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Owned by Terry Kaljo—a former model and founder of the Contemporary Hotels collection of upscale rental homes and villas—the Medusa Boutique Hotel offers 18 unique accommodations in Darlinghurst, an eclectic area and the epicenter of Sydney’s gay community. The 19th-century home is filled with wacky touches, from red Alice in Wonderland–style carpeting that runs up the grand staircase to pastel-pink walls studded with maple leaves in the entryway. The midcentury-modern rooms—with their retro primary colors, geometric patterns, and vintage chaises longues—attract fashion, media, and design professionals looking to get beneath the surface of one of Sydney’s liveliest neighborhoods. But there’s still the opportunity to relax, as guests can settle in next to the fireplace in the lobby to read the newspaper, enjoy a complimentary pastry, or make new friends. Longtime staff members offer the kind of local knowledge and personal attention that keeps guests coming back.

This bite-size coffee stand in the Victorian-era Strand Arcade building downtown is perfect for a midday lift. Run by the team behind Coffee Alchemy in Marrickville, Gumption serves coffee and only coffee (no food). Six single-origin bean varieties are on offer, three of them filtered hot, the other three dripped cold and served over ice. Don’t think about asking for milk, though, unless you mean a steamed drink. They’ll deny you. The staff is not snobby, just matter-of-fact. The coffees come small and extremely drinkable—even for dairy lovers.

If you’re visiting Tahiti with a large family or group of friends and hoping to surf the island’s most powerful wave, you’d be hard-pressed to find a better, more affordable place to stay than Green Room Villa. The 1,500-square-foot, four-bedroom property—the only vacation rental in the sleepy surfing village of Teahupo’o—practically opens up to the water and offers a unique place to rest your head. The main house is shaped like an octagon, with a huge mangosteen tree growing out of the open center, plus a large covered deck, teak flooring, and brightly painted walls that show off the owner’s creativity. The property even works well for a small destination wedding, as there’s a “honeymoon bungalow” near the fruit tree garden. Built on stilts, it sits over a purple-hued, lily-filled pond. It’s also the only room with air conditioning, although breezes keep the main house relatively cool. On a very local part of the island, Green Room Villa is extremely private, providing a relaxed place for your group getaway. Note: the owners require a credit card damage deposit and a three-night minimum stay.

Nearby reefs and big boulders keep Bermuda’s beaches calm and colorful for snorkelers and swimmers. Both Tobacco Bay & Church Bay offer great snorkeling conditions along beautiful shorelines. With one in the east and the other in the west, you could combine a day of snorkeling and sunrise/sunset viewing. Tobacco Bay is located on the northeastern side of the island near St. George. This small cove of calm water protects a variety of parrot, clown, and other tropical fish. Tobacco Bay has a snack bar and equipment rentals, restrooms, showers, and changing rooms. When you tire of swimming with the fishes, dry off with a short walk to the historic site of Fort St. Catherine. Its eastern location makes Tobacco Bay a prime sunrise spot. Located along the island’s western side in Southampton, Church Bay is a local favorite for snorkeling. Tucked into a small cove within cliffs of coral, the reefs are close to shore and offer lots of small hiding spaces in which to discover tropical sea life. Just watch out for the jellyfish. Youngsters will enjoy exploring the tidal pools formed by the many rocks. Forget to pack your snorkeling gear? No problem. You can rent equipment from Church Bay Beach Rentals during the summer months. Sunset seekers should not miss this beach.

The Bridges of Samaná, also called the “Bridges to Nowhere,” are a string of bridges connecting the small islands that stretch across the outside of Samaná harbor. They are remnants from a project in the 1960s and ’70s by President Joaquín Balaguer to build a restaurant on one of the islands, connected to the mainland by a pedestrian bridge. The restaurant never opened, but the bridges and the shell of the building remain as curious relics of recent history.

Home of the Venice Film Festival, the Lido is also where you’ll find Venice‘s beaches—Shelley and Byron went horseback riding here back in the day—as well as the Grand Excelsior Hotel, whose bar is often crowded with celebrities during the festival (and other times of the year, as well). If you’re a classic film fan, the hotel might look familiar: Luchino Visconti’s Death in Venice was shot here. The island has a decidedly lively feel compared with Venice itself, less a museum piece and more a buzzing destination, popular with Venetians and visitors looking to spend a day by the sea.

Bantayan Island’s fine white sand beaches and clear light blue waters are as enchanting as far busier Boracay, minus the noise and go go go night life. The island’s Ogtong Cave Resort offers a well-kept landscaped garden, a pool, and individual cottages, but the real draw is a cave below the resort grounds, where you can explore and wade in the waters. Rooms at the resort are simple and comfortable. The resort offers doubles up to family rooms with plenty of room for kids. There are two pools on the ground, with one reserved for resort guests. The usual jump off point is Cebu, a one-hour flight away from Metro Manila. You then take an almost 3-hour bus ride from North Terminal to Hagnaya for a 75-minute boat to Santa Fe, Bantayan. You can also opt to take a private van or taxi for a more comfortable and faster ride. Don’t be put off by the long travel time--the beach, cave, and everything else at the resort are well worth what it takes to get there.

The Hyatt brand is world renowned for its service and experience. Their Maui property checks all the boxes for creating the perfect island vacation. From the beautifully executed integration into the ocean environment, to the services and activities at your flip flopped feet, life’s stresses give way to island time the moment you arrive. Close enough to Lahaina town to skip a car rental, yet buffered from the distractions of the world, it’s a great balance in one location. The onsite restaurants are top notch, easily keeping your calorie intake therapeutic. The bars offer a wonderful mix of island cocktails to melt away any residual tension from your stand up paddle board lesson. The little bay on the south end of the resort is home to a healthy group of huge sea turtles, easy to paddle up to in a kayak or board. Walking everywhere is easy and entertaining. Whaler’s Village is just a mile up the beach on a paved path the takes you through some of the other resorts in the neighborhood. Rooms are crisp, spacious and have some ocean views. The resort is medium-sized so you don’t feel overwhelmed by the physical plant. Speaking of plants, there are hundreds of native flora dotting the grounds. Also wondering about are flocks of flamingos and penguins. The Hyatt is a first-class operation leaving you free to relax to your heart’s content.

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.

This private island features stunning views of Mount Otemanu and Matira Bay from its own motu just a few minutes’ boat ride across Bora Bora’s truly stunning fifty shades of blue (one minute it is turquoise, the next emerald or aquamarine) from sister resort Sofitel Marara. The private property is the perfect pick for romantic getaways (it’s geared toward couples, and children are not allowed). Privacy and intimacy are emphasized here with only 31 bungalows (20 are overwater, another 10 are located on a lush garden setting on a hill with stunning views) and one luxury villa that while not overwater, features direct lagoon and sandy beach access and a private jacuzzi (the only one on the property). There is no swimming pool, but guests can use the pool and all amenities at the Marara resort via free water shuttle. Should you not wish to leave your little slice of paradise, however, the onsite Manu Tuki restaurant does excellent French Tahitian fare; order lobster anything. There is also a bar, the Mako. Whether staying overwater or on the hill, the layout is the same, and all rooms feature contemporary Polynesian decor, gorgeous wood floors, and luxury toiletries in oversize bathrooms. Overwater bungalows also boast glass viewing panels in the floors and direct access into the lagoon. Make sure to book the “Romantic Soiree” for one night. It combines sunset champagne on top of the hill, followed by a romantic dinner on the beach under the stars. The breakfast delivered by canoe also is a must.

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.

Once an oyster-farming backwater, this area was held sacred to the shark goddess Ka‘ahupahau. But it’s forever etched into America’s psyche due to the 1941 Japanese surprise attack on the naval base, which launched the U.S. into WWII’s Pacific theater. Today, more than a million visitors pay their respects annually at the museums and memorials, which include the USS Bowfin, the USS Missouri, and the wreck of the USS Arizona. Buy tickets online to avoid the inevitable long wait. Ford Island also houses the Pearl Harbor Aviation Museum here: Historic hangars showcase vintage aircraft like a Japanese Zero and a Curtiss P-40E Warhawk. Plane buffs should add on a $10 combat-simulator flight.

When eating at the Sea House Restaurant, it’s hard to decide what is actually better: the view of Molokaʽi across the water, or the Molokaʽi sweet potatoes used in the frittata. Either way, both combine for a memorable breakfast on the island’s northwestern corner. Opened in 1963 when tourists were just discovering Maui, the Sea House restaurant celebrated its 50th anniversary in 2013—thereby making it one of the oldest restaurants in West Maui. Even with the history, fame, and ocean views, it’s one of the island’s most affordable restaurants. Most items on the breakfast menu will cost you $12 or less, and when you’re done with your meal, you can splash in the waters of protected Napili Bay. The Sea House sources many of their ingredients from local Hawaiian farmers (such as the Molokaʽi sweet potatoes), and they also follow traditional fishing calendars when choosing their fish for the menu. This is a great option for beginning the day on the island’s northwestern coastline and is a filling starting point for later adventures toward Honolua Bay and beyond. Or, just relax on the sands of Napili beneath the shade of a rustling palm. After all, there are only three hours between the end of breakfast and the start of the Sea House happy hour—an affordable menu that starts at 2 p.m. and has been voted one of the best on Maui.

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.

Why we love it: A family-run hotel with eye-catching design and sustainable architecture

The Highlights:
- Rustic wooden cabanas surrounded by water
- Private plunge pools in each room
- Tasty local food, including breakfast, snacks, and dinner upon request

The Review:
Holbox is becoming more and more popular, thanks to its chill vibe, powdery beaches, and relative privacy compared to Tulum. Among the island’s best places to stay is this family-run retreat, just a few blocks from the shore. Here, the unique geometric design features 12 whitewashed, thatch-roofed cabanas surrounding a flooded central deck-cum-pool. Each room opens directly onto a private plunge pool that connects to the main one, creating the feeling of an overwater bungalow.

Guest room interiors are carved from sustainable cedar wood, lending a rustic air that melds perfectly with Holbox’s laid-back, eco-conscious atmosphere. There’s not much in the way of furniture beyond a few shelves and a bed clad in organic sheets, but that helps keep the focus on the fragrant cedar. Daily breakfast is included as are afternoon snacks. With advance notice, the chef will also cook you an authentic Mexican dinner using local ingredients. If you’re in need of a tipple, a tower adjacent to the lobby area has a bar with well-made cocktails and stunning ocean views. Just don’t expect fast Wi-Fi or much in the way of amenities—here, it’s all about island time.