Cruising Area of Lucky Me

Pref. Pick-upCompass Point Marina, STT
Other Pick-upCompass Point Marina, STT
Summer PortGrenada, Windward Islands
Summer OperationsCaribbean Virgin Islands
Winter PortVirgin Islands
Winter OperationsCaribbean Virgin Islands

Lucky Me Specification

Length51 Feet
Beam28 Feet
Draft4.7 Feet
A/C NightYes
Sun AwningYes
Bimini TopYes
Children AllowedYes
InverterYES 115V
Voltages12 Volt and 115v onboard
Water MakerYES
Water Capacity254 GAL
Ice MakerYes
Internet AccessOnboard WIFI
Max Speed12 knots
Cruising Speed7-10 knots
Fuel Consumption1.5 US Gall/Hr
Range1000 miles
Engines2 Yanmar engines and 1 generator


Wash Basins4
Electric Heads4
Accommodation Details


Salon StereoYes
iPod/Device HookupsYes
Board GamesYes


Special DietsYes

Water Sports

Dinghy (Feet)13
Dinghy Hp40
Dinghy Pax8
Snorkel GearYes
Floating MatsYes
Standup PaddleYes
Boarding LadderAft Sugar Scoops
Beach GamesYes
Fishing GearYes
Gear Typetrolling rods x 2(Shimano and
Fishing Rods3
Deep Sea FishingYes
Under Water CamYes
Under Water VideoYes

Scuba Diving Scuba Diving Symbol

Resort Course$155
Full Course$190 for eLearning, then $350 for check out dives
Air CompressorNot Onboard
Weight Sets8
Num Divers8
Dives/Weekup to you
Dive Lights8
Diving Info
The crew, are PADI MSDT Instructor and a PADI Dive Master onboard.
Dive Costs
We offer Full PADI Instruction (costs depends on which course), Fun Diving ($90 for two tank dives), Discover Scuba Diving ($155), Night Dive ($75)

Lucky Me Crew Profile

Crew Number2
Crew SmokeNo
CaptainMichael Wilcox
LicenseUSCG Master Captain / PADI Master Instructor, Dive Master /
CrewJesica Wilcox
LicenseUSCG Master Captain / Ashburton Graduate Chef / PADI master

Michael started loving the water when he first went to Chicago and one of his friends had a sailboat, he learned to sail and yearned for his own boat. Till then he served his country, worked as a Surgical Nurse, then into Medical Sales. Michael met his beautiful wife, they spent a few years in the US before adventuring to Central America for several years. Michael is a USCG Master Captain, a web designer, marketer and a PADI Dive Master with over 400 dives.

Jes worked in Corporate Management and realized after several years and meeting her Prince Charming, life had more to offer than her current position. Jes continued to challenge her mind and became a Holistic Health Coach, Yoga Instructor, Thai Masseur and an PADI Open Water Scuba Instructor. During all her training she longed for a place to call home and now has settled in the Virgin Islands. After deciding to settle in the Virgin Islands, Jes became a USCG Master Captain and for her guests´ further enjoyment, an Ashburton Cookery School trained Chef. Thai, Greek, Italian, Fish & Seafood, and Patisserie are just a few things Jes is specialized in cooking.

Michael and Jes are a vibrant and passionate crew ready to treat their guests to a fun and memorable holiday aboard Lucky Me. They have transformed their deep affection for having fun above and below the water into options (including excursions, paddle boarding, scuba diving, snorkeling, and water sports) for an active vacation package for family or friends wanting to create a trip of a lifetime.

Lucky Me Calendar

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Lucky Me Reservations & Port Locations

Start DateEnd DateDetails (Holds can be challenged)
Jul 16, 2021Jul 23, 2021Booked: Yacht Haven Grand to Yacht Haven Grand
Jul 24, 2021Dec 26, 2021Unavailable: St Thomas, USVI* to St Thomas, USVI*
Dec 27, 2021Jan 03, 2022Booked: Yacht Haven Grand to Yacht Haven Grand
Jan 04, 2022Jan 21, 2022Unavailable: Yacht Haven Grand to Yacht Haven Grand
Jan 22, 2022Jan 29, 2022Booked: Yacht Haven Grand to Yacht Haven Grand

Lucky Me Rates / week

The prices shown are for the entire yacht for a week-long (7 nights) charter.
Low price: $12,000
(normal rate)
High price: $16,200
(normal rate)
The high and low prices of this yacht depend on both the number of guests and the traveling season. Send us an inquiry for exact pricing.

Lucky Me Special Offer!
Fam. Special!
Offer: $250 off for each child age 12 and under. Age is based on the charter date NOT the date of booking.
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 Lucky Me.

Lucky Me Guest Reviews

Sailing and Scuba Certification

Just returned from fabulous 5 day trip with Micheal and Jess to USVI. Two adults, two teens and an 11 year old, two of us got out open water scuba certification with Jess, and my eleven year old when did a discover scuba dive with her. She was very patient and a great teacher, even when I had to try on 3 different BCD’s and even kicked her in the mask and got stung by a Coral! No idea how she did this while cooking is the best meals we could imagine in a ( seemingly) effortless way.
Micheal was an amazing captain and guide, taking us to amazing places we hadn’t seen ( and we’ve been coming to USVI for years), along with great hidden restaurants we didn’t even know about, that could only be accessed by dingy. We couldn’t have had a better time, and are planning on booking a 7 day trip with them again in August. Absolutely a 5 star experience, beautiful, clean boat, good food, good company, couldn’t ask for more.

The Best Trip

My group of 5 just finished a seven day sail through the USVI and BVI’s with Michael and Jess. I can’t say enough about our wonderful experience. We visited 9 islands and Michael and Jess took great care of us all along the way. Their knowledge of the islands makes sailing a cinch for those that have been to the islands or first timers. Jess is truly an amazing chef and no matter whether it was breakfast, lunch or dinner, she never disappointed us. Each day we anxiously awaited to see what she would create for us to devour. I’m sure we each gained 10lbs... Thanks Jess. LOL
We also did an orientation dive with Jess that made our trip truly memorable. Michael is a wonderful captain and very careful to make sure everyone is very well taken care of from a safety stand point. “Lucky Me” is a beautiful catamaran and provides multiple areas for lounging. We never felt we were on top of each other and sleeping with an air conditioned room made our nights a dream. It was also a huge benefit to have dependable wi-fi onboard for watching shows in the evening or just catching up on news worthy events. I can’t wait until our next adventure together.

Amazing vacation amazing people

The vacation of a lifetime, Michael & Jess are a great team the boat was spacious with great bedrooms. The food Jess made was out of this world. The since of comfort and care they show their guest is like no other. I highly highly recommend them. They are very knowledgeable of the area and always make you feel safe. I will be seeing them again hopefully sooner the later. If your even thinking of chartering a boat Lucky Me is a must you will not be disappointed..

Thank you for such a great time and making our vacation so much fun. Can’t wait to see you again!!

Great Adventure on the Lucky Me

My husband Doug and I (Melinda) had an awesome 6 night, 7 day adventure on the Lucky Me with Captain Jess and Captain Michael. The first positive experience we had was from the moment I notified them that we were interested in a charter trip through the BVI. I notified them through their web site and Michael contacted me immediately and he gave me a lot of information that I had not received through the other companies we had contacted. I was totally impressed. He sent me an email and stated all that the trip included. No hidden costs or secrets. When we arrived at the pier in St Thomas we were greeted by Michael and his wonderful wife Jess. Jess gave us a warm and inviting smile, that made us feel so welcome. It was a wonderful beginning of an awesome journey through the BVI on the Lucky Me. One of many great experiences of our trip was being able to plan where we wanted to go and how flexible the captains were regarding our trip. They gave us some awesome ideas on the islands that we should visit and the places we needed to explore. We were not disappointed, ever!
A few but not all of the positive moments on are trip was the tasty meals that were prepared by Captain Jess. She made entrees that were healthy and exactly what we enjoy. The rooms were comfortable and the Catamaran Lucky Me was strong a mighty. The snorkeling and diving places that we experienced were outstanding and beautiful. It was so much fun sailing through the BVI on the Lucky me with Jess and Michael. We plan to go back next year since the trip was one of a lifetime, but we´re going to make it a yearly adventure. I highly recommend a Charter on The Lucky Me with Captain Jess and Captain Michael. They are not only great hosts they are now awesome friends that Doug and I will revisit yearly. If you have the opportunity to explore the BVI on the Lucky Me, please take the opportunity, its amazing.

Anegada Lobster Fest (Woooooo!)

Mike and Jes are without a doubt a dynamic duo! Once we boarded the boat they made it very clear that our safety was at the forefront of their minds and will continue to be throughout the trip. They both made everyone feel safe and comfortable while enjoying the time of our lives. Everything they did to ensure we had a super-fantastic time was spot on. The entire boat, both interior and exterior was immaculate. Our suite was clean, private and cool at night. I slept like a rock!.
Waking up to coffee and a beautifully prepared breakfast every morning was all I needed. Thanks to the chef, I´ve added guacamole and tomatoes to my list of foods I like.Only took 49 years for me. Thank you Chef Jes. Your talents definitely do not go unrecognized.
Our time on this boat was definitely one for the books. It´s easy to see Captain Mike (a military veteran) has complete 24-hour command and control of Lucky Me and with impeccable management skills. I´ve enjoyed learning a lot from Mike and getting to know him. I felt like we clicked on many levels.
This dynamic team were in sync with each other the entire time and never missed a beat. Captain Mike and Jes are a team you can trust and I strongly recommend Set Sail and Dive to anyone visiting the islands.

Thank you both!

Ready to book again!

As I’m sitting here in 45 degree weather I was dreaming about our amazing vacation aboard Lucky Me. This trip was celebrating my 50th birthday, Michael and Jes made it extra special with a gift, cake and decor, so sweet! I thought I had already reviewed it, but maybe I never finished it. We travel a lot and this by far was my favorite trip we’ve taken, what I loved was that it was truly a vacation to relax and chill, I didn’t have to cook, clean, or really even make any decisions which was quite amazing. We never wore shoes the whole week, which was wonderful too! The rooms are air conditioned and comfortable to retire to at bedtime. The food Jes prepared everyday was delightful. Hanging out at night underneath the stars is quite incredible. Had an amazing time snorkeling with Jes also. Michael and Jes are both very nice people and take immaculate care of their home/boat. We sailed the British Virgin Islands mostly and moored most of the nights. I thought we may get bored or antsy not even one moment, we actually preferred to stay on the boat the majority of our time. Sorry if we drank more than you expected, I warned you guys! We will be booking again soon!


If you are looking for an amazing trip and love to be in the water and sun, BOOK THIS NOW!!!! Captain Michael and Captain Jes will accommodate you. We spent 6 days traveling the VI and BVI on Lucky Me, but LUCKY US!! This was a trip of a lifetime. Island hopping, fishing, snorkeling, scuba diving- Jes is a great teacher, great chef, food was amazing, both are very knowledgeable and love what they do, which shows in how they made our vacation special and very relaxing. We were worried about space, 3 couples, but not once did any of us feel like we were cramped. Our rooms were perfect, clean and very comfortable. Plenty of room to do your own thing. We have already started planning our next trip with them. You will not be disappointed.

Unbelievable Vacation

No amount of words will do justice to the trip 6 of us had the unbelievable pleasure of booking with Michael and Jes. They are the best captains and team on the sea. I had expressed to Michael that we love “non tourist” spots, but also wanted to see the can’t be missed spots. They accommodated our dreams by taking us to wonderful places; I truly felt they were as excited as we were. We visited 11 islands in 7 days. He’s was so calm and patient and we grew in our snorkeling experiences. We were so fortunate that two of those were at Anegada island. Jes is a wonderful chef and very accommodating. They joined us on the islands and for evening games. Even though we booked as paying guests, I feel we left as friends. We will be doing this again, and only with them. Thank you Michael and Jes for helping me have the best 60th Birthday celebration at sea! See you soon


Top Ten Reasons to Book with Lucky Me:

1. Jes’s amazing food - nothing on St. Thomas, St. John’s, Norman, Peter or Virgin Gorda islands even really compare. Fresh, filling, healthy and delicious.

2. Hot water to shower in (most boats don’t have it). Forget hot water, these guys make their own fresh water. Lots of fresh water.

3. Diving direct from the boat. No rendezvous diving. No lost time. Instantaneous ability to go!

4. Dive master on board - available 24/7 (think night dives) who is excited to dive and knowledgeable about sites, standards and reef life

5. Impeccable vessel (comfortable, clean, safe, stocked, organized)

6. Gear at your fingertips (fishing, snorkeling, diving (day and night), relaxing) Pretty much all you need is a suit and sandals. They’ll cover everything else.

7. Flexibility - the knowledge and ability to adjust to the elements no matter what gets tossed at you. Nothing is set in stone. So you get the most out of EVERY MOMENT. You miss nothing and get to do it all.

8. Two people you really don’t mind being around day after day. Fun and funny.

9. Knowledge - these two know a lot about the area - the geography, the people, the history, where to go, what to avoid. They saved us a ton of time and headache.

10. Kindness. Mike and Jes are truly two of the kindest people you’ll ever meet. They help everyone they come across. People who need it and even those who don’t deserve it. They watch out for others when they have nothing to gain by doing so. They never once made us feel like clients. We were friends right from the start. It’s just one of those things that matters oh. so. much.

We spent five days/four nights with Mike and Jes and loved every second of it. They are amazing in every way. Relentless at making every detail perfect. They effortlessly make waiting on your every need look easy even desirable. Don´t think, just GO!!

Incredible trip with S/V Lucky Me

Captain Michael and Chef Jes (she’s a captain too) are an amazing couple who love being on the water, love to teach you things and see all the wonders under the ocean. If you are looking for the perfect blend of romantic getaway or a family fun vacation, relaxation and a beautiful backdrop, a trip with the crew of S/V Lucky Me is just where you need to be!! We have gotten to see and experience something amazing, snorkeling with sea turtles at Diamond Cay, deep sea fishing for Black Fin Tuna (have to get a fishing license), fresh sushi made from the Black Fin Tuna with friends, scuba diving a secret spot, learning how to read the wind & trim the sails, and a beautiful evening in a hidden cove off of Norman Island... S/V Lucky Me is the best of everything for everyone! Families with kids, group of friends, couples and honeymooners are all treated with comfortable accommodations, wonderful food & drink, awesome hospitality and all the water activities you could want on board. I can´t wait for our next trip aboard S/V Lucky Me and eating all the great food Chef Jes made for us. Wow!! Is all we could say about her food. Thanks guys!!!

Perfect way to enjoy the USVI

My friend and I had a great time aboard Lucky Me. The boat was beautiful and the hosts were very accommodating. We enjoyed some sailing, saw dolphins and even sea turtles. We were even able to scuba dive where we anchored that first afternoon. The meals were amazing and we want to stay again on Lucky Me with Captain Mike and Jes.

Trip of a life time

I have to be honest and say that I was very reluctant to take this trip with my husband. I get sea sick and was anxious about going out on a boat in the ocean. My husband was so excited about the trip and reassured me that everything was going to be ok. We picked Lucky Me because of Michael and Jesica. They are both Master Captains with sailing experience, hospitality experience and scuba divers. Jes is a Dive Instructor and Michael is a Dive Master. My husband and I are both advanced divers and really wanted to dive during this trip. I´m so happy we chose this crew and boat. Diving with Michael and Jes was relaxing and peaceful. They let me go at my pace and see what I wanted. I´ve always dove with a group, being led on a predetermined dive by a guide. With them we were able to stop and just look at little stuff, stay as long as we wanted and go on without any group pressure. The majority of my anxiety was actually being out on the ocean. We are from Colorado and I´m much more comfortable on dry land, I just didn´t know if this would be my thing. Michael is an experienced and capable captain and I felt completely comfortable and safe with him. Jes is level headed, calm and competent, the two of them ran the boat flawlessly. Both of them had just returned from the UK cooking school at the Ashburton´s School of Cookery. The food was absolutely amazing. I had to pinch myself several times to realize that this was real. I really couldn´t imagine myself enjoying sitting on a boat all day and night, what would we do, it´s so small, you can´t just get off when you want. All these thoughts were in my head. The opposite was actually the truth. I read, enjoyed music, lounged on the deck. We sat up on top with Michael while under way. He is a great conversationalist. They catered to our desires and we had significant input into the itinerary. The boat is NOT small. The cabins are queen sized, each with a full bath. It didn´t feel like the box of a cruise ship. The galleys are large and quite comfortable. I never imagined that I would have such a marvelous experience on a boat in the ocean, but found that it was very relaxing, peaceful and calming. This was the best vacation I´ve ever had and I can´t wait to go back. I know I´ll see ´Lucky Me´ again and hope it is soon. As we left the dock, I took one look back at her and thought to my self...…Lucky Me for having taken this adventure! Kathy

Lucky Me Sample Menu Picture
Lucky Me Sample Menu Picture
Lucky Me Sample Menu Picture
Lucky Me Sample Menu Picture
Lucky Me Sample Menu Picture
Lucky Me Sample Menu Picture
Lucky Me Sample Menu Picture
Lucky Me Sample Menu Picture
Lucky Me Sample Menu Picture
Lucky Me Sample Menu Picture