Sail the Caribbean – Sail Jester Review

There may be no better way to see the islands than by sailboat. Many of us may have dreams on what it would be like to simply raise the sail on your boat and drift off a few miles or so while you bask in the sun with no cares on where you may land. Of course that takes quite a bit of money to make that dream a reality so the next best option would be to have someone else invest the money, take the helm and do all the work while you take in the scenery. That being said, if you’re ever heading to the Virgin Islands, I would truly recommend a day sail on board one of the many charter companies that have called St. Thomas home. With all of the many options, our decision came rather easily. It just so happened that the apartment we rented for the week on our vacation was owned by, you guessed it, a sailer. How convenient for us, but when you’re not too sure about what to expect, the hesitation still persists. 

Do Your Research

There seemed to be dozens of these day sail options when you do an internet search, and even though we clearly had an option from the get-go, it didn’t change my OCD research method of checking almost all of the charters out to see their pricing. When choosing, you have to know exactly what you want out of your trip. If you’re sailing from St. Thomas, are you simply wanting to take a trip around the island for a half day, or are you looking for a fun day of sun while your captain plays a game of connect the dots among the many islands that await you in the clear blue water. Maybe your idea of a sail is take it a step further and visit some of the British Virgin Islands by taking in lunch in Tortola, playing around in the massive rocks at the Baths in Virgin Gorda or maybe you’re looking for a complete destressor by taking a few wet bills, jumping off the side of the boat and heading over to the Soggy Dollar Bar in Jost Van Dyke. No matter what your pleasure is, there’s a charter to make it happen. You could even combine most of these by taking a different “wave” of transportation altogether and utilizing the services of the many speedboats that can whisk you quickly to all of your destinations with very little time elapsing from your jetsetter schedule. There are even some packages that manage to fit in all of your sandy destinations within the timeframe of a single day!

The Daysail

For us, it was a matter of price and, well price. Ok, I’m exaggerating just a tad. Our family has learned over the years that a majority of our saving for trips comes on the front end. We will try not to worry so much about money once there, within reason. I tend to approach it with a “How long will it be before I have this opportunity again?”  Although you’d love to say soon, that usually isn’t the case. Would you agree? So, if we’re going to do it, we’re going to do it right. Based on location, price and just the simple fact of meeting our captain/renter, we had decided on Jester Sailing. It didn’t hurt that the reviews were incredible across the board over an extended period of time. Keep that in mind with any trip, excursion, or travel itinerary in general. The reviews will always tell you the complete story…if there are enough of them. Too few reviews and you may walk away with an incomplete picture. We had read the reviews: “Highlight of our trip!”, “Can’t miss!”, “The one thing you will take away from your trip!” Obviously, the expectations were pretty high and the picture you carry with you of sailing the Caribbean is pretty tough to beat also.
As morning broke, our family of 4 gathered ourselves and met Captain Jim at Secret Harbor near Red Hook. As he stocked the boat just 75 yards off the beach, we took our obligatory pictures and tried to contain our excitement. Moments later Captain Jim arrives in his dinghy to whisk us off to the Jester. Once on board, we heard the opening shot that always makes you feel good at mid-morning in the Virgin Islands. “We have plenty of drinks on board!” Well, Captain Jim, they won’t be there for long!

Rough Seas Ahead

As we make our way out into the open blue water, we discover the clear blue water that you see along the shore is just as clear as you steer into deeper waters. We went into this day with no clear destination or timeframe and that is the perfect way to do it. We found us a nice spot to sit, grabbed a drink to start the trip and let Jim do all of the work. I  must say that he has everything you need for the trip. All the snorkel gear, food, drinks, and good music playing in the background, it’s all there.  We knew there was a chance of storms, but Jim felt we could make our way around them. In fact, we did avoid the storms for the most part, but not completely. Only 20 minutes into the trip and the clouds gathered on us and then the bottom fell out. 3/4 of the family searched for cover underneath. The other 1/4 sat out there in the sideways rain that Forrest Gump affectionately called “stingin’ rain”. Ever the tough guy, I sat at the front of the boat while we dipped up and down, getting stronger and more deliberate with each passing moment. Lost cause? Not quite. The best thing about being out in the sea around these islands is the ability to see the breaks in the clouds. We knew our destination at that very moment, wherever the sun is shining! So that’s where we went, and that’s where the best part of our trip began.

Christmas Cove

One thing is for sure, calm waters treat your body much nicer than choppy waters, so the little jaunt to Christmas Cove inbetween St. John and St. Thomas was a welcome change of location. Whereas I enjoyed the feeling of a sailboat out in the water, being anchored in the crystal clear waters of the cove definitely had its advantages. It’s at this point that Captain Jim lets us know the day is ours to laze away as we choose. The Cove offers plenty of good snorkeling with varying depths that allows you to see plenty of colorful fish, sea turtles and the like, all the way to being in water so shallow you find yourself sucking in your chest to avoid the many sea urchins just inches away. Almost like a mini-minefield, you find yourself being quite creative with your acrobatic moves to avoid the pain of being a human pin cushion. Jim makes sure you have all you need, even for the youngsters. Our daughters are 9 & 12 so we were unsure if we would have all we need, but “No Worries!” Jim has it all. Floats for you to sit on and waste the day away, plenty of gear to choose from and best of all, lots of Jester Juice to help ease the pains of any stress you may have left in your body by this point. I can assure you we had very little stress, and that was before the Juice! After that, the feelings numb somewhat. While you soak the day away, Captain Jim is firing up the grill to cook up some rasta-style chicken, corn on the cob and pasta salad. How sweet to be sitiing on the boat, bobbing up and down, Killin some jester juice and showing that chicken who the boss really is. Epic experience and a feeling of
not wanting the day to end. But, the best part? Knowing that you’re completely happy with the expense. Now that’s the sweet knowledge that keeps you traveling right there. Plus, we mastered the recipes once home…Sorry Jim. Your view is still better than mine though.

Best Part of our Trip

Sound cliche? Well, it was that good. Sailing in the Caribbean on a beautiful, intimate sailboat was a dream come true. One that, honestly, we never thought would happen in our lifetimes. And, the opportunity to have something like that marked off my kid’s bucket list before they ever hit the teen years? Priceless! It’s experineces like this that keep us motivated to live the way we do, save the way we do, and, of course, travel like we do. It simply makes us thirsty for more. Captain Jim afforded us the chance to live like someone who has the resources to do so. It just goes to show that you can travel above and beyond and make memories that will last a lifetime. As we closed in on the final destination of our trip, we stared at our two young girls as they sailed us back into Secret Harbor, and we realized our dreams are coming true. As I continuously say, “Live within your means, but travel beyond them!”

“Beware of missing chances: ortherwise it may be altogether too late someday.”
-Franz Liszt


  1. Virginia Blady

    The advice is very sound and the sailing vessel does look very nice. I have never really tried that, wish I had taken his advice and gone along.

    Oh we’ll, there is always another island like Belize and maybe I will check into a sailing trip….but I will take my Dramamine the night before!


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