House boat

Sailing the Grenadines and Lesser Antilles 2023/2024

Sailing the Grenadines and Lesser Antilles 2023/2024

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Jalapeno Guests
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Captain Ray
The Baths, BVI
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Overview of Sailing the Grenadines and Lesser Antilles 2023/2024

Reviews
9.8 out of 10 Exceptional
2 bedrooms2 bathroomsSleeps 4

Popular amenities

  • PoolPoolPool
  • Breakfast includedBreakfast includedBreakfast included
  • KitchenKitchenKitchen
  • Barbecue grillBarbecue grillBarbecue grill
  • Ocean viewOcean viewOcean view

Explore the area

Map
St. Thomas
  • Popular LocationSecret Harbour Beach8 min drive
  • Popular LocationSapphire Beach11 min drive
  • Popular LocationCoki Point Beach14 min drive
  • AirportSt. Thomas (STT-Cyril E. King)31 min drive

Rooms & beds

2 bedrooms (sleeps 4)

2 bathrooms

Bathroom 1

Bathroom 2

Spaces

Deck or patio
Porch or lanai
Kitchen
Dining Area

About this property

Sailing the Grenadines and Lesser Antilles 2023/2024

Charter Schedule for 2023-2024:

St. VINCENT and the GRENADINES;
December 2023 to early February 2024:
After a first trip from Grenada to the Grenadines in December, we will be sailing the area of St. Vincent and the Grenadines until early February when we will be heading to St. Lucia.

St. LUCIA and MARTINIQUE;
early February 2024 and late March to late April 2024:
In early February we can squeeze in a St. Lucia and Martinique charter prior to Jalapeno taking a rest at Rodney Bay Marina while the crew is back in the states for a month., We will return in late March for more St. Lucia and Martinique charters until late April.

MARTINIQUE, St. LUCIA, St. VINCENT, the GRENADINES, and GRENADA;
late May to the end of June 2024:
Returning to St. Lucia again in late May, charters will first be in St. Lucia and Martinique, next in St. Vincent and the Grenadines, and finally ending with Grenada at the end of June for out next hurricane season haul-out.

VIRGIN ISLANDS:
Jalapeno is currently hauled-out in Grenada for hurricane season. Our new season started in the Fall of 2023 from Grenada through the Grenadines. We are not planning any sailing in the Virgin Islands this season, but we will be doing charters in lots of great locations throughout the Lesser Antilles.

Contact us for details.

Jalapeno Charters offers personalized sailing vacations in the Virgin Islands, the Grenadines, and the Lesser Antilles island chain 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.

By example when in the BVI 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 can get you doing things ashore.

In the Grenadines we love Bequia for exploring, dining ashore, and a nice anchorage along Princes Margaret Beach. The Tobago Cays Marine Park offer natural beauty with a unique snorkel experience. Salt Whistle Bay on Mayreau is a fun place to visit. And of course a day in remote Chatham Bay on Union Island with a private beach dinner hosted by our friend Shark Bite is a must. A climb to the top of Fort Duvernette at Young Island Cut combines history with a commanding view of the Grenadines.

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!

Property manager

Captain Ray

Amenities

Pool
Breakfast included
Kitchen
Ocean view
Barbecue grill

House Rules

Flexible check-in available (contact host in advance of arrival)
Flexible check-out available (contact host to arrange)

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

No pets allowed

Smoking

Smoking is not permitted

Damage and incidentals

You will be responsible for any damage to the rental property caused by you or your party during your stay.

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit

We should mention

A car is not required for transport to and from this property

About the area

St. Thomas

Located in St. Thomas, this houseboat is on the beach. The area's natural beauty can be seen at Virgin Islands National Park and Secret Harbour 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.
Map
St. Thomas

What's nearby

  • Bolongo Bay - 8 min drive
  • Secret Harbour Beach - 8 min drive
  • Smith Bay Beach - 10 min drive
  • Sapphire Beach - 11 min drive
  • Coki Point Beach - 14 min drive

Getting around

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

Restaurants

  • The Tap & Still - 4 min drive
  • Hook’d - 4 min drive
  • Captain Quin's Rum Bar - 4 min drive
  • Sapphire Beach Bar - 6 min drive
  • Tarpon’s Table - 4 min drive

Frequently asked questions

Does Sailing the Grenadines and Lesser Antilles 2023/2024 have a pool?

Yes, this property has an outdoor pool.

Is Sailing the Grenadines and Lesser Antilles 2023/2024 pet-friendly?

No, pets are not allowed at this property.

Where is Sailing the Grenadines and Lesser Antilles 2023/2024 located?

Nestled on the beach, this St. Thomas houseboat is within 2 mi (3 km) of Nazareth Bay, American Yacht Harbor and Vessup Bay. Beverhout Point and Secret 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.
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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

10/10 Excellent

Tracy C., Nottingham, Pennsylvania

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

10/10 Excellent

James B.

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

10/10 Excellent

C R.

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

10/10 Excellent

John M.

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

10/10 Excellent

Ryan G.

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

About the host

Hosted by Captain Ray

Host profile image
Captain Ray Bryan grew up skiing and hiking the Sierra Nevada Mountains and has been sailing for over 40 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 30 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.

Why they chose this property

Jalapeno Charters offers personalized sailing vacations in the Virgin Islands, the Grenadines, 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 property 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.
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