Docked boat in Caribbean
4 guests · 2 bedrooms · 2 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this docked boat rental
Sail with us for an adventure of a lifetime. See reviews, additional photos, and YouTube video at our VRBO/HomeAway/Expedia listing for the Virgin Islands #3584222.
Charter Schedule for 2025-2026:
St. VINCENT and the GRENADINES;
December 2025 to January 2026:
After a first trip from Grenada to the Grenadines in December, we will be sailing the area of St.Vincent and the Grenadines then heading to St. Lucia.
St. LUCIA to St. MAARTEN;
March 2026 to April 2026:
After Jalapeno takes a rest at Rodney Bay Marina while the crew is back in the states for a month, we will return in March for itineraries along the way from St. Lucia to St. Maarten until April.
St. MAARTEN to the GRENADINES, and GRENADA;
May to June 2026:
Returning to St. Maarten again in May, charters will be along the way south back to
the Grenadines, and finally ending with Grenada in June for out next hurricane season haul-out.
VIRGIN ISLANDS:
Our new season starts in the Fall of 2025 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 Eastern Caribbean.
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!
Charter Schedule for 2025-2026:
St. VINCENT and the GRENADINES;
December 2025 to January 2026:
After a first trip from Grenada to the Grenadines in December, we will be sailing the area of St.Vincent and the Grenadines then heading to St. Lucia.
St. LUCIA to St. MAARTEN;
March 2026 to April 2026:
After Jalapeno takes a rest at Rodney Bay Marina while the crew is back in the states for a month, we will return in March for itineraries along the way from St. Lucia to St. Maarten until April.
St. MAARTEN to the GRENADINES, and GRENADA;
May to June 2026:
Returning to St. Maarten again in May, charters will be along the way south back to
the Grenadines, and finally ending with Grenada in June for out next hurricane season haul-out.
VIRGIN ISLANDS:
Our new season starts in the Fall of 2025 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 Eastern Caribbean.
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!
Map of Caribbean
Ratings and reviews
10 / 10Outstanding·May 2023
We booked this trip almost a year in advance with a stay on Young Island resort surrounding 7 nights on the Jalapeno. We were picked up from the resort and headed directly to Bequia for the first night. Captain Ray and Jenn are excellent hosts and made us feel welcome from the start. The Jalapeno was beautiful and immaculately maintained. They are also excellent chefs, we've never eaten so well! With us being novices at snorkeling, thanks to their expert guidance we've gained the skills and confidence to do it again. They know the area and were the best of guides to it. We felt like we were sailing with old friends from the start and will definitely sail with them again!
10 / 10Outstanding·Jan 2023
We all had an amazing adventure aboard the Jalapeno! Ray and Jennifer were great hosts and very knowledgeable of the area we were exploring. We were able to snorkel in some amazing venues! The boat and equipment were clean and comfortable. Traveling by sailboat was mostly new to us all and we encountered some minor surprises regarding living aboard a sailboat but we fully expected to.
10 / 10Outstanding·Jan 2019
See reviews, additional photos, and YouTube video at our VRBO/HomeAway/Expedia listing for the Virgin Islands #3584222.
$$$$
Top rated by guests
10Outstanding
(3 Ratings)
"We booked this trip almost a year in advance with a stay on Young Island resort surrounding 7 nights on the Jalapeno. We were picked up from the resort and headed directly to Bequia for the first nigh..."
Leslie M.Don't miss out! Price and availability may change
