Experience the Magic of a Caribbean Sunset on the Water

There’s nothing quite like watching the sun dip below the Caribbean horizon from the deck of our sailboat the “Frances Anne”. Our St. Thomas sunset sailing cruise offers the perfect ending to your day in paradise. Departing from the stunning Sapphire Beach on St. Thomas’s east end, you’ll sail the pristine waters between St. Thomas and St. John as the sky transforms into brilliant shades of orange, pink, and purple.

Whether you’re celebrating a special occasion, looking for a romantic experience, or simply want to enjoy the natural beauty of the US Virgin Islands from the best seat possible, our sunset sail provides an intimate and unforgettable way to experience island life. Feel the gentle trade winds, listen to the water against the hull, and watch as the islands are bathed in golden light.

The Sunset Sailing Experience

Departure from Sapphire Beach

Your journey begins at Sapphire Beach, one of St. Thomas’s most beautiful locations. The convenient east-end location offers easy access, ample parking, and stunning views right from shore. Our crew will greet you at the beach and help you board our vessel, ensuring you’re comfortable and ready for your sail.

Sailing the Virgin Islands Waters

As we set sail from Sapphire Beach, you’ll immediately understand why the Virgin Islands are world-renowned for sailing. The protected waters between St. Thomas and St. John offer ideal conditions for a smooth, enjoyable cruise. We’ll position the boat to give you the best possible views of the sunset while you relax and take in the scenery. You might spot sea turtles, dolphins, or rays as we glide through the crystal-clear Caribbean waters.

The Golden Hour

As the sun begins its descent, the entire seascape transforms. The islands of St. Thomas and St. John create a dramatic silhouette against the colorful sky. This is the moment sailors and photographers dream about – when everything is bathed in warm, golden light. Your captain will position the boat perfectly, allowing you to capture photos, enjoy cocktails, or simply soak in the peaceful atmosphere.

Comfort and Hospitality

Throughout your cruise, enjoy complimentary beverages and light refreshments as you relax on deck. Our experienced crew handles all the sailing while you focus on the experience. Whether you want to learn about sailing, hear stories about the islands, or simply enjoy quiet conversation with your group, we create the atmosphere you’re looking for.

Cruise Details

Our Reviews

 
 
 
 
  EXCELLENT  
  
 Based on 134 reviews 
 
 
  
 
 
 
 
 
 
 
 
 
  
 
 
 
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 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 
 
 
 
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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 
 
 
 
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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 
 
 
 
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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 
 
 
 
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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 
 
 
 
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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 
 
 
 
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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 
 
 
 
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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 
 
 
 
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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 
 
 
 
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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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Why Sail with VI Day Sailing?

VI Day Sailing specializes in creating memorable experiences on the water around St. Thomas and St. John. As locals who have spent years exploring these waters, we know exactly where to position the boat for the best views, when the conditions are ideal, and how to make your time on the water special. Our commitment to small groups ensures personalized attention and a more intimate experience than the crowded commercial tours.

Sapphire Beach provides the perfect launching point for our sunset cruises. Unlike departures from Charlotte Amalie or other crowded harbors, Sapphire Beach offers quick access to open water and the beautiful sailing grounds between the islands. You’ll spend more time sailing and less time motoring through harbors.

Perfect for Special Moments

Our St. Thomas sunset sailing cruise creates the ideal setting for romantic evenings, marriage proposals, anniversary celebrations, family gatherings, or simply enjoying one of nature’s most beautiful displays. Many guests tell us their sunset sail was the highlight of their Virgin Islands vacation. There’s something magical about being on the water as day turns to night, surrounded by the natural beauty of the Caribbean.

Book Your Sunset Sailing Cruise

Sunset sails are our most popular offering and fill up quickly, especially during peak season. We recommend booking in advance to secure your preferred date. Whether you’re planning months ahead or looking for availability during your current visit to St. Thomas, we’re here to help make your sunset sailing experience perfect. Ready to sail into the sunset? Book Your Sunset Cruise. Questions about our sunset sails?  Contact us – we’re happy to help you plan the perfect evening on the water.

We can Accommodate Larger Groups – up to 18 People!

Explore More Sailing Options

Looking for a longer adventure? Check out our full day sailing charter or combine the best of both with our full day sail with sunset add-on. We also offer private charters for a truly personalized experience. Learn more about sailing from Sapphire Beach and discover why this location is perfect for exploring the Virgin Islands.

Frequently Asked Questions