Join us for the greatest vacation of your life – De Caribbean Regatta! This is where we list the skippers, their boats and crew.
Boat 1 – The Great Escape – SOLD OUT!!
Cruise aboard the luxurious catamaran Great Escape to experience the sailing lifestyle. We greet each beautiful sunrise with a swim and breakfast or boat yoga, coffee and chill time. I offer ASA 103 Coastal Cruising, 104 Bareboat Chartering, and 114 Cruising Catamarans on the trip, so learning is integrated into our daily routine. Each day we sail and explore the natural beauty of the BVIs. In the evening we anchor and celebrate with a sundowner, flotilla party, or relaxed dinner on the boat or at a local restaurant. Make your escape! You’ll never regret it.
Boat: Moorings 5000 5 Cabin Exclusive
Entry Fee $2,326
1. Skipper: Sara B
2. Marc K
3. Barbara O
4. Anthony T
5. Rena S
6. Patrick J
7. Matthew W
8. David R
9. Keenan S
10. Maneesh S
Boat 2 – Sailing & Sundowners – SOLD OUT!!!
The name says it all. We like to sail hard and party hard. Take your sailing skills to the next level while perfecting your Dark & Stormy technique. We’ll be doing the 103 and 104 classes. Anne’s has been developing the next generation of badass sailors for over 10 years, and she’s back for her second year at Caribbean Week. If you ask her how last year went, she’ll tell you the truth: what happens in the Caribbean stays in the Caribbean.
Boat: Moorings 5000 5 Cabin
Estimated price per person: $2,207
1. Skipper: Anne P
2. Jessica T
3. John P (103)
4. Karen Q (103)
5. Galiya C
6. Lori M
7. Omar R
8. Mike A
9. Angela A
10. Craig D
Boat 3 – Mercedes VII – SOLD OUT!!
Fair seas and safety.
Boat: Moorings 5000 4 Cabin Exclusive
Price: $2,566
1. Skipper: Jesse W
2. Doug R
3. Debra V
4. Trish D
5. Charlie B
6. Christina B
7. Daniel C
8. Pam S
Boat 4 – Sea Ya – SOLD OUT!!!
Returning to the BVIs for a third time, Katie’s excited to say “Sea Ya” to winter and spend a week cruising from island to island, enjoying the friendly banter between boats for the most important items of the week… spirit, sail trim and swimming support gear. Katie’s an ASA101-105-certified sailing instructor and while she’s not teaching on this trip, she loves sharing her knowledge and is looking forward to a trip where everyone participates in every part of the voyage—from planning and provisioning to helming and trimming. If you’re looking for a week of fun, chill vibes, a tiny bit of friendly competition (after all… what do you call two boats heading in the same direction? A race!), and as much swimming/snorkeling as we can fit in, then say hello to the BVIs and say “Sea Ya” to NYC for a week.
Boat: Moorings 4500 Club
Entry Fee: $2,003 per person
1. Skipper: Katie M
2. Robyn S
3. Brittney D
4. Eleanor P
5. Orest B
6. Esther E
7. Jon G
8. Joshua N
Boat 5 – Seas the Day! – SOLD OUT!!!
Boat: Sunsail 51
Price: $1,710
1. Skipper: Hector S
2. Eugene S
3. Ann Marie S
4 Veedoola R
5. Jeffrey R
6. Silvia G
7. Amanda W
8. Tracy S
Boat 6 – OMAKASE – SOLD OUT!!!
Boat: Moorings 42.1 Club
Entry fee: $2,390
1. Skipper: Kinya T
2. Yuichiro H
3. Akira O
4. Kazuaki S
5. Atsushi O
Boat 7 – Rum Runner – SOLD OUT!!!
Under the watchful eye of our English skipper who now mostly hides out in Miami FL, the Rum Runner will assume primary responsibility for making sure the party never dries up. Life on board will consist of working on our sailing skills by day, with everyone (who wants to) taking responsibility for all positions on the boat. We love sailing and will try to sail as much as possible, but will also leave plenty of time for exploring, snorkeling, paddleboarding, and taking epic photos with drones and cameras. Then as the sun goes down we will get the music going and head ashore together to show the BVIs how to take the party to the next level. DJ, mixology and cooking skills will be especially prized, and enthusiasm on the dancefloor an absolute requirement.
Boat: Moorings 4500 Lounge
Entry Fee: $2,291 per person
1. Skipper: Tom L
2. Tom L guest
3. Eric D
4. Justin P
5. Alan W
6. Percy W
7. Julia S
8. Jerry N
Boat 8 – Flagship 2023 – SOLD OUT!!
Fun, Sun & Sailing. “Flagship 2023” is in charge of the regatta which means all the skippers come to our boat for the morning skipper meetings. It’s fun to watch and you get a behind the scenes look at how we create a great regatta. I’ve sailed the BVIs many times. This year, we want to make it the best ever so let’s put our thinking caps on and do it right. One thing about our boat, we are looking for active participants who are ready to steer, trim the sheets, raise the sails, cook the breakfasts, etc. We sail during the day, go to all the parties and encourage dancing every night.
Boat: Moorings 5000 catamaran
1. Skipper: Michael F
2. Sarah R
3. Jim C
4. Wilson K
5. Steven V
6. Nicolas F
7. Valencia T
8. Katherine G
Boat 9 – Storm Rider – SOLD OUT!!
We’ll do lots of participation sailing and partying (with some concession to my advanced age.)
Boat: Moorings 4800
Price: $2,056
1. Skipper: David S
2. Alex P
3. Bill S
4. Pam S
5. Laura V
6. Antolin R
7. Roger P
8. Peggyann W
Boat 10 – Happy Bubbles – SOLD OUT!!!
Leave the cold and darkness of the winter behind and enjoy the warmth and beauty of BVI. With our experienced skipper Thomas you’ll explore secret spots in the BVI while sailing on a luxurious Catamaran. During the day, we’ll do a lot of sailing, snorkeling and swimming. In the evening, we’ll have dinner on board or at unique local restaurants and we’ll hang out with our MYC friends. Register now for this exciting event and experience the great spirit of The Caribbean Regatta.
Boat: Sunsail 484 4 Cabin Cat
Entry Fee: $1,842
1. Skipper: Thomas H
2. Jan K
3. Andy M
4. Christoph H
5. Lu W
6. Kim B
7. Sveta K
8. Anjali M
Boat 11 – L’Avventura – SOLD OUT!!
Come with me as I step away from my duties aboard Arabella to captain a fifty foot sloop for a week’s sailing in the Caribbean! Be my crew and share our love for the sea while singing and dancing through the tropical twilight. Every day will be filled with wind, laughter, and sail, while every night will stand replete with the joys of good food, good company, and the stars above. Practical seamanship and navigation, morning swims and evening festivities, Italian music and cooking are all on the menu. Hello. I’m Nicolas. A mariner with experience in the Mediterranean, Pacific, and Atlantic. Join me for a Caribbean adventure of your dreams aboard L’Avventura.
Boat: Sunsail 484
Entry Fee: $1,841
1. Skipper: Nicolas C
2. Heather S
3. Suelyn B
4. Sarah R
5. Christine O
6. Michael H
7. Janet A
8. Maurizio A
Boat 12 – Knot on Call – SOLD OUT!!!
Come escape the cold Northeast and relax on the Caribbean ocean for a week with skippers Yvette and Hollin who are Knot on Call! We will explore the beautiful islands, sip wine and cocktails, snorkel, grill and play music on the back of the boat, and maybe some dancing will be involved… we will improve our sailing skills, and enjoy the company of fun friends while having the best trip of the winter!
Boat: Moorings 48.4
Entry Fee: $1,708
1 & 2. Skippers: Yvette & Hollin
3. Sasha
4. Jenna B
5. Theresa O
6. Mihai B
7. Lorena E
8. Mike B
Boat 13 – Momentum – SOLD OUT!!
Evan’s excited to return to the BVI’s. Momentum is named for the laws of physics that allow boats to move through the water, and it’s also a metaphor for gaining momentum in life and our sailing careers—especially since COVID. Momentum is all about enjoying sailing, the local cuisine and every water sport the BVIs have to offer.
Boat: Moorings 4500 Lounge
Entry Fee: $2,291 per person
1. Skipper: Evan S
2. Han D
3. Wanshen W
4. Carlos O
5. Katie L
6. John A
7. Sophia A
8. Leo B