Yacht Charters……Your First Time Out


There you are in the car waiting for a bridge to close and out of nowhere a huge motor yacht glides through the opening heading out towards some wonderful destination. You see the crew all smartly dressed and with communication headsets on passing vital information to the Captain as he navigates the narrow passage. On the back of the boat a stewardess is serving drinks and snacks to a group of sunbathers lounging in the sun and enjoying life!

How quickly your mind wanders and, within a few shorts seconds, you see yourself having a similar adventure on a majestic yacht somewhere in the tropic warmth and clear blue waters of the Caribbean or passing through some verdant archipelago in the Greek islands….and then the car behind you honks its horn bringing you back to reality and, as you  drive through over the bridge, you manage to get one last glance at the motor yacht and that momentary daydream swirls through your consciousness for the rest of the day.

For many this daydream will unfortunately remain a dream and for others it will be an adventurous and memorable reality. It often begins by word of mouth.  You may have heard from a colleague or friend about their family charter vacation or from a blog you found on some travel site.  It’s important to know that each charter is going to be unique and it’s up to you to do some homework.  Having worked as a charter Captain for many years I always knew the best charter guests were the ones that communicated needs, wants, desires, and asked a lot of questions.  The key is to have fun and enjoy the process of picking a charter agency, the boat and most importantly your crew. A good charter agent will require a short bio of your group and your photographs to share with the crew and in return you will get a bio of your crew as well as their pictures.  It is commonplace and vitally important to have multiple conversations with the Captain, your Chef and the Chief Stewardess well in advance of your scheduled dates.

Your travel dates will often dictate the cruising area you would like to explore. The vast options throughout the Caribbean make it a great destination for first timers. I am partial to the U.S. and British Virgin Islands as it was my home for many years. Many charters start off by flying into St. Thomas and within minutes your crew will whisk you onto your charter yacht and get you settled in.  If chartering in March you might see hundreds of racing sailboats compete in the Rolex Regatta while you are safely anchored off of Cruz Bay in St. John.  A Fortune 500 travel recommendation is across the harbor and that is to visit with the irrepressible troubadour of Jost Van Dyke, Foxy Callwood, and the world famous Foxy’s Bar. It is an unforgettable piece of heaven that I highly recommend. Your next stop might be an overnight mooring at the Bight at Norman Island.  It is a wonderful anchorage and within swimming distance are shore side caves that offer an incredible snorkeling experience.  The harbor is also home to the vessel William Thornton, fondly known as the “Willie T”, a partially sunken steamer that for many years charter guests flocks to for food, libations and high jinks.

After you all enjoy a morning swim and a delectable breakfast your crew pulls the anchor and the Captain steams to the southern tip of Virgin Gorda to once again drop anchor so your group can explore the Baths. The Baths are cave-like natural formations of exotic pools and grottos formed by enormous boulders strewn across the beach. You will revel in ankle deep crystal clear water and white sands in hidden rooms of rock with slivers of sunlight peaking in from above. As you emerge back onto the beach your crew patiently wait to bring you back aboard for a sumptuous “down island” surf and turf lunch of fresh Caribbean lobster, French baguettes and thinly sliced Kobe beef. While you relax your crew once again weighs anchor as the ship heads along the coast to The Bitter End Yacht Club.  Enough can’t be written in this article about how wonderful the Bitter End Yacht Club is, just go!

After a day or two playing at the Bitter End it’s time to experience a little open sea. I would leave early morning while my charter guests are still sleeping and slowly steer the 85 miles to St. Maarten.  Your chef is busy in the galley making eggs with black truffles and crepes with salted butter smothered with Chantilly cream, sautéed apples and a swirl of caramel topped off with a small bowl of chocolate chaud.  Once you all arrive topsides and relax in the fresh sea air and finish breakfast it’s time to increase speed and make the late afternoon bridge opening into the Simpson Bay lagoon and your reserved slip at the Port de Plaisance Yacht Club. 

St. Maarten is half Dutch and half French.  Both sides have much to offer and since the French side is a short ride from Port de Plaisance, a trip into Margot to visit the many chic European shops and eateries is a must. I have always enjoyed spending time on the Dutch side in  Phillipsburg strolling through the shops on Front street and sipping ice cold Heineken offered by street vendors for pocket change. If traveling in May, the island is overtaken with an international collection of the greatest match racing boats in the world. Generally there are over 200 boats in several classes all racing in the world famous Heineken Regatta. When the day’s races are over the parties across the island are legendary. The nightlife doesn’t get any better than in Maho where you can enjoy Vegas-like entertainment, visit the clubs, or just head straight to Club Bliss for the Heineken Regatta after-party.  My last trip there was memorable watching the Black Eyed Peas performing on the beach.

Finishing out your charter wouldn’t be complete without a two-hour run from Simpson Bay to Gustavia Harbor in French St. Bart’s. Your Captain called well ahead and reserved you a slip in the inner harbor. Now it’s time to watch your crew in action as the boat makes her way in and the Harbor Master buzzes alongside to pass a mooring line to the crew on the bow, and the Captain slowly turns and backs down within a few feet from the pier while lines are set and the boat gently teeters between the bow mooring and the tight aft lines.  It’s called a Med Tie and is common in the Caribbean and throughout the Mediterranean. Downtown Gustavia is filled with duty-free chic European shops, amazing restaurants and quaint little bakeries.  A favorite with visitors for many years is Le Select restaurant, home of the “Cheeseburger in Paradise”.  A great time to schedule a charter is the first week in December when hundreds of sailboats that departed from St. Tropez in the Route De Rose’, and loaded with cases of rose’ on board, all arrive for a massive celebration that goes on all week.  There is certainly no shortage of wine!  So here your charter ends with hugs from your crew and a handful of zip drives with pictures they took during your time aboard as a parting gift, and a final toast or two with the last of the Veuve Clicquot.

When you finally get back home it’s time to start planning the next leg of your Caribbean adventure further down-island, but that’s a story for another time.