Catamaran Playtime

Catamaran Playtime is a 2014, 56' Lagoon catamaran offering crewed yacht charters in the BVI and USVI. She features a fly-bridge deck, on-board scuba diving and instruction, and accommodations for up to 8 guests in 1 Master Queen Suite, plus your choice of 3 Queen cabins or 2 Queen cabins and 1 upper/lower Twin cabin. Catamaran Playtime is a Carefree Yacht Charters mid-range, luxury option for families, couples, divers, or special occasions.

Here's what Tyler & Kelsey told Carefree Yacht Charters about their fun-factor aboard Playtime: "You should know it’s all in the name! It’s PLAYTIME! This is your vacation and there are opportunities for activities at every turn. We know this area very well and can get you moving in the right direction. We have water skis, tubes, wakeboards, paddle boards, scuba diving, snorkeling, cliff jumping, board games, movie nights, comfy places to read your book, cocktails, party games, pirate shows, and more. Or if fun means relaxing in the sun away from other people and listening to nature pass you by we have plenty of that as well. Be sure to come up with a few good jokes if you’re heading our way though. We’re always looking for a laugh."

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

Contact Us

To learn more about this crew or for further details about PLAYTIME, 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 repeat client and group of couples that we booked aboard 56' Catamaran Playtime in May, 2018 said: Hello Lynne, Just a quick note to let you know that our week spent on Playtime was absolutely fabulous. Our one complaint would be that the trip didn't last long enough :) Thank you to Carefree charters and to Kelsey and Tyler for such an awesome time. PS We would love to receive your newsletters. Kelly & Claudio M., Canada




Season Passengers
2 3 4 5 6 7 8 9 10 11 12
Summer 2018 $22,500.00 $23,250.00 $24,000.00 $24,750.00 $25,500.00 $26,250.00 $27,000.00 $0.00 $0.00 $0.00 $0.00
Winter 2018 to 2019 $22,500.00 $23,250.00 $24,000.00 $24,750.00 $25,500.00 $26,250.00 $27,000.00 $0.00 $0.00 $0.00 $0.00
Summer 2019 $22,500.00 $23,250.00 $24,000.00 $24,750.00 $25,500.00 $26,250.00 $27,000.00 $0.00 $0.00 $0.00 $0.00
Winter 2019 to 2020 $22,500.00 $23,250.00 $24,000.00 $24,750.00 $25,500.00 $26,250.00 $27,000.00 $0.00 $0.00 $0.00 $0.00

Special Offer

  • 56 feet
  • Accommodates up to 8 guests in 4 cabins
  • Rates from $20,000 to $27,000
  • Save $250 for each child 15 or under at the time of the charter
  • Maximum of 4 child discounts
  • May be pro-rated to 6 nights

Price Details

HOLIDAYS: 2019 Christmas Flat Rate $36,000 St Thomas pick up and drop off. 7 night minimum. Charter must end on or before 12/28/2019 New Years Flat Rate $36,000 St Thomas pick up. 7 night minimum. Charter must start no earlier than 12/29/2019 2020
 Christmas Flat Rate $36,000 St Thomas pick up and drop off. 7 night minimum. Charter must end on or before 12/26/2019 New Years Flat Rate $36,000 St Thomas pick up. 7 night minimum. Charter must start no earlier than 12/27/2019 
 ***3 lunches and 4 dinners ashore at client expense***  
***Does not combine with child discounts***

 CHILD DISCOUNT: $250 off for each child age 15 and under.  ***Does not combine with half board options*** 
***Age is based on the charter date NOT the date of booking***
 ***Max discount - 4 children*** 

 ***(Rate divided by 6N X number of nights*** For 6 nights divide rate by 7 X 6N. 

SLEEP ABOARD: $1,500 Sleep aboard the night before the charter departs Guests arrive to the yacht at 5pm. Snacks and welcome drink served, this is not an open bar. Dinner is ashore on clients expense. Continental breakfast provided next morning. Vessel departs on a timing agreed by both Captain and guest.


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)


  • Summer Base Port: VI
  • Summer Operating Area: Caribbean Virgin Islands, Caribbean Windwards
  • Winter Base Port: VI
  • Winter Operating Area: Caribbean Virgin Islands, Caribbean Windwards
  • Preferred Pickups: Red Hook, St. Thomas
  • Other Pickups: PR
  • Turnaround: 48

Reviews from our Carefree Clients

A family that we booked aboard Playtime in June, 2019 said:

You were right! Playtime, Tyler and Kelsey were the way to go!!! More people should do this with their pre-adult children.

It was absolutely amazing!!!! Tyler and Kelsey took wonderful care of us. It was so evident that they CARED about our experience. They are wonderful captains, chefs and people. The food was extraordinary. It was truly top notch. They were our own private chefs and the food presentation and taste was 5 star. I personally tried foods that I typically don’t eat and loved it! Tyler and Kelsey guided us through the BVI’s and joined us at most times. This enabled us to see the true gems of the island and to experience them not just as tourists. The catamaran was spotless and roomy. We all had our own space and enjoyed eating together. The memories made around that dinner table, unforgettable. The memories made during every activity, unforgettable! I will start saving now for 2020!!! Oh, and the map they gifted us with - I will take a picture when it is framed and hung!!!!

Thank you! Thank you! Thank you!!!

Kimberly G., New York

A multi-repeat client and family that we booked aboard 56' Catamaran Playtime in May, 2019 said:

Hi Lynne,

I’m happy to report we had a terrific week aboard Playtime!!

The yacht was a great choice and very comfortable for my family. The layout was great and provided ample space for us to be together or find private space if needed.

Tyler and Kelsey were a great team! They were very accommodating in developing a flexible daily itinerary-we were able to hit anchorages we had never seen in our previous two trips. Tyler led us on a great tour of The Baths, and the boys commented on Kelsey’s guidance and expertise on their scuba excursions.

The menu planning and meal quality/preparation was excellent!

Thanks again for advising us through the process of picking the yacht and making preparations for the voyage.

Best regards,

Rick B., Ohio

A multi-generational family group that we booked in tandem aboard 56' Catamaran Playtime and 52' Catamaran Island Hoppin' said:

Lynne, first of all, a summary of who we are: There were three generations totaling 18 people ranging in age from 5 to 77. The occasion was a family trip to celebrate grandma and grandpa's 50th wedding anniversary. We have chartered sail boats in the Caribbean over a dozen times and three of those were with two generations, including some cousins. All three of our sons and four of our grandsons like to fish, no matter where they are. Our general conclusion is that this week long experience on two catamarans could not have been better! The two crews easily met all of our preferences for sailing, family activities, food, and overall provided a fun experience for everyone.

Regarding your services, you confirmed our initial impression of the Island Hoppin' crew (Jamie and Sue), and then suggested an equally good crew/boat for the tandem charter (Tyler and Kelsey). You also stayed in frequent communication and made sure all the details were covered and that the contracting and payment process was timely. Thank you.

The two yachts were well equipped, laid out so that everyone could easily and safely move around, which provided both a comfortable and safe sailing adventure for all.

The two crews fulfilled all of our expectations and specific preferences and did so with a very positive spirit and hospitality. We especially wanted to experience sailing daily, weather permitting, and this was done.

The food was excellent. We had a couple of food allergies in our group and it was apparent from the first few minutes on board that this was handled appropriately and would not be a problem. The meals, appetizers, snacks and anything to do with food and drink were responsive to our preferences, well prepared and presented, and always added to the experience.

Overall, several adults observed that, "it could not have been better!" We agree.

Cheryl & Jim W., Illinois


Captain/Chef: Tyler Dunn
Tylers southern charm and hospitality will make you feel right at home as soon as you step aboard Playtime. An athlete, his aquatic adventures began at Camp Merrie-Woode, where he grew up kayaking and rafting the many lakes and white-water rivers that the North Carolina mountains have to offer. At the age of 10, Tyler became scuba certified. He played varsity college lacrosse, and graduated with a degree in Outdoor Experiential Education from Appalachian State University. After college, he pursed his dream to live on the ocean by moving to Key Largo, FL, where he began
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Crew Pictures

Cabins & Amenities


Accomodation Details

Play Time features 4 guest suites, 4 with queen berths, all with full A/C and ensuite toilet and shower.

Guest Cabins

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


  • AC: Full
  • Voltages: 110v & 220v
  • Hairdryer: Yes
  • Water Capacity: 260 gals
  • Water Maker: Yes 75 gal
  • Ice Maker: Yes
  • Deck Shower: Yes
  • Jacuzzi: No
  • Specifications

    • Size: 56 feet
    • Builder: Lagoon
    • Year Built: 2014
    • Beam: 31
    • Draft: 5


  • Kids okay: Yes
  • Salon Stereo: Yes
  • Salon TV/DVD: Yes
  • Sat TV: 0
  • Board Games: Yes
  • Special Diets: Yes
  • Kosher: Yes
  • # Dine In: 8
  • BBQ: Yes
  • Crew Smokes: No
  • Guest Smoke: Transoms only pls
  • On-board Water Sports and Diving


    2 onboard dive instructors - 1 male, 1 female

    • License: Instructor
    • Costs: 3 dives per week included for certified divers - charters 6 nights or more.

      Additional dives $25 per dive per person.

      Online course required before charter commences.

      DSD Course $150
      Open water Referral $
    • Number of Dives: 3
    • Tanks: 8
    • BCs: 8
    • Regulators: 8
    • Resort Course: 150
    • Scuba:Onboard
    • Air Compressor: Not Onboard
    • Wet Suits: 0
    • Dive Lights: 0
    • Night Dives: 0

    On-board Water Sports

    • Dinghy: 15 ft
    • Dinghy Horsepower: 50
    • Dinghy Pax: 8
    • Water Skis: No (Adult) 0 (Kids)
    • Wake Board: Yes
    • Tube: Yes
    • Knee Board: No
    • Snorkel Gear: 12
    • Underwater Camera: No
    • Kayak: 0 (1 Man) 1 (2 Man)
    • Stand Up Paddle Boards: 2
    • Floating Mats: Yes
    • Beach Games: Yes
    • Fishing Gear: Yes
    • Jetskis: No
    • Other Toys: 2 Stand-Up Paddleboards
      Adult Water Skis