Catamaran Gambit

Catamaran Gambit is a 2008, 50’ Lagoon catamaran offering crewed yacht charters in the BVI. She features a raised seating area, crew of 2 and accommodations for up to 8 guests in 3 Queen cabins plus 1 upper/lower Twin cabin. Catamaran Gambit is a Carefree Yacht Charters affordable pick for families, couples, divers or special occasions.

Here's what Doug & Val told Carefree Yacht Charters about life and charters on Gambit: "Living aboard Gambit, and the experience we offer charter guests, is a life style choice, as opposed to a job. We have no real retirement plans, no home base elsewhere. What we strive to achieve with each and every charter, is an extension of that freedom for their week aboard."

Noteworthy Details: Gambit and her crew of Doug and Val took the award for "Runner Up for Best Multihull Under 57 Feet" at the November, 2018 crewed charter yacht show in the BVI.

Rates from $20,000 to $27,000. View availability and rate details.

Contact Us

To learn more about this crew or for further details about GAMBIT, call us in our South Florida office at (954) 980-9281 or fill out our Quick Request Form.

What Our Carefree Clients Said

A family that we booked aboard 50' Catamaran Gambit for Christmas 2021 said: Dear Lynne, You have serviced our family for many years but this trip you outdid yourself!!! Covid threw its own set of problems into the mix which required you to prepare us for all the U.S and British requirements. Your relationship with Michelle (at Island Time Water Taxi), plus Doug and Val made for a wonderful team. Each of you played a big part in allowing our family to have a wonderful holiday. Best, Michael B., California



Watch a short video featuring 50' Crewed Catamararan Gambit!


Season Passengers
2 3 4 5 6 7 8 9 10 11 12
Summer 2023 $20,000.00 $20,000.00 $20,000.00 $21,000.00 $22,000.00 $24,000.00 $26,000.00 $0.00 $0.00 $0.00 $0.00
Winter 2023 to 2024 $21,000.00 $21,000.00 $21,000.00 $22,000.00 $23,000.00 $25,000.00 $27,000.00 $0.00 $0.00 $0.00 $0.00
Summer 2024 $21,000.00 $21,000.00 $21,000.00 $22,000.00 $23,000.00 $25,000.00 $27,000.00 $0.00 $0.00 $0.00 $0.00

Price Details

Gambit is a BVI based yacht currently accepting BVI ports only. 48 hours between charters except between Christmas/New Years. Gambit also accepts 6 night charters at the pro-rata rate. For charters 5 nights and shorter, please enquire for rates. For Tandem Charters, please add $1500 and maximum of two boats applies. Half Board Rates Please inquire for rates. Sleep-aboard Inquire for availability. Rate is calculated as 1/2 the regular daily rate 7 night min. Discounts do not apply. Non Comm. GENERAL RATES NOTE: All rates are for 7 nights 8 days. Christmas 2023 - 1-8 pax- $33,350 New Year 2023/24 - 1-8 pax $34,800 7 night minimum. Christmas charters must end no later than the 26th December. New Years week charters cannot begin earlier than 27th December Gambit is a BVI based yacht. Permits and fees are included in the BVI only. Other locations fees will be extra. Please inquire for any delivery fees for "down island" charters.


To find the best dates for your charter, call us in our South Florida office at (954) 980-9281 or fill out our Quick Request Form.


Highlighted dates are booked, on hold, or unavailable. We may be able to challenge the dates on hold. Please contact us for details. All other dates not highlighted are available. You can use the arrow icons to navigate through the months.


Dates Color Key

If no color is noted on calendar or in the detailed list below, the dates are available for your charter. Dates can change quickly, so please contact us as soon as possible to begin booking your charter. Highlighted colors mean:

  • Booked (Booked by another client group already)
  • Hold (Held by another client group, not yet booked, and can be challenged)
  • Unavailable (Blocked out by the Owner and unavailable to challenge)


  • Location Details: Based in the the British Virgin Islands
  • Summer Base Port: BVI
  • Summer Operating Area: Caribbean Virgin Islands (BVI)
  • Winter Base Port: BVI
  • Winter Operating Area: Caribbean Virgin Islands (BVI)
  • Preferred Pickups: Village Cay
  • Other Pickups: Village Cay
  • Turnaround: 48 hrs Firm

Reviews from our Carefree Clients

A family that we booked aboard 50' Catamaran Gambit as part of a 3 yacht tandem charter said:

Hi Lynne!

Sorry for the delay! Reality gave us a bit of whiplash :)

Our family had a fabulous time aboard Gambit! Val and Doug were wonderful and we felt right at home. They are both so friendly and were really great with our kids. They were always up for playing games with them or making sure they had the right snack or soda. Our six-year-old, Celia, particularly loved their company. :)

Val and Doug really did a great job making the boat both beautiful and comfortable and it was always spotless!

Val is a fabulous cook and we were always very pleased with her meals (this is not an easy task with our kiddos). The level of culinary was truly an expected treat!

Doug is extremely knowledgeable regarding the waters and the BVI's in particular, which made for a very seamless experience. He always had great suggestions and we felt very comfortable having him as our captain.

We hope to return and this time with our drivers licenses.

As for Carefree Yacht Charters and your services, we could not be more pleased. You truly were top notch Lynne and we are very appreciative of the countless hours you spent making sure our trip was perfect, which it was. Thank you!!!


Angelle S., Georgia

A group of couples that we booked aboard 50' Gambit for Thanksgiving 2022 said:

Hi Lynne,

We had a wonderful time sailing with Doug & Val on Gambit!

Since it was our first charter, we weren’t sure what to expect, but it far exceeded our expectations. Especially with your guidance and help. You were so helpful and guided us through the whole process and made it so easy step by step. Otherwise, we would have been lost. We really appreciated your prompt and thorough responses to our many questions!

Doug and Val ended up being a perfect match for our crew. Doug was a fantastic captain. He knew all of the places to take us and the right time of day to avoid too many others (especially helpful at the Baths, Virgin Gorda). He was also very funny and shared lots of stories with us. We enjoyed hikes he suggested and he even led us on one to the Bat Cave. Doug also arranged a driver for us on Jost Van Dyke that was also a mini sightseeing tour of the island. He was more than willing to serve up the perfect tropical cocktail for us, or was perfectly okay if we just helped ourselves. We felt right at home.

Val was a fantastic chef! There wasn’t a meal that we didn’t care for. She has a talent for presentation and also all of the meals were spiced perfectly. I don’t know if you know what I mean, but nothing was too salty or spicy, etc. She served us a great variety of meals with the small amount of information we provided on our preference sheets. Meal times were consistent as well as the daily snack/appetizer tray around happy hour. Can’t say enough good things about the meals. Val also made us feel right at home by sharing with us where all the snack goodies were in case we needed an extra snack in between meals : ) As much as we loved Val’s cooking, we did have a lunch and dinner out on shore which I recommend and I’m sure Val appreciated the break.

Since this was our first charter, I don’t have any other boats to compare her to, but our accommodations were very comfortable. Bed was comfy. Air conditioning at night made sleeping great. We took the cabin with the “wet bath” which turned out to be in our favor because it had more room in it. Plenty of toys on board. Paddle boards, kayaks, water skis, snorkel equipment, water tubing – we used it all! Doug was more than happy to get things out and ready for us.

Lynne, can’t thank you enough for all of your help. Especially with the last minute, almost fiasco! So glad we were able to go. I’m sure I left out some things, so feel free to ask if I left something out.

I would love to sign up for your newsletter. I think all of us would like to do this again some day.


Maureen H., South Carolina


Hi Lynne!

Back to reality is no fun! We had a fabulous time. Thank you for recommending the Gambit. Doug and Val were great and a great fit for us. They had lots of knowledge for the kinds of spots we liked and things to do. Less crowds, more natural activities. The snorkeling and hiking were great. Their boat was beautifully decorated and clean. All the extras were included. Val is a terrific cook and had just what we requested. Doug is very charismatic and knowledgeable. We felt right at home. I hope we can charter again with them. Highly recommend the Gambit and Doug and Val.

Thank you for your help in arranging this trip. You made everything fall right into place. The hotel was a perfect first night. Very clean and comfortable. The water taxi was the way to go. It was fun and easy both ways.

Not one complaint!

Thanks again,

Cyndy M., Tennessee

A group of couples that we booked aboard 50' Catamaran Gambit in May 2022 said:

Hi Lynne,

Of the eight guests in this charter, TJ and I were the least involved with planning/communications with Carefree Yacht Charters. The emails you sent were informative and we have no recommendations. We appreciate Carefree Yacht Charters working with us on the re-bookings due to COVID.

Doug and Val graciously provided us with a treasured and memorable holiday. TJ and I appreciated their open communication on things such as Gambit protocol, itinerary options, and evaluation of our scuba skills. During our stay, they tenaciously pulled off the arduous task of accommodating four couples with sometimes different interests. One of Doug and Val's most impressive traits is their patience and dedication to providing the experience of a lifetime to their guests. Their sailing knowledge and experience in the British Virgin Islands afforded extraordinary cruising under sail, snorkels, scuba dives, hikes, and/or shore excursions each day. One of our treasured memories is Doug serenading the sunset on his Conch Shell Horn- truly magical!

Val's talent and training in culinary skills were evident. Every meal reminded us of a Michelin 3-star (out of 3) restaurant experience. And I appreciated their conscious effort toward sustainability (tableware, stainless steel straws, yeti water bottles, cloth napkins/tablecloths, instead of single-use plastic and paper items). The Gambit is pristine, efficiently organized, and comfortable. This holiday had to be rescheduled twice due to COVID restrictions. That Doug and Val honored our 2020 booking in the inflated economy of 2022 is reflective of their character. If we were to vacation in the BVI's again, spending a week on the Gambit with Doug and Val would be our first choice.

Best Regards,

Mary K., Tennessee



To ease you into life at a slower pace are Doug and Val Fairfield, an English speaking, husband and wife team from South Africa, with many years combined cruising, travel and charter experience. To date, Doug and Val have successfully completed over 180 charters in the Caribbean making them one of the most experienced charter crew in the region.

Doug holds a Yachtmaster Offshore Qualification, reinforced with many ocean crossings and coastal voyages, not least those accomplished with his family aboard. Doug started sailing in his mid twenties, based

Read More

Crew Pictures

Cabins & Amenities


Accomodation Details

Gambit offers sleeping accommodations in 3 queen size cabins and 1 twin bunk room. All offer AC and ensuite head and shower.

Guest Cabins

  • Max Guests: 8
  • Total Cabins: 4
  • King Cabins: 0
  • Queen Cabins: 3
  • Double Cabins: 0
  • Single Cabins: 0
  • Twin Cabins: 1
  • Pullman Cabins: 0
  • Showers: 4
  • Heads: 4
  • Electric Heads: 4


  • AC: Full
  • Voltages: 115v and 230v
  • Hairdryer: Yes
  • Water Capacity: 254 Gal
  • Water Maker: 80 gal/hr
  • Ice Maker: Yes
  • Deck Shower: Yes
  • Jacuzzi: No
  • Specifications

    • Size: 51 feet
    • Builder: Lagoon
    • Year Built: 2008
    • Refit: 2021
    • Beam: 28
    • Draft: 4


  • Kids okay: Yes
  • Internet Access: Onboard WIFI
  • iPod/Device Hookups: Yes
  • Salon Stereo: Yes
  • Salon TV/DVD: Yes
  • Sat TV: No
  • Board Games: Yes
  • Special Diets: Inq
  • Kosher: Inq
  • # Dine In: 8
  • BBQ: Yes
  • Crew Smokes: No
  • Guest Smoke: Transom Only
  • On-board Water Sports and Diving


    3 Dives per week included in the rate for certified and current divers based on 7 night charter.

    Extra dives available at a cost of $115 and includes equipment and tank refills.

    Diving is for CERTIFIED and CURRENT divers only. If divers have not dived within the last 3 years, a refresher course must be done before diving. This can be done before through a certified dive operator or onboard GAMBIT at a cost of $150 per diver.

    Guests rent or bring their own wet suits, specialized gear and dive computers.

    • License: Master
    • Costs: 3 Dives per week included in the rate for certified and current divers based on 7 night charter.
      Extra dives available at a cost of $115 and includes equipment and tank refills.
      Diving is for CERTIFIED and CURRENT divers only. If divers have not dived within the last 3 years, a refresher course must be done before diving. This can be done before through a certified dive operator or onboard GAMBIT at a cost of $150 per diver.
      Guests rent or bring their own wet suits, specialized gear and dive computers.

    • Number of Dives: 3 Dives pp
    • Tanks: 10
    • BCs: 8
    • Regulators: 8
    • Resort Course: N/A
    • Full Course: N/A
    • Scuba:Onboard
    • Air Compressor: Onboard
    • Wet Suits: 0
    • Dive Lights: 0
    • Night Dives: 0

    On-board Water Sports

    • Dinghy: 13ft AB
    • Dinghy Horsepower: 60
    • Dinghy Pax: 7
    • Water Skis: Yes (Adult) Yes (Kids)
    • Wake Board: Yes
    • Tube: 2
    • Knee Board: No
    • Snorkel Gear: Yes
    • Underwater Camera: No
    • Kayak: 2 (1 Man) 0 (2 Man)
    • Stand Up Paddle Boards: 2
    • Floating Mats: Yes
    • Beach Games: Yes
    • Jetskis: 0

    Contact Us

    At Carefree Yacht Charters®, we specialize in arranging extraordinary crewed yacht charters in the BVI as well as other Caribbean destinations. For full details, call us in our South Florida office at (954) 980-9281 or fill out our Quick Request Form.