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Join us for the greatest vacation of your life – De Caribbean Regatta!  Below is a listing of boats, skippers & crew.  See which boat you would like to join and then contact the skipper.  Keep in mind that the final boat and price can change.  Boats are not booked until the crew is full.  Once filled, we check to see if the requested boat is still available.  If not, your crew can choose the next closest boat.


1. “Mercedes III” – SOLD OUT!!
Sailing with Mercedes III is all about having fun. We will race every day and enjoy the evening’s festivities so come have fune with us.
Yacht: Sunsail 444, 4 cabins, 4 heads – $1,750
Skipper: Doug Riehl
2. Debra Valenti
3. David Wren
4. Susan Tonks
5. Nickie Andrews
6. Kim Byrne
7. Wayne Pickering
8. Steve Kougioumtzis

jim mcnally

2. “Fat Buddha” – SOLD OUT!!
Come join me on Fat Buddha, the perfect mix of sailing and fun. If you want to overload on sailing…we’ve got you covered. I’m a racing instructor at the club and am getting my PhD in Ocean Engineering. So FEAR NOT sailing nerds you have found a home. But what is more important than the technical mumbo jumbo, is the moment when that is forgotten, and you become one with the wind and the water. Hence the name of the boat. The Fat Buddha is another name for the Laughing Buddha (Budai). The Fat Buddha reminds us to have a good time while trying to become enlightened. A little rum might help too and that’s OK cause’ Fat Buddha won’t hate on you. If you are interested in Coastal Cruising or Bareboat Chartering that can be arranged as well.
Yacht: Sunsail 54.5, 4 cabin – $1,590
Skipper: Jim McNally
2. Steven Rawlings
3. Julia Vassalotti
4. Tracy Steele
5. LaGrande Till
6. Laura Valentine
7. Meghan Conlin
8. Mike Jordan


3. “Delos” – SOLD OUT!!
It is the middle of January and you are on a boat!!! There is really not much more you can ask for – except for returning home with a tan and a ton of pictures of your relaxing sail around this tropical sailing paradise. The goal of “Delos” is to provide a relaxed environment for sailors and non-sailors alike to enjoy the BVI to its fullest. I love sailing, snorkeling, diving, and cooking (self professed foodie). I also have been told that I am a pretty mean mixologist. I have a love of logistics and planning, which will make this a very easy trip for any first-timer. This will be my third trip to the BVI and I aim to share the beauties of the islands and my love of sailing with the entire crew of “Delos”. Delos’s name comes from the mythical Greek island created by Poseidon. Poseidon created it to offer a beautiful and rich home to shelter and nourish the outcast Leto and her twin children Apollo and Artemis 🙂
Yacht: Moorings 50.5 Club – $1,490
Skipper: Michael Turon
2. Lauryn Arkin
3. David Forest
4. Ditte V Olesen
5. Martine Champagne
6. James Karklins
7. Kelly Dunn
8. Kim Sielbeck


4. “DoBeDoBeDo” – SOLD OUT!!
Looking for a crew of serious sailors ready to earn their BVI BS (British Virgin Island Bachelors of Sailing). DoBeDoBeDo embarks on her fourth BVI expedition to teach her crew how to become skippers. ASA Certifications for Bare Boat Cruising (104) and Cruising Catamaran (114) are the goal. These courses require Basic Costal 103 prerequisite and are taught in tandem. By Friday, you will be able to skipper a 30-50 foot Catamaran by day in costal waters. We’ll spend a few hours each day going over seamanship knowledge. Do sailing drills. Sharpen marlinspike skills. We will rotate skippers and first mates everyday and have fun as we become better sailors. After sailing hard, we play hard… It’s a little work, a little prep and a lot of play. A BVI University on island time, mon. Limited to seven. First crew cocktail dates are coming up soon, so get in touch and see you on docks!
Yacht: Sunsail 464
Skipper: Tracy Spinney
2. Jose Cordones (Bareboat & Cruising Catamaran)
3. Maximilian Brancaccio (Bareboat Chartering)
4. Veronica Washington (Bareboat Chartering)
5. Shivpal Kulhari (Bareboat & Cruising Catamaran)
6. Aleksandar Yonkov (Bareboat & Cruising Catamaran)
7. Kristine Rozan (Bareboat & Cruising Catamaran)
8. Geoff Parker (Bareboat & Cruising Catamaran)


5. “Squid Squid Squid!” – SOLD OUT!!
There is nothing more surreal than when you leave the bitter cold of New York and you find yourself on a warm sandy beach bar drinking “Pain Killers” with a 100 fellow club sailors! Be part of a crew with a vision for a harmonious balance of sailing, showing off your onboard cooking skills, performing heave-to’s for a quick pit stop to swim in the clearest of ocean waters with a smile and drink in hand. Forget NYC spas, sailing in such beautiful weather with a steady 15-20 knt wind is unlike any other way to relax and wind down from fast paced lives we all have become too accustomed, reminder you are in Caribbean Time! That is…until the sun sets and under the stars is when “real” night life begins. So come on board, have a cool rum drink and learn the secret handshake of The Squid!
Yacht: Sunsail 44i/3/3, 3 cabins, 3 heads – $1,540
Skipper: Jon Gimpel
2. Esther Eberhart
3. James Larsen
4. Jessie Purton
5. Allison Green
6. Ashley Rogers


6. “SS Shenanigans” – SOLD OUT!!
Welcome aboard the SS Shenanigans! Expect outrageousness. There’s no experience necessary on this boat, just a decent attitude and a willingness to work hard and play harder. Trip planning and crew duties and will be shared betwixt yourselves and the captain, Alexe, who’s a sailing school instructor and recent college grad with some BVI cruising experience and a penchant for history and adrenaline sports. If you have questions or concerns or just want to chat, shoot her an email at Bring your party hats, bring your game faces, but more importantly bring your fine selves and we’ll have a legendary week. P.S. Standby for a beer/ pizza/ itinerary and provisioning planning session once crew is finalized!
Yacht: TBA
Skipper: Alexe Taylor
2. Martin Winslow
3. Christopher Russell Fowler
4. Katie Foster
5. Brian McAllister
6. Jackie Balzer


7. “The Lido Deck” – SOLD OUT!!
/lēdō dek/ Noun: Outdoor area, often near the pool on a cruise ship, designated for sunbathing, entertainment, and good times. Popular usage: “Tonight’s boat party will take place on The Lido Deck.” Crew on The Lido Deck will enjoy a hands on experience including ample time at the helm, navigating the deep blue waters of the BVIs, playing DJ, and freshening drinks. Expect sun, wind, and cold beer on The Lido Deck. Come aboard, we’re expecting you!
Yacht: Moorings 50.5 Club – $1,490 pp
Skipper: Emre Cumali
2. Mihai Badoiu
3. Andrea Samdahl
4. Zeynep Dereli Korkut
5. Ekaterina Casali
6. Natasha
7. Serkan Eren
8. Dan Shilo


8. “Starship”- SOLD OUT!!
Let’s go sailing; period. De Caribbean Regatta will be the best vacation ever. For further details contact me directly at 787.460.4783 / Boat type to be determined by consensus.
Yacht: Footloose 4600, 4 cabins, 4 heads – $1,650
Skipper: Felix Garcia
2. Hooman Mehran
3. Alice Lustig
4. Kim Mizrahi
5. Cynthia White
6. Ben Katz
7. Ivan Rodin
8. Dana Richards


9. “Paradise” – SOLD OUT!!
What are your plans for January? Fighting through the snow to get to work, or sailing through crystal clear turquoise water under the warm sun to reach your perfect beach? Come and join me for a sailing adventure in Paradise. The Virgin Islands are my favorite place in the world – the beaches, water and wind are what dreams are made of! Take the helm, trim the sails, relax on deck, read a book, put some tunes on the stereo or simply soak up that Caribbean vibe. Pick up a mooring, swim to the shore, get a rum punch and then go back for more! At the end of each day on the water we’ll be perfectly tuned up for a good meal and entertaining evenings making friendships that may last a lifetime. This could be your best vacation ever! If you have any questions you can reach me at
Yacht: Sunsail 53, 4 cabin – $1,490 pp
Skipper: Tom Bollen
2. Matt Davis
3. Sarah Dickson
4. Peter Cody
5. Ingrid Adamsons
6. Veronica Knepp
7. Julia Bykhovskaia


10. “Internal Affairs” – SOLD OUT!!
With years of skippering at MYC, multiple charters on both coasts, and overnight distance racing, cruising and delivering of yachts along the Atlantic coast I am looking forward to cruising the wonderful BVI with you. I’m an assistant navigation instructor in the US Coast Guard Auxiliary and, as anyone who has sailed in the Fleet Captain program with me knows, I’m focused but relaxed, a pretty good wit, and like to help others become better sailors. We have a great crew coming together! Come for the good conversation, and good times we’ll have aboard! Bring your free spirit, desire to participate and get ready to relax! I guarantee you’ll learn, laugh and have a lot of fun!
Yacht: Moorings 43.3 Club, 3 cabins, 3 heads – $1,540
Skipper: Craig Kayaian
2. Carrie Booth
3. Laura Zygas
4. Jay Parekh
5. Matt Gajewski
6. Erich Templin


11. “Kismet” – SOLD OUT!!
Golden sand.  Turquoise water.  Clear skies.  Gentle breezes, crisp and cooling.  Sun, floating warm above smiles.  Music, inviting toes and ears.  Stars, brilliant beyond counting.  Nighttime halyards in the mast at anchor.  The joy of friendship.  The surprise of discovery.  Paradise found, and awaits again.  All combined for a week of blissful kismet.  Come dance your way from island to island with us!
Yacht: Moorings 54.5 Club – $1,590 pp
Skipper: Chris Fletcher
2. Chris Baker
3. Brendan Fletcher
4. Gail Brunje
5. Lauren Baker
6. Nicholas Kircos
7. Jesse Weeks
8. Anissa Becherair

2015 boat options and expected cost per person

  • Footloose 4000 catamaran, 4 cabin, 2 head, – $1,340
  • Sunsail 41/3/2. 3 cabin, 2 head – $1,440
  • Moorings 41.3 Club, 3 cabin – $1,470
  • Sunsail 53, 4 cabin – $1,490
  • Moorings 50.5 Club – $1,490
  • Sunsail 44i/3/3, 3 cabins, 3 heads – $1,540
  • Moorings 43.3 Club, 3 cabins, 3 heads – $1,540
  • Moorings 54.5 Club, 4 cabins, 4 heads – $1,590
  • Footloose 4600, 4 cabins, 4 heads – $1,650