My Sailing Regatta & Flotilla Experience

A First-hand Encounter

So, I was all set to go to my first ever sailing regatta.  I already had numerous personal charter vacations stamped in my passport and loved each one, but I was quite intrigued about the different experience a sailing regatta would be. And this was the Helly Hansen NOOD BVI Championship – no little regatta event here.  Thirteen boats, a set itinerary and a whole lot of strangers cruising together.  Sure, I knew the competitive sailing and Caribbean location would be ideal, but what I didn’t know was that this would turn out to be a sailing flotilla vacation unlike any other charter vacation I had experienced. And it was incredible.


Arrival in the British Virgin Islands

The fun started immediately on arrival day, which kicked off with an evening poolside party where Mount Gay pain killers were awaiting us.  For most, this was the first-time meeting of the people with whom we would be cruising with for the week.  The instant connections were obvious though our collective love of travel and boating.  Our stories were similar, yet each unique in what brought us here.  Some of the guests were new sailors, some were simply friends along for the adventure, and the rest that were competing on the race teams, well, they were true sailors to their core with the strongest of the connections that were clearly resonating through us all.


Setting Sail

The first day began with an early morning captain’s meeting to discuss the race itinerary and what to expect during the week at each anchorage.  Following that, it was the highly anticipated moment of throwing off the dock lines, bidding the base team farewell and starting the voyage across the Sir Francis Drake Channel towards Cooper Island, around which the first race of the regatta would take place.   The hearty smiles and excited hearts of each boat’s crew were highly visible as hands were raised with friendly waves shared, boat flags billowed in the breeze and music filled each boat’s decks with the spirit of the Caribbean.


The Flotilla Experience

Watching the teams each day as they roused their crew, prepared their boat and positioned themselves for the start surely played to my island soul with an excited anticipation of the starting horn.  Once underway, watching them sail off into the distance and execute the strategy of their course was an incredible high. I couldn’t help but appreciate my decision to join this event as I watched this regatta from my front row perch on the hardtop of my Sunsail 454 catamaran.  This was so incredibly cool.

The week ensued with exploring some of the most popular islands from the energetic Jost Van Dyke, to two Anegada days, one of which was a lay day for island cruising, relaxing along peaceful beaches and paddleboard racing around the mooring field full of our flotilla charter sailboats.  

To enhance the obvious overtaking the island vibes were executing on our pirate-like souls, teams were excited to create an entry into the Mount Gay Rum Drink Contest mid-way through the week during our overnight docked at Leverick Bay on Virgin Gorda. I can’t say I minded being a part of the Judging Team.  I can say I sipped some very interesting recipes and took a new favorite home with me, too.   The revelry, laughs and singing echoed through the early evening until slowly small groups broke away to their own dinner agendas. 

We enjoyed a progressive style party planned aboard a few of the mothership boats, sunset evenings with relaxing moments and shared stories, dancing nights ashore, morning aft deck gatherings with floating groups as we laugh and recall the previous evening’s fun.  From dingy surfing, to snorkeling, to catching rays beachside, I was clearly seeing this was an experience that delivered all of the aspects of a charter experience.  And so much more. 


Everything I envisioned, yet so much more.

Meeting new friends, hearing stories of the day and adventures in their sailing careers was simply the beginning.  By the end of the week, mere strangers had turned into friends.  Friends that I would sail with again anytime when provided the opportunity.  Friends who are now connecting through visits to cities around the US to strengthen the bonds formed first through collective passions of sailing and boating vacations.

In the lyrics of Jack Johnson and Donavon Frankenreiter’s “FREE”, I am confident that as we all sailed our way back to base at the end of our week, the verse “on a lifeboat, sailing home, with our drunken hearts and our tired bones” echoed though the salty veins of us all.

Interested in joining a regatta event or flotilla sailing vacation, including our Sail By The Cabin vacation options? Click here for more information on upcoming events.

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