Windward Description

The Bali 5.4 is a “Multihull of the Year” award-winning catamaran. The design was new to the market in 2019 and provided a fresh approach to sailing. It is revolutionary in how space is accessed, with deliberate attention to flow and open space and it succeeds in producing a scale that feels less like a boat, and more like an upscale floating condominium.

Bali catamarans are known and appreciated for their unparalleled success in blending luxury, space, and performance; producing a sailing experience that is unparalleled. This new design further capitalizes on that reputation with the advent of the “Bali garage door” that is the centerpiece of the yacht. It allows for the aft wall of the yacht to simply disappear, opening up the back of the yacht to an unobstructed view of paradise. This also affords indoor/outdoor dining options and gives the ever-present Caribbean breeze ample opportunity to make its way through the yacht with ease.

With her solid foredeck gone are the forward trampolines, replaced by a large relaxing lounge area complete with cushions for sunbathing. A full-sized door provides access directly from the lounge area into the salon, allowing free movement through the yacht. A walk up to the flybridge unveils a seating area perfect for cocktails and taking in sunsets. There is also another area for sunbathing on the flybridge where you can take in the sights of the islands from the highest vantage point on the yacht.

The Bali open space design is further complimented by the superior outfit and aftermarket items available on Windward. No detail has been left unnoticed from the fine linens, pillows and throws to the wine glasses, serving and flatware that make every day feel luxurious. She has been stocked full with every appliance and kitchen accessory to allow the chef to fully showcase the mastery of their art. And the water toys abound, allowing guests to fully experience all the Caribbean has to offer, both in and out of the water.

Windward will accommodate 8 charter guests in 3 spacious queen cabins and 1 sprawling master cabin for those who desire more space. She has a 50hp dingy with stereo system, underwater lights and ski pole, Starlink, portable projector on the flybridge, Code 0, solar panels, air conditioning, water maker, ice maker, full sized refrigerator, a fully customizable menu, Caribbean made ecofriendly and reef safe toiletries, a bar stocked to guest preference, coffee/espresso machine, rendezvous scuba diving, snorkeling gear, underwater scooters, subwing, kneeboard, 2 stand up paddle boards, wakeboard, 2 water ski tubes, 10 ft. floating dock, fishing gear, board and card games, television in the salon, Fusion 3 Bluetooth enabled sound system with 3 sub woofters, 4 separate zones and speaker color changing lights as well as Windward giveaways.

Cruising Area of Windward

Pref. Pick-upScrub Island
Other Pick-upTortola, BVI
Summer PortBVI
Winter PortBVI


Wash Basins4
TP in HeadsYes
Electric Heads4
Accommodation Details
4 queen berth guest cabins each with a private en-suite electric head, stall shower and sink/vanity. All cabins with exception of starboard aft cabin are dry heads.
All cabins have individually contract air-conditioning for each cabins comfort.
Top desk fly-bridge with lounging and seating with a 360 degree view.
Forward cockpit and lounge and dining area.
Aft cockpit with seating and dining accommodations.
Main deck has a bright and airy main salon (fully air-conditioned) as the galley direct access to the forward cockpit lounge area.

Crew take starboard mid-ship cabin (twin cabin), but will move to starboard aft cabin on request for $800 fee.

All queen berths are 5´w X 6´6´L
Bunks: Top bunk 32´W x 75´L; bottom bunk 36´W x 75´L


Length54 Feet
Beam29 Feet
Draft4.85 Feet
A/C NightYes
A/C SurchargeNone
Sun AwningYes
Bimini TopYes
Num HatchLots
Guest SmokeYes, only off transom
Children AllowedYes
Min Child AgeWater Safe
Water MakerYes
Water Capacity264 Gal
Ice MakerYes
Internet AccessOnboard WIFI
Cruising Speed8 Knots
Engines2x80HP Yanmar 21.5Kw Onan Generator

Water Sports

Dinghy (Feet)12 Ft
Dinghy Hp40 HP
Dinghy Pax6
Sea ScootersYes
Snorkel GearYes
Wake BoardYes
Floating MatsYes
Standup Paddle2
Swim PlatformsScoop steps
Boarding LadderS/S ladder of scoop steps
Beach GamesYes
Fishing GearYes
Gear Type2 trolling, 2 casting
Fishing Rods4
Fishing PermitYes
Under Water CamYes
Under Water VideoYes
Other Toys
10 ft. floating dock
Underwater lights
Floats / Noodles

Scuba Diving Scuba Diving Symbol

ScubaYacht offers Rendezvous Diving only
Air CompressorNot Onboard


Salon Tv/DvdYes
Salon StereoYes
iPod/Device HookupsYes
Board GamesYes


Special DietsYes

Green Initiatives

Make Purified Drinking WaterYes
Re-Usable Water BottlesYes
Other Green Initiatives
Reef safe/eco-friendly sunscreens, toiletries and cleaning products.

Windward Crew Profile

Crew Number2
Crew SmokeNo
CaptainJonathan Crews
Chef/MateTracy Shepherd

Jonathan Crews

Born and raised in Cape Town, South Africa, it wasn´t until Jonathan and his family moved to Australia where his passion for the outdoors and adventure began. He comes from a family of avid sailors which is where the intrigue for sailing started. Jonathan began his working career as an engineering Tradesperson in Heavy Fabrication & Welding. That experience gave him a broad background for all things mechanical.

In 2015, he decided to turn his dream of working as a Professional Yacht Captain into a reality and he obtained his Offshore Yacht Master´s in South Africa.
Jonathan has since had a vast amount of experience working on charter vachts in the Mediterranean, Caribbean, French Polynesia, Thailand, Australia and South Africa, working as both a Charter Captain, Delivery Captain and Lead Skipper of a flotilla company.

In his free time, between charter seasons, Jonathan also started a Safari company taking guests through South Africa, Namibia and Botswana.
Experiencing the vast landscapes, animal safari´s and 4wding (which is definitely not for the faint hearted). Jonathan´s first love however, will always be sailing, feeling most at home being in and around the water!

Jonathan spends his spare time participating in water sports, diving, fishing and travelling (anything that involves water really). Jonathan self-admits that he much prefers the relaxed lifestyle that comes with yachting and would WARD eventually like to purchase a yacht of his own and sail around the world with his partner, Tracy.

• RYA Yachtmaster Offshore 200gt
(Commercially Endorsed)
• RYA Powerboat Level |I
• International Marine Radio License
• Quarter Deck, Skipper Academy
• Cert 1 & 2 Tourism & Distribution
• PADI Open Water Diver
• Advanced First Aid
• ENG1 Medical

Tracy Shepherd

Born in the coastal South West of Australia, this is where Tracy´s love of the great outdoors began. Tracy grew up on a farm and started boating from a young age. Living on the coast allowed her to flourish on the beach and in the water.

Over the years Tracy has worked in several cafes and restaurants in Western Australia, well known for it´s famous wine regions. Tracy worked as a supervisor, chef and barista with over eight years experience in the hospitality industry.
Tracy also studied Occupational Therapy, at Curtin University, which lead to a career in the disability sector supporting adults with Autism.
Tracy has always had the urge to support other´s in need. She has since returned to working in the hospitality industry, having travelled overseas to a vast variety of countries, Tracy fell in love with the yachting lifestyle. After all, what could be better than travelling from place to place whilst working onboard a yacht!

Tracy has sailed around the western and eastern coasts of Australia, Mediterranean and French Polynesia. Her broad cooking style incorporates an array of seafood, Asian delicacies and comforting Italian cuisines to make you feel like you´re experiencing different cultures.

• STCW10
• ENG 1 Medical
• Recreational Skippers Ticket
• Provide First Aid - HLTAID003
• Level 2 Food Safety and Hygiene
• Ashburton Cookery School
• W.A Barista Training
• Working with Children´s Check
• National Police Clearance
• Soft Tissue - Level 1 & 2
• Occupational Therapist

Windward Calendar

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Windward Reservations & Port Locations

Start DateEnd DateDetails (Holds can be challenged)
Aug 15, 2023Oct 19, 2023Unavailable: Fort Lauderdale, Florida* to Fort Lauderdale, Florida*
Oct 20, 2023Oct 29, 2023Transit: Fort Lauderdale, Florida* to British Virgin Islands*
Nov 04, 2023Nov 12, 2023Booked: Scrub Island - BVI to Tortola, West End, BVI
Nov 15, 2023Nov 21, 2023Booked: British Virgin Islands* to British Virgin Islands*
Nov 23, 2023Nov 30, 2023Booked: Scrub Island - BVI to Scrub Island - BVI
Dec 01, 2023Dec 07, 2023Unavailable: Scrub Island - BVI to Scrub Island - BVI
Dec 20, 2023Dec 27, 2023Booked: Scrub Island - BVI to Scrub Island - BVI
Jan 09, 2024Jan 12, 2024Transit: British Virgin Islands* to Saint Marten, West Indies
Jan 13, 2024Jan 20, 2024Booked: St Martin to St Martin
Jan 21, 2024Jan 25, 2024Transit: Saint Marten, West Indies to British Virgin Islands*
Jan 27, 2024Feb 03, 2024Booked: Tortola, TBD to Tortola, TBD
Feb 10, 2024Feb 17, 2024Booked: Tortola - Nanny Cay to Tortola - Nanny Cay
Feb 21, 2024Feb 28, 2024Booked: Scrub Island - BVI to Scrub Island - BVI
Mar 08, 2024Mar 13, 2024Booked: Scrub Island - BVI to Red Hook, St. Thomas, USVI*
Mar 16, 2024Mar 23, 2024Booked: Scrub Island - BVI to Scrub Island - BVI
Mar 28, 2024Apr 03, 2024Booked: Scrub Island - BVI to Scrub Island - BVI
May 27, 2024Jun 03, 2024Hold: Scrub Island - BVI to Scrub Island - BVI
Jun 21, 2024Jun 29, 2024Booked: Tortola, Nanny Cay, BVI to Tortola, Nanny Cay, BVI

Windward Rates / week

The prices shown are for the entire yacht for a week-long (7 nights) charter.
Low price: $28,500

High price: $31,500

Season2 Pax3 Pax4 Pax5 Pax6 Pax7 Pax8 Pax
2023 Summer$28,500$29,000$29,500$30,000$30,500$31,000$31,500
2023/24 Winter$28,500$29,000$29,500$30,000$30,500$31,000$31,500
2024 Summer$28,500$29,000$29,500$30,000$30,500$31,000$31,500
2024/25 Winter$28,500$29,000$29,500$30,000$30,500$31,000$31,500

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, cruising permits, premium beverages and scuba activities. Inquire for more information.


For 6 night charters, divide weekly rate by 7 nights X 6 nights. For 5 nights or less, divide weekly rate by 6 nights X number of nights.
Please inquire if you need a cabin change

SLEEP ABOARD: Sleep aboard the night before charter dates. Available for $300 per cabin, with a 3 cabin minimum.
Includes boarding after 4pm, welcome cocktail and canapes plus a light breakfast the next morning. Dinner is to be taken ashore at client expense.

LOCAL FARE: Includes: 7 breakfasts, 5 lunches & 5 dinners. Requires 2 lunches and 2 dinners ashore at client expense.
-For local fare, deduct $150 per person off the charter rate

7 night minimum. Scrub Island ports required.
CHRISTMAS 2023: 1-8 guests @ $31,500
NEW YEARS 23/24: 1-8 guests @ $37,500 - charter may not start prior to 12/27

Relocation fee of $2,000, minimum 72 hour turn required on either side of charter dates for boat transit. Please inquire for availability.

St Thomas Drop off - $1000
Due to threats of provisions being dumped at the border, we will only drop off in the USVI.

St. Vincent & the Grenadines Relocation Fee:
Relocation fee of $4,000, minimum 72 hour turn required on either side of charter dates for boat transit. Please inquire for availability.

Windward Guest Reviews

June 2023

Tracy is an amazing cook, the food was excellent! We were blown away with every meal!
Jon and Tracy were very laid back and read the room well- when to let us have family time or to join in with discussions and activities. I had the trip planned for the most part but they helped bring it all together. Extremely nice, informative and glad we got to spend 5 days with them!! Tracy and Jon actually came recommended to me from a friend that booked with them last summer. We loved the crew. The yacht was very clean, comfortable and well ventilated.
The six of us have discussed this trip and would not have changed a thing!!! One of the best family trips ever!! My husband and I, summer 22 years old with boyfriend and Savanna and her husband are 26.


The Ferrell Family

March 2023

Our family of 3 couples from Kansas City, MO and Memphis, TN, in the US spent a week in March 203 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-Destination

Jon and Tracy were extremely attentive to our group throughout. For 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 night trip, we had 7 distinct BVI stops that will all provide their own unique memories.

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

Thank you so much for giving us the most memorable week! We look forward to doing this again with y´all!
-Madison & Jenny

You two are incredible! Thanks for making our family trip great!!
Kristi and Chad
Hope to see you next year!

March 2023

Jon & Tracy,

Thank you, thank you, thank you. From the moment we stepped on the boat, you outdid yourselves. We all came in not sure what to expect. Some of us thought we would be getting turkey, or even PB&J sandwiches for lunch. Each and every meal blew us away! We were saddend that we planned to go off the boat at all to eat. And while your suggestions on those places were wonderful, the meals and services (especially Jon´s A+ dish washing that he so enjoys) never were as good as on the boat. Tracy was amazing in knowing and anticipating our needs and accommodating gluten sensitivity. Jon was an amazing, calm captain who happily entertained our guys´s 1000 million questions. This trip far exceeded our expectations and we can´t wait to come back, but only if you will be our crew because we know anyone else would be disappointing. And don´t worry, next time, we´ll plan multiple speedo days and make sure to pre-order ours with faces on them for you too! Oh and thanks for putting up with Leroy. Cheers to next time!

#itsnottahitijon #delicious #thisdoesnotsuck

Love your friends from Cincinnati and Nashville

February 2023

Absolutely incredible trip!

Jon & Tracy, you made this a truly special memory for those of us who have done this a few times as well as the BVI virgins! The meals were incredible... far better than some of our favorite restaurants back home. And the effort to find the best spots in the BVI is seriously appreciated!

We had a lot of fun planning this adventure, and more than exceeded or ambitions. Thanks again for the great drinks, special experiences and lifelong memories!

Come see us in Dallas sometime soon!

Andrew, Jennifer, Scott, Brice, & Louie

February 2023

Best vacation/escape ever! John and Tracy treated us like royalty which started before our trip and continued throughout our fantastic adventure. We will definitely return, but only with this crew! The food was amazing. The boat was perfect and stocked with everything we could possibly need. I could go on and on and still not adequately express our appreciation for the top notch professional service we received.

-Chip & Michelle Martens

January 2023

John & Tracy,

We came with old friends to celebrate our 20 year wedding anniversary and are leaving with new friends, priceless memories, and unforgettable experiences. 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!!
Thanks for everything!

-Danny & Lisa Sauyer

January 2023

To John & Tracy,

Captains are a dime in a dozen… but chefs(like Tracy) are irreplaceable. Thank you from the bottom of our Indiana hearts for an amazing week sailing. You went above and beyond to make each day and each meal something we will never forget.

We appreciate all the adventures, answered questions, laughs, drinks, and memories. You two are sincerely something so so special.

We hope to be back. No stress, No shoes, No shirt, No problem!

With big love,

Dan & Kim Keers
Emmett & Jenn King
Ben & Allison Hession
Jay & Kristen Oswalt

Christmas 2022

Thank you so much for all you did to make our Christmas week the most wonderful trip! Tracy, your cooking is just amazing and far surpassed the restaurant meals we had! John, thank you for the bar tour and for keeping us safe on our journey. Never forget the, Wonkey Donkey, the Stanky Wanky and especially “No Bananas!” Much love & best wishes for a happy New Year. Thanks for spoiling us!


The Bhojwair family

December 2022

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 over sell it, but this is going to be the trip of a lifetime!´ And truer words have never been said. John and Tracy were beyond amazing 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 John and Tracy for providing us an excellent experience that’s surpassed our wildest dreams! You two are the very best.


Matt & Sarah Pavek
Mike & Marhya Molepske
Josh & Nicky Shepherd

Best Week Ever!

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 the incredibly delicious meals, our week was unforgettable!
Our first meal was absolutely fabulous and really got better from there. We will never forget the amazing views and incredible hospitality! Great music and beautiful sunsets and awesome friends and crew made for the best trip ever!!

-Cam & Bobby Cowen + Kelli & Time Carlson

June 2022

Wow! We had a spectacular trip. First trip to the BVI and Jon+Tracy made it a memorable vacation. The itinerary was prefect - hitting all the beautiful coves and islands. We were spoiled each day with wonderful meals and adventures. Tracy and Jon were delightful, professional and accommodating.

Thanks Tracy & Jon!
Best, Mike & Marie

June 2022

Spent the last 8 days with the wonderful crew of the Oceana touring the nooks and crannies of the BVI. Tracy is a wizard in the kitchen, presenting amazing meals every day. Jon is the sailing guru and kept everything running smooth the entire way. Jon and Tracy having the talent, knowledge and attention to detail made this experience most memorable and leaving a lasting impression of how much they care about making sure you are comfortable and happy the entire voyage.
Ricky and Amy

June 2022


We had an amazing vacation in the BVI on Oceana from the moment we entered the boat and were greeted by our strikingly good looking crew, Jon and Tracy. Jon and Tracy beautifully decorated the boat with striking, elegant coastal decor! Every detail is accounted for with the very best equipment and decor.

Jon is an impressive captain! We felt safe with his skilled competence and confidence! Impressive how knowledgeable he is! He also strives to create the ultimate experience for his guests.

Tracy is a 5 star chef! Every meal was a work of art and delicious! Tracy´s calm, patient style made our vacation an exceptional experience! We especially appreciated their taking us to the very best places in the BVI! We didn´t have to think about anything! The ultimate vacation! Thanks Jon and Tracy!

June 2022

From start to finish this trip was AMAZING! Captain Jon did an excellent job of picking just the right spots for us to enjoy the good life. We had some great snorkeling and lots of fun playing with all the toys. Tracy did an amazing job on all of our meals, it is going to be difficult to get back in a routine of not eating as much. Oh, and I almost forgot! Kelly started this whole adventure off with some delicious rum punches when he picked us up at the airport. Thank you so much Tracy for making this family vacation so memorable!
-Beth, Kees, Matthew, Kaitlin, Jen and Jema

May 2022

I´ve been excited about this trip for months and dang near everything about the last week has exceeded my expectations! The boat is wonderful, but Jon and Tracy were absolutely phenomenal! They added so much to the experience of cruising the BVI. If I could, I´d pick them to crew any charter I ever take in the future. Thank you both so much for this awesome week of sailing!

May 2022

My first trip to the BVI is one to remember! I cannot imagine a better crew than Tracy and Jon. Everything was absolutely perfect. Food, fun, sailing and everything in between. I don´t know if I´d ever be able to sail with any other crew. I´m coming down with friends and Jon and Tracy will be the captain and chef no doubt!

Cheers to the best (and a BVI sail to remember)!

Love, Jodi

May 2022

It is difficult to imagine anything greater than sailing in the BVI, until you meet John and Tracy and discover a paradise vacation like no other! Both John & Tracy were the most amazing hosts we have ever had the pleasure of meeting. We felt an instant connection with them and consider them our close friends now. John is an unbelievable captain. He knew all there was to know, sailed the vessel perfectly, and even taught us anything we wanted to know about sailing. Tracy is so kind and fun. Her food was 5 star and every meal was so impressive. We were so excited they accepted our invitation to enjoy our time together by eating with us, playing games, and going out to dinner with us. They truly made our vacation one of the best we have ever had and we are already talking about another charter with them soon. I cannot recommend John and Tracy enough. So amazing!
Thank you!
Thank you!
Thank you!

Tim & Julie

May 2022

This was our first trip to the BVI and our first time sailing. This experience was out of this world! John and Tracy were absolutely amazing. John took the time to teach us all about sailing. Tracy made the most amazing meals, and delicious drinks. They were so kind to us and showed us the most gorgeous spots all around the islands. I never knew how much fun wakeboarding and subwinging in the ocean could be. Wee are obsessed with playing games and John and Tracy were always willing to learn them and play along with us! This experience was something we will never forget! New friends and new places. We are already planning our next charter with John and Tracy next year.

Cheers to anchor beers!
Carson and Meredith

May 2022

Tracy and Jon have been the best captain and chef! Every meal has been fantastic and every step along the way has been great! And I have asked many questions and Jon and Tracy have answered all of them. The time has flown by and I hate to leave, but all good things must come to an end. I would request Jon and Tracy again.

Tracy´s skills in the kitchen were awesome. So much talent and every meal was so tasty! Thank you Jon and Tracy for the most wonderful week aboard Oceana. Hopefully we will see you again.

Safe sailing and good health to both of you.
-Lee and Jake

May 2022

To put it simply, I did not want this trip to end! The BVI is one of the best places on earth and this charter reconfirmed that feeling for me. The Oceana is a fabulous vessel and it was amazing to be part of the group to be it´s first quests.

Tracy and Jon, thank you for creating an easy going and relaxing experience. From the sailing to the water sports, to the beyond delicious meals, to chilling with a glass of wine or other ´beverage´ ;) it was all incredible!
Bet of luck with your future charters and once again - an open invite if you are ever in Boston!

May 2022

It was a distinct pleasure to be one of the first charters on this fantastic boat! Great to enjoy all its fantastic toys from the swim platform, the drone, and jet pods. The boat really makes you feel at home. Now the best part and the most enjoyable is the crew!! Tracy and Jon are wonderful, gracious hosts. Words cannot express their warmth and attention to the needs and wants of their guests.
Tracy´s meals were out of this world. Each day, morning, noon, and night. We didn´t want for anything. She always had a smile. Jon, what can you say, but he made sailing a pleasure. His knowledge and experience was evident in how he managed the boat. They are a great team and we enjoyed their company on and off the boat.

In summary, Oceana and Tracy and Jon. Great! Great! Great!