Jalapeño Description

Sailing Vessel “Jalapeno” offers personalized sailing vacations aboard our 52 foot ketch in the BVI, USVI, and the Spanish Virgins, plus the Grenadines and all along the Eastern Caribbean island chain in-between. Join us for a few days, a week, or more sailing and exploring these Caribbean islands. Jalapeno provides one or two couples, or small families up to 6 with possibly the most exotic, relaxing, and fun vacation experience they have ever had. More than just a charter, it´s a taste of the cruising lifestyle.

“See our 2020-2021 charter schedule on the Rates page.”

Cruising Area of Jalapeño

Pref. Pick-upBlue Lagoon, St Vincent
Summer PortLeewards/Windwards
Winter PortLeewards/Windwards


Length52 Feet
Beam15.6 Feet
Draft5.6....13.0 Feet
A/CAt Dock
Sun AwningYes
Bimini TopYes
Children AllowedYes
Min Child AgeWater Safe
InverterHart 2500
Water MakerVillage Ma
Water Capacity380 Gal.
Generator7.6 KW
Max Speed9+ Kts
Cruising Speed7.5 Kts
Turnaround24 hours
EnginesPerkins 85/hp Diesel 7.6 KW


Wash Basins2
TP in Heads-
Accommodation Details
V-Berth bed is King size at the head and narrows at the foot (like a pizza slice)
All cabins ensuite with head and shower
Sleeps 4 adults comfortably- inquire for 5/6 passengers with small children

Water Sports

Dinghy (Feet)Walker Bay 10ft
Dinghy Hp9.8 HP
Dinghy Pax6
Snorkel GearYes
Floating MatsYes
Standup Paddle1
Swim PlatformsYes
Boarding LadderAft
Beach GamesYes
Fishing GearYes
Gear TypeHand Lines
Under Water CamYes
Other Toys
Snorkel Gear with variety of sizes
Floating Noodles, Rafts, Kickboards
Stand Up Paddle Board
Fishing for Offshore Trips

Scuba Diving Scuba Diving Symbol

ScubaYacht offers Rendezvous Diving only
Air CompressorNot Onboard


Salon Tv/DvdYes
Salon StereoYes
Board GamesYes
Other Entertainment
Storage for 20 lbs. of ice in freezer


Special DietsInq

Jalapeño Crew Profile

Crew Number2
CaptainRay Bryan
License100 Ton Masters, STCW 95
Chef/ First Mate
Chef/ First MateJennifer Bryan

Captain Ray Bryan grew up skiing and hiking the Sierra Nevada mountains and has been sailing for 35 years. He holds a 100 ton US Coast Guard Captain´s license and is a avid diver and snorkeler. Ray has degrees in Mechanical Engineering, holds a Professional Engineering license, and has a very successful engineering firm specializing in product development for over 25 years.

First mate Jennifer met Ray skiing and shares his love of the outdoors. Jennifer taught school and has been a school administrator for many years, but her love of the sea and sailing has called her to a different life. Ray and Jennifer have both worked hard to fulfill their dream of sailing their own charter yacht in the Caribbean. Their goal is to insure you relax, enjoy your time on board, and experience the beauty of the Caribbean.

Jalapeño Calendar

Jalapeño does currently not provide a calendar or bookings list. Please inquire for more information.

Jalapeño Rates / week

The prices shown are for the entire yacht for a week-long (7 nights) charter.
Low price: $7,800
(normal rate)
High price: $9,200
(normal rate)

Jalapeño Special Offer!
Discount: 5%!
Old price: $7,800 - $9,200 / week
New price: $7,410 - $8,740 / week (Save: $390 - $460 / week)
Travel between: Nov/01/2022 - Dec/14/2022

Season2 Pax3 Pax4-6 Pax
2022 Summer$7,800$8,500$9,200
2022/23 Winter$7,800$8,500$9,200
2023 Summer$7,800$8,500$9,200

Yacht terms: Plus Expenses

The price includes a professional crew operating your chartered yacht, but all running expenses such as fuel, tax, provisions and any other costs are extra. Calculate between 15-25% for a sailing yacht and 25-35% for a motor yacht on top of the given rate with an APA cash payment made to the ships agent or captain, who will keep an open tap and produce full accounts of all expenditures. Inquire for more information.

Send us an inquiry to get specific pricing for Jalapeño.

Jalapeño Guest Reviews

Top Condition and Very Comfortable

I loved spending a week with Jennifer and Ray aboard the Jalepeno. The boat was in top condition and very comfortable. Ray and Jennifer were very welcoming and made us feel at home. They went out of their way to make sure that we experienced what the islands had to offer including snorkeling, paddle boarding, sightseeing on the islands and meals ashore. The meals aboard were great and plentiful and gave me the opportunity to try some new things. I feel as if I have made some new friends and can´t wait until I book another vacation aboard the Jalepeno.

Gracious Hosts

Ray and Jennifer were very gracious hosts, and extremely knowledgeable about the Virgin Islands and Culebra. The trip´s itinerary included sailing, snorkeling, walks on the beautiful beaches, and hikes to an abandoned lighthouse. Our every need was met. The food was delicious and plentiful and the conversation lively. A thoroughly wonderful and highly recommended experience.

Our Best Vacation Ever!

Our trip aboard Jalapeno was our best vacation ever! The experience, views, and the time on the water was something you could not get from a hotel or villa. Being able to visit all of the different islands was absolutely amazing. We were able to discover so many different beaches, restaurants, and enjoy each of the islands´ awesome scenic areas. And we were able to spend so much time in the beautiful Caribbean water swimming and snorkeling. What a wonderful sailing experience!

We CANNOT say enough about Ray and Jennifer. They welcomed us aboard Jalapeno with open arms and graciously shared her with us for our week away. Their attention to detail was second to none. All of our wants and needs were taken care of, from planning months ahead to the last time we stepped off the boat. All aspects of the trip -- from the islands we visited, to the delicious food they prepared for us, to all of our activities -- were completely centered around our interests. Ray and Jennifer made it a priority to make sure our experience on board went well above our expectations!

We can´t wait to sail with them again!!!

Both our Boys Learned to Sail

We had an incredible week aboard Jalapeño! Captain Ray and Jen were wonderful hosts who worked tirelessly to make our trip unforgettable. Ray plotted a course that adjusted to our desires and everyone enjoyed each of the islands we visited (St. John, Peter, Jost, Virgin Gorda, Anegada and Sandy Spit). Jen went above and beyond to make sure our youngest son (age 7) had a great time and both of our boys learned to sail. Ray and Jen were outstanding hosts providing us history, information, beach and restaurant suggestions. We miss the gorgeous views, boat drinks and great conversation!

A Better Team, You Could Not Find

From the moment Captain Ray met us at the marina with a friendly smile, we knew this was a great vacation choice. We sailed for a week throughout the BVI´s and really had the vacation of a lifetime. Captain Ray and First Mate Jennifer, a better team, you could not find, were accommodating, happy and extremely knowledgeable. They made us feel right at home on their beautiful boat and were just so easy to be around. It was very comfortable and all amenities really were supplied. This was a first time experience for us so it was nice that options were presented to us each day with lots of information about what we might be choosing. The meals were wonderful and with three teenagers, there was no shortage of food. We especially loved ´Cocktails´ every night with well planned out appetizers and fruity drinks. We also had three meals onshore and we were always given lots of ideas as to the best places to go. Ray and Jennifer have this charter business down to a tee. They know all the best snorkeling spots (and will accompany you if you want). They know everything you will see when you are out and can teach you a ton about marine life. Hiking to amazing vistas is an option on several of the islands. We paddle boarded, swam and sailed (and what a great job they did teaching my children about sailing). I really wanted a nice, relaxing week with nothing to think about except which island we were going to next. The week was perfect. Some nights we were moored in bays with one or two other boats. To look at the stars in complete darkness, lying in a hammock, is just incredible. Other nights, we went onshore where there was more action and once were treated to an authentic pirate show. I really felt, the whole week, that it was both Ray and Jennifer´s mission, to make sure we had the best vacation ever. If you are looking for an awesome sailboat excursion, choose this boat. We love the Jalapeño and the incredible memories we made. We can´t wait to go on another trip. Thank you Captain Ray and First Mate Jennifer.

Above and Beyond Service

´The best vacation ever!´ That is a quote from our 17 year old daughter. I couldn´t agree more. We were looking for something different for our holiday vacation. We wanted a unique, relaxing and uncrowded experience. The Jalapeño, Ray and Jennifer came through in a big way. From the first hour, I knew we´d made the right choice. Once we left the marina and stopped for a snorkeling swim, I realized I left my backpack in the taxi. Jennifer immediately got on her cell, used her local contacts, and tracked down my backpack in 10 minutes. After a ´no big deal´ trip back to the marina, my backpack was soon returned. That type of above and beyond service is the standard. Ray and Jen were not just the crew of the boat, they were an integral part of our vacation and I couldn´t think of two better people to spend it with. Friendly and funny and full of all kinds of interesting info about the Virgin Islands, sailing, marine life...you name it. What was most amazing to me was, at one of the busiest times of the year, several times, Ray would find an anchorage with few or no other boats. The weird thing is, they were in such fantastic places that you wondered why everyone else wasn´t there! The best snorkeling I´ve ever experienced, by far. Beautiful beaches to explore. Hikes from our private beach, over a ridge to a busy beach with lots of people and local food stands, or to an old lighthouse with thousands of butterflies and hermit crabs along the way. Unbelievable. We opted to have several meals on board...good choice. Great food from salmon, to chicken, empanadas, to pork. The food was amazing and all prepared fresh. Served with a smile and a glass or two of wine. Some nights that was followed by a guitar session with Ray and our daughter or an astronomy lesson. I´m telling you, this is a great trip. The boat is spotless, safe and provided ample space for all of us. Ray and Jen´s knowledge of sailing is vast and we always felt safe, even in 7´ waves in the open water. I could go on for a while about how special this trip was, but the best thing I could say, is just experience it for yourself. I was amazed how connected I felt to the places we were and Ray and Jennifer too. Great people, great boat, great food, great sights. No complaints. Do it!

Floating Heaven

Our stay with Ray and Jennifer on the Jalapeño was just as expected = terrific. A beautiful boat based out of a lovely harbor in St. Thomas. Our trek around the BVIs was an amazing adventure. Our hosts knew the ins and outs of every stop and even had a huge social network amongst the bar, restaurant, motor bike rental and other locals.

The Jalapeño was in tip-top shape, clearly owned and maintained by intelligent and detail oriented people.

We were spoiled all week. From Bloody Mary second breakfasts to treks to fabulous lobster restaurants via Zodiac Boat. Top notch across the board.

We would absolutely recommend the trip to family and friends. My one word of caution is that an extremely tall person (I am 6´4´) could be challenged in the front bed with a tall partner (5´8´) due to the shape of the bow of the boat. Doable but tight. There is a second bedroom just feet away.

We had an amazing trip and adventure and recommend the Jalapeño and Ray and Jennifer highly!

We Hit the Jackpot!

We chartered Jalapeno after the boat we initially booked fell through, and we hit the jackpot! Everything about our trip could not have been better. We had never done a charter before and Ray was very friendly and easy to work with. Since we had already booked our flights, Ray offered us the option to stay on board the night before we left the marina and on the last night. We arrived back in port just in time to catch a ride (that Ray arranged) to the airport.

Jalapeno is a beautiful boat! She is comfortable, spacious and full of character. Jalapeno is well-loved by her owners, Ray and Jennifer, and well equipped and provisioned. Anything you could want or need is on board. I believe there is a tremendous advantage to chartering from someone who owns the boat. Ray and Jennifer know all the nuances of Jalapeno and every day flowed seamlessly into the next. Safety was a priority and we always belt VERY safe and secure even on ´windy´ (for us!) days.

Our itinerary was ´loosely´ discussed before we started. We did hit all our ´must see´ locations. Being flexible enabled us to discover some amazing spots that were off the beaten path. Ray has some ´secret´ spots that included one night with not another boat in sight! We stargazed in one of the darkest places I´ve every been, saw the water glow with phosphorescent creatures, did a little hiking, paddle boarding, scootering on Anegagda and lots of snorkeling (which was amazing). We saw brilliant coral gardens, and Ray showed us sea creatures that we never knew existed. We held furry (and slimy) sea cucumbers, sea biscuits, sand dollars, conch and more. Ray found lobsters, rays and turtles and took amazing underwater pictures for us. I could go on and on about the snorkeling, it made us all want to get SCUBA certified. Ray is very familiar with the islands and when there were too many boats at one place, he always had a plan B (or C or D...)!

Ray and Jennifer are really fun and interesting hosts. We learned about the history of the islands and heard great stories about the locals and islands. Speaking of locals, it seems like Ray and Jennifer know them all--restaurant owners, bartenders, and various other island characters. Food and drink on the boat was wonderful and plentiful, and we had some very nice French wine every night. Afternoons we were treated to rum punch, margaritas and painkillers (or painkiller juice only for our 16 year old daughter).