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This is a peaceful spot to land when you want to soak up the tranquil breezes off the Chesapeake Bay. Head down south and enjoy a quaint stay in this hopeful little town still showing forth the glory of its historic roots. Grab a bicycle from the Hope & Glory Inn’s bike stand and head on over to their namesake vineyard. Taste a few of the delicious wines and dine at the Inn’s restaurant where the grub gives ‘country’ food a new meaning.

The VIP Room comes with proper clubbing experience as a backing, with previous ventures like Taboo and Cocoon Lounge before it, this venue offers only the cream of the crop to it’s patrons. In the heart of the Sandton business district at the Michelangelo Towers, the club is conveniently located near top hotels like The Michelangelo, The Davinci, The Sandton Sun, etc, and restaurants in the square should you want to grab a bite before heading out for the night,

Woodstock is the creative heart of Cape Town, filled with galleries, studios, street art, and artsy types galore. The Woodstock Exchange is a hub for the design set, home to a rotating legion of furniture shops, coffee shops, and furniture shops combined with coffee shops. Because, why not? Right when you enter the space, you’ll be greeted by this mammoth sculpture of a sleeping dog. Proceed with caution: this doesn’t look like the kind of guy you’d want to wake up.

At Boschendal, guests can slow down and savor “Le Pique Nique,” a pre-packed picnic basket that you can order in advance of your visit to the vineyard. When you arrive, collect your wicker basket filled with sweet and savory treats, pick up a bottle of wine to pair with your snacks, and find a spot under the pine trees to sit for the afternoon, relaxing and enjoying the sunshine.

Boschendal is right on the edge of Stellenbosch, about an hour’s drive from Cape Town through the beautiful hills and valleys of the winelands. The owners transformed several farm laborers’ cottages into luxury accommodations, should you wish to spend the night after a day of vineyard tours, winetastings, and dining at the estate’s several restaurants.

The Cederberg Mountains are where Capetonians go to hike and camp in the Western Cape. After a very bumpy (7km or so) ride deep into the hills and valleys of the Cederbergs, you’ll arrive at Gecko Creek Lodge. Each evening, watch the sun fall snugly between the mountains from your tent, pictured here. You can bring your own tent or opt to use Gecko’s, which was setup with two twin beds and included linens. Gecko also offers wood cabins with hammocks on a small front patio. With a swimming pool, hiking trails to wander, a nearby river, plus a lapa and boma (dining/cooking area) for mingling with the other guests, there was no shortage of activities to partake in.

The Portland Art Museum has been a fixture of the Rose City for longer than you’d expect—it’s the oldest art museum on the West Coast, opened in 1892. The current location, on the South Park Blocks, debuted in 1932 with a design by Pietro Belluschi. Today, the permanent collection includes 42,000 works along with a rotating selection of exhibits. Among the highlights in past years: pieces by Rodin and Andy Warhol, and what is thought to be the largest cat painting in the world. The 2.5-block campus also includes the Northwest Film Center.

The best of several great Atlantic beaches around Punta Rucia, Playa La Ensenada is made up of a fishing village and 4.5-mile stretch of sand with calm, crystal-clear water. Here, you can snorkel around submerged reefs in waist-deep water, or take a 12-minute boat ride through mangroves to a dreamy sandbar (named Cayo Arena but also called Cayo Paraiso, or Paradise Island) to see even more colorful fish. The size and shape of the sandbar change depending on the currents and season, so you’re always in for a bit of a surprise.

Day-trippers in search of awesome views, cool drinks, and light bites score at this oasis in the middle of Arikok National Park. The menu is simple and heavy on island favorites, from fried whole fish to seafood served with plantains, salad, and pan bait (a pancake-like bread). There are also hamburgers and cold sandwiches, along with frozen cocktails and local beer. Still, it’s the views that really stun. From its perch between Boca Prins Bay and the Fontein Cave, the restaurant has sweeping vistas of desert, hills, and sea.

Located on the beautiful white sand beach motu, this is Maupiti’s swankiest pension with spacious bungalows decked out with modern conveniences like air-con and televisions (rare for Maupiti still). The location, on a small strip of beach, offers blue-green lagoon vistas amid rows of swaying palms -- the water is very shallow here so swimming isn’t so great, but hop in a house kayak and take yourself to deeper waters. Airport transfers, kayaks and snorkels are free. Also opt for the full-board option as the owner is an excellent cook, specializing in French meets island dishes including excellent fresh seafood.

When you arrive in Corfu, you may notice it doesn’t look a great deal like the other Greek islands—in fact, it has a distinctly Venetian feel. That’s because, unlike the rest of Greece, Corfu was never ruled by the Ottomans. The Old Town is a perfectly preserved Venetian town and a UNESCO World Heritage site. Renaissance, baroque, and classical touches can be found between every alleyway and square. Some points of interest: the Old Fortress, Spianada (the largest square in the Balkans), and the Liston (an arcaded promenade where wealthy aristocrats used to gather).

One of the best destinations in Greece for SCUBA diving is off the coast of Corfu. Divers of all skill levels can appreciate the level of underwater visibility around the island, especially on the northwest coast, near Paleokastritsa. Caves, reefs up to 40 metres deep, underwater arches, and more can all be found in the turquoise seas of the Mediterranean, and you’ll never be bored around Corfu.

A fairly new addition to the Waikiki waterfront, the seven-year-old Modern was a dream come true for those young urbanites who never quite felt at home in the more traditional Hawaiian resorts. It’s not directly on the beach—the closest is the lagoon and expansive beach in front of the Hilton Hawaiian Village, a quick walk on the hotel’s ramp—and instead overlooks the picturesque Ala Wai Boat Harbor, where many of the island’s boating excursions depart. Designed by George Yabu and Glenn Pushelberg, celebrities in the world of fashionable hotels, the look is warmly modern, all whites and creams and luxurious wood, and some striking art pieces, including a large surfboard installation in the lobby (titled “Wreck-tangles”). There’s a fun nightclub and some seriously good restaurants, though the real scene is out on the Instagram-worthy two-tiered teak pool deck, lined with lots of cushy chaises and shady corners to curl up. Upstairs is the adults-only pool—less a pool than a shallow water prop for frequent DJ-hosted dance parties. But for as much as the Modern is a hipster haven, the service is surprisingly good at making sure guests never feel like they’re crashing someone else’s party.

Watching the sun set on Jamaica‘s west coast is a bona fide activity. The island’s red skies are a sight to behold. I have yet to experience a better Caribbean sunset than in Jamaica. From Montego Bay all the way to Negril--famous for having the best--to Whitehouse, get your camera and Red Stripe ready for the last hours of daylight. You won’t lack for choice of seafront bars or scenic spots--from the trendy Pier One in Montego Bay to the wooden shack watering holes along Negril’s West End cliffs. Wherever you end up, there’s a very good chance you’ll get hooked on this daily sunset viewing routine.

This tiny island is north of Isla Mujeres and Cancun and is only 26 miles long and offers visitors in search of a “Robinson Crusoe” experience the perfect escape. Long, sweeping beaches beckon with water sports, snorkeling, sport fishing, and total R&R. A shallow lagoon gives sanctuary to thousands of flamingos, pelicans and other exotic birds and creatures, allowing visitors the perfect spot in which to commune with nature. Several good restaurants and hotels are available and tours to area attractions can be arranged by ferry and small plane. Getting around the island is via bicycle or golf cart.

Wine is an integral part of life on the Dalmatian Coast, a region with many indigenous varietals; a visit to Dubrovnik shouldn’t go by without a glass of local wine. Tucked away on Palmotićeva Street off the main Stradun, D’Vino offers cozy interiors as well as atmospheric seating at tables set on the narrow thoroughfare outside. Try a glass of something new from the impressive selection of local producers—the knowledgeable staff can help guide you in choosing one. D’Vino features several tasting experiences that highlight the region’s star wines: the Konavle Valley’s refreshing Malvazija, potent Plavac Mali reds from the Pelješac Peninsula, and Korčula Island’s fruity Pošip whites. Pair the wines with a platter of prosciutto and Croatian cheeses for a wonderful welcome to Dubrovnik and its wine region.