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The past two decades have seen the dozens of islands scattered across Boston Harbor transformed from barely noticed dots on the horizon to one of the city’s most popular attractions. The Boston Harbor Island National Recreation Area, established in 1996, has propelled them into prominence, with ferries carrying day-trippers and overnight campers from downtown Boston, Hingham, and Hull to eight of the islands (19 more are accessible by private boat or charter excursions). Most visitors head to Georges Island, home of the Civil War–era Fort Warren, or the beaches and hiking trails of Spectacle Island, the one closest to downtown Boston. (Don’t skip the concession stands here: The food is from James Beard Award–winning Boston chef Barbara Lynch.) You can also camp on Peddocks, Grape, and Bumpkin islands, or take a tour to Little Brewster Island to witness the 300-year-old Boston Light, the nation’s oldest lighthouse.

What do Al Capone and Bruce Willis have in common? They both did time here at Eastern State Penitentiary. (OK, Willis wasn’t an inmate, but he did shoot the film 12 Monkeys here.) The facility’s first inmate was brought through these doors in 1829, and the prison was in use until 1971. After closing, it became a target for vandals and housed a sizable colony of stray cats. Real estate developers proposed repurposing it as condominiums (high-security, of course), but preservationists won out. They raised funds to stabilize the crumbling interior and remove trees that were growing inside some cells. Wander through its stark interior and learn about the fascinating history of this unique site and its previous tenants, including Capone. Don’t miss the special art installations that are on display here all year round.

Pass over limestone rocks and through a protected landscape and you’ll arrive at this enchanting pool, which gets up to eight feet deep at times. Surrounded by volcanic outcroppings, it’s so removed from other island attractions that it feels undiscovered and romantic. The water is warm and bubbly and there are some ledges for sitting, all of which make you feel as if you’re in a natural Jacuzzi. Whether you arrive by foot, mountain bike, or jeep, the journey is as exciting as the destination itself. For a dose of adventure, opt for the half-hour guided horseback tour, which winds past caverns and other rock formations on its way to the pool.

The Caramoan area, on the eastern tip of the Caramoan Peninsula in Bicol, is a rugged and remote landscape of white-sand beaches, rich woods, swampland, lakes, and caves. Numerous seasons of the reality TV show Survivor have filmed around this region, including at Gota Beach. Most travelers explore the pristine Caramoan Islands by small outrigger boat. There are too many to scope out in one trip, but don’t miss famous Matukad Island with its pure white sands, exotic rain forest, limestone rock formations, and even a hidden lagoon. Another must-visit is Manlawe Island, a one-kilometer-wide sandbar surrounded by ankle-deep water. Other highlights include Cotivas Island, Gota Island, and Sabitang-Laya, a triangular landmass with powdery sand, caves, and superb snorkeling. Accommodations in Caramoan include family-run inns that are equipped with modern amenities but rustic enough to accentuate the region’s remote and unspoiled ambience.

Among the three Cayman Islands, Brac is the most topographically endowed, thanks to its distinguishing feature: the Bluff, a limestone cliff rising along the length of the island and topping out at about 140 feet at the eastern end. Between that and the island’s densely forested interior, the local hiking options have a lot to offer—one of the best cases in point being the Lighthouse Footpath, a trail that runs two and a half miles (one way) along the bluff’s edge and that serves up endless sea views and likely encounters with the absurdly adorable brown boobies and soaring frigate birds. Try to go in the morning or late afternoon, and of course, take along plenty of water: You’re looking at a two-hour outing to the most beautiful of boonies.

Why we love it: A boutique hotel that puts guests in the heart of it all

The Highlights:
- Allergen-free Pure Wellness rooms
- A convenient location right downtown
- An award-winning steak house on site

The Review:

A boutique stay in the heart of downtown Boise, Hotel 43 seamlessly blends cozy charm with urban style. Works by local artist Amy Westover enliven the cathedral-like lobby (its ceiling soars to 60 feet), while vibrant drapery and bathrobe-clad teddy bears on each bed make the 112 guest rooms feel both chic and homey. If you need more than William Roam bath products and a jetted tub to feel pampered, book one of the Pure Wellness rooms, which offer purified, hypoallergenic accommodation for even the most sensitive of guests.

Hotel 43 also provides travelers with a free pass to the Boise Art Museum, plus loaner bikes for cruising to the Shakespeare Festival or farmers’ market. Come dinnertime, however, you’ll want to stay put for a meal at on-site Chandlers Steakhouse, where Kobe-style beef and fresh seafood are accompanied by live jazz each evening. In the morning, head to Metro Café for Caffé D’arte coffee, freshly baked pastries, and house-made granola, or grab the complimentary airport shuttle to catch your flight home.

Why we love it: A faithful reimagining of a classic travelers’ hotel

The Highlights:
- Conveniently located right next to East Tennessee State University and near downtown
- Delightfully comfortable sleigh beds
- Historically accurate decor, including oil paintings and antique furniture

The Review:
While the original Carnegie Hotel in Johnson City was lost to a fire in the early 20th century, guests can get a taste of history at this faithful re-creation, which offers upscale accommodations for both business and leisure travelers. Today, the hotel combines historical grandeur with modern amenities, such as a state-of-the-art fitness room, a heated outdoor pool, and a full-service spa for massages and body treatments. In the 128 rooms and 11 suites, guests also find sleigh beds with mattresses so comfortable they’d be wise to set two alarms for the morning.

The on-site restaurant, Wellington’s, serves elevated Southern cuisine made with traditional Appalachian ingredients, while the bar offers craft cocktails and a wide selection of whiskey. After your meal, take a nightcap down the hall to the clubby Roosevelt Library lounge, where you can admire original oil paintings, dark wood accents, and antique furniture that recall the Carnegie Hotel of yore.

Come to this neighborhood corner establishment for the seafood, but don’t overlook the beef tartare, complemented by radish, nori, and ranch (and don’t be ashamed to order two if you’re with a party of three or more). Pricing is akin to the Ordinary, without that big brother’s fancy full experience, but it’s worth a visit for treats like tempura blowfish tails—bone-in adult lollypops of crispy, savory flavor, with lemon and spicy mayo on the side. Unconventional entrees like the smoked fish curry (amberjack one week, mackerel the next) with pumpkin and peanuts and hints of citrus, make each bite a pleasant and surprising adventure of textures and tastes. The tiny dining room gets packed quickly on weekends, and the residential setting means they still haven’t acquired a liquor license a year in, but the flavor is worth any sacrifice. The small but excellent wine list includes creative sparkling varietals, and the restaurant is one of a few places in town to serve Life Raft Treats desserts—don’t leave without a waffle-flavored ice cream in the shape of a small chicken leg, coated in toasted corn flakes, wrapping a frozen cream-filled chocolate wafer.

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.

Of the many draws of this upscale property on 26 pine-clad acres, the biggest is arguably its beach, one of the longest private stretches on Lake Tahoe, where guests can relax in cabanas and lounge chairs, rent jet skis, boats, or kayaks, and even stay in one of the 26 luxury beachside cabins. The lobby, with its massive timbers, flagstone walls and fireplaces, and huge windows, recall some of the great National Park Lodges; the rooms, however, are modern and spacious, swathed in soothing neutral colors. (Rooms on the upper levels of the 12-story tower have the best views.) And because the resort resides on the Nevada side of the North Shore, there’s a 20,000-square-foot casino. Other amenities include a spa, fitness center, and an indoor/outdoor swim-out pool that—along with a lazy river and water fountains—is heated year-round, as well as a kiddie pool and two large whirlpools. And no need to leave Fido behind: the resort accepts your furry friends, too.

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.

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.

This property hits the sweet spot for Yosemite lodging—it’s conveniently located in the heart of the valley, is more affordable than the Majestic, and has better views than any other accommodation, looking directly out to Lower Yosemite Falls. All 241 rooms, spread among 15 two-story buildings, were recently updated to include TVs, mini fridges, phones, coffee makers, and Wi-Fi. While not air-conditioned, they come with fans and some even have patios or balconies. There are also four larger family rooms, complete with a king bed and two bunk beds. The lodge has its own pool, gift shop, and outdoor amphitheater, where rangers and naturalists give presentations during warmer months, as well as two restaurants. The more formal Mountain Room features soaring ceilings, waterfall views, and dishes like lobster beignets and grilled pork mole, while the Mountain Lodge—popular with the valley’s climbers—serves beer, cocktails, and a small but tasty bar menu, which can be enjoyed either inside by the double-sided fireplace or outdoors on the deck. There’s also a food court, which is slated for a complete makeover in the spring of 2018.

At the Hyatt Centric, luxury amenities meet front-door access to 7,300 acres of ski terrain, including the 314 trails, 40 chairlifts, and six natural half-pipes that make up the Park City Mountain area of Canyons Village. For even more adventure, the hotel’s in-house activities company, Wasatch Adventure Guide, can arrange for dogsledding, fly-fishing, heli-skiing, hot-air ballooning, and even ice-climbing excursions. If you’d rather soak up some culture, there’s complimentary seasonal transport to Park City’s charming Main Street and its dozens of galleries. After a long day of exploring, guests can unwind in the resort’s heated outdoor pool, or in front of their own stone fireplace. The 120 guest rooms and apartment-style residences offer a home-away-from-home feel, with even the standard rooms featuring a partial kitchen stocked with china for four. In case you don’t feel like entertaining, the on-site Escala Provisions Company Restaurant & Bar offers après-ski fare like classic fondue as well as a dinner menu with dishes like a grass-fed beef burger with tomato jam, pork belly, and pommes frites.

On a hilltop perch overlooking 8,000 acres of grounds designed by famed landscape architect Frederick Law Olmsted, the Inn on Biltmore Estate’s 210 rooms and suites evoke traditional 19th-century manor houses, with dark mahogany beds and desks, billowing window treatments, and comfortable overstuffed chairs; book a room with a balcony to breathe fresh mountain air while appreciating views of rolling hills—or simply take in the vista from the hotel’s veranda. The formal dining room showcases seasonal specialties using estate-raised cattle and lamb, vegetables from the on-site garden, and wine from the property’s own winery, where you can participate in a free tasting, then ride back in a complimentary shuttle. If you’re looking for something more casual, the lobby lounge and library bar offer salads and sandwiches—and no dress code. But the main attraction is the 250-room Biltmore château, the Gilded Age mansion George Vanderbilt built here in the late 1800s, and its 16th-century tapestries, Renoir and Sargent originals, and 65 fireplaces.