Unforgettable! Caribbean sailing vacations aboard Island R&R | iYachtClub

Welcome aboard Island R&R the newest Leopard 46 in the iYachtClub fleet, ideally suited for up to 6 charter guests to enjoy a catamaran sailing charter in the Caribbean in perfect comfort. Check out the transformation process this boat went through to become a luxury yacht charter!

Island  R&R features 3 queen staterooms for guests, each with semi-walkaround beds, ample drawer and closet space and private bathrooms with electric flush toilets and separate walk-in showers.

Best Caribbean sailing charters are aboard Island R&R. Book your next catamaran vacation | iYachtClub

The plush interior design and bed linens create a beautiful serene environment on board, encouraging everyone to truly discover some real Island “R&R” during their Caribbean sailing charter.

The serene salon sitting area is an inviting area to relax in the A/C in the evenings to discuss the next day’s itinerary with the crew.

Call iYachtClub to book Island R&R today for Caribbean sailing charters like no other! | iYachtClub

The big salon seating area aboard Island R&R is the ideal place to escape the heat and relax with a book.

Still, guests generally prefer to spend the majority of their time in the spacious outdoor, shaded aft lounge area.

The big table easily accommodates 8 people with comfortable cushioned seating, and the nearby bar-fridge keeps the cocktails cold! An additional padded bench is the perfect place for gearing up for the next snorkel adventure.

Sail catamaran Island R&R - Affordable Caribbean sailing charters | iYachtClub

The big trampolines forward in the bow are also popular for sun-seekers  and a great  front row seat while the boat sails between the destinations planned for your Caribbean sailing charter.

Book Island R&R for the ultimate Caribbean sailing charters! | iYachtClub

The cockpit seating area is where the meals are served on board and a comfortable shaded area to relax during the sailing.

Island R&R is indeed a great choice for friends or family groups looking for a catamaran sailing charter in the Caribbean aboard a vessel that feels more like a high-end resort hotel than a boat.

Water Toys

Book Island R&R Catamaran Sailing Charters | iYachtClub

Did you know this yacht wasn’t always called Island R&R?

Book Island R&R for amazing Caribbean sailing charters for the whole family! | iYachtClub                                                                                 14′ Dinghy with 40hpWater fun aboard Island R&R during a Caribbean sailing charter | iYachtClub

3- Riviera Stand-up paddleboards
1- Bote stand-up paddle board
1- two person kayak
1- giant floating mat
1- kneeboard
1- wakeboard (to arrive soon)
1- water basketball
1- subwing
3- inflatable floaties (Uni, Baby Uni and Goldi)
1- inflatable tube
8 sets of snorkel, mask and fins





Yacht Photo Gallery


Step aboard the beautiful  Island R&R and experience the comfort and style of this modern and stylish catamaran – your floating home during your Caribbean sailing charter.


Island R&R Layout


Book Island R&R for Caribbean sailing charters like not other | iYachtClub

Island R&R accommodates 6 guests in 3 queen cabins featuring private bathrooms with electric heads and walk-in showers.



Meet Your Crew: Matt and Casey

A crewed Caribbean sailing charter gives you the opportunity to completely relax with all of the details taken care of – itinerary, meals, cleaning up are in the hands of your capable crew.

Island R&R is ready to take you on an amazing Caribbean sailing charter. Join Captain Matt and Chef Casey for the best of the BVI | iYachtClub

Captain Matt worked as a private captain for the past 2 years showing guests the best of the BVI.

Book Island R&R for your Caribbean sailing charters | iYachtClub

Casey and Matt look forward to showing guests all of their favorite places in the US and British Virgin Islands.

Captain 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 42×12 houseboat in Key West, Fl. called the “Sassy Lady.” 

The move to Key West spurred Matt’s love for the ocean.  Spear fishing and lobstering, scuba diving and snorkeling were, and still are, on the top of the list of his favorite activities!

Matt played soccer for the Key West High School Fighting Conchs and later in Oklahoma for college; and still has a love for the game, today.  Matt’s favorite off time activities include reading and visiting with family, enjoying good food with friends and anything outdoors.

Matt is a USCG certified 100GRT Master, with sailing and towing endorsements, as well. He also has an Able-bodied Seaman Unlimited/Any Waters License, an STCW 95’, and 5 day Lifeboatman Certificate, and has been sailing in the Virgin Islands for the last two years working as a captain for a busy private daysail company.

Book catamaran Island R&R for Caribbean sailing charters like no other! IYachtClub

Captain Matt and Chef Casey share a passion for the water, adventure, exploring the outdoors, and sharing good food with friends.

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 (or unique culture?).  Hiking, snorkeling, wakeboarding, paddle boarding and exploring new areas are all things she hopes to share with her charter guests. 

Caribbean yacht charters aboard Island R&R - great CREW! | IYachtClub

Casey received honorable mention for her cocktail in the 2016 Fall Yacht Show Cocktail competition.

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, Florida.  After 3 years in corporate America, she found herself working countless hours to make money but not having any time to enjoy life. 

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!

Casey holds STCW -95, CPR/First Aid Certifications, Crowd & Crisis Management Certifications and is currently awaiting the documentation to arrive for her Captain’s License.

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 catamaran Island R&R.


Sample Charter Menu

Delicious cuisine with a Caribbean flair is all part of the crewed sailing charter experience. Chef Casey is happy to accommodate any dietary needs or preferences. 

Book Island R&R for the most AMAZING sailing charters in the Caribbean! | iYachtClub

Chef Casey delights in surprising guests with beautiful fruit arrangements.

Standard Ships Bar

Soft drinks, sodas, water, beers & well drinks are available all day for your enjoyment .

Spirits include: Smirnoff and Stoli Vodka, Gordons Gin, Jack Daniels Bourbon, Souza Tequila, 

Cruzan Rum, and an assortment of liqueurs.

Red & White Wines are served with dinner. 

Beers include: Bud & Bud Lite, Coors Lite, Corona, Miller Lite, Caribe and Presidente/Presidente lite. 

Please remember to let the broker know your preferred brand.  If you require premium wines or spirits not included in the above please let us know and we will be happy to put them on board for you but at additional cost to the charter.

What We LOVE about Island R&R

Book a Caribbean sailing charter aboard Island R&R | iYachtClub

Captain Matt is also an expert fishing guide if catching dinner is on your todo list for your Caribbean sailng vacation.

The Leopard46 may be the most perfectly designed sailing catamaran for charters in the Caribbean. The generous cabin designs with semi-walkaround queen beds and ample storage, the bathrooms with separate walk-in showers, the big sofa in the salon and huge cockpit seating area all make this an ideal catamaran for groups of 6 seeking a Caribbean sailing charter like no other.

We love the crew of Casey and Matt and believe that guests are bound to experience the best week of their lives with this exceptional couple as their guides.

They are committed to creating your ideal vacation, whether that means an active charter with lots of fishing, snorkeling and hiking then dancing the night away at a beach bar, or a total relaxing charter floating on the lilypad with a cocktail in hand, or a week of reconnecting with family. Casey and Matt know where to go and how to optimize every minute of your time aboard Island R&R.

Green Boating Aboard Island R&R

Green boating - Caribbean yacht charters with iYachtClulbIsland R&R practices “green boating” to protect and preserve the marine environment. The BetterLife brand of cleaning products is exclusively used on board as well as the Pharmacopia line of toiletries.

These products are all-natural and do not contain petrochemical solvents or petroleum based cleaning agents, synthetic fragrances, dyes, alcohol or sulfates.

Ask your crew what you can do to be an environmental steward during your charter aboard Island R&R!

Guest Testimonials

We Love Everything About This Trip

Book Island R&R for the BEST Caribbean sailing vacations | iYachtClub

Island R&R Caribbean Sailing Vacations

Thanks so much for opening your boat and home to us. We loved everything about the trip especially the union and its babies! We were looking for a way to get away and you guys provided just that! We all 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

You Made Every Day of the Trip 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 are…Island R&R!

~Mitch, Judy, Bob, Natalie, Keith, and Todd -AKA The Aquaholics!

The Best Trip I've Ever Been On

Thank you for making my first out of country vacation an amazing adventure. Every single place we went to 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 I’ve ever been on.

I couldn’t 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 possibly be.

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.


The Meals Were Absolutely Incredible!

Book Island R&R for amazing Caribbean sailing vacations - great for families! | iYachtClubOur 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
Family fun aboard a Caribbean sailing vacation. Book Island R&R for all-inclusive charters | iYachtClubWe 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

Visited February 2017

Having a Local Captain and Chef Added So Much to Our Trip!

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

Matt and Casey Knew the BVI's 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 judgment 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 foredeck. 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!


Caribbean Sailing Charter Rates

Best Rate
Passengers 2 3 4 5 6
Summer 2016
Per Person $6,250 $4,333 $3,375 $2,800 $2417
Totals $12,500 $13,000 $13,500 $14,000 $14,500

Winter 2017

Per Person $6,250 $4,333 $3,375 $2,800 $2417
Totals $12,500 $13,000 $13,500 $14,000 $14,500

Rates are All Inclusive

Additional Rate Details

Captain Only Rates: $9000 all running expenses additional.

Book Avalanche For a Special Discounted Rate before Jan 31, 2017

$500 Discount for All-Inclusive, 7-Day Charters. May be combined with a maximum of 2 Child Discounts

SLEEP ABOARD: $200 per cabin, 2 cabin minimum. Dinner ashore at client expense. Includes boarding after 4pm, welcome cocktail and breakfast the next morning.


2/$12,200 3/$12,550 4/$12,900 5/$13,250 6/$13,600

Includes: 7 breakfasts, 4 lunches & 3 dinners. Requires 3 lunches and 4 dinners ashore at client expense. Also see Local Fare option below.


2/$12,350 3/$12,775 4/$13,200 5/$13,625 6/$14,050

Includes: 7 breakfasts, 5 lunches & 6 dinners. Requires 2 lunches and 1 dinner ashore at client expense

Xmas and New Year’s Weeks

$15,950 flat rate for Xmas and New Year’s weeks

Honeymoon/Anniversary Discount:

$1000 discount on 2 pax rate.

***Child Discount*** 

$250 per child 17 and under
limit 4 per charter



Charter Calendar


Currently booked or requested dates:

Date Start Date End Status
Aug 18, 2017 Sep 30, 2017 Unavailable: Compass Point, St Thomas* to Compass Point, St Thomas*
Oct 09, 2017 Nov 08, 2017 Unavailable: Compass Point, St Thomas* to Compass Point, St Thomas*
Nov 09, 2017 Nov 16, 2017 Booked: Compass Point, St Thomas* to Compass Point, St Thomas*
Nov 22, 2017 Nov 29, 2017 Hold: Compass Point, St Thomas* to Compass Point, St Thomas*
Dec 02, 2017 Dec 08, 2017 Booked: Compass Point, St Thomas* to Compass Point, St Thomas*
Dec 27, 2017 Jan 04, 2018 Booked: Compass Point, St Thomas* to Compass Point, St Thomas*
Jan 15, 2018 Jan 22, 2018 Booked: Compass Point, St Thomas* to Compass Point, St Thomas*
Feb 08, 2018 Feb 16, 2018 Booked: Compass Point, St Thomas* to Compass Point, St Thomas*
Feb 17, 2018 Feb 24, 2018 Booked: Compass Point, St Thomas* to Compass Point, St Thomas*
Feb 27, 2018 Mar 07, 2018 Booked: Red Hook to Red Hook
Mar 24, 2018 Mar 31, 2018 Booked: Tortola, West End, BVI to Red Hook
Apr 25, 2018 May 02, 2018 Booked: Compass Point, St Thomas* to Compass Point, St Thomas*
May 04, 2018 May 12, 2018 Booked: Compass Point, St Thomas* to Compass Point, St Thomas*
May 21, 2018 May 28, 2018 Booked: Compass Point, St Thomas* to Compass Point, St Thomas*
Jun 03, 2018 Jun 09, 2018 Booked: Compass Point, St Thomas* to Compass Point, St Thomas*
Jun 23, 2018 Jun 30, 2018 Booked: Compass Point, St Thomas* to Compass Point, St Thomas*
Dec 22, 2018 Dec 29, 2018 Hold: Compass Point, St Thomas* to Compass Point, St Thomas*



Catamaran Specifications



Yacht Type Multihull
Yacht Name Island R&R
Builder Robertson & Caine
Yacht Length 46′
Year Built 2008
Retrofit No
AC Yes
Cabins 4
Total Sleeps 6
Heads 4
Electric Heads 4
Showers 4
Pets No
Captain Only Yes
Price Under 15K
Internet Yes
Location USVI, BVI
Dingy Size 12 ft
Dingy Engine 18hp
Generator Yes
Children OK Yes
Children Age Limits water safe
Gay OK Yes
Nude OK Yes