Private Day Charter Classic Sailboat

If you’re dreaming of a day cruising the crystal-clear waters of St John aboard a classic 40-foot sailboat, this private day charter could be the highlight of your trip. While we haven’t personally taken this exact tour, reviews and detailed descriptions suggest it offers an authentic, relaxing, and customizable sailing experience.

What we love about this trip is the combination of private exclusivity—just your party and the crew—and the chance to enjoy two snorkeling stops in secluded, beautiful spots. The second is a well-included gourmet lunch, paired with a well-stocked open bar, making it perfect for those seeking both adventure and indulgence.

On the flip side, a point to keep in mind is that this experience requires advance booking—on average, travelers book about 65 days ahead—and it’s priced at $1,395 for up to 6 people. While this might seem steep, the privacy, personalized service, and all-inclusive amenities tend to deliver good value for those wanting a special day on the water.

This tour is best suited for small groups or families looking for a luxury, hassle-free experience. If you’re craving a personalized, scenic, and relaxing day with the option to snorkel, sip, and enjoy gourmet food, this could be your perfect choice.

Key Points

• Private and Intimate: Only your group participates, ensuring personalized attention.
• All-Inclusive Experience: Snorkeling gear, gourmet lunch, drinks, and Wi-Fi included.
• Flexible and Customizable: Two snorkel stops, Sunbathe, and swim at your leisure.
• Convenient Pickup: Pickup offered from the St John ferry terminal.
• Highly Rated: Consistently 5-star reviews reflecting excellent service.
• Great Value for Small Groups: For up to 6 people, it offers a premium experience for a fixed price.

The Itinerary Breakdown: A Day on the Water

Start at Cruz Bay and Transfer to Your Sailboat

Your adventure begins at the Saint John Ferry Terminal in Cruz Bay. From there, a quick boat ride in an inflatable tender takes you out to your private sailboat, docked and ready for the day’s journey. The transfer adds a bit of excitement and sets the tone for an intimate voyage.

Having your own sailboat means you’ll avoid the crowds and enjoy a personalized experience. The boat itself is a classic 40-foot vessel, comfortable with shaded cockpit, fully functional restroom, and WiFi onboard—valuable amenities that contribute to a relaxed and connected day.

Setting Sail and First Snorkeling Spot

Once aboard, you’ll set out toward Cruz Bay. The water views are truly stunning, with the Virgin Islands’ clear, calm waters offering excellent visibility for snorkeling.

The first stop typically involves a snorkel session in a popular yet accessible location. Using provided snorkeling gear, you’ll get close-up views of the vibrant marine life. This is a highlight for many travelers, with reviews emphasizing the quality of the snorkeling spots—“beautiful spots to snorkel” and “accessed only by private boat” are common praise.

Secluded Anchorage Near Honeymoon Beach

After the initial snorkeling, you’ll head to a secluded anchorage off Honeymoon Beach near Caneel Bay. This is the second stop and a favorite among guests. The spot is peaceful, with calm waters perfect for swimming, sunbathing, or simply relaxing on deck.

Guests often mention that this area offers a “beautiful place to swim or sunbathe”, and the seclusion makes it feel like a private paradise. You can take your time here, enjoying the scenery, taking photos, or just soaking up the sun.

Lunch and Libations

The highlight for many is the gourmet lunch included in the price. The menu features 9 deli sandwiches and 5 salads, sourced from the North Shore Deli. Expect fresh, satisfying fare that provides enough fuel for the afternoon’s activities.

Throughout the day, the open bar is stocked with beer, soda, juice, water, and spirits including vodka, rum, gin, and tequila—plus sparkling wine. Reviews praise the “very open bar” and the “expert bartending”, which adds a festive touch to the trip.

Ending the Day

After a relaxed afternoon of snorkeling, sunbathing, and eating, you’ll return to Cruz Bay via the tender. The entire experience lasts between 4 to 5 hours, making it a perfect half-day escape that leaves plenty of time to explore the island or relax afterward.

What Makes This Sailboat Adventure Stand Out?

Personalization and Privacy

Unlike group tours, this private charter ensures your party won’t be mixed with strangers. This allows for a more relaxed, tailored experience. Captain Mike and his crew are lauded for their attentiveness and friendliness—“Captain Mike is the best, thoughtful and attentive”—and their ability to teach sailing or suggest spots suited to your interests.

Quality of the Amenities

From snorkeling gear to WiFi, the sailing experience is designed for comfort and convenience. The fully functional restroom onboard means you don’t need to worry about long waits or roughing it, which can sometimes be a concern on smaller vessels.

Scenery and Marine Life

The Virgin Islands waters boast incredible clarity, and the selected snorkeling spots tend to be lesser-known, giving you a sense of discovery. Travelers mention “beautiful snorkel spots” they wouldn’t have accessed on their own, which adds to the appeal of a private trip.

Food and Drink

The gourmet sandwiches and salads are well-reviewed, with some guests calling the lunch “delicious” and the drinks “top-notch”. The inclusion of both food and drinks in the price simplifies planning and budgeting—no hidden costs or last-minute errands.

Value for Money

While $1,395 might seem high at first glance, it covers a full day of tailored service, gourmet food, snorkeling gear, drinks, and private transportation. For small groups, this can translate into a more affordable and enjoyable alternative to booking separate activities or multiple excursions.

Authentic Experiences and Guest Feedback

Many reviews highlight the personal touch of Captain Mike and crew. One guest noted how Mike even offered to give a sailing lesson, describing it as a “highlight” of their trip. Others appreciated the friendly, knowledgeable staff who made everyone feel comfortable, regardless of sailing experience.

Snorkeling in secluded areas, swimming with dolphins, and the chance to enjoy “a once-in-a-lifetime experience” are common themes. The overall consensus is that this trip offers both adventure and relaxation—a perfect combo for travelers wanting a memorable day on the water.

Practical Details for Your Planning

The tour operates year-round, from early morning until late evening, so you can pick a time that suits your plans. Most travelers book about 65 days in advance, indicating it’s popular among those planning ahead. Pickup is offered from the Saint John ferry terminal, simplifying logistics.

The tour is suitable for most travelers, including those with service animals, and they accommodate weather-related cancellations with full refunds. Remember, cancellations less than 24 hours in advance aren’t refunded, so scheduling carefully is wise.

Who Should Consider This Experience?

If you’re traveling with a small group or family and want a luxurious, private day on the water, this charter offers excellent value. It’s perfect for those who enjoy snorkeling, gourmet food, and a relaxed, scenic sailing experience.

Couples celebrating a special occasion, friends looking for a memorable adventure, or families seeking a comfortable, hassle-free day will find this trip offers a perfect blend of fun and tranquility.

On the other hand, if you prefer large group tours or budget options, this might not be the best fit. But for anyone wanting to enjoy the Virgin Islands in style and comfort, this private sail could easily become the highlight of your trip.

The Sum Up

This private day charter combines the best of St John’s natural beauty with personalized service, comfort, and a touch of luxury. You’ll love the beautiful snorkeling spots, the gourmet lunch, and the friendly crew who make you feel like a guest rather than just a passenger. The privacy means you can relax and enjoy the sea at your pace, making it ideal for small groups seeking an exclusive day on the water.

The experience is well-suited for travelers who value quality, convenience, and authentic marine adventures. While the price is on the higher side, the all-inclusive package and personalized nature make it a worthwhile investment in a memorable day. Whether celebrating or simply escaping the crowds, this trip offers a true taste of Virgin Islands sailing.

FAQ

What is the price of this private sailboat tour?
The tour costs $1,395 for your group of up to 6 people, covering all amenities, lunch, snorkeling gear, and drinks.

How long does the tour last?
The experience takes approximately 4 to 5 hours, offering enough time to snorkel, relax, and enjoy lunch without feeling rushed.

Is pickup included?
Yes, pickup is offered from the Saint John ferry terminal, making it convenient for travelers arriving by ferry.

What is included in the experience?
Snorkeling equipment, gourmet lunch from North Shore Deli, alcoholic beverages (beer, spirits, sparkling wine), WiFi, restroom, and shaded seating are all part of the package.

Are there any restrictions or special considerations?
Most travelers can participate, and service animals are allowed. Cancellations are free if made 24 hours in advance; bad weather might lead to rescheduling or full refunds.

Is this trip suitable for children or non-swimmers?
While specific age restrictions aren’t listed, the snorkeling and swimming stops could be enjoyed by most guests comfortable in water. It’s best to discuss with the provider if you have young children or concerns.

Can I bring my own drinks or food?
No, all food and drinks are included in the tour price, and the open bar features a selection of beverages provided onboard.

In all, if you’re after a private, comfortable, and scenic day on the Virgin Islands, this sailboat experience offers an excellent mix of adventure, leisure, and authentic island charm—an investment in memories you’ll cherish long after your trip ends.