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Sailing in the Grenadines 2018/2019

Bedrooms 2
Property type yacht
Minimum Stay 3 nights


About the property

A Truly Personalized Sailing Vacation.

For the Fall of 2018 we will be sailing in the Grenadines. Looking forward to having you join us there for this extra unique experience. Contact us for more details. Description for our Virgin Island charters follows:

Sail the US, British or Spanish Virgin Islands for an adventure of a life time. Jalapeno Charters offers personalized sailing vacations in the BVI, USVI, and the Spanish Virgins aboard our 52 foot ketch, Jalapeno. Join us for a few days, a week, or more sailing and exploring these Caribbean islands. Jalapeno provides one or two couples, or families up to 6 with possibly the most exotic, relaxing, and fun vacation experience they have ever had. Why take a cruise ship when you can have your own private sailing yacht take you to destinations the cruise ship passengers never go. Relaxing and reading, swimming, snorkeling, or learning to sail, your crew is ready to meet your vacation needs. Work with the captain directly to customize your personal sailing cruise through Caribbean waters.

Factors to consider when planning your trip:

* Do you want to do a little or lots of sailing?

* Balance between dining aboard and meals ashore?

* Private anchorages or nighttime entertainment?

* Been here before, and want to go to different places while definitely hitting a few of your prior favorites?

* It is all good, and your crew likes to be flexible.

* Never been here before? No problem. We will make sure you see all the 'not to be missed' attractions.

* Been here a dozen times? We will still take you to new places you have not seen.

We can take you to Anagada where being on the beach at Cow Wreck or Loblolly Bay feels like you are at the end of earth. Day stops at places like the Baths, the Indians, pirate caves, Sandy Cay or Sandy Spit may be high on everyone's list. Perhaps you want to add a stop at the Dogs or Monkey Point. Don't forget Jost Van Dyke! This island has great hang-outs like the Soggy Dollar, Foxey's, Ivan's, Sydney's, Abe's and many more. On Virgin Gorda in the North Sound privacy can be had off Mosquito Island or Prickly Pear, while Leverick Bay, Saba Rock, and the Bitter End Yacht Club get you doing things ashore.

This is a truly custom made vacation and is designed around the desires and wishes of you and your party. Your crew will do their best to make sure your charter is a fantastic experience that you will remember with fond memories and want to repeat. The crew will act as your chef, bartender, waiter, tour guide, activities director, and sailing instructor (should you desire)!

Two cabins, each with its own head (bathroom), accommodate 2 couples with two additional bunks available in the salon. Each stateroom is made-up with bed linens, pillows, bath towels, and beach towels. A change of linens and bath towels is provided mid-week. We also supply soap, shampoo and sunscreen.

Jalapeno is well equipped with all the comforts of home. Our large galley is a delight to cook in and holds plenty of food and beverages for your cruise. In the Caribbean, rum is king -- and a favorite of the crew for making the guests “boat drinks” before sunset, and sipping after dinner.

Your crew will prepare all your meals and beverages specified in your preference sheet. Many guests like to eat a few meals ashore to enjoy the local cuisine and ambiance at some of the local establishments, which can range from a fancy dinner to a traditional island beach barbeque (guests are responsible for any meals ashore). You might invite the crew, which is a special treat, but it is not expected. The point is for you to enjoy the islands.

The Caribbean has some of the most beautiful water in the world and beautiful fish to go with it. You can bring your own mask and snorkel, or use a set from the assortment aboard Jalapeño. We also have fins as they can be a bit more difficult to travel with.

Come sail with us for a relaxing yet adventurous vacation personalized to meet your needs. We look forward to spoiling you!

More Details

Captain Ray
Member since: 2010
Speaks english
Response time
Within 12 hours
Response rate
Calendar last updated:
13 April, 2018

About Captain Ray

Captain Ray Bryan grew up skiing and hiking the Sierra Nevada Mountains and has been sailing for 30 years. He holds a 100 ton US Coast Guard Captain’s license and is an 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 20 years.

First mate Jennifer met Ray skiing and shares his love of the outdoors. Jennifer taught school and was 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.

Captain Ray purchased this yacht in 2007

Why Captain Ray chose St. Thomas

Jalapeno Charters offers personalized sailing vacations in the BVI, USVI, the Spanish Virgins, and other parts of the Caribbean aboard our 52 foot ketch, Jalapeno. Join us for a few days, a week, or more sailing and exploring these Caribbean islands. Jalapeno provides one or two couples, or families up to 6 with possibly the most exotic, relaxing, and fun vacation experience they have ever had. Why take a cruise ship when you can have your own private sailing yacht take you to destinations the cruise ship passengers never go. Relaxing and reading, swimming, snorkeling, or learning to sail, your crew is ready to meet your vacation needs.

What makes this yacht unique

A sailing charter provides you with your own personal yacht and the opportunity to see and experience what very few people get to in the Caribbean. Get off the plane, settle in on Jalapeno and enjoy the rest of your vacation. Go where you want, when you want, linger away the day or not! Where ever you adventure Jalapeno is with you, providing all the comforts of home while being worlds away.

Guestbook comments from the owner

We thoroughly enjoyed our sailing trip on the Jalapeno! Captain Ray and first mate Jen met or exceeded all of our expectations as the crew. They are doing a great job putting all their experience together and running the business. Clear instructions, great service, good food, respectful behavior, professional yet relaxed environment. We really liked being included in the decision-making. Great information was provided about both sailing and the areas we explored. It was a fantastic vacation.
Jan 2016
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Accommodation and facilities for this holiday yacht rental in St. Thomas, Virgin Islands

Property Type:
  • yacht
  • Catering available
  • Breakfast - Included in Price
  • Lunch - Included in Price
  • Dinner - Booking Possible
House Rules:
  • Max. occupancy: 6
  • children welcome
  • pets not allowed
  • Adventure
  • Away From It All
  • Budget
  • Family
  • Historic
  • Romantic
  • Sports & Activities
  • Tourist Attractions
  • Linens Provided
  • Towels Provided
  • Coffee Maker
  • Dishes & Utensils
  • Kitchen
  • Microwave
  • Oven
  • Pantry Items
  • Refrigerator
  • Stove
  • Toaster
  • Dining
  • Dining Area
  • seating for 6 people
  • 2 Bathrooms
  • Bathroom 2 -
    Bathroom 1 -
  • Each stateroom has its own head.
  • 2 Bedrooms, Sleeps 6
  • Jalapeno offers two staterooms for our guests. The forward cabin is a V berth and the second cabin has a double berth.
  • Books
  • DVD Player
  • Games
  • Music Library
  • Stereo
  • Video Library
  • Boat
  • Kayak / Canoe ...
  • Outdoor Grill
  • Water Sports Gear ...
  • wheelchair inaccessible
Leisure Activities:
  • beachcombing
  • eco tourism
  • photography
  • sight seeing
  • walking
Sports & Adventure Activities:
  • sailing
  • diving
  • swimming
Jalapeno is your home for your cruise and has most every amenity you would have at home. Your itinerary is based on your personalized preferences. In addition to sailing, charters offer swimming, snorkeling, sunning, relaxing, hiking, reading, sight-seeing, napping, eating, and drinking. Your crew can also recommend and arrange additional activities like diving, parasailing, island tours, and other excursions depending on each island's offerings. The Virgin Islands offer a tremendous variety of bays and anchorages to visit. A varied menu will be designed around the food selections on your preference sheet as are the beverages. Guests select which meals to eat aboard and which to eat ashore.


Wonderful! 4.8/5 -
(19 traveller reviews)

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Sailing in the Grenadines 2018/2019
average rating of 4.8421054 based on 30 reviews

Exceeded my expectations

  • 5 of 5

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.

  • Review Submitted: 06/04/2017
  • Date of Stay: March 2017
  • Source: VRBO, from HomeAway
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The boat was very clean, well maintained and more than met our expectations.

  • 4 of 5

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.

  • Review Submitted: 11/12/2016
  • Date of Stay: December 2016
  • Source: VRBO, from HomeAway
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Great time on the Jalapeno

  • 5 of 5

Jalapeno is a well equipped 52' ketch with a knowledgeable husband/ wife team as owner/ operator, both with extensive experience operating in the US and British Virgin Islands. You can't go wrong spending a week or more visiting the many sights in the area.

  • Review Submitted: 19/11/2016
  • Date of Stay: November 2016
  • Source: VRBO, from HomeAway
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  • 5 of 5

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!!!

  • Review Submitted: 21/07/2016
  • Date of Stay: June 2016
  • Source: HomeAway
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Spectacular week aboard Jalapeño!

  • 5 of 5

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!

  • Review Submitted: 11/04/2016
  • Date of Stay: March 2016
  • Source: HomeAway
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Favorite Vacation Ever

  • 5 of 5

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.

  • Review Submitted: 21/02/2016
  • Date of Stay: January 2016
  • Source: VRBO, from HomeAway
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Car: not necessary

Jalapeno offers her guests adventure sailing in the U.S. Virgin Islands, British Virgin Islands, and the Spanish Virgins.


Rates & Availability

Rental Rates for this holiday yacht in St. Thomas, Virgin Islands

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly Event
My Standard Rate
3 night minimum stay
Notes: Rates are based on 2 guests; add AU$101 per night, per additional guest

Additional information about rental rates

Above rates are for 2 people, all breakfasts and lunches included with 1/2 dinners ashore. Please contact us for more options.

Other typical FULL Crew rates:
(Weekly Rates) 1 couple/2 people - 2 couples/4 people - Family of Six
All Dinners Ashore: $6,230 - $7,170 - $8,110
1/2 Dinners: $6,500 - $7,580 - $8,660
All Dinners Aboard: $6,770 - $7,990 - $9,210

Owner's Cancellation Policy

Please ask the owner or check their rental agreement when booking the property.
Contact Owner