Leeway Description

This elegant 58´ Leopard catamaran offers the best in large open decks and spaces for lounging, including a comfortable indoor salon, a breeze-filled fly-bridge with a dance floor and seating for 12, and the fun forward netted space to experience sailing firsthand in the day and star gazing at night. All 3 guest staterooms include en-suite bathrooms, air conditioning, and everything you would need to create sailing memories with families and friends. Guests will never forget their charter experience on Leeway!

TOYS: 2 Stand Up Paddle Boards, Snorkeling Gear, Floats, eFoil, 1 2-Person Kayak, 2 Fishing Rods, Yoga Mats & Onshore Games.

Cruising Area of Leeway

Pref. Pick-upAYH
Other Pick-upYHG
Summer PortSt. Thomas, USVI
Summer OperationsCaribbean Virgin Islands
Winter PortSt. Thomas, USVI
Winter OperationsCaribbean Virgin Islands


Wash Basins3
TP in HeadsYes
Electric Heads3
Accommodation Details
6 Guests in 3 Queen cabins with private heads


Previous NameLady Susan
Length58 Feet
Beam27.9 Feet
Draft5.10 Feet
A/C NightYes
Sun AwningYes
Bimini TopYes
Num Hatch10
Guest SmokeNon-smoking boat
Children AllowedYes
Min Child AgeWater Safe
Water MakerYes
Water Capacity400
Ice MakerYes
Internet AccessOnboard WIFI
Max Speed12
Cruising Speed8
Turnaround48 hrs preferred, Inquire for
Engines2 Yanmars 110hp Northern Lights

Water Sports

Dinghy (Feet)13 ft.
Dinghy Hp40 hp
Dinghy Pax5
Snorkel GearYes
2-Man KayakYes
Floating MatsYes
Standup Paddle2
Swim PlatformsScoop Steps
Boarding LadderStern Sugar Scoops
Beach GamesYes
Fishing GearYes
Gear TypeTrolling and Casting
Fishing Rods4
Deep Sea FishingYes
Fishing PermitUSVI only
Under Water CamYes
Under Water VideoYes
Other Toys
WELLNESS CHARTERS: Turn your yacht vacation into a rejuvenating retreat facilitated by Chef Jessica, a certified yoga teacher and health coach.

Each package includes a pre- charter health consultation to curate a menu based on your dietary preferences, as well as the customized itinerary based on your wellbeing & fitness goals.

For wellness charters, we run with a crew of 3 in order to provide a high level of service.

A Wellness Charter includes all of the adventures and amenities of a regular charter, but your experience will be augmented with intention setting, daily yoga, meditation, breathwork, healthy food, transformational workshops, and deep authentic connection.

Please inquire if interested


Wing Foil

Leeway is also now offering to their guests on charters completed before July 31st, 2023:
• Free use of their eFoil
• One free group yoga class per day
• Onboard Diving: 2 dives at no service charge. No more than 4 people per dive. Gear not included.

Scuba Diving Scuba Diving Symbol

ScubaYacht offers Rendezvous Diving only
Air CompressorNot Onboard
Weight Sets8
Num Divers2
Night Dives1
Dive Lights2
Diving Info
• Onboard Diving: 2 dives at no service charge. No more than 4 people per dive. Gear not included.
Dive Costs
Gear not included


Salon Tv/DvdYes
Salon StereoYes
iPod/Device HookupsYes
Board GamesYes
Other Entertainment
Bow Thruster, Raymarine Axiom Electronics Package including 12´ MFDs at helm and inside nav station, radar, autopilot and AIS, Northern Lights 20kw Generator (under 2,300 hours), Webasto AC Chiller units, Custom granite countertops, 2 x custom wooden tables, one on aft deck, one on flybridge, wine fridge and beverage prep station in salon, inside throttle control for engines and autopilot control / nav station so you can drive your yacht from inside, 6 x Walk on 140Watt Solar Panels with Victron Smart Controllers, watermaker, electric furling genoa, 75lb Anchor with Swivel, Flybridge/Helm Isinglass Enclosure, Custom 1.5´ stainless steel sold rails all around main decks, 3´ high, additional railings going to fly bridge, additional grab bars on fore deck, , 48´ Flatscreen TV on a Lift System, Auxillary Fuel Tanks, Blue Underwater lights, Washer/Dryer, Dishwasher, additional freezer, center console tender & outboard, flybridge with sink, fridge, icemaker bbq and prep station

Yoga Mats

REFIT DETAILS: During the 2022/2023 season, Leeway has had these items replaced or upgraded: New flybridge BBQ, new, solar installed, new ice maker, new refrigerator, New Tender lift system


Special DietsYes

Green Initiatives

Make Purified Drinking WaterYes
Re-Usable Water BottlesYes
Other Green Initiatives
Grow herbs via hydroponic system Recycling RO to spring water quality restructuring system

Leeway Crew Profile

Crew Number3
Crew SmokeNo
CaptainTerrance “Bubba” Gainan
Chef / First Mate
Chef / First MateJessica Filkins

Capt. Terrance “Bubba” Gainan
Terrence was born in the water. Surfing by the age of five, picking up a fishing pole shortly after and becoming fascinated with the ocean throughout his experiences. He bought a Hobie ´16 before he even had his driver´s license and was a state champion surfer for six years straight. The love and respect he has for the ocean is indescribably fascinating. He is a lover of life and people are drawn to the good energy he brings along with him wherever he explores.

Chef Jessica Filkins
Jessica enjoys cooking all types of cuisine. She specializes in catering to guests´ specific dietary preferences such as vegan, gluten free and keto. She is skilled in preparing food that tastes delicious, looks beautiful and adheres to her high standards of quality, sustainability, health and nutrition. Jessica´s passions are creating food art, surfing, spearfishing, kiteboarding, dancing, traveling, taking underwater photos, and hosting retreats.

Jessica offers her services as a yoga teacher and energy healer on board the yacht as requested. Imagine starting your day on a beautiful catamaran with meditation, breathwork, and yoga! Jessica is also available to teach paddleboard yoga, and host bonfires on the beach, ecstatic dance pirates, cacao ceremonies, authentic relating workshops, chakra workshops, and rapid rewire sessions. She has a wide network of local body workers in the USVI and BVI for guests who want to experience other healing modalities and plant medicine ceremonies. Jessica´s life purpose is to merge the wellness industry with the yachting industry through hosting wellness charters and yoga retreats on yachts.

Jessica has had a lifelong passion for cooking. Her parents indulged her from an early age in baking and meal prep. Jessica grew up on Block Island and was homeschooled on her parent´s wooden motorsailer in the Bahamas. She graduated from Colorado College in 2011 with a BA in philosophy and psychology. In the summers she captained a launch (water taxi boat) in the harbor on Block Island. Following an illness her junior year of college, Jessica learned the value of healing herself through specific diets and alternative medicine. She became interested in the study of the gut microbiome and the science of treating food as medicine. In 2013 she attended the Institute of Integrative Nutrition and became a certified health coach. She subsequently started a turmeric tea company called Jahmu in 2014 which she ran for 6 years.

Her career as a yacht chef began in 2019. Since then she has cheffed on both sailing and motor yachts ranging from 50ft to 120ft in the Caribbean, Bahamas and New England. She has become very proficient at provisioning in the islands, sourcing the highest quality produce, meats and seafood. Jessica enjoys making deep, authentic connections with new people and holding space for transformation. Her mission is to provide the best experience possible for her guests and for them to leave feeling well nourished, satisfied, healthy and inspired!

Stewardess Heather Hanson
Heather is an outgoing and spontaneous Texan who wants to see what the world has to offer. She has been working on boats for 3 years starting off in Hawaii, ending up in the Caribbean. She recently got her 100 ton Captains license. Heather is attracted to all outdoor activities such as surfing, hiking, diving, fishing, foiling, and keeping her guest stoked while doing it. Her life goals are to immerse herself into as many different cultures to learn, experience, and grow along the way.

Leeway Calendar

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Leeway Reservations & Port Locations

Start DateEnd DateDetails (Holds can be challenged)
Jun 09, 2023Jun 16, 2023Booked: St Thomas, USVI* to St Thomas, USVI*
Jun 26, 2023Jun 30, 2023Booked: St Thomas, USVI* to St Thomas, USVI*
Jul 29, 2023Aug 04, 2023Booked: Red Hook, St. Thomas, USVI* to Red Hook, St. Thomas, USVI*
Aug 07, 2023Oct 31, 2023Unavailable: Puerto Rico* to Puerto Rico*
Nov 09, 2023Nov 17, 2023Boat Show: Boat Show, USVI* to Boat Show, USVI*

Leeway Rates / week

The prices shown are for the entire yacht for a week-long (7 nights) charter. Inquire for lowest rate.
Low price: $27,700
(normal rate)
High price: $31,500
(normal rate)

Leeway Special Offer!
Discount: 20%!
Offer: 20% discount for charters booked and completed on Leeway between now and July 31st, 2023. This special cannot be combined with other offers.
Old price: $27,700 - $31,500 / week
New price: $22,160 - $25,200 / week (Save: $5,540 - $6,300 / week)
Minimum nights: 5
Travel before: Jul/31/2023

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


CURRENT SPECIAL: Charters booked and completed on LEEWAY between now and July 31st, 2023 will receive a 20% reduction off of the current charter rate. For the discount to apply, the charter must have a minimum of 5 nights.

Leeway is also now offering to their guests on charters completed before July 31st, 2023:
• Free use of their eFoil
• One free group yoga class per day
• Onboard Diving: 2 dives at no service charge. No more than 4 people per dive. Gear not included.

This offering cannot be combined with other offers or specials

This vessel is legal to conduct charters in the BVI

Preferred pick up is St. Thomas. BVI pick ups are possible but limited to 7 per season.

MINIMUM NIGHTS: 5, Inquire for less
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.

BVI PORT FEE: B.V.I. customs and cruising permit fees are included in the rate.

SLEEP ABOARD: Available for half of the daily rate. Includes boarding after 4pm, snacks, welcome cocktails & continental breakfast. Dinner ashore is additional. Select option upon booking. EXCLUDES: Christmas and New Year´s weeks.

Discount of $150 per person
Includes: 7 breakfasts, 4 lunches & 3 dinners. Requires 3 lunches and 4 dinners ashore at client expense. Also see Local Fare option below.
2@$27,700 | 3@$28,050 | 4@$28,400 | 5@$28,750 | 6@$29,100

Discount of $75 per person
Includes: 7 breakfasts, 5 lunches & 6 dinners. Requires 2 lunches and 1 dinner ashore at client expense.
2@$27,850 | 3@$28,275 | 4@$28,700 | 5@$29,125 | 6@$29,550

CHRISTMAS 2023: 1-6 pax @ $37,500 - must end no later than 12/26
NEW YEARS 2023: 1-6 pax @ $40,000 - may not start prior to 12/27

Leeway Guest Reviews

Previous Yacht NameLady Susan
March 2023

I enjoyed the most incredible retreat from start to finish - everything was so thoughtfully planned and curated to ensure each guest felt seen, heard, and so taken care of while on the boat. I would absolutely recommend to anyone who wants to enjoy a once in a lifetime experience.
Awaken The Waters Retreat was the most life changing experience of my life. St Thomas’s magic was undeniable with incredible food , host and captain! Bioluminescence and shooting stars were the highlight of the trip. I will be back again and again.

What was the highlight of your experience on Leeway?

Oh gosh, this is a hard one. The highlight would be witnessing the passion that you have infused the experience with. Each detail was carefully curated based on your own experience and your love for the lives you have created. From the presentation of the flowers on the boat to the tours, the excursions, the snorkeling, the sailing, the FOOD! It was all offered with such pure intentions of bringing the best possible experience for us all.
The entire trip was the highlight - from start to finish it was an experience I will never forget.
The bioluminescent waters, the shooting stars, the private experience, the food was absolutely phenomenal.

How was the food? What was your favorite meal and what was your least favorite?
The food was incredible!! I miss Jess´s cooking so much - although I did invest in an airfryer when I got home! haha My favorite meal was the lobster - both evening and morning breakfast with it. YUM! I´m not sure I had a least favorite.
Insane! It was like dining at a 5 star restaurant every meal - so delicious. You could taste all the love, energy, and effort that went into the meals.
I loved them all so much. No least favorite. I loved day 1 food. I loved the pancakes!! I loved the fruit mandalas. I loved it all.

February 2023

We were a party of four and spent one night out on Leeway along the south side of St. John. Bubba, Jessica, and Heather were awesome! They were attentive to the needs of our group and always on top of things before we had to ask. The boat is absolutely beautiful! The beds are comfortable, the crew keeps the boat immaculate, and the AC worked perfectly. The living areas on the boat are the best – there is so much space and so many different spots to hang out, take a nap, or eat Jessica’s amazing and healthy food.
The boat is loaded with water toys and fun things to do on a mooring or at anchor. We did one dive at Ledges and the corals and sea life were magnificent. Bubba and Heather are awesome divers and Jessica is a great hype girl and underwater photographer! We spent hours trying out the hydra-foil which is a must! And paddle boarding around was a blast. I highly recommend a trip on Leeway! 10/10

January 2023

Thank you Chef Jessica, for a once in a lifetime experience of constant fun and good times! From amazing meals to helping us with spiritual growth, you have been way beyond nice! Your food was absolutely delicious and fueled all of our fun times together! Thanks for connecting to each of us on a personal level and reaching all of our hearts through our tummies!

January 2023

I have to say that the experience on the Leeway was one of my all-time favorites thus far! Being on the yacht provided an intimate container to simply BE. The food was incredible; colorful, flavorful and plentiful! The extra attention to the care and delivery of the excursions and adventures allowed us to experience the beauty of the local area without the overwhelm and crowded tourist aspect. I thoroughly enjoyed the extras that the boat offered such as fishing, paddleboarding, snorkeling, efoiling, and snuba diving. Every detail down to the towels, the bedding, and the pillows offered a feeling of luxury. I will definitely be back!