Catamaran Island R&R

46ft · 6 guests · St Thomas, US Virgin Islands

 7-Night Rates

From $12,500 (2 passengers 7 nights)
To $14,500 (6 passengers 7 nights)*
*Price range is subject to change. Please Contact Us for pricing for various party sizes, number of nights and seasons. Best price guarantee: We endeavor to offer the lowest prices available and will always match lowest rates. We accept Visa, MasterCard and AMEX, no fees. We accept Visa, MasterCard and AMEX


   Guests    Cabins Length
6 3 46ft
Guest cabin configuration:
3 Queen en-suite cabins with A/C
Designer Robertson and Caine
Built 2008
Children Allowed Yes (Min. age: Water safe)
Home port Compass Point Marina, St Thomas, US Virgin Islands
Scuba Rendezvous only

Special Offer

$1,000 discount for Honeymoon and Anniversary charters
Island R&R offers a $1,000 discount for Honeymoon and Anniversary charters. Excludes holiday weeks.
Available now through 14 Dec 2019.
Confirm before 7 Dec 2019.
The elegant and spacious salon seating area. Huge shaded aft cockpit lounge. Queen Cabins with ensuite head Queen Cabin with ensuite head Beautiful bed linens create a beautiful experience on board Separate showers in each head The salon The galley Cockpit seating area Great sailing aboard Island R&R Aft sugar scoops Island R&R on her mooring. Island R&R Layout

Catamaran Island R&R Overview

Island R&R is a 2008 Robertson & Caine designed Leopard 46 catamaran, perfectly suited for crewed yacht charter vacations in the Caribbean.

The yacht offers a great platform for relaxing and watersports in the warm Virgin Islands waters.

The yacht offers 3 queen size cabins each with private, en-suite bathrooms complete with electric flush toilets, separate walk-in showers (dry heads) and air conditioning.

The yacht’s salon flows into the outside shaded cockpit seating area where a large table and additional bench seating gives everyone plenty of space to be together and enjoy a relaxing and fun sailing vacation.

Head forward to relax on the trampolines or for an excellent spot to enjoy the warm breeze while under sail to the next bay or Caribbean island.

Ports and Available Cruising Areas

   Home port: Compass Point Marina, St Thomas, US Virgin Islands
Winter cruising area: Caribbean Virgin Islands
Summer cruising area: Caribbean Virgin Islands, Caribbean Windwards


Island R&R Sleeps 6 guests in 3 Queen cabins with ensuite heads, all electric and separate walk-in showers.


WiFi Internet: WiFi available
Air Conditioning: Full
Salon Stereo
Deck Shower
Hair Dryer
Board Games
Sun Awning
Ice Maker
Water Maker

Water Toys

2-Man Kayak
Floating Mats
Snorkel Gear
Underwater Camera
Fishing Gear
Fishing Type: Light tackle
Fishing Rods: 2
Dinghy: 14'
Dinghy Outboard HP: 40
Other equipment includes:

4 Stand Up Paddleboards, 2 man Kayak, Giant floating Lilypad, Inflatable Party Island for 6, SUB Wing (underwater flying device), Projection Screen that turns the cockpit lounge into a movie theater, Inflatable Swan and Flamingo, KneeBoard, Wakeboard,

Crew photo

Meet the Crew

Matt & Casey

Matt's love of the water began at an early age fishing the lakes and rivers of the North Woods in Wisconsin, Minnesota, and Illinois, and was escalated quite a bit when his parents decided to sell the lake house in Wisconsin for a 42x12 houseboat in Key West. The move to Key West spurred Matt's love for the ocean. Spear fishing and lobster fishing, scuba diving and snorkeling on the top of the list of his favorite activities. Matt's favorite off time activities include reading and visiting with family, enjoying good food with friends, soccer and anything outdoors.

Matt is a USCG certified 100GRT Master, with sailing and towing endorsements. He has been sailing in the Virgin Islands since 2014 where he started working as a captain for a busy private day sail company before moving over to captain of a crewed charter catamaran.

First Mate/Chef Casey knew she would find herself living on an island from the first time she visited the Caribbean with her parents. Casey grew up in Maryland and her love of the water began at age 4 when she learned how to water-ski on her Grandparent's lake. Casey thrives off adventure and loves to embrace the beautiful island atmosphere and unique culture. Hiking, snorkeling, wakeboarding, paddle boarding and exploring new areas are all things she hopes to share with her charter guests.

Casey received a Bachelor of Arts degree from the University of North Carolina at Wilmington. She has owned a boat for 10 years, and frequently found herself as captain taking her friends to the nearby coastal islands. Casey moved further South to attend law school in Jacksonville, more

In the summer of 2015, Casey made the decision to leave her corporate life behind and move to St. Thomas to help her family with their day charter business.

Casey has a passion for cooking and exploring new cuisines, but she still loves to follow her grandma's recipes for good old-fashioned comfort food. She admits to having a serious sweet tooth!

It was on the St. Thomas dock where Casey and Matt (introduced by Casey's father) first met. They share a passion for the water, adventure and enjoying good food with friends. Casey and Matt look forward to making your Caribbean sailing charter dreams come true aboard Island R&R.

  Weekly Charter Rates by Group Size

Passengers: 2 3 4 5 6
Winter 2017 to 2018 $12,500 $13,000 $13,500 $14,000 $14,500
Summer 2017 $12,500 $13,000 $13,500 $14,000 $14,500
Winter 2018 to 2019 $12,500 $13,000 $13,500 $14,000 $14,500
*Price range is subject to change. Please Contact Us for pricing for various party sizes, number of nights and seasons. Best price guarantee: We endeavor to offer the lowest prices available and will always match lowest rates. We accept Visa, MasterCard and AMEX, no fees. We accept Visa, MasterCard and AMEX

Availability for Island R&R:

Listed below are any confirmed reservations or unavailability, as well as current holds / options. Note: this calendar is not always 100% current. Please contact us for more information about available dates aboard this yacht.

Upcoming 12 Months Reservation Calendar:

Available weekend day:
Caribbean off season:
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Reservation Calendar with Port Locations:

Transit: Wednesday, 17 October 2018 to Wednesday, 31 October 2018: Transit: Grenada, St Georges to Compass Point, St Thomas*
Boat Show: Friday, 9 November 2018 to Saturday, 10 November 2018: Boat Show: Yacht Haven Grand to Yacht Haven Grand
Booked: Sunday, 11 November 2018 to Saturday, 17 November 2018: Booked: Compass Point, St Thomas* to Compass Point, St Thomas*
Booked: Thursday, 29 November 2018 to Friday, 7 December 2018: Booked: Compass Point, St Thomas* to Compass Point, St Thomas*
Booked: Saturday, 8 December 2018 to Saturday, 15 December 2018: Booked: Compass Point, St Thomas* to Compass Point, St Thomas*
Booked: Wednesday, 19 December 2018 to Thursday, 27 December 2018: Booked: Red Hook to Red Hook
Booked: Friday, 28 December 2018 to Friday, 4 January 2019: Booked: Compass Point, St Thomas* to Compass Point, St Thomas*
Booked: Saturday, 5 January 2019 to Thursday, 10 January 2019: Booked: Compass Point, St Thomas* to Compass Point, St Thomas*
On Hold: Friday, 8 February 2019 to Saturday, 16 February 2019: Hold: Red Hook to Red Hook
Booked: Friday, 22 February 2019 to Friday, 1 March 2019: Booked: Red Hook to Red Hook
Booked: Sunday, 10 March 2019 to Sunday, 17 March 2019: Booked: Compass Point, St Thomas* to Compass Point, St Thomas*
Booked: Tuesday, 19 March 2019 to Tuesday, 26 March 2019: Booked: Red Hook to Red Hook
Booked: Sunday, 7 April 2019 to Saturday, 13 April 2019: Booked: Compass Point, St Thomas* to Compass Point, St Thomas*

Hours required between charters: 24

Contact us

Contact us for rates and current availability or to book a charter aboard Island R&R!

Reviews for Island R&R with Matt & Casey:

Matt & Dana (Dana filled in for Casey) were very friendly and clearly knew what they were doing. Matt’s knowledge of the islands led us to many places others may not have the opportunity to experience and we took home several recipes and ideas from Dana’s cooking. My 83 year mother traveled with us and Matt & Dana were very patient and willing to help her so she had a wonderful experience.

We found the boat very comfortable for 6 people and the crew. We really only slept in the cabins, but they were big enough to sleep well. We had plenty of space on the deck, whether we were up front when sailing or sitting in the back for dinner/lunch. The boat is a little bit older which we knew going in but is well maintained and very comfortable.

The water toys really added to the experience, wake boarding, snorkeling, paddle boarding, the go-pro and Peggy & Ursula made sure we had plenty to do in the water.

The food was fantastic, really nice variety and plenty to eat. Dana did a great job creating menu options for my vegan daughter who probably had more variety on the boat than any other time. Very locally focused, which was nice in terms of experiencing new tastes.

Eddie Y, aboard Catamaran Island R&R June 2018  sailing the British Virgin Islands

Matt and Dana (standing in for Casey) were stars. They were more than friendly they were like family. Matt's knowledge of the islands, special stories and the history were amazing. They accommodated our gluten-free needs as well as fresh and healthy with flavors Galore and presentation of a Michelin meal. The breakfasts were exquisite with poached egg on portobello mushrooms to spectacular Portuguese sausage and Spanish omelets.

Matt encouraged us, with little bit of a nudge, to try things that we were a little apprehensive to do but we're so thankful that he did.

The Virgin Islands were way beyond our expectations. Matt knows his stuff when it comes to balancing each day with as much as you could possibly do and yet fully enjoying each moment.

This was a bucket list trip but because Dana and Matt made it beyond our expectations we have high hopes to repeat this vacation. We are fortunate to be youthful in our late 50s and 60s and this trip reconfirmed that we want to continue to push and enjoy this part of life.

Robert H, aboard Catamaran Island R&R May 2018  sailing the Virgin Islands

We had a wonderful cruise with Matt and Dana (standing in for Casey). They were incredibly responsive to any request and took us to spots that they somehow knew would delight us. We had some concerns about the boat and the Islands after the hurricanes. John kept us informed all along the way as more information became available about the islands, our boat, and general conditions. We found everywhere to be safe, comfortable, beautiful, and welcoming. Dana did a wonderful job preparing our meals. One in our group has celiac disease and creating gluten free meals was no problem for her. The cabins were very comfortable and clean. There were ample water toys and sports for every ability. It was our first experience chartering and cruising in the BVI's and we can't wait to go again. A 5 star experience!

Margie E, aboard Catamaran Island R&R March 2018  sailing the Virgin Islands

We were a group of three couples for 7 nights on the Island R and R Catamaran “Leopard 46” with crew Matt and Casey. They simply delighted us from start to finish with a well-rounded tour of so many delightful bays, beaches, bars and daily activities of hiking, snorkeling and site seeing. Their flexibility and range of options made for a truly wonderful trip. We were always in awe of what was offered in both the British and US Virgin Islands. The onboard hospitality, food and drink was truly 5 star.

Matt and Casey were in touch with us prior to arriving in St Thomas, very helpful with getting us from our hotel to the boat. Met us with open arms at the Dive Bar prior to boarding. A great option to “overnight” with Casey and Matt before we sailed. We all got to know each other, we got to settle in, and it allowed us to get a great early start on the first day. They had great and extensive knowledge of all the sites along the way. They were very helpful in giving us a range of options and choices for things to do, places to visit and sites to see. Extremely helpful and flexible in planning out each and every day.

Island R&R was clean and comfortable. The front bean bags were a great option. The dining area at the back was also one of our favourites for breakfast lunch and dinner. Of course we must give special mention to Darnell the Duck for floating on. Snorkeling equipment in great form. The floating “mat” was also a great place to lolly gag when tied up.

Oh my, the food! Casey and Matt did an extraordinary job. Case did handle the bulk of cuisine but Matt assisted on many occasions. Casey had us totally delighted and the dietary customization made our one “non seafood fan” very happy. Some terrific creations. We’ve asked for recipes.

The itinerary was awesome. It was really great to start off with a quick sail and then a snorkel for us all to get comfortable with the boat, as well as the crew. A special treat was Pizza Py in the first bay we visited before sailing on for a few hours that afternoon.

Great service from Sailing Directions - always straight forward - informative. The website is clean, informative, straight forward.

Ferg D, aboard Catamaran Island R&R March 2018  sailing the Virgin Islands

We had a fantastic trip. Matt and Casey were awesome and a perfect fit for us.

Ted O, aboard Catamaran Island R&R January 2018  sailing the Virgin Islands

Matt and Casey were wonderful. We couldn't have picked a better crew to be a part of our vacation. Our entire group would all agree that this was the best vacation we have ever had. I can't imagine going on another charter without Matt & Casey!

We enjoyed the Island R&R greatly. We found it clean, comfortable and well ventilated. The beds were very comfortable, and the a/c at night was wonderful. I am not sure if there was anything in particular that would be a favorite aspect as we were 110% satisfied the Island R&R. The accommodations were great, the water toys were great ( and the sling shot was really great ! ).

Casey did an outstanding job with our meals, everything was well presented and delicious. Casey took very good care of us for all the meals, snacks, appetizers and desserts. Not to mention the beautiful view you get to enjoy at every meal !

Our itinerary fit what we were looking for perfectly. We talked a bit about a few stops we wanted to make and left the rest to Matt. Matt did a great job guiding us to places that fit exactly what we were looking for. We were even fortunate enough to have some dolphins join us one day while we were in the water which was one of the high lights of the trip ! ( of which there were many )

Cant say enough how much we enjoyed spending time with Matt and Casey, I fact as we tell others about our trip, we all consider them part of the Family.

Kevin M, aboard Catamaran Island R&R July 2017  sailing the Virgin Islands

Matt & Casey could not have been better! They were amazingly welcoming from the moment we walked on the boat. We have 3 teenage kids and they knew how to relate to them perfectly. They gave us the perfect amount of history of the islands, let the kids participate in the sailing, made us very comfortable, provided amazing food, good music and gave us the perfect balance of private time and together time. Matt had us all jumping off the boat by the end of the trip! Would definitely book with them again!

The Island R&R was beautiful. It is maintained very nicely. All of the amenities were great - we had bean bags to really enjoy the cruising from place to place, great coffee in the morning, air conditioning for sleeping, everyone had their own bathroom, we all had our own cup, towel and snorkel gear. For fun in the water, we had the big blue mat to lay on and play on, Matt pulled us behind the dingy on a kneeboard, we had paddle boards - everything we needed.

The food was perfect. Casey can do some amazing things that should not be possible on a boat. She made things that I would find too difficult in my full sized kitchen. Her meals were well presented, delicious, creative, flavorful and more than enough food. She customized the food as needed (my semi-vegetarian daughter got a separate main dish for a couple of meals), the food choices fit perfectly with our family, we had snacks that we could grab during the day and drinks at any time we wanted. They really listened to our preferences and had everything we asked for or should have asked for.

Matt really listened to what we wanted out of our itinerary. We got a good balance of relaxing boat time, time in the water, snorkeling, beaches, 30 minutes hikes, luxurious stops and historical stops. We visited The Baths, the north sound, the RMS Rhone, the Indians, Foxy’s, Willie T’s and so many more.

John with Sailing Directions answered all of our questions quickly and thoroughly. Booking the trip was easy.

Best vacation ever!

Sara H, aboard Catamaran Island R&R March 2017  sailing the Virgin Islands

Additional reviews:

Every Day Was Totally Different!
We planned this vacation for our 20th anniversary. It is a trip my husband and I always wanted to do. We booked the island R&R for our active family of 5. First of all, there was plenty of room for my husband and I and our 3 kids. From the minute we got on the boat we knew we were going to love Matt and Dana! Matt planned our itinerary every day after asking what we were in the mood for. He is so active our crazy kids could barely keep up with him! I could not pick one favorite place or activity, since every day was totally different! It was the perfect blend of snorkeling, exploring, relaxing and learning. I can't imagine that there could be a more knowledgeable captain! Everyone knows and loves him! We loved getting to know Dana as well. Her meals were amazing and perfect and we enjoyed hanging out with her and getting to know her. We felt like we had 2 new family members at the end of the week!! We can't wait to do it again!!
It Just Doesn't Get any More Personalized and Customized Than That!
In early March of 2018 we boarded the Island R&R motor sailing catamaran. The boat is a comfortable 46 footer with 4 cabins in the hulls. The cabins are nicely appointed with a choice of putting on the air conditioning, or enjoying the air of the Virgin Islands. We were three couples joining the hospitable, kind and courteous crew of Matt and Casey. What an experience of a life time! Although you may have an idea of “what do do, where to go, what to see”, Matt and Casey quickly put you into an exploring mindset. Much of your trip will depend on sea conditions, mooring ball availabilities or the mood that you are in for the adventure that you wish to undertake. We experienced local beach bars and boutiques and solitary bays and beaches where we were the lone vessel overnight. We snorkelled, swam, paddle boarded, lounged, hiked, ate on board (breakfast lunch and dinner), visited beach bars, toured islands, partied at the full moon party in Trellis Bay and explored the Conch mountains on Anegada Island. Each morning you awaken to Matt and Casey reviewing “what’s possible” for your sailing journey. It just doesn’t get any more personalized and customized than that! We even had the wonderful opportunity to explore Necker Island (Richard Branson’s private island) with exclusive tour guide Gumption. Matt and Casey are simply the best. Flexible, helpful, safe, courteous and wow...prepare for some awesome culinary delights. 5 star, top notch. Thanks for the wonderful experience and hospitality provided. We’d gladly respond to any inquiries inquiring minds might have.
We are HOOKED on the Boat Life!
I just got back from a week on the Island R&R with Matt and Dana (filling in for Casey) and I am already ready to go BACK for MORE. I am not sure how this vacation could be topped. From the moment Matt met us at the dock until we left him at the dock he was on top of everything and make sure we didn't need for anything.
We let him plan our itinerary and he didn't disappoint - from Christmas Cove for some pizza from the Pizza Pie boat, to an afternoon in White Bay sipping Pain Killers from Soggy Dollar, a hike through the Baths on Virgin Gorda, the Bubbly Pool on Jost Van Dyke, Snorkeling at the Caves and Indians, an afternoon at the exclusive Oil Nut Bay, pirate songs in Leverick Bay, shopping eating and drinking in St John, and an afternoon on our own private secluded beach. The trip was a perfect combination of relaxation and activities and it was catered just for US. Matt knows the islands so well and I was always intrigued to listen to him share information.
Dana cooked some amazing meals in that tiny kitchen... every breakfast, lunch and dinner was fantastic. They were Delicious and with beautiful presentation. She has an infectious laugh and smile and such a sweet personality. The crew on this boat MADE the trip!!!

This kind of trip is a once in a lifetime experience (although I plan to repeat) that you MUST do. I don't know how a trip to a Caribbean island at an all inclusive resort will ever fit the bill for us again. We are HOOKED on the Boat Life!
Thanks Matt and Dana - you are forever in our hearts - thanks for the time of our life!- Monica
The Crew Knew the BVI Like the Back of Their Hand
Matt and Casey are the perfect crew!! 6 of us enjoyed an amazing vacation and felt completely safe with them and their judgement at every turn. We ate every meal on the boat and loved the chef inspired cuisine. I truly cannot thank them enough for being so helpful and skillful!! They knew the BVI's like the back of their hand and guided us as we snorkeled, hiked, swam, paddle boarded and kayaked when we weren't sunning on the fore deck. One of the women on the trip was originally a bit apprehensive about a sailing vacation, but by the third day she said 'I will never do a cruise ship vacation again when I have such a great option with Matt and Casey. There is no comparison to a sailing charter and a cruise ship because the sailboat takes our experience to another level. Thank you very much for making our vacation a memorable one!
The Boat Has Everything, The Food Was Unbelievable, Matt and Casey Are the BEST!
We just got back from 6-person/6-day trip aboard the Island R&R with Matt & Casey. None of us had sailed on a 46' catamaran and everyone had a fantastic time. The islands are great on their own but having a local captain and chef added so much to our trip and allowed us to see & learn more than you get from travel books.

Matt and Casey are so experienced, they can help with anything related to the trip (such as less experienced snorkelers). I have provisioned and captained a few times in the past, but this was much more safe, fun, and relaxing. The boat has everything, the food was unbelievable, and Matt and Casey are the best. They took care of everything and we are planning next year's trip already! ~J. Wilmes
The Crews\' Knowledge of the Islands is Very Impressive. An Amazing Family Trip!
Our family of four spent an amazing week in the USVI and BVI with Captain Matt and first mate Casey aboard the Island R&R. The beauty of this trip is that you can be as lazy or active as you want - and Matt, Casey and the boat can accommodate any and all desires. We were fairly active so we snorkeled, hiked, sailed a Hobie Cat, knee boarded, paddle boarded, and kayaked.

The boat is fully equipped with all the water toys you could imagine - including a dinghy with a 40hp motor that can take you knee-boarding or wake-boarding. Packing for the trip is so easy as the boat is perfectly provisioned based on your favorites and things such as snorkel equipment, towels, sunblock, and linens are provided

We all know the islands are beautiful and a treat to sail, but a trip such as this can only be as good as the company you keep. Matt and Casey are so pleasant to be around and acted as our guides on some snorkels and hikes but were also willing to pull back and allow family time.

The meals were absolutely incredible - using many native fruits and vegetables and locally caught fish (Matt was able to get a newly caught Tuna on the day we arrived so we had fresh sashimi for the first couple days of the trip). The crew's knowledge of the islands is very impressive so you can get a great history lesson if you are interested. And if you want to learn about sailing or tying knots, that can be done as well. Captain Matt also captures many photos throughout the trip and was good enough to send all the photos electronically a few days after the trip ended.

Overall, you can't go wrong on the Island R&R. It was truly relaxing because everything is taken care of and you know that the family is in safe hands. Go sailing with Matt and Casey - you won't regret it! ~The Thompson family

Yacht Island R&R customer review image
I Cannot Say Enough About This Trip!
This was the best family vacation - I cannot say enough about this trip! Captain Matt and Casey gave us the most wonderful experience! It was the perfect balance of activity (snorkel, hikes, water sports, jumping from Willy T's) and relaxation (sailing, sunsets, fabulous cocktails and food). Our meals were top restaurant quality - healthy, delicious and beautifully plated.

My children 11 and 14 enjoyed every bit of it of this trip too. There are so many other highlights but the biggest take away was that my husband and I were able to relax and not have a care in the world because Matt and Casey took care of everything. ~ JLT
You Made Every Day The BEST DAY EVER!
From the flexibility to the recommendations for snorkeling to the tasty cuisine to the hospitality to the breadth of knowledge about the beautiful islands to the phenomenal playlist, we could go on and on! Thank you for the most amazing time! You guys made every day of this trip the Best Day Ever! We areIsland R&Red
Mitch, Judy, Bob, Natalie, Keith and Todd -AKA the Aquaholics!
I Couldn\'t Have Picked a Better Team
Thank you for making my first out of country vacation an amazing adventure. Every single place we went was beautiful and an experience I could not find anywhere else. Both of you made sure me and my family were as comfortable as possible, and we all appreciate it extremely. Thank you for making my last Christmas as a high school senior the best trip Ive ever been on. ~Chloe

I couldnt have picked a better team. Wow! You guys Rock! No experience can replace an Amazing Chef (Casey) or Captain (Matt). You guys made my last family trip with my girls the best it could possible be. Gary
We Loved Everything About the Trip
Thanks so much for opening your boat home to us. We loved everything about the trip especially the inflatable unicorn and its babies!

We were looking for a way to get away and you guys provided must that. We all had lead very busy lives, and we loved being able to disconnect for a little bit. We loved hiking Salt Island, the Indians and the Baths!

Thanks for everything,. We hope we can do this again in the future!

Shannon, Thomas, Sara, Jake, Kurt and Kate
Contact Us

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