Sailing the Grenadines and Eastern Caribbean 2025/2026

Photo gallery for Sailing the Grenadines and Eastern Caribbean 2025/2026

A compact kitchen with wooden cabinets, a sink, and a small countertop.
A compact living space with a blue sofa, a wooden side table, and a framed photograph on the wall.
A bed with a floral pillow, a teddy bear, and a black bag.
A sailboat with passengers on deck, surrounded by clear blue water and a forested island in the background.
A sailboat docked near a beach with a house in the background.

Reviews

9.8 out of 10
Exceptional

Popular amenities

  • On beach
  • Patio
  • Outdoor pool
  • Breakfast included
  • Barbecue grill
  • Refrigerator

Explore the area

View in a map
St. Thomas

Rooms & beds

2 bedrooms (sleeps 4)

2 bathrooms

Bathroom 1

Bathroom 2

Spaces

Deck or patio
Porch or lanai
Kitchen
Dining area

Add dates for prices

Similar properties

Interior
Vacation/Sail in Style: Luxurious Catamaran "SeAtitudes" Dream Vacation
Charlotte Amalie
  • Pool
  • Hot tub
  • Breakfast included
  • Kitchen
10.0 out of 10, Exceptional, (39 reviews)
Vacation/Sail in Style: Luxurious Catamaran "SeAtitudes" Dream Vacation

About the area

St. Thomas

Located in St. Thomas, this houseboat is on the beach. The area's natural beauty can be seen at Sapphire Beach and Lindquist Beach. Scuba diving, sailing and swimming offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours nearby.
View more Houseboats in St. ThomasOpens in a new window
Map
St. Thomas

Getting around

  • St. Thomas (SPB-St. Thomas Seaplane Base) - 21 min drive

Restaurants

  • ‪Jimmy Buffett’s Margaritaville - ‬11 min drive
  • ‪Duffy's Love Shack - ‬4 min drive
  • ‪The Ritz-Carlton, St. Thomas - ‬6 min drive
  • ‪Sunset Grille @ Secret Harbour Beach Resort - ‬5 min drive
  • ‪Picaso's Coffee Bar - ‬10 min drive

Frequently asked questions

Does Sailing the Grenadines and Eastern Caribbean 2025/2026 have a pool?

Yes, this property has an outdoor pool.

Is Sailing the Grenadines and Eastern Caribbean 2025/2026 pet-friendly?

No, pets are not allowed at this property.

How much is parking at Sailing the Grenadines and Eastern Caribbean 2025/2026?

On-site parking is available at the property.

Where is Sailing the Grenadines and Eastern Caribbean 2025/2026 located?

Nestled on the beach, this St. Thomas houseboat is 1.1 mi (1.7 km) from Nazareth Bay and 2.4 mi (3.8 km) from Sapphire Beach. Secret Harbour Beach and American Yacht Harbor are also within 2 miles (3 km).

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 23 out of 26 reviews
Rating 8 - Good. 3 out of 26 reviews
Rating 6 - Okay. 0 out of 26 reviews
Rating 4 - Poor. 0 out of 26 reviews
Rating 2 - Terrible. 0 out of 26 reviews

10/10

Cleanliness

9.6/10

Check-in

10/10

Communication

10/10

Location

9.6/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

The Jalapeno was a fantastic vacation opportunity. Would love to go back.

The week we spent on board Jalapeno exceeded our expectations. The boat was very comfortable and the food both tasty and plentiful. Ray and Jennifer are excellent "tour guides" and a lot of fun.
Stayed 7 nights in Jan 2019
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Dream Vacation

We had a fantastic time on Jalapeno. Ray and Jennifer were amazing host and took great care of us. The meals were delish and were never without a drink in hand. We learned so much about the area and they provided an itinerary that was really customized to accommodate everything we wanted to see. My husband learned a ton about sailing and my daughter mastered snorkeling and the SUP with Ray and Jennifers help. If you have a chance to take this vacation, I highly recommend you take it on Jalapeno.
Stayed 7 nights in Jan 2024
Response from VrboOwner on 30 Jan 2024
It was wonderful having the three of you aboard. Maggie was a delight and it was so fun to see her conquer snorkeling and the paddle board so quickly. We will continue to teach Ed more next time! Hope the trip provides good memories throughout the year.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beyond Expectations!

Super Hosts, great boat, and magical places we would have never thought to visit!
Stayed 7 nights in Jan 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Jalapeno May 2021

Our time with Captain Ray and First Mate Jennifer was fantastic. They were a joy to be with and for our first charter trip we were pleasantly surprised at how fun sailing was. Food and service were very good. We were on a short trip of 3 nights but got all we wanted from it. They have many options for anchorage depending on your duration of trip and interests. We had 3 that really fit our desires. First night in Brewer's Bay and morning snorkeling was great. Then it was off to Bucc Island sanctuary where it was just us, 2 Catamaran and the birds. So awesome to go out on deck and night and see the Milky Way and so many stars without all the light pollution of civilization. Then off to St. John and anchor at the National Park with beautiful clear water and semi-private beach. We are tall (over 6 ft) and the main cabin was a wedge shaped bed but it was manageable for our stay. You are definitely ready for sleep by the time you get to that point. Our son stayed in the Port cabin and had his own space and head which was nice. Ray and Jennifer had so much local knowledge which made our time on the boat and afterwards very enjoyable. Would recommend you book a trip on the Jalapeno.
Stayed 3 nights in May 2021
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Trip of a Lifetime

A few friends and I stayed on the Jalepeno for a week with Ray and Jennifer and had a trip of a lifetime. They built us an itinerary the fit our preferences perfectly, cooked us wonderful meals, sailed us to secluded bays and beaches, and showed us the best snorkel and swimming spots. Most importantly, they were a joy to spend a week with. 10/10 vacation — Ray and Jennifer took care of us and we’ll plan to travel again with them in the future.
Stayed 6 nights in Jul 2020
Verified review

10/10 Excellent

Sailing adventure

We had an awesome time!! It was so relaxing! Ray and Jennifer are so nice and always were sure we had everything we needed. I can’t say we won’t be back! Such a fun trip!! 😊
Stayed 5 nights in Mar 2019
Verified review

10/10 Excellent

A Great Taste of the Virgin Islands

We were looking for a sailing vacation in a warm, sunny locale with lots of activity. From the moment I connected ‘live’ with Jalepeno’s Captain Ray, I knew he would help us design a trip we’d enjoy. With his questions to get to know us, briefing documents and preference checklists, I had no doubt we would be well taken care of. The 2nd member of the crew, his first mate Jennifer, made sure our stay on Jalapeño was comfortable and took our interests into consideration at every step. She helped us get used to ‘life on the water’ very quickly. They both know the US and BVI extremely well and guided us effortlessly on land and in the beautiful blue Caribbean.waters telling tales and giving us a few history lessons at every island.
Stayed 5 nights in Dec 2018
Verified review

10/10 Excellent

Awesome sailing vacation

A week aboard Jalapeno is a trip of a lifetime – and my family and I have been fortunate to have sailed on her twice! It is difficult to put into words what a wonderful experience sailing the islands is. To be on the water, smelling the salt air, feeling the sun on your face, and enjoying a breeze is a feeling that can’t be topped. We were able to visit beaches that wouldn’t be accessible without a boat. We were able to enjoy the best meals prepared by welcoming locals that we would have never know about since they are off the beaten path. We were able to learn sailing basics and, if we wanted, help with some of the sailing duties. Both trips Ray and Jennifer were the ultimate hosts. They planned the itinerary around our interests – from snorkeling, to exploring the islands, to relaxing on the beach. Delicious onboard meals were prepared according to our likes and dislikes, all the while being able to try new delicacies only the islands were able to offer. Our comfort and enjoyment were their number one priority! Even though we just returned from our sailing vacation, my family and I are already planning, and very much looking forward to, our next trip onboard Jalapeno with Ray and Jennifer!
Stayed 7 nights in Jun 2018
Verified review

10/10 Excellent

Advenventurous & Relaxing - All in One Trip

Nothing like ripping along at 8+ knots with all the sails out. Then dropping the sails and anchoring off a bright white, sandy beach with crystal clear turquoise blue waters lapping the shore. Ray & Jen are great hosts and know all the awesome spots to visit in the Windward Islands (Martinique, St. Lucia, St. Vincent, Bequia Island, Union Island, Tobago Cays, etc.). They're great hosts and their boat was amazingly comfortable.
Stayed 15 nights in May 2018
Archival

10/10 Excellent

Exceeded my expectations

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.
Stayed 8 nights in Mar 2017
Archival

8/10 Good

The boat was very clean, well maintained and more than met our expectations.

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.
Stayed 3 nights in Dec 2016
Archival

10/10 Excellent

Great time on the Jalapeno

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.
Stayed 10 nights in Nov 2016
Archival

10/10 Excellent

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!!!
Archival

10/10 Excellent

Spectacular week aboard Jalapeño!

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!
Archival

10/10 Excellent

Favorite Vacation Ever

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.
Archival

10/10 Excellent

The Best Vacation Ever

"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!
Archival

10/10 Excellent

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!
Stayed 8 nights in Nov 2015
Archival

10/10 Excellent

Sailing adventure with no worries

Captain Ray and the First Lady provide a relaxing, safe sailing adventure. They have thought of everything in terms of their guests comforts and preferences. The forms provided before sailing cover all necessary subjects and help them to provide you with the kind of trip you prefer. Jalepeno is a beautiful boat, and kept in pristine condition. Captain Ray makes sailing look easy, and is a calm presence. We ate two meals a day on the boat, and each meal was different, very tasty, and a nice blend of flavors and textures. The shore restaurant recommendations were "spot-on". Captain Ray has an intimate knowledge of the BVI, and his telling of the history and lore is very entertaining. It was a delightful week and one we would highly recommend to others.
Archival

10/10 Excellent

Amazing Family Vacation!

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). Highly recommend!
Archival

10/10 Excellent

AMAZING...a great adventure!

We had a GREAT time...well beyond my expectations! Ray and Jennifer took into account everyone's wants and needs and did a great job of making the trip interesting, fun and safe! We had a wide variety of ages on our trip and all were accommodated very well! The boat was extremely well cared for and comfortable. I felt completely safe...could just relax and have a great time sailing, snorkeling and having a couple of "Painkiller" cocktails! (A favorite on our trip!) It was a great experience that I would recommend to anyone interested in sailing!
Archival

10/10 Excellent

Absolutely great.

It was everything I expected, and more, especially the knowledge and insight Capt. Ray shared while sailing. And the onboard food was outstanding. Best breakfast ever. Would I recommend this vacation to a friend? Indeed I would, and as a matter of fact, I already have. Would I take the adventure again? Hard questions to answer. It's like wanting to climb Mt. Everest. Once you reach the summit you begin to think of other challenges, likes sailing from the West Coast to Hawaii.
Archival

8/10 Good

A sailing adventure to remember

We were very well taken care of by Captain Ray and his wife and first mate Jennifer. The boat was clean and the accommodations were comfortable. I drifted off to sleep each night to the gentle rocking of the boat and the warm breezes coming in through the hatch. We were joined by our friends on the trip, and were able to enjoy stops and moorings at many wonderful Islands. Ray adjusted the itinerary to our wishes. We especially enjoyed the sailing, snorkeling(me in particular) the food and of course the comradery, and fun that eight days on a boat engenders.
Archival

10/10 Excellent

A wonderful experience - highly recommended

Our family of four (myself, my husband, and two college age kids) had a wonderful four day trip on the Jalepeno. Ray and Jennifer were extremely welcoming and a pleasure to spend time with. We chose to focus on sailing, snorkeling, swimming and relaxing, but Ray and Jennifer will facilitate whatever else you want to do as well. We would highly recommend an expedition on the Jalepeno and would love to go back some day for a longer trip.
Archival

10/10 Excellent

Amazing!

My husband, daughter and I recently completed a trip I’ve been dreaming of for 30 years and planning for two years. We met Ray, Jen, and Jalapeno in St. Thomas and had a 16 day adventure to the Leeward Islands, including stops at St. John (US Virgins), St. Kitts, Nevis, Montserrat, Antigua, St. Barts, Anguilla, and Virgin Gordon and Tortola (British Virgins). Our sailing conditions included long passages with little wind, nice wind, and more than enough wind! We encountered rough, sloppy seas, broken boat parts, and engine troubles. Through it all, Ray and Jen maintained unfailing good humor and accommodated our every need and want. We had great drinks and meals, even if it required Jen setting the toaster up in the floor of the cockpit to keep it from flying around. We had an awesome, day-long celebration for our daughter, who turned 21 on the trip, completely with mimosas to start the day and homemade birthday cake to end it. Ray and Jen joined us for many land adventures and gave us recommendations for several others that we enjoyed on our own. When our plans for activities one day didn’t work out as expected, Ray jumped to the rescue and cleared customs for us to visit some unplanned harbors, replacing frustration with delight for all. Ray was a gracious escort for several adventures – star gazing, scuba diving, dinner at Dune Preserve to see Bankie Banks, a late night dinghy ride back to the boat at Cane Garden Bay, and a hike to the top of the hill overlooking Colombier. This was our second charter on Jalapeno, and the boat was, as always, well equipped and spacious. When Ray and Jen didn’t join us for land excursions, it was because they stayed behind to do maintenance, food prep and cleaning to ensure that everything was in top condition for us. We were spoiled rotten the entire trip! We made family and friendship memories to last a lifetime. I have tears in my eyes as I write this – tears of sadness that our trip is over and tears of joy at the wonderful reminiscences. Thank you Ray and Jen.
Archival

10/10 Excellent

Sailing Nirvana

We wanted a unique sail, combining the benefit of experienced crew and personalized attention. What we received exceeded all expectations. From the raucous nightlife of Willie T's, to the edge-of-the-world feeling approaching Anegada for a Christmas Eve feast of lobster, every day was more amazing than the last. After relaying to Ray the desire for an informal ceremony "at some point" along the trip, he adjusted the itinerary to include an early morning stop at the tiny island of Sandy Spit. Who knew he and Jennifer were consummate wedding planners along with all of their other skills. After thoughtful words from Ray and exchanging of vows, we enjoyed the surprise of champagne and fluted glasses, smuggled aboard the dinghy by Jennifer. It was the perfect spontaneous moment to remember for a lifetime. Of course, the food was wonderful and we were always well-supplied with a variety of tasty drinks. Bloody Mary's are now ruined for me, because no other bartender can measure up to Ray's concoctions. At the end of the trip, we were sad to leave not only the Islands, but our 2 newest friends. I have a feeling we will be back for an anniversary!
Tell us how we can improve our siteShare feedback