Odyssey Sailing Festival
Picture this: your ultimate week-long getaway on the water. The sun is blazing, the breeze is just right to keep you cool as you zip through the crystal-clear waters between the breathtaking British Virgin Islands on a pristine, spacious new catamaran. What could possibly make it better?
How about adding seven of your favourite YouTube sailing stars, world record holders, and TV celebrities as your skippers? Throw in some rum, costume parties, more rum, beach parties, even more rum, and racing so close you could practically high-five your competitors. Well, buckle up, because we’ve got the vacation of a lifetime for you.
Recently, Brioni and I were thrilled to be invited to skipper one of the seven boats in this year’s Caribbean Odyssey Sailing Festival. Hosted by our good friend Andy H of The Ocean Cruisers Podcast, The Odyssey website promises ‘a week on the water learning about sailing and cruising around the oceans, stories about breaking world records and making history from some of the best sailors in the world.’ Needless to say, we were humbled to be part of it.
Our fellow skippers for this third Odyssey Sailing Festival included Captain Glen Shepherd (Below Deck Sailing), Raf & Sash (Spear It Animal), Laura Dekker (World Sailing Foundation), Kiana Weltzien (Women and the Wind), Erica & Warren (WESail), and Lauren Landers (Soul De La Mar). Quite the lineup, and everyone as genuine and fun as you’d imagine.
The week kicked off with welcome drinks and introductions at Nanny Cays, Peg Legs bar, before everyone loaded up their bags onto their chosen Navigare yacht and home for the festival. But there was just enough time to crack open the first beer before lines were slipped and the fleet was underway to the first anchorage of many.
A typical Odyssey Sailing Festival itinerary involves the fleet gathering at various anchorages to enjoy the evening’s frivolities. But there are also plenty of opportunities while sailing for each boat to break away from the pack and explore everything the BVI has to offer. Discovering rum distilleries, the Virgin Gorda Baths, and more are all at the skipper and crew’s discretion, so everyone has plenty of stories to share when the sundowners are flowing.
The anchorages are handpicked too, with most providing the opportunity to raft up and boat hop all night long. These parties are where the real fun takes place. Passing from boat to boat, meeting all the skippers, and sharing tales of the day’s adventures. While the week is an all-access pass to hang out with your chosen skipper, the raft-ups are a great way to get to know everyone a little better. If it isn’t the disco lights of WESail’s boat that draw you in, then the guarantee of a wild time over on Spear It Animal’s floating nightclub is always a fender hop away. But there’s something for everyone, with the more relaxed spaces onboard Captain Glen’s Gin Palace, where I almost expected to see a harpist and smoking jackets appear, and the chilled vibes of Kiana’s, aliens to her, air-conditioned luxury boat, you can always find a comfortable spot to enjoy your evening.
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