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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.

One of Bermuda’s most historic resorts—there’s even a 300-year-old sea captain’s cottage on the property—Cambridge Beaches is a traditional rose-hued confection that matches its four pink-sand shores. Though an English country club vibe prevails in many of the public spaces (think tennis whites and croquet on the lawn), the rooms are anything but stuffy, outfitted with vibrant coral and lime-green sofas, zebra-striped rugs, and in some rooms, private plunge pools. Relaxation can be found in the marine-sourced treatments on offer at the Ocean Spa, but if you’re looking to excite the palate, the acclaimed Tamarisk restaurant plates up local takes on creole specialties, from the iconic Bermudan fish chowder to fresh-caught lobster baked in garlic and coconut oil.

Borrow a bike and get down by the Charles River to explore this popular linear park, which runs along the river through the Back Bay and the Beacon Hill neighborhood (albeit separated from both by the Storrow Drive expressway). A paved, 18-mile multiuse path popular with cyclists, runners, and in-line skaters helps connect the Esplanade to the parklands of Boston’s Emerald Necklace and provides easy access to landmarks like the Hatch Memorial Shell (the summer stage for the Boston Pops and other performers) and Harvard Bridge (aka the Smoot Bridge). The landmark Community Boating boathouse has kayaks, stand-up paddleboards, and sailboats for rent when you want to get out on the river.

Moorings Village has a setting out of an island fantasy, stretched along one of the largest private beaches in the Keys, with more than 1,000 coconut palms shading its 18 guest villas. After a direct hit from Hurricane Irma, the resort reopened in January 2018 with 100 newly planted coconut trees, a new picturesque dock, and a refurbished swimming pool—while still maintaining its eclectic design and luxurious feel. The individually styled villas—each with a wraparound veranda—have kitchens, living and dining spaces, and a selection of artwork collected during resort owner Hubert Baudoin’s travels. Ocean activities rule the day here (unless you’re lolling in a hammock) and the property offers complimentary kayaks, paddleboards, and bikes, in addition to coordinating excursions like scuba diving, kitesurfing, sailing, and fishing. And because the resort takes up both sides of the Key of Islamorada, guests can catch the sunrise and then witness sunset while dining at either Pierre’s (an upscale spot with French fusion cuisine) or the Beach Café (a casual bistro serving Caribbean-American food). Pro tip: Book your visit to coincide with the full moon to attend the Mooring’s monthly beach party for live music, fireworks, and bonfires on the beach.

Every Thursday night during the months of November to June, San Jose de Cabo’s galleries stay open late for Art Walk. You can join other art lovers on a casual stroll through the Art District’s many galleries, enjoying work in various media from both local and expat artists. Several local restaurants participate in the Art Walk, too, offering specials or discounts as part of the weekly event.

Before World War II, Falls Church experienced its most significant growth during the Victorian era (1837-1901). Today, the city’s Victorian-era legacy lives on in the charming homes and churches along East Broad Street, in between Roosevelt and Washington Streets. A few years ago, the Victorian Society of Falls Church created a self-guided walking tour map for locals and visitors highlighting Victorian architectural styles and buildings like Tallwood (see above picture), an 1870 home whose previous occupants included a descendant of the founder of Yale University, and a brother of President Dwight D. Eisenhower. An important note: all houses except Cherry Hill are private residences and are therefore not open to the public.

Located just footsteps from the hustle of Columbus Circle, Mandarin Oriental New York serves as the ultimate urban escape. More than 240 rooms and suites showcase stunning views of Central Park, the Hudson River, and the Manhattan skyline, while carrying their own perks within (Diptyque amenities, cherry wood furnishings, walk-in showers). The 14,500-square-foot spa feels like a true getaway in the heart of the city, with a tea lounge and a number of treatments ranging from Jet Lag Cure to Thai Foot Therapy.

The MO Lounge offers dramatic park views and an all-day menu with American cuisine centered on sustainable local ingredients. Come evening, MO Lounge’s hand-crafted cocktails paired with Central Park vistas are perfect for impressing out-of-towners.

Crosby Street Hotel founders Tim and Kit Kemp are behind this Midtown property, which opened its doors in February 2017. Each of the 86 guest rooms exudes a personality of its own, complete with playful pieces of artwork and color-forward design by Kit. High ceilings, long foyers, and walk-in closets help guests feel more at home than on the road, as does a stop at the Drawing Room before lights out. It’s here that floral curtains, oversize armchairs, and book-lined walls greet guests who want a nightcap from the honor bar, which is always stocked with top-shelf liquors, wines, and pre-batched cocktails. Pick your poison and enjoy it in your deep-soaking tub, where a TV and lineup of bespoke bath products await. Come morning, head to the light-drenched Orangery for well-executed breakfast favorites like avocado toast, acai bowls, and brioche French toast.

Perched on a not-so-lonely nude beach on the northern end of Sauvie Island is an enigma. Well above waterline lies a 30-foot orb that piques the imagination and challenges explanation. The “spaceship” origin is not interstellar but certainly presents itself as other-worldly. The craft is actually a ferro cement experimental boat built around 1970 just upriver. It was designed as a self-righting sailboat and carried a local family on adventures for a couple decades before it got away. Now covered in moss and graffiti, it sits as a testament to Oregon innovation and exploration. To do some of your own exploring of this mysterious craft, take Reeder Rd out to where the pavement ends at a spot called Collins Beach, aka the nude beach. (Yes, if you venture out in summer, you will see naked people.) There’s a parking area (permit required) and trails down to the beach. Sitting up in the trees, just above the sand, sits the stripped-out hulk of a dream. The tri-hulled beast looks more like a lifeboat than a spaceship, but alien nonetheless. Be careful climbing around if you decide to explore inside. The rusting steel framework is losing its cement skin in places and can be dangerous. Cycling to the site is a great way to spend an afternoon on the island and get a great workout in the process.

It appears small from the outside, but Gale South Beach manages to pack a lot into a modest space, including Italian restaurant Dolce, a cocktail lounge, and a nightclub. These attractions, and its prime location on Collins Avenue, just a block from the beach, make the Gale a social hot spot. The landmarked art deco building is, like many of its neighbors, protected from structural changes; as such, the hotel harks back to the golden age of American architecture. Inside, the decor evokes 1940s–1960s style, with throwback typography, black-and-white family photos, newspaper clippings, and mid-20^th-century memorabilia providing atmospheric design touches. The rooms are on the smaller side but tend to let in lots of natural light. The color scheme is nautical, with blue carpeting and white walls, and crisp, bright white linens embroidered with the hotel name in blue. Guests can take advantage of an outdoor bar on the fourth floor, and a rooftop pool. An annex of the hotel is set to open just a few feet away in December 2014. The Gale Suites at Kaskades is a 25-suite complex with a focus on luxury and privacy. It features rooms with Jacuzzi tubs and rain showers and has its own rooftop deck with cabanas.

Just when it seemed like the Riviera Maya Riviera had become nothing but a sea of all-inclusive beach resorts, you stumble upon the quaint little Mexican village of Puerto Morelos. There are almost no huge developments, no shopping outlets, and no chain restaurants. The place is absolutely magical and is like traveling back in time. There is a small town square or plaza lined with palm trees, small cafes, and local boutiques. You can always find a good margarita to sip on at the super hip little bars scattered around the small town. If you find yourself on the Yucatan peninsula don’t miss this opportunity to travel back in time 50 yrs and experience the “old” Mexico.

Nearly hidden behind a tall row of hedges is Delano South Beach, a landmarked hotel built in 1947 and renovated by Ian Schrager and Philippe Starck in 1995. Schrager and Starck wanted Delano to feel like a home; to that end, Starck created a series of discrete “living spaces,” with mismatched furniture, in the hotel’s common areas. Each of the spaces is intended to evoke specific images and experiences from his childhood, such as a wall of nightlights. The Delano’s backyard and pool area are an extension of the lobby’s “living room,” and that’s why a table and two chairs sit in a shallow section of the pool, and why the hotel’s veranda features the kind of comfortable furniture usually found inside a building, rather than outside it. In rooms, guests will find oversized marble bathtubs, said to be a favorite among NBA players because of their seven-foot length, along with Malin + Goetz toiletries.

One of the more relaxing evenings away from home was spent at the Outrigger Hotel in Kailua-Kona on the Big Island of Hawaii. I checked in with no problems and was even upgraded to a partial ocean view room! I had enough time to mosey on through town to grab some dinner and watch the sun sink to the ocean (complete with a green flash). The hotel was comfortable and situated next to a beach filled with a all sorts of fish and sea turtles. Snorkeling at Kahaluu Bay Beach Park, right next door to the hotel in the morning was one of the best snorkeling experiences I have had in Hawaii. The water was clear and the marine life was over-abundant! Sitting at the beach bar in the evening with live music and the sound of the surf was enough to relax the body and soothe the soul for a great night of sleep! If you are local, make sure to book their Kamaaina rate. **Unfortunately, the Keauhou property has closed. However, the Outrigger has several other properties on the Big Island.

Families will find lots to love at this 241-room high-rise property on Palm Beach. Children under 12 stay and eat for free, and the Treasures of the Caribbean kids’ club—complimentary to guests—organizes supervised scavenger hunts and sand castle–building competitions by day and film screenings, complete with popcorn and Shirley Temples, in the evenings. There’s also loads of space for the whole gang to spread out: Even the lowest-tier studio suites are amply sized, featuring a full kitchen, a dining table, and a private deck or balcony. But Divi also offers plenty to keep adults occupied while the little ones play, including two pools (with a swim-up bar and cabanas), a full-service spa, and two beachside restaurants with tables situated just steps from the water’s edge.

One of the world’s best beaches according to UNESCO, this beautiful palm-lined stretch of golden sand 40 minutes north of Punta Cana is known for its top-rated surf school and its oceanfront restaurants that serve delicious, Dominican-style fish plates. Catch some waves at one end of the beach, then swim in the calm water at the other, where fishing boats loaded with red snapper and lobster pull ashore. Mid-beach, you’ll find food and drink stands alongside activity concessions, from buggy rides in the dunes to stand-up paddleboarding, horseback riding, and surf lessons.