virgin islands
day Sailing

Sunset Cruises & Boat Charters in St Thomas

All-Inclusive

From Drinks, Food, Water Toys – We’ve got You Covered!

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We are an Award Winning, Top-Rated St Thomas Sailing Charter

Experienced Crew

Visit the insider spots and local secrets other tours never find. Welcome aboard!

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Simon Nold profile picture
Simon Nold
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This is perfect for small groups. Kendal was an awesome captain that really gave us a great sailing experience. Full of knowledge of the local area and had great snorkeling spots. Would recommend to anyone who is looking for that smaller intimate sailing experience!
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Jenn Douglas profile picture
Jenn Douglas
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Our sailing trip with Captain Kendall was absolutely unforgettable! ⛵🌊 From the moment we set out, his incredible experience and deep knowledge of sailing made us feel confident and safe on the water. You can immediately tell how passionate he is about the island and about sailing—he shared so many interesting insights that made the entire trip feel like both an adventure and a learning experience. It was my first time sailing, and I’ll admit the waves made me a little nervous at first. But Captain Kendall’s great sense of humor quickly eased my anxiety and had us all laughing and enjoying the ride. His calm confidence made the whole experience even better. One of the highlights was the delicious home-cooked lunch he prepared for us—seriously amazing flavor! 🍽️ And the wildlife sightings were incredible. We saw beautiful, colorful fish and even two baby turtles swimming nearby, which felt like such a special moment. If you’re looking for an authentic, fun, and memorable sailing experience, Captain Kendall is the one to go with. Highly recommend! 🌴🐢
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Jennifer Elkins profile picture
Jennifer Elkins
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BOOK IT!! After our experience I would trust Captain Kendall with my life. Experience beyond comprehension. Good company. Delicious lunch. Great snorkeling spots. Don't miss this opportunity everyone!
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mo gatto profile picture
mo gatto
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Absolutely perfect day spent with Kendal. He was captain, chef, bartender, lifeguard and entertainment. I have no idea how he did all that without ever breaking a sweat! The boat was well equipped with everything needed for a day of sailing, snorkeling, eating and drinking. Kendal is an extremely skilled sailor. He navigated unusual Caribbean winds and weather with ease. Watching him solo the boat ( even picking up the mooring ball while simultaneously controlling the helm and sheets) was nothing short of amazing. He put extra effort into getting us to the best snorkeling locations and to make sure we had a great sail in between. Like I said…an absolutely perfect day.
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V H profile picture
V H
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We looked for the best day trip on the water and found it here. Captain Kendall was a wonderful host, guide, history teacher, cook, beverage server and overall safe keeper for the passengers. Lots of hats! The boat is well equipped and clean. If you’re looking around for a high value excursion, this is for you!
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Marianne Langlois profile picture
Marianne Langlois
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Spend the day sailing with Kendall who has years of experience. He shared the history of the many islands. He took us to private bats for snorkeling and prepared a very filling lunch. Highly recommend if looking for a day trip
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Cari Grundman profile picture
Cari Grundman
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What a great day!! Tommy the captain and Kayla, his first mate, were delightful and so easy to plan our day trip with. They picked us up in the 40’ Beneteau promptly at 9 am. The boat was clean and well maintained. Tommy is knowledgeable and confident at the helm and made even the first time sailor feel right at home! We sailed to 3 blissful coves, Lovongo, Scott and Christmas where anchor was dropped and off we went snorkeling. All equipment was supplied. The locations were picture perfect and empty (due to being off season!) A lunch of grilled chicken, pasta salad and watermelon was provided and plenty of rum punch, painkillers and tequila. Tommy is a wealth of knowledge about the islands, their history, and fun facts. The 6 hr day flew by and we’d definitely book with Tommy and Virgin Island Day Sailing again!!
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Robyn Calhoun profile picture
Robyn Calhoun
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We had the BEST day ever sailing and snorkeling with Kendall. This is our 1st visit to St Thomas and our 1st time to book with VI Day Sailing. We have traveled to many places and taken similar trips but this one was by far the best! Kendall took us to the best spots to snorkel, cooked a delicious lunch and made sure all our needs were met.
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Colleen Wise profile picture
Colleen Wise
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Mark is a great captain and Rusty is a great first mate! They’re both very friendly, accommodating and knowledgeable. The drinks were perfect and the food was delicious. It was really fun to go ocean sailing, I highly recommend it!
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Alan C profile picture
Alan C
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Captain Mark and Rusty did a great job We had a great day of sailing and snorkeling Michelle even got a great video of herself swimming with the turtles. Lunch was absolutely delicious Highly recommend this trip
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