Cruising Area of Windward 5.4

Pref. Pick-upScrub Island
Other Pick-upTortola, BVI
Summer PortBVI, STV
Winter PortBVI only at this time
Winter OperationsCaribbean Virgin Islands

Windward 5.4 Specification

Length54 Feet
Beam29 Feet
Draft4.85 Feet
A/C NightYes
A/C SurchargeNone
Sun AwningYes
Bimini TopYes
Num HatchLots
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


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.

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

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
Gear TypeInquire
Fishing PermitInquire
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 5.4 Crew Profile

Crew Number2
Crew SmokeNo
CaptainJonathan Crews
NationalitySouth African
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 yachts 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 eventually like to purchase a yacht of his own and sail around the world with his partner, Tracy.

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.

Windward 5.4 Calendar

AvailableBookedHold (can be challenged)Unavailable
Jan 202312345678910111213141516171819202122232425262728293031
Feb 202312345678910111213141516171819202122232425262728
Mar 202312345678910111213141516171819202122232425262728293031
Apr 2023123456789101112131415161718192021222324252627282930
May 202312345678910111213141516171819202122232425262728293031
Jun 2023123456789101112131415161718192021222324252627282930
Jul 202312345678910111213141516171819202122232425262728293031
Aug 202312345678910111213141516171819202122232425262728293031
Sep 2023123456789101112131415161718192021222324252627282930
Oct 202312345678910111213141516171819202122232425262728293031
Nov 2023123456789101112131415161718192021222324252627282930
Dec 202312345678910111213141516171819202122232425262728293031
Jan 202412345678910111213141516171819202122232425262728293031

Windward 5.4 Reservations & Port Locations

Start DateEnd DateDetails (Holds can be challenged)
Jan 28, 2023Feb 04, 2023Booked: Tortola - Nanny Cay to Tortola - Nanny Cay
Feb 06, 2023Feb 12, 2023Booked: Scrub Island - BVI to Scrub Island - BVI
Feb 16, 2023Feb 23, 2023Booked: Scrub Island - BVI to Scrub Island - BVI
Feb 25, 2023Mar 03, 2023Booked: Tortola, West End, BVI to Tortola, West End, BVI
Mar 05, 2023Mar 12, 2023Booked: Tortola, West End, BVI to Tortola, West End, BVI
Mar 18, 2023Mar 25, 2023Booked: Tortola, Nanny Cay, BVI to Soper´s Hole Marina, Tortola, BVI
Apr 01, 2023Apr 08, 2023Booked: Tortola - Nanny Cay to Tortola - Nanny Cay
Apr 10, 2023Apr 17, 2023Booked: Tortola - Nanny Cay to Tortola - Nanny Cay
Apr 18, 2023Apr 26, 2023Booked: Tortola - Nanny Cay to Tortola - Nanny Cay
Apr 27, 2023Apr 28, 2023Unavailable: Tortola - Nanny Cay to Tortola, West End, BVI
May 05, 2023May 12, 2023Hold: Scrub Island - BVI to Scrub Island - BVI
May 23, 2023May 28, 2023Booked: Tortola - Nanny Cay to Tortola - Nanny Cay
Jun 03, 2023Jun 08, 2023Booked: Tortola - Nanny Cay to Tortola - Nanny Cay
Jul 04, 2023Jul 18, 2023Unavailable: British Virgin Islands* to British Virgin Islands*
Nov 04, 2023Nov 12, 2023Booked: British Virgin Islands* to British Virgin Islands*
Dec 20, 2023Dec 27, 2023Booked: Scrub Island - BVI to Scrub Island - BVI

Windward 5.4 Rates / week

The prices shown are for the entire yacht for a week-long (7 nights) charter. Inquire for lowest rate.
Low price: $30,700
(normal rate)
High price: $37,000
(normal rate)

Windward 5.4 Special Offer!
8th Night Free!
Offer: Windward 5.4 is offering the following (for new bookings only, only one option): 8th night free when you book 7 nights OR Book 6 or more nights and we will include spa treatment at Scrub Island Resort and Spa for all guests as well as include a sleep aboard at no additional cost
Minimum nights: 6
Travel before: Aug/01/2023

Season2 Pax3 Pax4 Pax5 Pax6 Pax7 Pax8 Pax
2022/23 Winter$31,000$31,500$32,000$32,500$33,000$33,500$34,000
2023 Summer$31,000$31,500$32,000$32,500$33,000$33,500$34,000
2023/24 Winter$34,000$34,500$35,000$35,500$36,000$36,500$37,000

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.

Send us an inquiry to get specific pricing for Windward 5.4.

Windward 5.4 Guest Reviews

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!