Private Day Charter Classic Sailboat

Looking to add a touch of elegance and adventure to your trip to the US Virgin Islands? This Private Day Charter on a classic sailboat offers an intimate, all-inclusive experience that promises the kind of relaxed luxury you’ll remember long after your trip ends. It’s tailored for small groups—up to six people—who want to sail, snorkel, and enjoy gourmet food in the company of friendly, knowledgeable crew.

What we love about this experience is the chance to escape the crowds on a private boat with personalized service, and the opportunity to visit some of the most beautiful snorkeling spots around Cruz Bay and Honeymoon Beach. The inclusive lunch and open bar add real value, turning what could be a simple boat ride into a full-day indulgence. The only potential drawback? The price tag of $1,395 for up to six guests might seem steep, but for the quality, intimacy, and unique access, it’s a fair investment—especially if celebrating a special occasion or seeking a memorable family outing.

This tour suits travelers who appreciate comfort, want to avoid large tour groups, and are eager to explore the Virgin Islands’ waters with a professional crew. It’s perfect for celebrating a special day, enjoying a romantic escape, or simply wanting to experience the islands in a relaxed, authentic way.

Key Points

Personalized experience: Small groups and private charter mean you set the pace and enjoy dedicated attention.
All-inclusive value: Gourmet lunch, open bar, snorkeling gear, WiFi, and restroom access are included—no hidden costs.
Beautiful itinerary: Snorkel stops near Honeymoon Beach and Caneel Bay offer pristine water and quiet hideaways.
Expert crew: Captain Mike and his team provide safety, local knowledge, and a few sailing lessons if you’re interested.
Comfort and convenience: Pickup from the cruise terminal or other locations, shaded cockpit, and onboard restroom make for a comfortable day.
Highly rated: With a perfect 5.0 rating from 69 reviews and 100% recommendation, this experience clearly delights past guests.

Contents

• Key Points
• The Itinerary and What to Expect
• Why This Experience Delivers Value
• Who Will Love This Tour?
• Final Thoughts
• FAQ
• Our Top Picks in St John
• More Private Tours in St John
• More Boat Tours & Cruises in St John
• More Tour Reviews in St John
• Not for you? Here's more things to do in St John we have recnetly reviewed

The Itinerary and What to Expect

Starting from the Saint John Ferry Terminal in Cruz Bay, your day kicks off with a short transfer to the boat via inflatable tender, setting the scene for an effortless transition onto the water. The 40-foot sailboat is spacious enough for comfort, featuring a shaded cockpit and onboard restroom, so you won’t feel cramped or uncomfortable during your cruise.

The first stop is a bit of sailing, offering a chance to relax and enjoy the breeze. As you cruise out into the Virgin Islands, your crew will serve soft drinks and alcoholic beverages—think beer, soda, juice, sparkling wine, and even some spirits like vodka, rum, and gin. Many reviews highlight how Captain Mike mixes drinks skillfully and keeps the atmosphere lively yet laidback. One guest even remarked, “Mike is the best, thoughtful and attentive to ensure we had a great time. He even gave my husband a sailing lesson,” making it clear that this experience offers more than just sightseeing.

The first snorkeling spot is typically an accessible, beautiful area with clear waters—perfect for beginners or those looking to explore underwater life. Guests can use the provided snorkeling gear to see colorful fish, coral, and perhaps even a turtle or two. As one reviewer put it, “He took us to a couple of fun snorkeling spots that we could not have accessed otherwise,” emphasizing the exclusivity of these hidden gems.

The second stop is a secluded anchorage off Honeymoon Beach near Caneel Bay. Here, you can swim, sunbathe, or simply relax on deck with a drink in hand. It’s a peaceful setting that feels a world away from the busy cruise ships, and many guests describe this as the highlight of their day. “A rare experience to swim with dolphins in Scotts Bay,” one reviewer exclaimed, highlighting how flexible and personalized this tour can be.

Lunch is a true treat, featuring gourmet deli sandwiches and salads prepared in collaboration with North Shore Deli. The menu includes 9 different sandwiches and 5 salads, catering to various tastes and dietary preferences. Guests rave about the quality, describing it as “delicious, fresh, and satisfying,” perfect for fueling the rest of your day on the water.

Throughout the trip, WiFi on board adds a modern touch, allowing you to share your experiences or catch up on messages—if you want to. The crew’s friendly attitude, combined with their local knowledge and sailing skills, creates a relaxed atmosphere that makes everyone feel at home.

Why This Experience Delivers Value

At $1,395 for up to six guests, this private charter packs a lot of value. You’re paying for exclusivity, personalized service, and access to some of the Virgin Islands’ best snorkeling spots—something that larger group tours often can’t match. The all-inclusive nature means stress-free enjoyment: gourmet lunch, drinks, snorkeling gear, WiFi, and on-board facilities are all covered.

Guests consistently mention the professionalism and friendliness of Captain Mike and his crew. One comment read, “He is so experienced, safe, informative, and really communicates what he needs from you as a passenger clearly,” which hints at the calm confidence you want when sailing in unfamiliar waters. Their local expertise ensures you’re likely to visit spots that are both beautiful and less crowded.

The flexibility of the tour’s schedule offers good value. It runs from morning into the evening, with the ability to reschedule if weather conditions aren’t ideal—something many travelers appreciate. And since this is a private experience, your group can customize parts of the day, whether that’s spending more time snorkeling or relaxing on deck.

Who Will Love This Tour?

This private sailboat experience is best suited for travelers seeking a more intimate, personalized adventure. Families, couples, or small groups looking to celebrate a special occasion will find it perfect. It’s also ideal for those wanting to learn about sailing or enjoy a laid-back day on the water with quality food and drinks.

If you’re a water lover, the snorkeling stops offer a real bonus, especially given the reviews praising the visibility and access to spots that are otherwise hard to reach. Those who enjoy good wine and cocktails will appreciate the “very open bar” and the opportunity to sample local spirits as you cruise along.

However, if your group prefers a quick, budget-friendly, large-group tour, this might not be the best fit. It’s an experience designed for comfort, quality, and exclusivity—worth considering if you’re after a memorable, luxury day on the water.

Final Thoughts

If you’re after a relaxed, luxurious day on the water with personalized service and stunning views, this private day sail in St John offers tremendous value. The combination of beautiful scenery, excellent snorkeling, gourmet lunch, and a friendly crew makes it more than just a boat ride—it’s an experience that captures the essence of the Virgin Islands’ charm.

The thoughtful details, like WiFi and onboard restroom, show how much the crew cares about your comfort. The reviews confirm that this tour delivers on its promises—friendly hosts, beautiful locations, and memorable moments. For those wanting to escape the crowds and enjoy a tailored adventure in paradise, this sailboat experience is a top choice.

FAQ

What is included in the tour?
The tour covers the sailing, snorkeling, and sunbathing along with a gourmet lunch, alcoholic beverages, snorkeling equipment, WiFi, and access to a restroom on board.

How many people can join?
This is a private charter for up to six guests, ensuring a personalized experience.

Where does the tour start and end?
It begins at the Saint John Ferry Terminal in Cruz Bay and concludes back at the meeting point.

Is transportation provided?
Pickup is offered from the ferry terminal or other locations, but private transportation is not included.

What should I bring?
Bring swimsuits, sunscreen, sunglasses, and any personal items you might need. The boat provides snorkeling gear and drinks.

What is the typical duration?
Expect about 4 to 5 hours for the entire experience, offering plenty of time to snorkel, relax, and enjoy the scenery.

Can the schedule be changed?
Yes, the tour runs daily from morning to evening, with flexibility for rescheduling due to weather conditions. Cancellations are free if made at least 24 hours in advance.

This private sailing adventure offers a chance to see the Virgin Islands in comfort and style, with enough flexibility and personalized touches to make your day truly special. Whether you’re celebrating or simply seeking a peaceful day on the water, it’s a well-reviewed, highly-rated option worth considering.