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  • 939 West 5th Avenue
    In 1964, a 9.2-magnitude earthquake—the second most powerful ever recorded—ripped through the south coast of Alaska, devastating much of downtown Anchorage. After surveying the damage, real-estate developer Walter J. Hickel, who would later go on to serve two terms as the state’s governor, vowed to build Alaska’s biggest and best hotel. The result, a massive 546-room complex spread out over three towers, is still the city’s most luxurious, known for its attentive concierge, excellent athletic club, and wealth of dining options. The elegant Crow’s Nest restaurant offers dishes that incorporate French technique with regional ingredients, like king crab–studded bouillabaisse, along with a 10,000-bottle wine collection; on a clear day, 360-degree views include the iconic peaks of Denali. One more reason to visit: The property was inducted as a member of the Historic Hotels of America in 2016.
  • Tordrillo Mountains, Alaska 99682, USA
    Just a 45-minute floatplane ride from Anchorage along the banks of the Talachulitna River and Judd Lake, this multistructure resort combines a six-room flagship lodge, which was renovated in 2017, with a lakeside bar and dining room (and 500-bottle wine cellar); a private four-room lodge; and two smaller individual cabins, all with views of either the Alaska or Tordrillo ranges. But guests don’t come here to just ogle the mountains—they take them on. With Olympic gold medalist Tommy Moe and Alaska heli-ski pioneer Mike Overcast behind the resort, plus access to 1.2 million acres of untrammeled terrain with runs that top out at 7,500 feet, world-class heli-ski adventures are practically guaranteed. And an exclusive partnership with Winterlake, another notable resort nearby, allows guests to heli-ski even further north into the Tordrillo Range and Neacola Mountains.
  • Talkeetna, AK 99676, USA
    There are several small towns around Alaska that make visitors of years past smile. Talkeetna sits pretty high atop that list. A good stopping point between Anchorage and Denali National Park, the town is at once a history stop, arty spot, beer fill-up, hearty food destination, and mountain climbing mecca. Talkeetna is the first step for everybody setting out to climb Denali. But it’s also the go-to for visitors who enjoy quirky little towns with huge personalities. Thanks to cruise-ship bus tours, the town does get a bit overrun during the summer months—but it’s still worth swinging in. And if you happen to be in Alaska during the winter and want to attend a very Alaskan event, don’t miss the Bachelor Auction. The entire town gets revved up and pretty darn drunk. It’s damn fun.
  • On the leeward side of Union Island, remote Chatham Bay Beach—one of a dozen on the island—is a favorite anchorage for boaters, a peaceful spot for sunbathers, and a great location for snorkelers. If you’re coming by land, there’s a trail that leads right down to the beach. There’s also a bar and a couple nearby restaurants should you get hungry from all that relaxing.
  • Antigua and Barbuda
    English Harbour is one of Antigua‘s crown jewels, so it should be no surprise that Fort Berkeley was erected to protect this excellent protected bay. Placed on the peninsula on the western entrance, this fort has been enforcing entry to the anchorage for nearly 300 years. Today, the fort is mostly ruins, but it still supplies visitors with stunning views of the harbor. From Nelson’s Dockyard it’s a fairly short 10-minute stroll to the ramparts and well worth the walk. From here you can see the dockyard’s waterfront, every boat that enters the bay, and beautiful Galleon Beach on the opposite shore.
  • 120 Wauwinet Road
    The Wauwinet makes the most of its coastal setting between the Atlantic Ocean and Nantucket Bay. Next to the Coskata-Coatue Wildlife Refuge, the resort has 32 rooms, plus four cottages with separate living rooms and the three-bedroom Anchorage House across from the main inn. In addition to private beach access and bikes to explore the island, guests can take out a kayak, play a game of tennis, or watch a movie in their room with hot buttered popcorn. A spa offers sea-inspired facials, massages, and body treatments. TOPPER’S restaurant is known for its Retsyo oysters, harvested only 300 yards from the restaurant, and offers transfers to and from White Elephant Hotel’s Brant Point Grill on its 21-passenger boat, Lady Wauwinet. The inn also provides regular shuttle services to the ferry and Nantucket town (about 10 miles away), and outside of peak summer season will drive guests to the village of ‘Sconset in its 1947 Woody station wagon.
  • 171 Lindblad Ave, Girdwood, AK 99587, USA
    Family-friendly Chair 5 Restaurant lures visitors with its gourmet burgers and pizzas, including pies with unique toppings (try its Thai Chicken pizza), as well as deep-dish options. Originally opened in 1983 at another location, the restaurant remains a go-to spot for locals in search of draft microbrews.
  • 33F+44Q, Route 37, St. Thomas 00802, U.S. Virgin Islands
    One of the island’s best lookouts, Drake’s Seat offers a panoramic view of Magens Bay and the U.S. and British Virgin Islands to the east. The site is named for Sir Francis Drake, who is said to have kept watch over the harbor from this vantage point. (Was Drake benevolently watching over his own fleet or looking for ships to plunder? The answer will depend on whether you subscribe to the British’s regard of him as a celebrated explorer or to others’ belief that he was a brutal privateer.)
  • 1343 G St, Anchorage, AK 99501, USA
    Fire Island, in the heart of South Addition, one of Anchorage’s oldest neighborhoods, handcrafts an astonishingly delicious array of baked goods, breads, sandwiches, and savory delights that keep locals lining up for more. The bakery uses as much local produce as it can squeeze into its scones and muffins, offers interesting flavor combos, and serves up a tofu banh mi that is one of the finest tofu sandwiches known to man. If you’re hanging out in Anchorage for more than a day or two, check out the class schedule. You could leave Alaska with some serious sourdough skills. Please note: Fire Island is closed Mondays and Tuesdays, as well as most of January.
  • White House Bay, St Kitts & Nevis
    While White House Bay is becoming more widely known since SALT Plage restaurant opened on its shores, it’s always had a reputation for offering the best snorkeling on St. Kitts. Off the rocky beach, you’ll find calm waters and two notable wrecks—a sunken tugboat and an 18th-century British troop ship—to explore. A popular anchorage, the beach also features a chic bar, making it a favorite of the yacht set.
  • 429 E Street
    Take your place in line, check the street sign to see what the flavors of the week are (or send somebody up to the shop door to take a peek), and start planning your order. Most of Wild Scoops’ ice creams are made with locally sourced ingredients. Even Alaska-made potato chips make an appearance. Are you a fan of coffee ice cream? Then don’t even play around. Order up a coffee ice cream baked Alaska. They’ll fill a freshly made waffle cone with the sweet cold joy, swirl marshmallow on top, and hit it with a mini blowtorch. You’ll be back for more the next day.
  • 27635 Seward Hwy, Anchorage, AK 99540, USA
    Don’t blast past this easy-to-drive-by restaurant on the Seward Highway. Open since June 2017, Froth & Forage looks like an unassuming sandwich joint. And it does serve some sandwiches. But you’re not going to get, say, a ham and cheese. Nope. You’re going to get an open-faced shrimp scampi sandwich served with house-cut fries that are topped with truffle oil, garlic, and Parmesan. Oh, and the view out of the window is of Turnagain Arm and the mountains. It’s crazy beautiful. So now you see why you shouldn’t blast past? You’ll want to eat there again—and you can do that on your drive back to Anchorage.
  • Park Road
    Each year, six million–acre Denali National Park and Preserve gets roughly 400,000 visitors, who come in hopes of spotting the park’s own version of the Big Five (grizzly bears, moose, caribou, wolves, and flocks of Dall sheep) and to take in majestic views of the highest mountain peak in the country. Only a fraction of that number, however, escape the crowds and tour buses to make their way to the tail end of the 92-mile-long Park Road, which winds deep into the heart of Denali’s rugged backcountry to the old gold town of Kantishna. Those who do are rewarded at this all-inclusive vacation resort with 42 rustic cedar cabins, some of which have private decks facing secluded Moose Creek. (All come equipped with private indoor bathrooms and heaters, welcome treats in these parts). Activities range from morning yoga classes and gold panning to guided hikes and mountain biking excursions. After an invigorating day outdoors, guests can pamper themselves in the new spa, which offers treatments like Swedish massage with hot stone therapy.
  • Magens Bay, St. Thomas, U.S. Virgin Islands
    This beautiful one-mile stretch was donated to the people of the Virgin Islands by Arthur Fairchild, a benefactor of the islands who’d made his fortune on Wall Street before retiring here. The usually calm waters of the heart-shaped bay make the beach the most popular on St. Thomas. Rent beach chairs and floats, and pick up lunch from stands selling burgers, pizza, and other snacks. Lifeguards are on duty every day.
  • One of the most popular anchorages in the BVI, Cane Garden Bay is home to a lively boating community. It makes a great day trip, whether you arrive by land or by sea. In this scenic cove, calm blue water laps a gentle arc of blinding white sand. Open-air beach bars offer lounge chairs and rum drinks; a few shops sell souvenirs, along with provisions for the sailors coming in off their boats to stock up.