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Spend the night nestled under the Golden Gate Bridge in the most dignified of accommodations: the former living quarters of high-ranking officers in the U.S. Army. Cavallo Point is the result of the luxurious reimagining of a cluster of military lodges located within the Golden Gate National Recreation Area, just over the bridge in Marin County. Today, the 142-room hotel serves as a retreat for in-the-know travelers and locals looking for an easy, elevated escape from everyday city life. Original brick fireplaces and beamed ceilings mingle with modern finishes and furnishings, such as butter-soft leather sofas and whitewashed Adirondack chairs. The expansive grounds are meant to be explored on foot or bicycle. The Wellness Weekend package includes all meals, prepared with an emphasis on health at Murray Circle restaurant, morning yoga classes, guided hikes, a spa treatment, nightly wine receptions, and plenty of free moments to soak in the serene meditation pool—the very best kind of boot camp.

One of Anguilla’s most secluded beaches, Little Bay is tucked beneath a series of bluffs on the island’s northwest. Usually reached by boat or kayak from Crocus Bay, this tiny, undeveloped stretch of sand hugs a cove with calm turquoise waters filled with small tropical fish, sea turtles, and starfish. Bring drinks and snacks, rent gear from Da Vida Restaurant, and kayak (or boat taxi) over in the morning to avoid the crowds and spend a couple of blissful hours away from it all.

This twin-peaked headland—and the ruins of the 18th-century Fort Shirley garrison—preside over Prince Rupert’s Bay, Dominica’s largest wetlands and a docking area for smaller cruise ships. An 1802 revolt here led to the British Empire abolishing all slave soldiers, making this Dominica’s most important historic destination—and now a worthy World Heritage site. A short climb leads to the restored buildings and a splendid viewpoint, complete with cannons. Longer trails spike out into the dry coastal woodlands, populated by crabs and grass snakes (Liophis juliae, known locally as kouwes).

Located in Messinia’s Mediterranean area, this popular beach is most well-known for its distinct “omega” shape. Locals and visitors come here to lap up the waves, admire the dunes, sunbathe on soft sand, hike, and bird watch. Other attractions located above the beach include Nestor’s Cave, the ruins of Old Navarino Castle, and the tomb of Thrasymedes (Mycenaean period). As you climb, you’ll enjoy aerial views of the Divari Lagoon of Gialova, Navarino Bay, and the olive tree-littered Peloponnesian Hills. Interestingly, Voidokilia Beach is believed to be the place mentioned in Homer’s Odyssey, where Telemachus (son of Odysseus and Penelope in Greek mythology) was greeted by King Nestor—who is thought to have used the beach as a port during ancient times—when searching for his father. For a guided experience, Navarino Outdoors offers a bike tour of the beautiful Voidokilia, with time to swim and enjoy views of Gialova Lagoon.

The Morada Bay Beach Cafe on the bay side of Islamorada is the perfect spot for a Keys lunch. Colorful chairs and tables dot the beach; the food is excellent and the restaurant regularly receives fantastic reviews. Try the Wagyu beef burger. It is delicious. Fresh fish and seafood are popular choices. The conch fritters and conch chowder hit the spot. The staff is very friendly, professional, and helpful. Island music or Jimmy Buffet songs waft across the beach.

What started as a simple hat shop has grown over the years to a full-scale boutique with a wonderful range of women’s clothing from local designers. And you’ll find accoutrements such as scarves, gloves, bags, and umbrellas, stationery sets, coffee table books, cute odds and ends for the home, as well as children’s books and clothes. However, the hats still reign supreme—with fedoras, cloches, caps, and berets from hatmakers like Bailey, Christy’s, and Goorin Brothers.

This stunning white-sand stretch, just a five-minute drive east of Port Antonio, is the only beach in Jamaica with waves high enough to surf. Boston Bay is also one of the few remaining public strands on the island. It continues to attract more locals than tourists and as such is nearly vendor-free. You can watch kids splashing about on their boards, or you can rent your own for a Surfing 101 lesson. Be forewarned: As at many beaches, sometimes the waves are flat, but you can console yourself with a short stroll down the beach to the famous Boston Bay jerk chicken stands.

Outdoor and culinary adventurers alike are drawn to this 11-acre property situated at the entrance of a stunning seven-mile fjord in Kachemak Bay. Guests can kayak through hidden coves to glimpse otters and porpoises, hike past alpine meadows, or deep-sea fish for salmon. But where Tutka Bay really separates itself from other Alaskan lodgings is in its culinary offerings. Visitors dig for steamer clams or stop by a local oyster farm for their evening’s feast, and continue the hands-on approach with lessons in the resort’s one-of-a-kind cooking school, housed in a repurposed crabbing boat. The focus ranges from Kachemak Bay cuisine to global influences, prepared with regional seafood and homegrown vegetables. After dinner, you’ll retire to one of six comfortably furnished oceanfront cabins, the most exclusive of which has three bedrooms and is surrounded by old-growth Sitka spruce trees.

While all of the beaches in St. Vincent and the Grenadines are technically public, some of the best ones are accessible only by sea. If you’re lucky enough to be cruising around the Grenadines, be sure to stop for a swim at the beautiful, remote Mahaut Bay Beach on the northern tip of Canouan. You won’t find any restrooms or facilities here but you’ll likely have the beach all to yourself.

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.

You’ll be hard pressed to find anything other than postcard-perfect scenery in the Exumas, and if you’re ambitious and up early enough, there’s a good chance that you can have Horseshoe Bay in Saddle Cay all to yourself for a few hours. A trip to a private Bahamian island isn’t out of reach for the intrepid traveler, as plenty of outfitters offer affordable tours, overnight adventures, and sightseeing cruises to these gorgeous islands.

While scouting out the remaining lighthouses left standing on the Oregon coast, I was lucky enough time my visit with two gray whales. There’s a vintage whale watching station just across the parking lot at the Umpqua River Lighthouse and with a few quarters, I was able to see the action. By flipping through my guidebooks, I learned that morning is the best time to scout for the views of the mighty whales, that like to hang out at the mouth of the Umpqua River where it empties into the ocean. In the morning light, the sun is at your back at the viewing station, meaning you can spot the whitecaps that the whales create (instead of the ones that the wind and waves create later in the day). At the station, you’ll find a sign with a few helpful suggestions to spot these magnificent creatures. You’re instructed to look for puffs of vapor that seem to hang in the air, just above the water. Those spouts usually rise twelve to fifteen feet into the air and when you spot one, you’re bound to see several in the same area. Soon, you’ll be able to observe the head, back and flukes as the whales roll on the surface.

To experience a peaceful and private Hawaiian morning, enjoy room service in the quiet of your own with a view of the Pacific Ocean. Listen to the waves roll on shore while enjoying pancakes and tropical fruit at the Mauna Lani Bay Hotel and Bungalows where you will feel like a Hawaiian King or Queen.

Opened in early 2018, Harbor Club is a modern resort housed on Rodney Bay Marina on St. Lucia’s northwest coast. The overall feel is crisp and aquatic, with the bright-white building resembling a cruise ship on the harbor. Given the hotel’s marina setting, there is no direct beach access, but there is a sparking complex of swimming pools with mountain and water views. The hotel also provides complimentary shuttle service via a fast boat to the beach on Pigeon Island Nature Preserve, as well as towels and chairs for a day on the sand. Guest rooms are like spacious ship cabins, decorated in cool shades of blue with views of the marina or mountains. Eight swim-up rooms on the ground floor even feature private patios directly over the swimming pool area. The hotel’s half-dozen restaurants include Caribbean-Asian fusion spot 14North on the top floor, a modern sushi bar, and farm-to-table eatery Julia’s, and more options are available a short walk from the property. A full-service spa and fitness center, nightly live entertainment, and sunset cruises round out the amenities.

No trip to D.C. is complete without ordering the district’s signature dish, the half-smoke. And while many restaurants serve it, there’s only one worthy of your order: Ben’s Chili Bowl. The popular landmark diner has been feeding the community and cultural icons since the area’s “Black Broadway” days, when jazz greats such as Miles Davis enjoyed this comfort food classic. When riots broke out after Martin Luther King’s assassination in 1968, Ben’s remained open and served both police and protesters. While the U Street Corridor has undergone an urban makeover, Ben’s has remained the same, serving its quarter-pound of half-pork/half-beef smoked sausage on a bun with mustard and onions, all smothered in spicy homemade chili sauce. The prestigious James Beard Foundation even took notice, deeming it one of “America’s Classics.” Bring cash and come hungry.