It’s always just before winter really hits, seems as if the whole town goes running off to some sunny and warm land down south for “off-season.”

This year my girlfriend Katie and I decided to join that stampede.

Our good friends Fitzy and Jannine who celebrated their rocking 80’s Wedding earlier this summer decided to honeymoon in the Caribbean during the off season. Their intent was to go down and rent a sailboat for a couple of weeks by themselves and then have any willing friends join them for another leg on a different boat.

This summer I had done some sailing with Fitzy on his boat up on Jackson Lake which prompted him to extend an invite to Katie and me, which, we immediately accepted.

The weeks before the vacation were hectic to say the least. We had to find friends to water our plants, work over time to pay for the trip and make sure out butts were covered at work for our time off. The cheapest tickets we could find from the rockies to St. Thomas in the US Virgin Islands were out of Salt Lake. After about a day of driving, we arrived on the islands and purchased our first cheap Cruzan Rum at the duty free store.

Our plan was to meet Fitzy and Jannine in Cane Garden Bay on Tortolla which is located in the British Virgin Islands. After a cab ride to a ferry ride to another cab ride (a frightening one on the steep roads) we found ourselves on the beautiful beach of Cane Garden Bay. Cane Garden Bay is everything you’d expect from a Caribbean beach, perfect turquoise waters, beautiful beach, friendly locals and plenty of rum. The second day we met up with Fitzy and Jannine the only way that seemed appropriate: while sitting on the beach drinking Pina Coladas!

We started the real adventure on a rented boat from North South Yacht vacations, which was what you might call the “economical” option of all the charter companies that rented sailboats. After an adventurous shopping excursion to Bobbie’s Grocery to stock up on provisions for the next eight days we finally boarded and stocked up “Emily T”, our 42 foot Catalina. The last of crew to arrive was Jannine’s parents, Mary Jane and Warren from Long Island, a hilarious and endearing couple who kept us laughing for the entire trip.

Mary Jane and Warren arrived to an fully stocked boat and after a short but frantic search for a dish sponge we set off into the beautiful waters of the BVI on the fabulous Emily T!

Our first stop was Norman Island, home of the famous floating bar, the Willy T. We moored there for our first night for $25 - a small price for not having to worry about an anchor slipping during the night.

We spent the days sailing from island to island, stopping at the smaller islands and exploring the intricate and rainbow-colored reef via snorkeling. We explored part of the shipwreck of the R.M.S. Rhone on Salt Island, snorkeled around the reef of the Dog islands and made friends with a stingray on Marina Cay. The winds were amazing for the entire trip, it was like going to ski resort and having a powder day every day. The seas were varied, sometimes we had eight to 10 foot swells and sometimes it was much calmer. Only a few times did we have frighteningly large ones up to about 20 feet (a bit different than sailing on Jackson Lake!)

Despite hopping from beautiful island to beautiful island, we were also lucky enough to visit the “Baths” on Virgin Gorda when there was not a cruise ship ferrying loads of people to the famous boulders that line the shore. Another day we moored in Leverick Bay near the swanky Bitter End Yacht resort where Fitzy and I burned away a few hours racing each other on a couple of rented 14 foot Hobie Cats, which we of course both flipped in our quests for speed. We also had the fortune of a full moon during our stay, which the Caribbean’s love to celebrate. While moored at Maria Cay we dingy’ed over to the full moon party at Trellis bay, a great festival with lots of local art and the Mocko Jumbie Stilt Dancers rocking out to the live steel drum band. Later in the party the artists set fire to a few sculptures they had placed a short distance out in the water. It was a damn festive time!

We stayed two nights on Jost Van Dyke, which was one of the best islands we visited. Jost seemed to be the island that retained it culture the best, the population of the island is about 220 and they just got electricity in the 1990s. We met many friendly locals and spent our last night on the boat in the incredible White Bay, home of the famous Soggy Dollar bar, named so because of the fact that people swimming to shore always pay with soggy dollars.

Sadly we set sail the next morning to return the Emily T back to North South.
We returned the boat in good condition, thankfully, and returned to Cane Garden Bay to finish out the remaining days of the vacation. We all remarked that beach life was for the birds and being on the sailboat was where it was at, but the beach wasn’t that bad! The last day Katie and I woke up and walked down to the beach for one last swim, in that warm nice water. It seemed surreal that in less than 24 hours we would be back in the snow.

But then again, who’s complaining!?

I highly encourage you to check out the Photo Slideshow Here.