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BUILT: 2021


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Bali 5.4 Cabins - Five with Twin


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Dedicated Captain and Chef/First Mate

Fully Customizable and Catered Menu 

Coffee/Espresso Maker

Full Sized Refrigerator

Ice Maker

Water Maker

Dingy / Yacht-tender

Outdoor Shower

Stand Up Paddle Boards

Rendezvous Scuba Diving


Sea Scooters

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10 ft. Floating Dock

Fusion 3 Zone Bluetooth Enabled Sound System 

Television in the Salon

Windward Branded Giveaways  







  • All-inclusive rates are for 8 days and 7 nights. For charters longer or shorter in duration (with at least a 4 night minimum), please contact us for details.

  • Embarkation is 12:00 p.m. / Disembarkation is 12:00 p.m.

       Guests          Full-Board USD/week  


2                    $28,500

3                    $29,000

4                    $29,500

5                    $30,000 

6                    $30,500  

7                    $31,000 

8                    $31,500


  • Christmas Week will be a flat rate of $31,500

  • New Year's Week will be a flat rate of $37,500


  • Tip. It is customary to tip your crew at the end of your charter. The amount you leave is at your discretion and should be based on the level of service provided. The suggested gratuity is 15-20% of the total charter fee.



William was born and raised in Bermuda. He started sailing at a young age whilst also enjoying rugby, swimming, cliff jumping and wakeboarding. William began as a Dinghy Instructor who taught sailing for five years during the Summer seasons in Bermuda, coaching students from 4 to 60 years old on a range of dinghy sizes.


Throughout this time he was also working as a Social Media Coordinator and Deckhand for a luxury charter motor yacht based in Bermuda. 


When William went to the University of Sussex in the UK, he studied for a Bachelor’s in Marketing and Management. He also obtained a Sports Scholarship for sailing at university whilst he trained and raced on a high-performance sailing boat called “49er”. 


He is a keen sportsman and has represented Bermuda at the Junior level Rugby competitions on multiple occasions. He has also represented Bermuda in the SSL Gold Cup where he raced top sailors from around the world. 


He has crossed the Atlantic twice, the Mediterranean once, and has worked as a Watch Leader which holds high responsibility for the vessel and the crew throughout the ocean passages. 


Since graduating from university three years ago, William has been living on sailboats, building a strong offshore sailing background with a huge sense of adventure. William is sociable, funny, professional, and passionate about sailing, and is always eager to share what he knows about yachting.

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Meet Kylie, a California native with an unbreakable bond with the water and a deep love for culinary arts. Growing up visiting lakes throughout the state, boats became her second home, while her mother's homemade meals kindled a culinary passion. This love for food and exploration led her to Spain during her college years, where she not only absorbed the rich culture but also embarked on her first formal culinary course.


After college, Kylie initially started her career in commercial real estate in NYC but felt the call for change. In 2022, she embraced her Croatian roots and started her yacht chef career in the Mediterranean. This not only satisfied her love for the sea but also allowed her to explore her culinary talents.


Kylie's voyage extended beyond cooking. She transitioned into an instructor role, sharing her culinary wisdom with aspiring chefs, from provisioning to the art of plating. Her galley became a classroom as she taught the intricacies of baking onboard a yacht.


Recently, Kylie enriched her skills through a highly accredited Yacht Chef course. Her journey as a chef remains ever-evolving, driven by her dedication to fresh ingredients, homemade craftsmanship, and an insatiable appetite for learning. With a fusion of global inspiration and culinary artistry, Kylie's culinary journey unfolds with each new creation.

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This was a trip to "paradise" for us. We loved every minute of the cruise. From sailing, to great places to drop anchor. The food offerings were amazing an Kylie - we loved your cooking and the welcoming table set ups! Will - you made amazing painkillers. Your knowledge of sailing and willingness to have "helpers" was kind. Our favorites were "Turtle Bay" and seeing the flamingos in the wild, and the night time games and laughter. Thank you for being great captain and crew!


We cannot thank you enough for the perfect week of sailing, sun, eating, drinking and lots of laughs! Tracy and Jon - you guys are a delight. You seamlessly integrated into our circle, creating a warm and comfortable atmosphere.

Tracy's culinary skills were exceptional, catering to all of our dietary needs. Tracy was always there with a drink, snack, and an unbelievable spread for each meal - not to mention the beautiful tablescape! Jon insured we always arrived to each cove safely, and we had so much fun on the water!

The yacht was over the top - Jon and Tracy were always calm and so knowledgeable about everything - we love you Tracy and Jon - we cannot wait to come back!!


First and foremost Jon and Tracy could not have been any more perfect. They are gracious, professional, pleasant, and a joy to be around. There are no words to explain all of their level of efficiency and attention to detail. Their knowledge of the islands and what each island has to offer was spot on.


Every single meal was over the top delicious. Every meal was made from scratch and all fresh ingredients. All personal preferences were followed to a "T".


The Windward was in stellar condition!


There are eight of us on board every single one of our wants and needs were meet immediately! 


We cannot thank John and Tracy enough for making our first catamaran adventure, perfection. From the amazing food for breakfast, lunch and dinner to gorgeous stops and helping us make the most out of our trip. John and Tracy made us feel like more than guests, we felt like family this week. I think all of us can say that this is the best trip we've been on. We will always hold these memories close to our hearts. Tracy always knew what we needed before we even asked for it. Every meal, drink, appetizer, and dessert was so delicious. John was our tour guide and the best captain. Both of them were so warm and easy to be around. They really made us feel like we were becoming friends this week! We were not sure how much the crew be around this week but we always wanted to hang out with them. They were an amazing addition to our family. We will miss them dearly and would stay forever if we could!


This week was probably one of the best family vacations we have ever had. Between the sea life, the meals, the boat and the two of you giving above and beyond, we could not have asked for a better trip. We enjoyed every second of family time but also loved talking with y'all and playing games all together. This was our first time in the BVIs (for all 6 of us) and we would recommend this trip and the two of you to anyone! We truly appreciate everything that both of you did to make sure we were all taken care of this week.

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It's very rare when I don't have the words or enough words to express how much something has meant. But the two of you have done exactly that so here is my attempt. This was not just a fabulous week on a beautiful boat in the BVI. That alone would have been one of the best weeks of our lives. What the two of you have added to that is what is almost, indescribable. The attention to detail, the anticipation of what we wanted or needed, the perfect balance of interacting and giving space. The teamwork that you have makes it all seem effortless and yet we know how hard you both worked to make this so amazing. We will all go home 5 pounds heavier and more knowledgeable about sailing and the BVI. When we do this again we will follow you to whatever boat you are on. You made the difference between the best vacation ever to thinking we will never be able to top this experience. Thank you so very much!!!

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Our family of 3 couples from Kansas City, MO and Memphis, TN in the US spent a week in March 2023 on Windward with Jon and Tracy. Our priorities when looking for a boat were in this order - 1) crew, 2) boat layout and amenities, 3) food/drinks and 4) the destinations.

Jon and Tracy were extremely attentive to our group throughout. Fun, professional, absolutely first class service. We had previously taken a trip on a 67' cat but this 54' Bali had an amazing modern layout that felt equally as spacious and was meticulously maintained. The meals, whether breakfast, lunch or dinner were like dining at a first class restaurant. During the 7 nihgt trip we had 7 distinct BVI stops that will all provide their own memories.

For anyone considering a BVI cat sail, we would highly recommend Jon and Tracy and the Windward boat. We would absolutely consider booking this combination again. A+ eperience!!!



Best Week Ever!

Jon and Tracy,

Thank you for the most perfect week ever!! You far exceeded every hope and expectation we had for the week. From the beautiful boat with the most amazing crew to our incredibly delicious meals, our weeks was unforgettable! Our first meal was absolutely fabulous and only got better from there. We will never forget the amazing views and incredible hospitality! Great music and fabulous sunsets and awesome friends and CREW made the best trip ever!


We came with old friends to celebrate our 20-year wedding anniversary and leaving with full bellies, priceless memories and new friends. Thank you so much for making this a trip we will never forget. You both are first class people and we have had a first class experience. Best wishes to you in your future adventures and we hope to meet again!


We can't put our words to paper. We are speechless! But, we will quote a guy we met on the beach the first day, "I don't want to oversell it, but this is going to be the trip of a lifetime!" . . . and truer words have never been said. Jon and Tracy were beyond . . . and made our trip magical. The scenic views, the gourmet food, the onshore adventures and the bond we made with each other will last a lifetime.

Thank you Jon and Tracy for providing us an experience that surpassed our wildest dreams! You two are the very best.


Thank you so much for an amazing trip. It was everything we ever hoped for and more. Truly wonderful in every way, thank you so much for your gracious hospitality and all your efforts. We hope we can sail with you guys again.


Windward and crew were the best, gave us a family vacation to see the BVI’s and enjoy all the wonders of the Caribbean. We enjoyed this awesome vacation, food, sights and water… so much fun. Had a fun relaxing time. We will be back.

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To my dearest Kelly and Wouts, Thank you!!! Y’all were amazing, this entire trip was amazing from start to finish, the food was absolute perfection. We loved having you join us at the bars and playing our games with us! Thank you for giving us new words to use and keeping us laughing. We all agree this was the best crew ever!! You survived the Bumpass family and the Diamonds, and Baxter. Thank you!


Thank you Kelly and Wouts for the absolute BEST week! I couldn't have imagined a better pair to entertain and play with our kids. Lulu and Webb loved absolutely every minute of our trip. The food was outstanding, I will be trying to copy so many of your meals Kelly and Wouts is the captain extraordinaire. Everyday was a fun and new adventure and we can’t thank you enough for helping us make so many fun memories.


This was the most wonderful family trip we have ever taken! The food, the scenery, the activities, but most of all Kelly and Wouts. They make the best team and we would definitely sail with them again. We love y’all!

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We expected a great trip and it exceeded our expectations. Kelly provided incredible food and Wouts gave us leadership in watersports and sailing. Can't imagine how it could be improved.


It was a blast! The water was clear and the beaches were nice. It was the best time ever, the snorkeling was fun. (10 year old).

Great food, ship and team, thanks! What a holiday. A beautifully appointed 5 star restaurant which went to the best locations in the islands. So comfortable and made even more so with Wouts and Kelly- always capable and helpful and so skilled at what they do. Great seamanship and teamwork- set the new record to Anegada. Hope to see you both again for another perfect holiday.

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Amazing trip! The sailing, the food, the views, the food, the islands, the food, the captain, the food, the amazing chef and her food. You both made our trip unforgettable, we hope to be back to the BVI. Specifically with you. PS, if you need the third crew member, I can fill the barista position.

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