Cruising Area of Rapscallion

Pref. Pick-upRH
Other Pick-upYHG, BVI
Summer PortVirgin Islands
Summer OperationsCaribbean Virgin Islands
Winter PortVirgin Islands
Winter OperationsCaribbean Virgin Islands

Rapscallion Specification

Length45 Feet
Beam26 Feet
Draft4 Feet
A/C NightYes
Bimini TopYes
Nude ChartersYes
Guest SmokeSugar scoops only
Children AllowedYes
Water Maker26 GPH
Water Capacity138 gallons
Ice MakerYes
Internet AccessOnboard WIFI
Turnaround48, Inquire for 24
Engines2 x 57HP Yanmar Onan 11KVA


Wash Basins3
Electric Heads3
Accommodation Details
Yacht has 3 queen guest cabins each fully air-conditioned with private en-suite head with separate shower stall and electric toilet. Lovely salon plus top fly-bridge bench seating with bimini top and padded sunbeds. Ample shade in the aft cockpit and U-shape forward cockpit for extra seating options.


Salon StereoYes
iPod/Device HookupsYes


Special DietsYes

Water Sports

Dinghy (Feet)11.8
Dinghy Hp30hp Honda
Snorkel GearYes
2-Man Kayak1
Floating Mats1
Standup Paddle2
Fishing GearYes
Gear TypeTrolling & Casting
Fishing Rods2
Other Toys
2 USB in each cabin
Floating mat

Scuba Diving Scuba Diving Symbol

ScubaYacht offers Rendezvous Diving only
Air CompressorNot Onboard

Rapscallion Crew Profile

Crew Number2
Crew SmokeNo
CaptainRichard Darling
LicenseUSCG 200-ton Master & MCA 200-ton Master of Yachts

Captain Richard hails from a small town in upstate New York near the Lake Ontario shoreline
where he learned absolutely nothing about sailing! That is until he spent some college years in Daytona, then went back to NY and was fortunate enough to enter the racing scene where he purchased his own sailboat and hasn’t stopped sailing since.

In 2003, Richard moved to the Virgin Islands and acquired his USCG Master’s License. Since
then, he has worked in the charter industry as Captain or Engineer on various sailing and motor
yachts up to 160 feet.
Calling St. Thomas home for more than 15 years. Richard has sailed thousands of miles through the islands and beyond, and he loves sharing some of the best kept secret anchorages and dive locations along the way along with his knowledge of the stars under the beautiful Caribbean night skies.

Rapscallion Calendar

AvailableBookedHold (can be challenged)Unavailable
Sep 2020123456789101112131415161718192021222324252627282930
Oct 202012345678910111213141516171819202122232425262728293031
Nov 2020123456789101112131415161718192021222324252627282930
Dec 202012345678910111213141516171819202122232425262728293031
Jan 202112345678910111213141516171819202122232425262728293031
Feb 202112345678910111213141516171819202122232425262728
Mar 202112345678910111213141516171819202122232425262728293031
Apr 2021123456789101112131415161718192021222324252627282930
May 202112345678910111213141516171819202122232425262728293031
Jun 2021123456789101112131415161718192021222324252627282930
Jul 202112345678910111213141516171819202122232425262728293031
Aug 202112345678910111213141516171819202122232425262728293031
Sep 2021123456789101112131415161718192021222324252627282930

Rapscallion Reservations & Port Locations

Start DateEnd DateDetails (Holds can be challenged)
Aug 01, 2020Oct 31, 2020Unavailable: St Thomas, USVI* to St Thomas, USVI*
Nov 01, 2020Nov 08, 2020Booked: Red Hook, St. Thomas, USVI* to Red Hook, St. Thomas, USVI*
Nov 09, 2020Nov 14, 2020Boat Show: Yacht Haven Grand to Yacht Haven Grand
Nov 15, 2020Nov 20, 2020Booked: Yacht Haven Grand to Red Hook, St. Thomas, USVI*
Nov 21, 2020Nov 27, 2020Booked: Red Hook, St. Thomas, USVI* to Red Hook, St. Thomas, USVI*
Nov 28, 2020Dec 05, 2020Booked: Red Hook, St. Thomas, USVI* to Red Hook, St. Thomas, USVI*
Dec 08, 2020Dec 15, 2020Booked: Red Hook, St. Thomas, USVI* to Red Hook, St. Thomas, USVI*
Dec 27, 2020Jan 03, 2021Booked: Red Hook, St. Thomas, USVI* to Red Hook, St. Thomas, USVI*
Jan 15, 2021Jan 23, 2021Booked: Red Hook, St. Thomas, USVI* to Red Hook, St. Thomas, USVI*
Feb 05, 2021Feb 13, 2021Booked: Red Hook, St. Thomas, USVI* to Red Hook, St. Thomas, USVI*
Feb 15, 2021Feb 21, 2021Booked: Red Hook, St. Thomas, USVI* to Red Hook, St. Thomas, USVI*
Mar 31, 2021Apr 07, 2021Booked: Red Hook, St. Thomas, USVI* to Red Hook, St. Thomas, USVI*
Apr 26, 2021May 02, 2021Booked: Red Hook, St. Thomas, USVI* to Red Hook, St. Thomas, USVI*
May 23, 2021May 29, 2021Booked: Red Hook, St. Thomas, USVI* to Red Hook, St. Thomas, USVI*
Jun 07, 2021Jun 14, 2021Booked: Red Hook, St. Thomas, USVI* to Red Hook, St. Thomas, USVI*

Rapscallion Rates / week

The prices shown are for the entire yacht for a week-long (7 nights) charter. Inquire for lowest rate.
Low price: $14,700
(normal rate)
High price: $17,000
(normal rate)

Rapscallion Special Offer!
Discount: $1,000!
Offer: Rapscallion is offering a $1,000 discount on any charter taking place between Nov. 1st and Dec. 16, 2020. Can not be combined with any other special offer and does not apply to existing bookings.
Old price: $14,700 - $17,000 / week
New price: $13,700 - $16,000 / week
Minimum nights: 7
Travel between: Nov/01/2020 - Dec/16/2020

Season2 Pax3 Pax4 Pax5 Pax6 Pax
2020 Summer$15,000$15,500$16,000$16,500$17,000
2020/21 Winter$15,000$15,500$16,000$16,500$17,000
2021 Summer$15,000$15,500$16,000$16,500$17,000
2021/22 Winter$15,000$15,500$16,000$16,500$17,000

Yacht terms: All Inclusive

An all-inclusive charter covers all provisioning and running expenses. This includes a captain and crew that is fully trained and committed to your safety and enjoyment of your trip. A chef will provide the kind of exceptional, personalized meal preparation that you would expect of a five-star restaurant. The listed rate may not include all local taxes, premium beverages or scuba activities. Inquire for more information.

Send us an inquiry to get specific pricing for Rapscallion.

Rapscallion Guest Reviews

July 2020

Dear Richard & Suzanne, The Rapscallion has been the prefect home for us this week and we can´t thank you enough for your generosity and hospitality. We loved tubing in Magens Bay, stargazing off St John and snorkeling in countless beautiful coves. Suzanne, the food was incredible - we especially loved the banana pancakes, crab cakes, sun dried tomato ravioli and ALL the deserts! Richard, you make the best ´Painkiller´, if this Captain thing doesn´t pan out, you´ll make an excellent mixologist. Thanks for sharing evening card games and giving us a vacation we´ll never forget..although a few dolphins would have been nice lol!

-Nick, Katherine, Sloan, Reese & Grace

June 2020

Sundowners and The Big Blue - what could be better?! Our time aboard SY Rapscallion was absolutely perfect! Captain Richard and Suzanne were THE BEST!! Great dynamics!! Very welcoming and genuine! Perfect for our family. Love the laid back atmosphere and even though the covid-19 threw us a challenge, we managed to stop in amazing anchorages and enjoy the vast snorkeling opportunities! The pier @ Fredriksted is an absolute must when visiting St Croix!

Suzanne, many thanks for your wonderful cooking skills! Everything was beautiful and so so tasty! (Kudos on the homemade sweet and sour mix!) Amazing job! Cannot stress enough! Above & beyond!

To both Captain Richard and Suzanne -
Humble thanks for sharing your sailing knowledge! As we´ve mentioned this is our dream to live aboard full-time. Appreciate your patience and involvement more than you know! Will has been in his happy place for the last 10 days for sure! haha

Seriously you both have been great! Many many thanks for making this a most memorable trip for our family! I bet Emory will talk (& talk, & talk, & talk..) about her time aboard for years to come! haha Until next time...

Fair winds & following seas,
Will, Rayna, Elle, Emory & Ryan

PS - Mind the ´sugar cubes´

June 2020

I´ve had several people ask about our recent vacation. It was AMAZING btw!! If you´re interested in booking a charter for your family, please reach out! Captain Richard and Suzanne were THE BEST!! And don´t worry, you won´t have to do ALL the work! Seriously what an experience! I highly, highly recommend!

March 2020

Richard & Leala,
We had a wonderful week with you. From Richards infectious smile and hearty handshake at Red Hook to our final cove on the North shore of St John, you made us feel welcome and our trip was very special - whether it was dropping the dinghy or pulling out water toys or making a cocktail you were more than happy to oblige.
Our highlights included the private cove at Beef Island, snorkeling the Indians, and our final cove on St John
Leala, thank you for waiting on us hand and foot and accommodating our 6 year old. My favorite dishes were the tuna steaks and the BBQ sliders.
Thanks to both of you!

Nev & Bethany
Atlanta GA

February 2020

Dear Richard & Leala,
Our family enjoyed a tremendous experience on Rapscallion. You are wonderful professionals who first and foremost care about your guests. We all appreciated how considerate and thoughtful you were to our needs and comforts. It was obvious you both wanted us to have an amazing vacation aboard Rapscallion and that we all did. Your provided us delicious meals (very impressive with a sailboat kitchen/little storage space) and attended to our likes and dislikes. Than you. From the breakfast tacos to the best burger I have ever eaten to the delicious desserts, thank you so much for the amazing food.. and thinking back to the snack tray you provided when we initially boarded the boat in Red Hook - perfect! Oh, and you´re both so attentive to beverage needs - from providing great coffee to delicious morning juices to perfect painkillers and awesome mojitos, great bartending! Richard, you make navigating and sailing the boat look so easy. It´s not! You are a true professional and we all felt 100% comfortable in your extremely capable hands. It was so enjoyable to watch you manage the boat. You are an amazing captain, professional and talented, willing to share your knowledge (thanks for that - I really enjoyed our conversations about sailing and navigation, very cool!) and your obvious love of boats. You are a timeless worker!

We leave you today but we all want to return. You both provided and experience we will look back with smiles and warm thoughts.

Thank you so much!!
Karl, Amy, Jillian, Anna & Jamie
Sherborn MA

Ask Richard for an astronomy lesson - he´ll be more than happy to oblige and it is quite fascinating

´The plan for today is to have no plan´

Thank you very much for this unique experience. This was an awesome vacation for the 2 of us.
Richard, you are an extremely professional Captain and you gave us a very impressive ride.
Leala, you conjured up meals that were beyond our expectation. We enjoyed so much the variety of the meals you prepared. Healthy and very delicious.
Richard & Leala, you showed us the best spot in the VI and made our trip the perfect stay. Also we enjoyed all the talks we had during our holidays. You are perfect hosts.
We loved your painkillers and think we´d like some more!!!
We are really looking forward to seeing you again on the Rapscallion (which is a perfect boat for a cruise like this)
Thank your very very much!! It was very nice to have met you. Take good care..
Uschi & Ralph

January 2020

Where do we begin? Ok - Red Hook! When we first met you both, instantaneously we knew we were going to have a great week! Since I´m older, my memory isn´t that great and I may get some of the ports/dates wrong!
First full day of sailing was quite an adventure. The seas were not cooperating, but Captain Richard and 1st mate/chef/mermaid Leala made the trip a lot of fun (and safe)
Cooper Island - Prickly Pear were a lot of fun (except losing our speaker on the beach) Thanks for naming an island for us!!!
Snorkeling at the Baths and the caves at Norman Island was one of the best highlights for me. I almost lost my ish getting in the water the 1st time, but you both calmed me down and gave me to courage to get on with it! Leala, you were THE BEST snorkel buddy, always making sure I was close and pointing out the amazing fish! But I was the one to show you the beautiful turtles!!! Snorkeling the next day at the caves was also amazing. When I panicked at the entrance - you didn´t pus me. You just said ´swim in & look & leave´ Getting in at the Bights Beach was also quote the snorkeling adventure. We hit the rock wall and swam in quickly!
Hanging with the guys all week long was the best! Willy T´s - dancing and drinking - bringing the dancing back to the boat and the ´pole dancing´ Richard - we decided you won the price for the best ´dancer´!
Captain Richard - we felt totally safe in your hands and we would all sail with you again (and bring more friends with us) You and Leala made the trip totally amazing. Chef Leala - every meal was better than the next...The two of you and how you work together made this trip for us!! I feel like we have 2 new amazing friends. Thanks for everything that your did for us and cannot wait for the next trip!!!
Michelle & David

Captain Richard - Captain of the year - rescuing the people on the capsized dinghy - that was really scary but really brave of you!!!

They are an amazing team!
First time sailing in the BVI and what an incredib;e team! Captain Richard made us feel so safe and while Leala was the best host and chef, after 2 days we felt like they were part of our vacation family. We loved spending time with them and having them join our adventures.
Loved The Baths, Jost Van Dyke & Prickly Pear
Defining episode - Captain Richard saving 4 people when their dinghy capsized
I would sail with them again - and again
Will definitely recommend Rapscallion with the Captain Richard and Leala1

New Years 2019/2020

Dear Richard & Leala,
We couldn´t think of a more perfect place to ring in the New Year! Thank you for such an amazing trip aboard S/Y Rapscallion! Leala, all of the food was so incredible and healthy - I can´t wait to try your recipes at home:) Richard, every stop was better than the last. Thank you for making all of us feel so well taken care of, safe & at home. Highlights of the trip were:
Prickely Pear - gorgeous beach
Oil Nut Bay - amazing snorkeling
Sandy Cay - more amazing snorkeling, great little beach
White Bay - Soggy Dollar and Hendos Hideaway
So much more too - everything was prefect. Thank you for the wonderful memories
Theron, Chloe, Sophie, Gracie & Jenn
Grenwhich, CT

Thank you so much for the best trip ever! The food was AMAZING! So so good! My favorite spot was at Sandy Cay when we went snorkeling and went on the beach! Also I loved seeing the dolphin at the front of the boat! It was so cool! Thank you so much again!

Thank you so much for all that you did on this boat! The food was absolutely amazing and everything was always so so beautiful. My favorite memories from this trip were tubing and seeing the dolphin swim with our boat - it was absolutely amazing! Couldn´t have asked for a better trip! Thank you so so much for having us on Rapscallion

Christmas week

Friday - out of St Thomas over to St John - cool town - get a bushwhacker!
Favorite spots - Maho Bay - woke up to beautiful scenery, mostly sunny, great breeze - Saturday morning -
The Baths - Virgin Gorda - amazing short hike
Leverick Bay - really nice spot - saw and spoke to Richard Branson - great bar, shops, and loved Michael Beans
Spent Christmas in Norman Island - very nice cove - bar & restaurant is awesome. Willy T´s is a must do!
Then on to Yost (Jost) lol - best spot by far. Would definitely recommend spending an extra day there or even longer. Best bars, shops & beach is amazing! Water crystal clear, calm and great to swim in.
Breakfast - lunch - dinner- ALL wonderful!
Th coffees in the morning were amazing. Grouper ceviche was bomb! Every meal was carefully thought out and delicious and plentiful. Eggs benedict, a Christmas tradition was phenomenal!
Great Captain - great Chef/1st Mate!


Awesome time

We had an amazing trip. The boat is spacious and stocked with all the ingredients you need for an awesome time- snorkel gear, paddle boards, towels, underwater camera, and many other accoutrements. You can explore caves and island ruins, go hiking or seek out interesting sea life, and then finish off the day with a cocktail on a gorgeous, obscure beach, away from the tourist stuff (unless you like the tourist stuff-and he can help with that too!). I can’t say enough about how perfect a hostess Leala was. She made us a yummy breakfast everyday and cocktails in the afternoon and was so sweet, coming with us to excursions and taking pictures whenever we’d forget. They had just the right balance of spending time with us and letting us be, as on any boat trip with a captain this can be a concern. This was one of the best trips I’ve ever had!

Awesome experience!

Always wanted to know what it might be like to Island hop in the Bahamas. Now I know! Loved it! Awesome Experience! Spent 5 nights for a father-daughter adventure. Leala cooked amazing meals for us, not to mention delicious rum drinks anytime upon request. Nice way to! They were both accommodating, friendly, and genuine! We really enjoyed the white sandy beaches and sailing along the bright blue waters. Beds were comfy, and hot showers too!

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