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Hundreds of years ago, at the height of Florence’s Renaissance heyday, visitors to this cultural capital wouldn’t have stayed in the kinds of luxury hotels that now line its picturesque streets. Rather, the well-heeled would have come at the behest of friends, lodging in private homes whose unassuming facades in the best neighborhoods belied their sumptuous interiors and private gardens, outfitted with art and artifacts collected from around the world.

A guesthouse to its core, Casa Howard continues this Florentine tradition; there is neither lobby nor restaurant, and the owner Massimiliano Leonardi di Casalino lives in his own apartment here while in town (note, it can be rented when he’s away). Jennifer Howard Forneris, one of the design-conscious proprietors who has since passed away, was the daughter of renowned textile designer Luciano Forneris. She gave each room its own look, with finds from her and Leonardi di Casalino’s world travels. A media room is the sole common area, and a hammam steam room and an on-site concierge service are the only nods toward traditional hotel services. Insider recommendations are personalized according to guests’ preferences, and the honor bar feels more like a friend’s (well-stocked) fridge.

Among the original guests to pop in at Dr. Thomas Bond’s 1769 Georgian home on South Second Street was none other than Benjamin Franklin. Together the duo chartered Pennsylvania Hospital, the first public hospital in America, and Bond was an influential figure in Philadelphia throughout the Revolutionary War into the first turbulent decades following the founding of the country. Today, the four-story red-brick home within Independence National Historical Park has been meticulously restored, offering history buffs a taste of Philadelphia at the dawn of America. Original architectural details restored to their full 18th-century splendor include the modillion cornice at the roofline, the parlor’s Rumford fireplace, and the grand staircase connecting the third and fourth floors that was subsequently copied in other prominent buildings around town, including the still-standing City Tavern.

Each guestroom has been furnished with Federalist-style reproductions, with a few antiques sprinkled around. Ten rooms offer queen beds, with the two original bedrooms nearest the first floor adding small sitting areas with working fireplaces.

An intimate gem whose only shortcoming (in some eyes) is that it does not sit on Pink Sands Beach, the Rock House Hotel & Restaurant was a labor of love for the late Wallace Tutt, an interior designer to the stars who was best known for designing Gianni Versace’s Miami mansion. Ten individually decorated rooms in the 1940s private home turned boutique hotel echo that property’s grandeur with king size beds and seaside motifs, as well as sumptuous linens and stone lion heads mounted on the walls in the restaurant. But the real story here is the service: There is always a picnic basket on-hand in every room, a library of games and books is available for perusal on rainy days, and the concierge is happy to arrange in-room pampering treatments if the walk to the neighboring spa feels like too much trouble.

The Saguaro Scottsdale is among the handful of downtown Scottsdale hotels that embrace the urban Southwest vibe. Although it began life as a 1970s chain motel—evident in its blocky structure and the compactness of most rooms—this now-hip address has blossomed into the visual equivalent of desert wildflowers at the height of a wet spring. Especially striking against the desert tan that coats just about every other structure in Scottsdale, both outside and in, are a riot of colors that go beyond orange and purple and pink and yellow to such wildflower shades as California Poppy and Red Desert Globemallow. Just as vibrant is the Saguaro’s pool-party scene, aided, no doubt, by water temps chilled or heated as the season dictates. A complete redo of the Saguaro’s rooms in January 2017 gave them a modern Southwest vibe (think pastel-colored prints of cacti and desert-hued furnishings), but not so much that guests will be asking the concierge where to shop for cowboy boots (which would be Saba’s, just down the street, in Old Town).

No visit to Ambergris Caye is complete without an afternoon at the Palapa Bar. Situated at the end of a dock surrounded by turquoise waters and cool breezes, Palapa Bar attracts a mix of locals, travelers, and some of the coolest bartenders on the island. On a warm day, eschew the barstools and opt instead to float in inner tubes beside the dock; you can even have cold buckets of Belize’s Belikin beers lowered down to you. In addition to beer and standard cocktails, fun creations like Scotty’s Palapa Punch (three different types of rum, triple sec, mango, pineapple, and a squeeze of lime) offer some island-inspired refreshment. Up in the palapa, recommended items from the menu include sausage dip, pulled pork sandwiches, and the immense half-pound burger. Palapa Bar is 1.5 miles north of town and easily reached by golf cart, taxi, bicycle, or water taxi, which drops you right off at the dock.

At Maui Brewing Co. in Kihei, visitors can take hour-long tours of the brewhouse, cellar, and packaging line, then adjourn to the tasting room with views of Haleakala and Molokini. There, they can sample beers, ciders, wines, and specialty cocktails while playing board games or simply taking in the vistas. Also on-site at the brewery is a restaurant with 36 craft and specialty beers on tap, plus a menu of burgers, fish tacos, and pizzas with MBC’s Bikini Blonde lager in the crust. Go for the live entertainment or the twice-daily happy hours, when you can enjoy steep discounts on house beers, classic cocktails, pizzas, and select appetizers.

The Bridges of Samaná, also called the “Bridges to Nowhere,” are a string of bridges connecting the small islands that stretch across the outside of Samaná harbor. They are remnants from a project in the 1960s and ’70s by President Joaquín Balaguer to build a restaurant on one of the islands, connected to the mainland by a pedestrian bridge. The restaurant never opened, but the bridges and the shell of the building remain as curious relics of recent history.

Blue Heaven is a favorite in Key West—Jimmy Buffett even mentioned it in one of his famous beach tunes. The whimsical courtyard is filled with brightly colored tables and chairs, twinkly lights, foliage, and stray animals. The bar and restaurant is owned and operated by a husband and wife whose creative backgrounds in art and literature inspired the space. There’s a mini art gallery, a sandwich shop, and roaming roosters on the grounds. Once a boxing ring (with Ernest Hemingway as referee), the spot now pays tribute to the Caribbean, with bright accents and Cajun seasonings on the menu. Menu highlights include the scallops, which are locally celebrated, served with white wine and lemon butter with tomatoes, onions, mushrooms, and lots of garlic. Locals say the Key lime pie is one of the best in town.

Perhaps it’s more interested in diner loyalty than in snagging prizes, but chef Elena Reygadas’s original Mexico City restaurant is still beloved—and busier than ever. So while a few greatest hits linger season to season, there’s always something new to try, inspired by food of the Mediterranean (or the Middle East, or Paris) but supported by the just-picked ingredients only Mexico knows. It invites repeat visits where patrons count on impeccable breads and pastas, delicate greens, and sauces that never cloy or overwhelm, plus some of the freshest fish and tenderest viands to be had in the city. The setting—a venerable town-house patio and parlors, decorated in florid, provincial filigree and anchored by lovely vintage furnishings—is one of the city’s most romantic.

Why we love it: An upscale stay in Victor with special fun for families

The Highlights:
- Proximity to Headwaters Club and its golf course
- Spacious log cabins that can accommodate large groups
- Tons of activities in every season

The Review:
Jackson Hole, on the Teton Range’s east side, hogs most of the high-end traffic, but this westside resort offers an appealing alternative, with big, open skies and out-the-door golf on a Byron Nelson–designed course at Headwaters Club. Guests here can also look forward to a 5,000-square-foot spa with a fireplace-equipped relaxation room, an on-site restaurant serving grill fare, and an outdoor heated pool with two hot tubs and a geyser play area for children.

Accommodations are spacious and appealing to families. Luxury suites feature fully equipped kitchens, dining areas, and living rooms with gas fireplaces, while freestanding log cabins—available in three-, four-, and five-bedroom configurations—afford groups some extra privacy. When not relaxing in your room, take advantage of the resort’s extensive activities, including hiking, kayaking, horseback riding, and hot-air ballooning in summer and heli-skiing and snowmobiling in winter.

Why we love it: A family-friendly resort with a dizzying array of accommodations and activities

The Highlights:
- A range of accommodations, from cozy cabins to boutique hotel rooms
- More than 65 year-round activities to entertain the kids
- A water-themed spa and two championship golf courses for when you need a break from the family

The Review:
Situated on the shores of Gull Lake, the historic Grand View Lodge has been hosting family vacations since 1916. With everything from a kids’ club and indoor water park to a game room and fire pit for s’mores, the resort caters to children of all ages but offers plenty for adults as well, including a water-themed spa and two championship golf courses. Guests here can take advantage of more than 65 year-round activities, including a range of water sports, or venture a short distance to local zip lines, riding stables, and ski resorts. There’s even a newly constructed recreation facility on-site, featuring a 3,779-square-foot pool area, state-of-the-art fitness center, yoga studio, tennis court, ice-skating rink, and more.

Accommodations are equally varied, ranging from lodge rooms and lakeside cabins to garden cottages and entire homes. Come July 2019, a 60-room boutique hotel that’s perfect for company meetings will also be available. When hunger strikes, there are eight dining venues on the property, including a steak house, beachside cantina, and wine bar with a 2,000-bottle cellar. Whether you visit in the summer for the lake or the winter for the nearby mountains, expect cozy accommodations, a high standard of service, and a family trip that will long be remembered.

Tucked into the hilly northwestern corner of Jordan, Umm Qais (or ancient Gadara) commands grand views of the Sea of Galilee and the Golan Heights from the edge of its plateau. It was here that Jesus is said to have performed the miracle of casting demons out of men and into pigs. The town has existed since the Hellenistic period, but is best known for its Roman ruins, which once sat along a prosperous trade route. Many ancient streets and buildings are still intact, as are several Ottoman-era stone houses, which remained occupied all the way until the 1980s. Grandest of all the ruins is the black basalt theater, located along the wide Decumanus Maximus that still holds its original paving stones. Visitors should also be sure to check out the small museum in what was once the home of the Ottoman governor, as well as the celebrated restaurant in the old Ottoman school. In recent years, Umm Qais has become a pioneer of community tourism in Jordan, and it’s even possible to take cooking classes, nature walks, or tours with a local beekeeper after enjoying the ancient ruins.

Wobbly floors, a crooked staircase, dusty books, an old piano, and a few hundred years of character mix together in the beating heart of old Dublin, the Temple Bar. I spend more than half of every year on the road, calling in at one hotel and the next, and I’ve been lucky to have spent time at some fabulous hotels and holiday homes. This joint at No. 25 Eustace St. is near the top of the list. From the Irish Landmark Trust website: “The Irish Landmark Trust saves heritage buildings throughout the island of Ireland that are at risk of being lost through neglect or inappropriate use; conserving and restoring these buildings so they can be let as holiday homes.” The next time you’re in Dublin with your family or a large group, forget about calling in on modern digs, and check out No. 25, or one of the other heritage properties managed by the trust. It was a beautiful experience, and I can’t wait to check in again. Next time I plan to visit an old lighthouse, fort, or country home.

The Jefferson Hotel has been the gold standard for discerning visitors to Richmond (including 13 U.S. presidents) since 1895. Not content to rest on their laurels, the hotel completed a renovation in 2016, restoring its landmarked public areas and refreshing and expanding the guest rooms and suites. The new rooms feel more like posh apartments, with doorbells, foyers to the sitting and dressing areas, and luxury touches like soaking tubs, walk-in showers, and in-mirror televisions. The alligator drawer pulls are a nod to the creatures who used to live in the lobby fountains in the early 20th century. The Rotunda and Palm Court lobbies, with their Tiffany stained glass ceilings, have overlooked many power meetings and celebrations, and provide a magnificent backdrop for decadent afternoon tea or the popular champagne Sunday brunch. The four-star Lemaire restaurant serves a New American menu of Virginia ingredients in their distinctive dining rooms, while the more relaxed TJ’s bistro is open for hearty breakfasts and classic lunch fare. Guests of the Jefferson may work off all that locally sourced food at the 3,000-square-foot gym or in the indoor pool with skylights and an outdoor pool deck.

How often does a king’s car pick you up at the airport? Arrival at Heritage Suites begins with a vintage 1962 or 1968 Mercedes—one of which used to belong to the late King Norodom Sihanouk—before you’re promptly whisked off to a historic cream-colored building of soaring arches, mahogany columns, and wrought-iron balconies. With just 26 rooms (most of which are suites), the boutique hideaway is often so serene as to feel more like a royal’s private compound than a hotel—if a royal’s compound had its own high-end tour agency and one of the trendiest jazz bars in town. Rooms are spacious and surprisingly modern in style—all suites have a lush private garden, and top-tier rooms also have a private hot tub—and welcome drinks and canapés help guests immediately acclimate to the villa’s languid and decadent atmosphere. The sprawling saltwater pool and its umbrella-shaded sunbeds beckon at all hours (including for romantic candlelit dining), while the intimate spa offers yet another way to unwind in between temple excursions.

Best of all, the hotel gives back: It works closely with the Sala Baï Hotel and Restaurant School, training and hiring students from this school that works with underprivileged Cambodians, especially women, and offers guests opportunities to participate in activities with the school.