisanal spirits straight up or in carefully crafted cocktails.

Cruise the Venice lagoon on one of the few remaining bragozzo boats still working this body of water. The vintage double-masted, flat-bottom fishing boat, once a common type of vessel here, dates back to 1946. The captain and owner, Mauro Stoppo, is also an excellent chef, which comes in very handy. Charter a daytrip (the boat comfortably carries 6–10 people) and sail to a lesser visited portion of the lagoon. The pace is slow; the food and wine decadent. If you want to charter a longer trip, you’ll explore more of the lagoon by day, learning its history and ecology, and then sleeping in private villas at night.

Downtown Orlando is a very social place, with blocks of bars and restaurants that stay busy from happy hour through late night. Along Orange Avenue—but delightfully removed from the more boisterous downtown stretch—this rooftop lounge overlooking Ivanhoe Row is a local favorite for drinking craft cocktails al fresco. Ride the glass elevator up the third-floor deck, where a horseshoe-shaped bar is shaded from the sun but open to the breezes. Seasonal sangrias spiked with whatever fruit is at peak ripeness go down easily. And another house favorite is the Majors Mule, which puts a tequila twist on the ginger beer and fresh lime classic.

The stars shine every night at the Ogunquit Playhouse, a theater with a rich history and an enviable reputation. Broadway professionals bring this 750-seat summer-stock theater to life from mid-May through October. Born in 1933 out of the Little Theater Movement, the current space dates from 1937 and is listed on the National Register of Historic Places. Don’t miss attending one of the five musicals, ranging from Broadway hits to world premieres, staged each season. Insider tip: Plan ahead to book a 90-minute Behind the Scenes Tour or a 45-minute Stage Door Tour to view the greenroom, wig and sound rooms, and original dressing rooms used by luminaries including Bette Davis, Myrna Loy, and Steve McQueen.

Disco ball, lounge, jungle, and cuisine all come together at this trendy restaurant located on Tulum’s main hotel-zone avenue. The venue is renowned for its eclectic style that blends unusual lighting, a lush outdoor setting, and live DJ nights for a cool, hippie-style vibe. Dinner is prepared over open-fire grills and in wood-burning ovens, resulting in flavorful Mexican favorites like taco samplers, quesadillas with epazote, grilled avocado, and slow-roasted pork belly. Gitano also specializes in strange but enticing cocktails from its mezcal bar, like ones that include ingredients like rum, hibiscus, and tropical fruits.

Located on a gorgeous, very private stretch of black-sand beach, Tahiti Pearl Beach Resort offers affordable, modern rooms, many of which feature spacious layouts, private Jacuzzis, and ocean views. Guests can also look forward a massive infinity pool, a luxurious spa, and meticulously maintained grounds, complete with fresh flowers and lush grass. The onsite Hita Mahana Restaurant and Bay Bar are outdoors but covered, offering sweeping views of the sunset across the ocean to Moorea. Note: This resort is very close to the airport so it’s ideal for those arriving late at night or leaving early in the morning.

One of the world’s most epic drives, the Hana Highway connects Kahului with Hana in eastern Maui. The scenic stretch is just 64 miles long but can take up to three hours to drive, thanks to 62 twists in the road as it winds through rain forests and past waterfalls, natural pools, and seascapes. Plan at least a half day to properly experience the drive, or slow it way down and spend a night in Hana so you can linger at places like Twin Falls, the Keanae Peninsula, the Garden of Eden arboretum, and the black sand beach at Waianapanapa State Park. Sun worshippers should also budget plenty of time for stops at Hamoa Beach and Ho’okipa Beach Park Beach Park.

Architects clearly had fun designing Saruni Samburu, an eco-lodge tucked away in the private Kalama Conservancy in central Kenya. Set on a giant outcropping of volcanic rock, stone serves as furniture and structure in the six spacious villas—jutting out of walls, punctuating the outdoor decking, and transformed into shower stalls with some clever pipework. Creative decor aside, the family-friendly resort enjoys spectacular views over billowing golden rangelands, a scene best appreciated from one of the two infinity pools on site, or with a gin and tonic in hand from the decked patio area. Just be sure to call it an early night: Guests are assigned their own jeeps and guides for daily safari excursions to spot elephants, giraffes, and endangered Grevy’s zebras.

This family-run hotel, originally opened in 1886, is steeped in history from its classic furnishings to its esteemed guests. Literary legends William Faulkner and Ernest Hemingway have stayed here; Tennessee Williams wrote about the hotel in his play The Rose Tattoo, and Truman Capote was known to prop up the Carousel Bar & Lounge on many a night. The merry-go-round–like bar (which makes a complete revolution every 15 minutes) is probably the hotel’s most famous feature, and a Vieux Carre cocktail there is de rigueur. Guests will also want to visit on-site restaurant Criollo, which offers an updated take on traditional N’awlins fare.

This very attractive sidewalk café in the Jewish district is a popular destination for dining as well as for relaxing during the day. The venue includes both an art gallery and theater, where events take place from September to May, along with a restaurant and coffee house. The food is an unusual and tastebud-tingling hybrid of Hungarian and Mediterranean – and the signature chicken with honey and garlic or the roast goose leg with steamed red cabbage is not to be missed. There’s live music every night from 7 p.m. and a klezmer concert every Friday at 7 p.m.

As the number of bars in Krakow has gradually increased, the spots from which to enjoy a sunset drink have also expanded. One of the most glamorous spots is the Sky Bar on the roof of the Hotel Stary, overlooking the main square. Order a cocktail or a decadent homemade dessert and watch as the bustle of the city plays out below to the occasional tune of the unfinished bugler.