St John in the US Virgin Islands is a sailor’s paradise. The calm, clear waters and steady trade winds make it an ideal spot for both relaxing days on the water and learning how to sail. Among the many options, two stand out for their quality and unique experiences: a Private Day Charter Classic Sailboat and Learn to Sail – Sailing Lessons All Inclusive. We especially love the private charter for its personalized approach and snorkeling stops, and the sailing lessons for those eager to gain hands-on skills and confidence on the water. If you’re dreaming of a day on a classic sailboat or mastering the art of sailing, these tours offer authentic Caribbean experiences.
Quick Overview
In this guide, we cover two top-rated sailing options in St John. The Private Day Charter Classic Sailboat offers a private, intimate experience with snorkeling, drinks, and a delicious lunch. The Learn to Sail – Sailing Lessons All Inclusive provides a full day of instruction, including swimming, snorkeling, and personalized sailing lessons. Both are rated 5 stars, making them excellent choices for different preferences and levels of activity.
1. Private Day Charter Classic Sailboat
At number one, the Private Day Charter Classic Sailboat is perfect if you want a tailored sailing experience just for your group. For around $1,395 per group (up to 6 people), you get 4 to 5 hours aboard a beautiful 40-foot sailboat. The tour departs from Cruz Bay, where you’ll take a small inflatable tender out to your vessel. Once aboard, you’ll cruise through the Virgin Islands, with the option to snorkel at two different spots in the pristine waters.
What makes this tour stand out is the combination of privacy and flexibility. The captain is attentive, with reviews praising Captain Mike’s thoughtful service and his ability to teach sailing if you’re interested. Many guests love the chance to snorkel in clear waters, with snorkel gear available to all passengers. The boat is stocked with soft drinks, alcoholic beverages, and a included lunch — ideal for a relaxed day in the sun. One guest described it as “a once-in-a-lifetime experience,” highlighting the dolphins and snorkel stops that added to the magic.
This tour is best suited for travelers seeking a private, customizable day on the water with good snorkeling and a laid-back vibe. The intimate size and personal service make it a memorable splurge for celebrating special occasions or just escaping the crowds.
Bottom Line: For a private, all-inclusive day on a classic sailboat with snorkeling and good food, this tour offers excellent value and memorable moments.
2. Learn to Sail – Sailing Lessons All Inclusive
At number two, the Learn to Sail – Sailing Lessons All Inclusive is designed for those who want more than just a boat ride. For approximately $1,395 per group (up to 6), you’ll spend about 5 hours with a dedicated captain teaching you the basics of sailing. This tour is perfect if you’ve ever wanted to understand how a sailboat works or simply enjoy a full day on the water with a hands-on approach.
What makes this experience stand out is its focus on instruction. The captain will guide you through sailing techniques, while also allowing you to relax or swim in the beautiful waters. Snorkeling gear is included, so you can explore the sea life at your leisure. Guests appreciate the personalized attention, especially the ability to learn at your own pace. One reviewer noted, “Captain Mike tailored a great experience for us and was fantastic with our daughter,” emphasizing how well the instructor adapts to different skill levels.
This tour is ideal for curious travelers or families wanting a memorable, educational experience. It suits those who prefer to actively participate rather than just sit back and watch. The inclusive meals and drinks add to the value, making this a full day of fun and learning.
Bottom Line: If you’re eager to learn sailing in a relaxed environment, this tailored lesson offers both instruction and plenty of time for swimming and snorkeling.
How to Choose
When deciding between these two sailing experiences, think about your interests and what kind of day you want. If a private, leisurely day with snorkeling and gourmet lunch sounds perfect, the Private Day Charter Classic Sailboat is a great pick. On the other hand, if you’re curious about sailing and want to gain practical skills, the Learn to Sail – Sailing Lessons All Inclusive offers hands-on instruction and a full day on the water.
Budget-wise, both tours are similar in price, but the private charter offers more exclusivity and customization, while the sailing lessons focus on education and active participation. Booking early is recommended, especially in peak season, to ensure availability.
Consider your fitness level and interest in learning new skills. The private charter is more laid-back, while the sailing lesson requires a bit more engagement. Also, think about the weather — both tours are best during calm, sunny days.
To sum it up, both options give you a true taste of life on the water in St John. For a special celebration or romantic getaway, the private charter delivers intimacy and comfort. For families or adventurous travelers who want to learn something new, the sailing lessons provide a rewarding, memorable experience. Whichever you choose, booking early guarantees a spot on these popular tours. Now, all that’s left is to pick your favorite, pack your swimsuit, and get ready for a fantastic day sailing in the Caribbean.