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Cheap house wine for sale on the side of the road outside of the village of Pyrgos. Santorini is famous for its tradition of small vineyards that produce fruity wines. Visitors can easily spend the day winery-hopping around the island.

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.

Opened in 1891, the city’s oldest hotel is a throwback to a bygone era. Individually decorated guest rooms combine old-fashioned details, like claw-foot tubs and antique wood headboards, with modern amenities like USB ports and Bose sound systems; other nods to the past include vintage brass keys with tassels and a second-floor writing desk with functional typewriter (rest assured the front desk will stamp and mail your letter faster than the Pony Express). Inspired by a bar on the Queen Mary, the Art Deco Cruise Room was Denver’s first drinking establishment to open after Prohibition; today it’s known for its collaborations with local distilleries and classic cocktails. Follow them up with the confit chicken pops at the Urban Farmer restaurant, or call it a night and wake early for a honey exfoliating scrub or chocolate-ginger wrap at the on-site spa.

“The menu at this authentic Japanese restaurant changes constantly. This place is legit authentic Japanese, they even make you take off your shoes and wear their slippers … Men have to wear a button-down collared shirt, so be ready. You can order from their menu a la carte, but the thing to do is make reservations and get their tasting menu. This is what we do every time and it never disappoints. The tasting menu is about seven to eight dishes depending on what the chef decides to send. The meal is unforgettable. In signature Japanese style, the dishes are small, but compact with tons of awesome flavors.” —Kevin Diedrich, a bar manager and consultant who grew up in Northern Virginia.

The Thermal Water Pool of Terra Nostra Park is without doubt a highlight of the Azores. Built in 1780, by Thomas Hickling, the American consul who had the original idea for Terra Nostra Park, the Thermal Water Pool began to form part of the assembly dominated by Yankee Hall, a holiday house owned by Hickling. The pool was significantly smaller at that time, but already consisted of an “island” in the middle, with a bridge linking it to the land. The Thermal Water Pool was enlarged in 1935, acquiring its present form, with the refurbishment of the Park, operated by Vasco Bensaude. It was also enhanced by quarry stone masonry, remaining unchanged to date, undergoing only a few minor repairs.

The ire of Mount Kilauea reforges the world before visitors’ eyes. Nicknamed “the World’s Only Drive-In Volcano,” it’s produced serious lava every day since 1983 with no signs of stopping. Pele—the fire goddess who lives here, according to Hawaiian lore—is on a roll. Occasionally the lava flows spill into the sea, releasing stunning plumes of steam. Don’t miss the petroglyphs, lava tube, lush rain forest, and more than 150 miles of trail, including the four-mile Kilauea Iki loop. The drive here from Kona or Kohala can take two and a half hours, a bit of a long day, so consider reserving accommodations in the town of Volcano. You’ll have plenty of time to explore this otherworldly landscape, and even see the lava glowing in the dark!

Jamaica’s interior beauty includes several botanical gardens. Shaw Park, located in Ocho Rios’ surrounding hillside at up to 800 feet above sea level, is a great stop for families, with a large waterfall cascading through, gorgeous flower gardens and plenty of picnic space. When you want to get away from the heat and chaos of downtown Ocho Rios, head up to the hills and relax here. It’s a US$10 entrance fee and the park is open during regular business hours.

Roseau’s only oceanside dining option, the elegant Palisades pairs sweeping water views with one of Dominica’s best culinary experiences. Here, creative dishes showcase the island’s natural bounty, including produce sourced from local farms and fish straight from the Caribbean Sea. Start with dishes like BBQ jerk octopus and sesame-crusted tuna with a soy-chili dip. Then, move on to the lion fish, served with green-banana croquettes and mushroom sauce. Fancy something lighter? Try a lentil-black-bean cake or callaloo soup, made with baby taro leaves, coconut milk, yam, and green bananas.

Across the bay from Puerto Ayora on Santa Cruz Island, Finch Bay is one of the few hotels in the Galapagos Islands located near a beach. While the hotel prides itself on its ecofriendly touches—such as its own water treatment plant, solar panels, a composting system, and the addition of 500 new mangrove plants surrounding the hotel—the atmosphere is more that of a contemporary resort than a rustic nature lodge. Outside, an oversized pool overlooks the ocean; inside, a Cordon Bleu–trained chef heads a modern restaurant. Dark volcanic stones line the walls in the suites, while standard rooms all come with hammock-slung wooden balconies. Like most hotels in the Galapagos, Finch Bay is all-inclusive, providing land and sea excursions to attractions like the highlands of Santa Cruz, to search for giant tortoises in the wild. Also included are daily excursions on the hotel’s private yacht to nearby islands like Bartolomé or North Seymour, national park highlights, which can be reached on day trips.

Hidden out past quaint Five Islands Village, Hawksbill resort is seamlessly sprinkled over 37 acres of Caribbean gardens right on the water. Sure, Antigua is known for its 365 beaches so it shouldn’t be a surprise when a resort has more then one beach, but Hawksbill has, an impressive, four secluded strips of sugar-white sand easily accessible to guests with a fifth accessible to truly intrepid sun worshipers. Besides the sheer quantity, Hawksbill also sports a one-of-a-kind beach for Antigua. Beyond the southern point of the the 99 non-smoking guest rooms, down a little path, through a white fence, and around the bend is Eden Beach — Antigua’s one and only extremely concealed clothing-optional shore. It’s here, a matter of meters into the Caribbean Sea, that you’ll find majestic Hawksbill Rock (so named for its uncanny resemblance to a hawk’s profile) from which the property gets its name.

Named after the reef it overlooks, the Alexandra Resort, located about halfway down Provo’s famed beauty, Grace Bay Beach, is a great spot for families or couples. Rooms are in groups of four-story buildings circling a lagoon-style swimming pool. There is also 600 feet of pink-sand beach in front of the hotel leading directly into the emerald waters of the South Atlantic. Beyond its mid-range accommodations and excellent location, the Alexandra recently debuted a new restaurant, Asu, which has a fantastic location right on the beach and does a barefoot al fresco dinner -- book for sunset and then after the sky blackens lantern baskets provide a romantic glow.

On Puerto Rico, horses roam the farms, the mountains, the town centers—and also the beaches. A couples’ horse ride at sunset is a perfect way to kiss the day good-bye. With Tropical Trail Rides, in the northwestern municipality of Isabela, you can take a two-hour ride through the forest and by the beach as the sun sinks down toward the water. Make sure you take the opportunity to break for a hike or a swim along the way. On the north side of the island in Manatí, Kerry’s Horses designs personalized sunset rides by the beach or through nature reserves.

In the heart of old town Kapaa, the Olympic overlooks Main Street with laid-back Hawaiian style. Upstairs in an old building that’s been converted into a collection of ragtag shops, the cafe has a commanding presence. Park and wander along the street to make your way to the stairs leading up to the bar and cafe. No pretense upon arrival. The tables lining the open windows in front are choice for people watching and catching the breeze from the prevailing trades. Late afternoon sun streams in and heats things up but is a welcomed delight. There’s always something cold close by to help with the temperature regulation. The bar is a mix of locals and tourists. Happy hour is a draw from four to six with discounts on drinks and select appetizers. I’m a big fish fan when near the source and the fish tacos at the Olympic take the gold. Dressed with a mango salsa and sides of beans and rice, they use two kinds of fish to keep your tastebuds guessing. There is a good selection of island beers and all the fruity umbrella drinks you can imagine. It’s right on the Kapaa multi-use path, so you can cruise in on your beach bomber for a refreshing break. Staff are friendly and service is casually good. Worth a stop when trolling around Kauai for someplace to take a break from vacation.

Updated in 2017, the rooms and public areas in this attractive, airy resort have an island-themed decor. Rooms now come equipped with marble bathroom vanities, Smart LED Samsung televisions, and Starbucks Coffee. But the star attraction remains a prime, crowd-free position on Grand Cayman’s Seven Mile Beach, famous for clear water and powder-fine white sand. Resort sun loungers are spread far apart to give guests a sense of privacy. A day camp with fun activities and a healthy meals program for kids (ages 4-to-12) means parents get guiltless downtime (or scuba diving and other water sports). Shopping and alternative dining are within walking distance.

Taking a trip to Fort Sumter gives visitors a chance to explore a little Civil War history (the first shot of that long bloody war was fired here in 1861) through an orientation in town at the education center, followed by a ferry ride out to the fort itself, built on an island at the mouth of the harbor, for a brief park ranger introduction and a self-guided tour. In addition to being a fascinating experience for the site’s historical significance, the excursion offers water views of Rainbow Row, the homes along The Battery, and the Holy City’s many steeples.