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The Best Sailing Destinations Around the World

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As the CEO of Oracle Team USA, the American sailing team, and defending champion of the America's Cup, Sir Russell Coutts is no stranger to experiential travel. Here are a few of his favorite places to stay, eat and sail around the world.
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Rovinj, Croatia
A trip to Rovinj makes you feel like you’ve stepped back in time. It’s a little old town with an active fishing port located on the Adriatic Sea, and it hasn’t been overrun by tourists. The RC44 Championship Tour—which consists of regattas in five...
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Auckland, New Zealand
A number of good sailors in Auckland can masterfully navigate the changeable westerly trade winds. Visitors often overlook the islands just off the Auckland coast. Two of my favorites are Waiheke Island and Kawau Island. Waiheke is a 40-minute...
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Cascais, Portugal
In the late 19th century, Portugal’s royal family started vacationing here and turned a simple old fishing village into quite the posh spot to vacation. Today, a jet-set Portuguese crowd comes here to sunbathe on the beaches and dock their yachts...
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Norman Island, British Virgin Islands
The BVI is all about fun, and you can have the most fun on a boat. If you visit, go to Willy T, a floating bar housed on a boat anchored in Norman Island’s Bight. Zeus, the bartender, really gets the crowd riled up with rum drinks. Back in the day...
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San Francisco, CA, USA
There are so many fabulous places in the city that you can go to see and photograph San Francisco and the entire bay area. Some of these are open for the public while others may only be available to guests staying at that particular hotel. So if...
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07021 Porto Cervo, Province of Olbia-Tempio, Italy
This island lies in the Strait of Bonifacio, between Corsica and the top end of Sardinia. The Strait of Bonifacio is famous among sailors for its notorious weather and fantastic wind. It’s quite an art to navigate around the rocks along the coast....
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Via Capodimonte, 14, 80071 Anacapri, Isola di Capri NA, Italy
It’s hard to say what’s the biggest draw at Capri Palace Hotel & Spa, a whitewashed retreat overlooking the Gulf of Naples with 68 rooms that blend stylish minimalism with beach-chic comfort. As the name implies, wellness junkies...
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Via Gesù, 6/8, 20121 Milano MI, Italy
Everything old becomes new again in Italy. I really admire how the Italians think of ways to make the old beautiful and relevant. The Four Seasons in Milan is such a lovely hotel and I get a kick knowing that it was actually a 15th-century convent...
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342 Howard St, San Francisco, CA 94105, USA
I like the informality of this San Francisco restaurant. The food is always good and the staff always friendly. The menu has a Southern influence so you can expect to see barbecue shrimp, gumbo, hush puppies, and of course fried chicken....