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.
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.
The big trampolines forward in the bow are also popular for sun-seekersand a greatfront row seat while the boat sails between the destinations planned for your Caribbean sailing charter.
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.
Did you know this yacht wasn’t always called Island R&R?
14′ Dinghy with 40hp
3- Riviera Stand-up paddleboards
1- Bote stand-up paddle board
1- two person kayak
1- giant floating mat
1- wakeboard (to arrive soon)
1- water basketball
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
Island R&R accommodates 6 guests in 3 queen cabins featuring private bathrooms with electric heads and walk-in showers.
Meet Your Crew: Jason and Dana
Jason and Dana’s fun-loving personalities will make you feel at ease as soon as you step aboard Island R&R!
Growing up as a competitive swimmer in Indiana, Jason has always been around the water. He found his passion in boats at a young age spending his summers as a water-sports instructor and swim coach. After attending Indiana University, he pursued his dream of working on the ocean and began his career as a parasailing captain. Jason found himself on a journey operating parasail boats in different places around the world such as Key West, New Zealand, and the Caribbean. From traveling the waters worldwide, he has gained sailing, fishing, and diving experience that he enjoys sharing with all of his guests. Whether its water skiing, hiking, snorkeling, or just cruising the waters, Jason is always eager to experience the next adventure with those aboard.
Chef/ first mate Dana was born and raised in Birmingham, Alabama. Growing up in a family of chefs from the South,her passion for cooking naturally developed at a very young age. Her mother always stressed the importance of fresh ingredients and supporting local farmers while also making sure every dish manifests comfort. She now seeks to incorporate local ingredients and flavors in her dishes while always aspiring to create something new for guests to enjoy.
Summers spent at the Gulf in Alabama led to her appreciation of the sea, but her interest in sailing was not discovered until she moved to St. Thomas in 2015. Since then, Dana has worked as a first mate and chef while aspiring to learn as much as possible about what the sea has to offer.
Jason and Dana love having guests aboard to share their passion for the islands, making memories in the beautiful place that they call home. They welcome you to enjoy a fantastic week with them full of fun, relaxation, and bliss on 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.
Chef Casey delights in surprising guests with beautiful fruit arrangements.
Fresh Fruit, yogurt, and granola are available each morning along with a selection of juice, coffee, and tea.
Lemon Ricotta Pancakes
French Toast with Pan-fried Cinnamon Bananas
Quinoa Breakfast Muffins
Caprese Egg Sammies
Made to order Omelets with a Home-fry Scramble
Smoked Salmon Eggs Benedict
Shrimp Quesadillas with Banana Salsa
Island Cheeseburgers on the grill
Avocado BLT Salad
Cilantro Lime Fish Tacos with avocado cream sauce
Sweet and Sour Chicken flatbread
Spicy Kale and Quinoa Black Bean Salad
Lemon Garlic Baked Ricotta with Broccolini and Toast Points
Charcuterie and Cheese Plate
Prosciutto Wrapped Scallops
Mezze Platter with Hummus and Tzatziki
Pear and Brie Crostini
Roasted Pineapple Rum Chicken with Black beans and Rice
Guinness glazed Steak with a Smoked Gouda Dipping Sauce and Cauliflower Puree
Garlic Shrimp with Arugula and White Beans on Toast
Hoison Glazed Caribbean Kebabs with Coconut Rice and Vegetables
Maryland Style Crab Cakes with Skillet Cornbread and Coleslaw
Seared Sesame Crusted Tuna over Quinoa and Seasonal vegetables
Caribbean-Style Pork Tenderloin with grilled plantains and pineapple salsa
Nutella Wontons with Strawberry Sauce
Key Lime Pie
Hot Chocolate Pudding Cake
Warm Apple Crisp with Vanilla Ice Cream
New York Style Cheesecake
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
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
Island 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!
We Love Everything About This Trip
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. ~Chloe
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. ~Gary
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!
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
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!
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
Rates are All Inclusive
Additional Rate Details
Captain Only Rates:$9000 all running expenses additional.
$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.
LOCAL FARE MEAL PLAN:
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
$1000 discounton 2 pax rate.
$250 per child 17 and under
limit 4 per charter
Currently booked or requested dates:
Mar 19, 2019
Mar 26, 2019
Booked: Red Hook to Red Hook
Mar 29, 2019
Apr 06, 2019
Booked: Yacht Haven Grand to Yacht Haven Grand
Apr 07, 2019
Apr 13, 2019
Booked: Compass Point, St Thomas* to Compass Point, St Thomas*