Catamaran Gambit

Catamaran Gambit is a 2008, 50’ Lagoon catamaran offering crewed yacht charters in the BVI and USVI. She features accommodations for up to 8 guests in 4 Queen cabins or 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 $17,000 to $22,750. 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, toll free at (888) 670-6884 or fill out our Quick Request Form.

What Our Carefree Clients Said About Us

A family that we booked aboard 50' Catamaran Gambit for Thanksgiving 2018 said: Lynne, Thank you for working what was magic in your pairing our family with Gambit for our recent Thanksgiving charter. The charter far exceeded our expectations...and that is saying something coming from 14 and 16 year old high school students !!! We would highly recommend (and already have !!!!) not only your knowledge of the charter industry and professionalism, but specifically the charter yacht Gambit and Doug and Val Fairfield to anyone who is seeking an “Over the Top” vacation of a lifetime. Sincerely, Hays O., Louisiana



Watch a short video featuring 50' Crewed Catamararan Gambit!


Season Passengers
2 3 4 5 6 7 8 9 10 11 12
Winter 2021 to 2022 $17,000.00 $17,750.00 $18,500.00 $19,250.00 $20,000.00 $21,500.00 $22,750.00 $0.00 $0.00 $0.00 $0.00
Summer 2022 $17,000.00 $17,750.00 $18,500.00 $19,250.00 $20,000.00 $21,500.00 $22,750.00 $0.00 $0.00 $0.00 $0.00
Winter 2022 to 2023 $17,000.00 $17,750.00 $18,500.00 $19,250.00 $20,000.00 $21,500.00 $22,750.00 $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 currently accepts a minimum of 7 nights for charter. No short charters please. 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 2021 - 1-8 pax - $26,200 New Year 2021/22 - 1-8 pax $27,500 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, toll free at (888) 670-6884 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 NOTE: All Grenadines Charters should be booked North to South, from St Vincent to Carriacou. We can pick up from Young Island Cut in the South and visit Bequia, Mustique, the Tobago Cays, Mayreau, Union and Petit St Vincent. Please contact for routing. Diving with local Dive Operators Only.
  • Summer Base Port: Grenada
  • Summer Operating Area: Caribbean Virgin Islands, Caribbean Leewards, Caribbean Windwards
  • Winter Base Port: BVI until Mid July
  • Winter Operating Area: Caribbean Virgin Islands
  • Preferred Pickups: BVI
  • Other Pickups: BVI
  • Turnaround: 48 hrs Firm

Reviews from our Carefree Clients

A repeat group of couples that we booked aboard 50' Catamaran Gambit in January 2020 said:

Hi Lynne,

My apologies for the slight delay in responding...we hit the ground running after a blissful vacation on Gambit. I must say, the Gambit pace is preferable!

I can only speak for myself, but I loved every minute of our time with Doug and Val. They are charming, interesting, caring people who are so clearly dedicated to creating a memorable guest experience. It was such fun to make a return visit and to know exactly what to expect so that we could fall into true relaxation as soon as we stepped aboard.

Gambit, (and Doug & Val) seem to be reverse aging. Everything is sparkling clean, well organized, beautifully appointed, and as comfortable as any home. The new bar area is such fun and garnered quite a few compliments from passers by.

We opted for a more low key itinerary this year and Doug took great care in helping us plan around some often challenging weather conditions to secure beautiful and secluded anchorages. We enjoyed the slower pace and spent hours floating, paddle boarding, kayaking, hiking, puzzling, and reading, stopping only for one of Val’s delicious meals and a refill from bartender Doug. One new fun addition was the nightly Left, Right, and Center game...we tallied the scores and at the end of the week crowned a winner. (ME!)  

Thank you again for pairing us so perfectly last year.  Getting to know Doug and Val, and having the privilege of being aboard Gambit twice has been such a treat.  I would highly recommend this experience.


Meg C., Virginia

A group of couples that we booked aboard 50' Gambit in March, 2019 said:

Hi Lynne,

My two cents:

The charter experience aboard Gambit is a superb experience. Being a first timer, I had expected sun, fun, and relaxation, but I had no idea the bounty of other elements that make for a magical week. I would like to thank you for laying the groundwork for our trip. I now understand the importance of matching a boat and crew to the pace and style of the guests, and you did that perfectly. Val and Doug were professional, proficient, experienced, and hospitable, and that alone would have made for a wonderful week. But they are also so much more. They keenly understand, almost innately it seems, how to craft each day around weather, meal pacing, water time, and our desires, while also positioning us well for each subsequent day. As far as creature comforts, the Gambit is sparkling clean, well appointed, warm, and inviting. The meals were beautifully presented, ample, and delicious, while respecting our dietary requests. Doug and Val make what they do seem effortless to guests, but I know it is far from that.

As I stare out the window at snow and sip coffee I had to pour for myself, I am still basking in the warm glow of a unique and marvelous adventure, and still feeling spoiled in every way having been under the spell of Gambit.

Best wishes to you and thank you again for all you did to make our trip nothing but smooth sailing.

Meg C., Virginia

A repeat client and 2 family group that we booked aboard 50' Catamaran Gambit in March, 2019 said:

Hi Lynne -

We did have a ball! Doug and Val as always are fantastic. I think the best comment was from my husband who said "I feel like I have known them my whole life". The charter with them just becomes one big family and they are wonderful hosts, telling stories and making sure everyone, including the kids, were having a great time. The food was fantastic... the proof being we are all on diets now, especially since my sister (on copy of this email) checked the "Desserts please!" section in the preference form. ha. Gambit is a beauty, we all loved her and it was very spacious for all of us.

Thanks again for making this so easy booking through Carefree, another stellar vacation in the books! I would love to be signed up for the Carefree newsletter. Thanks again Lynne.

Dana A., Colorado



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.

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 off the east coast of South Africa, where sailing and weather conditions are notoriously unpredictable and the coastline hazardous. Having grown up on the ocean with
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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
  • Hairdryer: Yes
  • Water Capacity: 254 Gal
  • Water Maker: 500 Gal
  • Ice Maker: Yes
  • Deck Shower: Yes
  • Jacuzzi: No
  • Specifications

    • Size: 51 feet
    • Builder: Lagoon
    • Year Built: 2008
    • Refit: 2016
    • 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 free dives included in Gambits rate for 7 night charters only.

    Maximum amount divers is 6.

    Maximum dives per day is 1.

    Extra dives at a cost of $75 dependent on itinerary.

    Diving is for certified and current divers only.

    • License: Master
    • Costs: 3 Dives per week included in the rate for certified divers based on 7 night charter. Extra dives at a cost of $55.
      Guests rent or bring their own wet suits, specialized gear and dive computers.
      Diving only offered in the Virgins.
      Rendezvous diving in the Grenadines at guest expense.
    • 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
    • Water Skis: Yes (Adult) Yes (Kids)
    • Wake Board: Yes
    • Tube: 2
    • Knee Board: Yes
    • Snorkel Gear: Yes
    • Underwater Camera: No
    • Kayak: 2 (1 Man) 1 (2 Man)
    • Stand Up Paddle Boards: 2
    • Floating Mats: Yes
    • Beach Games: Yes
    • Jetskis: 0