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On the North Fork of Long Island, Shinn Estate Farmhouse Inn is tucked away on a peaceful vineyard. Rooms are in the estate’s historic 1880s homestead, and guests get to experience life on the vineyard—and taste the final product in the winery’s tasting rooms. There is also a lovely front porch and gazebo for kicking back with a glass of wine. A cozy wood-burning stove in the reception area is an ideal spot on a chilly day. Breakfast here is a slow and civilized affair, starting with hot coffee and finishing with a full farmhouse hot breakfast from chef David Page, made from farm-fresh ingredients. This is the pastoral North Fork at its best, designed for lazy afternoons, sleeping in, and one too many glasses of wine.

A historic New York state resort, Mohonk Mountain House first opened in 1869 in the Hudson Valley, about 90 miles from New York City. This Victorian castle has welcomed five U.S. presidents (including Bill Clinton) in addition to countless artists, authors, and actors. Surrounded by thousands of acres of nature, the resort is perched on a cliff overlooking Mohonk Lake. Guests travel specifically for the dramatic, vibrant fall foliage and expertly manicured gardens. Rates are all-inclusive and comprehensive—all meals and activities are included for a single nightly rate. Yoga classes, boating, tennis, horseback riding, and rock climbing are all popular activities. During the winter, ice skating and cross-country skiing lure guests into the great outdoors. Rooms with wood-burning fireplaces and a huge spa with heated indoor and outdoor pool create a peaceful retreat.

Around since 1692, Spier is one of the oldest and best-known wineries in Stellenbosch. Not only does this historic estate continue to receive accolades for its wine, it’s also become a hot spot for travelers thanks to its family-friendly atmosphere. Visitors can easily spend anywhere from a couple hours to an entire day enjoying all the activities Spier has to offer, from picnics on the lawn overlooking the Eerste River to self-guided walking tours of the property. There’s also a farm-to-table restaurant on-site, as well as an outdoor playground for children. For something unique, book the “Eagle Encounter” program to learn how the estate rehabilitates wounded birds and uses them for natural pest control, or take an evening Segway tour of the vineyards, followed by a sunset tasting among the vines.

On the second Sunday of every month, bargain hunters, collectors, designers, tourists, and other curious shoppers head to the historic Rose Bowl Stadium in Pasadena, where 2,500 vendors of furniture, accessories, clothes, crafts, vinyl, and more line the perimeter of this 92,000+ seat venue. The sheer size may be overwhelming, the sun may be beating, and it may be early in the morning—but if you come prepared in sneakers, a hat, and with coffee in hand, you’ll be ready to hunt for treasure.

If you find yourself in Asheville, NC (and you should, as AFAR’s recent feature pointed out - there’s a lot to love in Asheville); stay at The Grove Park Inn. This historic hotel is part art deco/part arts and crafts with rambling porches and a view of the mountains to rival other properties in town. The Horizons restaurant serves up Michelin-worthy meals and their sommelier will not steer you wrong. The spa buried in the depths of the property has salt water pools and heated waterfalls, with trained masseurs who can erase any ill your body is suffering. Rooms are spacious and comfortable with updated bathrooms. The elevator is built into a massive fireplace. It’s an incredible place that does an excellent job of showing off the quirky character of the Southern town it calls home.

Hello, rooftop pool! Leave it to Chicagoans to remain optimistic that summer will be amazing, even if winter lasts well into May. The rooftop pool (open to restaurant as well as hotel guests), occupies a prime spot on one corner of Six Points, that crazy intersection where three major shopping streets cross paths. That means the regulars are a mixed bag, but all come in for a good time, whether that means for brunch in the newly redesigned Café Robey street-level restaurant, to drink until dawn at the poolside Cabana Club bar, or to sneak up to its new sister, the Up Room, at the top of the deco tower.

View along hike between these two villages.

Right on Key West’s famous Sunset Pier and next to Mallory Square, Ocean Key is at the center of the action, proven by the flocks of tourists who descend on the pier every evening at sundown. Inside the resort, the contemporary rooms are decorated in tropical colors like bright lime and turquoise, and have bathrooms with rainfall showers and whirlpool tubs and private balconies with views of the Gulf of Mexico or buzzy Duval Street. The angular pool is surrounded by cabanas and day beds; grab a ringside seat for the daily fashion show at Liquid, the kicking poolside bar. Prefer a quieter experience? The spa has a full range of treatments and packages that lean heavily on Asian traditions and ingredients, from Balinese massage to a Javanese rice-and-turmeric body scrub.

A larger, more luxurious alternative to an inn-style getaway, the ocean-facing Gurney’s Montauk Resort offers gorgeous views, plush accommodations, and top-notch amenities, including a whopping 2,000 feet of private sandy beach. The spa is the star attraction and includes a Finnish sauna, steam room, Roman bath, and saltwater swimming pool, all of which are only open to guests to maintain a quiet, exclusive ambience. Other property highlights include a salon, fitness center, and selection of restaurants, ranging from Scarpetta Beach (which serves Italian cuisine) to Tillies (a more casual bistro with hearty American fare and brunch specialties on weekends). Not surprisingly, the guest rooms and cottages are especially luxe, with lovely wooden floors, walk-in rain showers, and big windows with sweeping sea views.

In the heart of Old Québec’s Upper Town, Hotel Manoir Victoria blends 19th-century grace with an updated urban-chic vibe. A recently completed $8 million makeover of the 1830 property’s accommodations added a calming palette of ebony, gray, and cream and amenities like electric fireplaces and living areas, as well as iPhone chargers, rain showers, and pod coffee makers. Guests have no shortage of diverting destinations to choose from, including a spa, indoor saltwater pool, and fitness center. The hotel’s gourmet restaurant, however, usually beats out the competition, earning high praise for its thoughtful Nordic-inspired Québecois cuisine using seasonal, locally sourced, and foraged ingredients in dishes such as carpaccio of elderberry-marinated arctic char with cattail heart and milkweed pod.

Hilton Molino Stucky on Giudecca Island is a zippy five-minute boat ride (free for guests) away from bustling Piazza San Marco, and ideally located for those craving a tad more tranquility without missing out on any of those sweeping Venetian vistas. Once a working flourmill, this brick, industrial-era fortress has been reimagined as a luxury hotel with all of the modern bells and whistles. Take a break from museum hopping with a day spent surveying the city below from the city’s only rooftop pool (followed by quality time spent in the spa). Of course, with several dining options just steps from your room, you could happily spend most of your time right here.

If mixing business with pleasure, this hotel—with Executive Suites, a ballroom for events, several conference rooms, and a business center—makes for a superbly scenic day at the office.

Set within a century-old, Pantheon-inspired former bank building, the Ritz-Carlton, Philadelphia raises Center City living to classical heights. When the building opened in 1904, the Girard Trust marble dome was the largest in the country, and its columns and styling matched its inspiration down to its oculus 142 feet from the floor, the exact height as the Roman original. Today, every stay starts in this grandiose rotunda, where staff man the immaculately preserved bank-teller booths. Guest rooms and suites are in the attached 30-story office tower, gutted and transformed into a hotel by Ritz-Carlton.

All 299 rooms and suites bring classic Ritz-Carlton elegance, with wood furnishings matching gold, sage, and pumpkin hues. High ceilings and picture windows with stunning city views enhance the vibe, while spa-style marble bathrooms have rain showers.

Hotel Zelos brims with understated luxury. Rooms are kitted out with on-demand movies and music, in-room spa services upon request, and a complimentary honor bar stocked with organic treats. The hotel’s 4th and Market Street location puts it within walking distance of Union Square, AT&T Park and the Moscone Center. For further distances, guests can borrow free bikes. The hotel’s crowning jewel, though, is Dirty Habit, it’s rooftop restaurant and bar. A favorite among locals as well as tourists, Dirty Habit’s film-noir-inspired dining room offers guests a chance to play the part of old Hollywood glamour while nibbling on seasonally inspired dishes like seared king salmon and sipping inventive craft cocktails (try the Bonzai, a mix of whiskey, orgeat, grapefruit, lemon, and matcha green tea).

Reykjavík’s old harbor, built between 1913 and 1917, has seen quite the transformation in recent years, morphing from a mainly functional area dominated by ships and their fishermen to a lively, modern tourism area that’s almost a new city district of its own. The sparkling, award-winning Harpa concert hall and conference center has dominated the area since it opened in 2011, and several restaurants and cafés, along with offices, now line the harbor promenade, interspersed with the occasional cultural spot such as the fascinating Reykjavík Maritime Museum. The boats, trawlers, and whaling ships are still there, of course, and remain a big part of the atmosphere, but they’re today joined by a number of tourist boats offering whale-watching and puffin tours.

Set on the northern shore of Lake Union—a body of water the size of Monaco—this rustic-chic, nautical-themed restaurant offers dazzling views of the Space Needle and downtown skyline. Its menu blends Mediterranean flavors with local bounty: Expect highlights like grilled octopus with taramasalata, charred carrots with cocoa, and a salmon gravlax tartine with za’atar, green apple, and cauliflower labneh. Finish with a rhubarb-pistachio cheesecake or a cheese from Vashon Island’s Kurtwood Farms. For extra Northwest credit, arrive in a kayak or on a stand-up paddleboard, or rent a ride from the Center for Wooden Boats (cwb.org)—then moor near the waterside fire pit!