VIDEO: Sailing Regatta in Coral Bay, St. John

Join us on our day spent sailing in a regatta in Coral Bay, St. John!

Welcome aboard! Today, we’re spending the day aboard Mahala, my buddy Justin’s boat, as we help him navigate the route of an annual regatta in Coral Bay, St. John!

By no means are any of us seasoned sailors. We all know the very basics. So our two stated goals of the day were as follows:

1. Don’t Hit Anything. Justin works and lives aboard this boat as he uses it for the Boy Scouts program through Florida Sea Base. It’s his livelihood.
2. Have fun. Winning the race is likely out of the realm of possibility. So let’s lose but let’s have fun doing it!
3. Finish the race. We can at least do that, right?

Wrong. Turns out we could only complete 2 out of our 3 stated goals. See which ones we completed in our video below. Enjoy!

Sailing Charters on St. John, USVI

Although we were aboard my buddy’s vessel, there are quite a few options for sailing charters on St. John to do a similar trip. These are a few of my favorites:

• Sunset Sail: Cruz Bay Watersports departs the Westin on St. John every evening for a relaxing sunset cruise.
• Small-Group Sail to St. John from St. Thomas: Virgin Islands Day Sailing departs St. Thomas every day for a trip to St. John and the surrounding waters of Virgin Islands National Park.
• Sea Turtle Snorkeling and Pizza Boat Pitstop: Stormy Pirates depart St. Thomas aboard their catamaran as they head to Maho Bay for snorkeling with sea turtles before dropping anchor in Christmas Cove to visit a pizza boat.
• Sunset Sail from St. Thomas: The Lady Lynsey departs the Ritz Carlton on St. Thomas for a beautiful sunset sail with an open bar and tasty appetizers.
• All-Inclusive Private Day Sail: Hop aboard this private charter for an all-day sail and snorkel around St. John with all drinks and food included.

Photo Gallery: Sailing Regatta on St. John

Sailing in Coral Bay Video Transcript

At the start of the day

Welcome to Coral Bay on St. John in the US Virgin Islands. If you’ve ever been, you’ll know this place is unlike any other within the United States. It’s truly a forgotten corner of the Caribbean. I was once told, that Coral Bay is where sailors and sailboats go to die. But for my buddy Justin, it’s where he thrives.

We’re joining him today in a sailing regatta as he breaks in his recently purchased boat, Mahala. Now, we know how to sail, he knows how to sail, but by no means are any of us professionals.

Explaining the route

I’m going to stop you right there Justin. Let me explain with a better visual.

So this is a map of Coral Bay, this is where we are. And this is where the winds are coming from. The route we’re supposed to take heads directly into the wind as we leave the harbor. It’s easier said than done but it should be doable. After that, we circle around Flanagan Island before doubling back to Leduck Island where we should have the wind at our back. After wrapping around Lduck Island, it’s a straight shot back into Cora bay where we will hopefully be crowned champion. Easy, right?

And as I mentioned, this regatta is rather relaxed. No professional sailors. No teams. Just a group of salty dogs in the Caribbean looking for a little fun. so drink up!

A foolish technique

It didn’t take long into our sail to realize we weren’t doing so hot. We weren’t exactly traveling terribly too fast and the other teams were already leagues ahead of us. So we decided to take drastic measures to see if we could pick up our speed. Foolishly, we took down our main sail to see how it would change the interactions between our other three sails. It’s safe to say, it didn’t work to our advantage.

Unintended Route

Unfortunately, we were crawling into the wind and never quite made it out of Coral Bay. Our regatta was a wash. Instead, we decided to enjoy the day puttering around, testing new techniques, napping, and putting back a few cold ones. The day was saved.

So here’s how it ACTUALLY went. As we left Coral Bay we did a few unintended twists and turns, or accidental jibes, before making our way out into the ocean. We did wrap around Leduck island but never sniffed the vicinity of Flanagan Island. But hey a day at seas beats any day in the office.

Appreciating Coral Bay

There’s something about this place. Coral Bay. It feels wild and natural. A unique setting found nowhere else in the world. It’s beautiful. And I suppose that’s why people want to develop it. But I don’t know. There’s something about the rustic, salty charm of this place that seems so appropriately unchangeable.

It’s a place for people like me, Laura, and Justin to frolic around as our true selves. The island of misfit toys. A place to step back into time. It’s a place to live simply. It’s a place to live life to its fullest. And yes, it’s certainly a place where sailors and sailboats go to die. And there’s nothing wrong with that.