Do you ever feel like you need a vacation from your vacation? I arrived back in Southern California, and I really need a long nap after a week of sailing in the British Virgin Islands.
From the welcome party to the last night at Willy T’s, I had a nonstop blast.
Frankly, we needed more time together.
If you ever wondered what a vacation looks like when sailors, sunshine, and a whole lot of rum come together—this was it. The Lenny Shabes Sailing Festival brought the energy, the camaraderie, and the unforgettable moments that would’ve made Lenny himself raise a glass.
Between the flotilla’s energy and Lenny’s legacy of community, this wasn’t just a sail—it was a floating family reunion. We laughed, raced, danced, feasted, and fell in love with island life all over again. Honestly? We all needed a longer weekend to properly say goodbye.
So, yes—I’m home now, craving a nap. But I wouldn’t trade those seven days of sea-salty bliss for anything.
Highlights From The BVI Flotilla
Day One: Permission to board! We kicked things off with a bang—somehow squeezing about 30 people onto our catamaran for the ultimate floating welcome party. The top deck overflowed with laughter, rum drinks, and new friends. By the time the charcuterie was gone, we were practically family.
Day Two: The Cooper Island Rum Bar proved to be a fan favorite. My crew sampled nine different rums while I stuck to Chicken Roti and captain duties (note to self: upgrade my job next time).
“Your raft up looks like a banana”
Day Three: Picture this: 11 boats rafted together, music playing, the Rum Runner delivering drinks like a floating tiki bar, and people floating between boats like sea otters with cocktails. I heard someone say, “This is the best thing I’ve ever done,” and honestly, same. Also, I learned that managing dinner reservations for 80+ sailors is an Olympic sport—I personally greeted every guest to make sure they had a seat.
Day Four: Things got…frisky. Let’s just say “Can I touch you?” became the phrase of the day. We’ll leave the details to the BVI breeze and remember: what happens in the islands, stays in the islands.
Day Five: Baby shark sightings near Foxy’s Taboo and an adventure through the Bubbly Pool reminded us we weren’t just here to party—we were also here to explore. Soggy dollars and sun-kissed memories in Jost Van Dyke? Yes, please.
Day Six: Rule of the sea: you must finish all your provisions. Cue a progressive cocktail hour featuring gin, wine, beer, and yes, even more charcuterie. Our boats turned into floating lounges.
Day Seven: Saying goodbye is never easy, but we left with full hearts, new friends, and a shared sense that we had truly honored Lenny’s spirit.
Until next year, sailors.
Make New Friends Who Share Your Passion
Sailing brings people together like nothing else. You’ll share stories, laughter, and unforgettable sunsets with fellow adventurers who love the sea as much as you do. Whether you’re traveling solo or with a partner, you’ll join a community that feels more like family by the end of the trip.
Learn, Sail, and Grow with Confidence
These aren’t just sailing vacations—they’re immersive, hands-on experiences. Whether you’re a seasoned sailor or a curious beginner, you’ll learn skills, gain confidence on the water, and earn certifications that bring you closer to sailing your own boat one day. Every sail is a step closer to your goal.
A Different Kind of Luxury: Freedom, Adventure, and Serenity
This is the kind of luxury you can’t find in a hotel—the sound of the wind in your sails, waking up to a sunrise over the sea, anchoring in secluded coves where no crowds can reach you. It’s not just a trip—it’s the adventure of a lifetime, tailor-made for those who crave freedom, connection, and something truly unforgettable.
Do You Want To Join Us?
