Private Day Charter Classic Sailboat

Planning a day on the water in St John? A lot of travelers opt for tours that combine stunning scenery, good food, and a touch of adventure. But for those seeking a completely personalized experience, the Private Day Charter Classic Sailboat by Morningstar Sailing offers an intimate, luxe escape that ticks all the boxes.

This private excursion is highly rated, with an almost perfect 5-star score from 69 reviews, and it gets recommended 100% by past guests. The trip promises a smooth, relaxing sail with snorkeling stops, a gourmet lunch, and an open bar — all for a flat fee that covers your entire party of up to six. So, what makes this tour stand out? We love the private setting, the quality of the inclusions, and the friendly, knowledgeable crew.

One thing to keep in mind is that this experience is most suited for those who want a leisurely, customizable day on the water. It might not appeal to travelers looking for a large group or a more structured, guided tour. But if you value exclusivity, comfort, and great service, this private charter could be your ideal Caribbean adventure.

Good To Know

• Private Experience: Perfect for intimate groups or special occasions.
• All-Inclusive: Gourmet lunch, open bar, snorkeling gear, WiFi, and restroom on board.
• Flexible Itinerary: Enjoy stops at Cruz Bay and Honeymoon Beach for snorkeling and swimming.
• Professional Crew: Captain Mike and his team are praised for their attentiveness and expertise.
• Great Value: The flat rate of $1,395 covers up to six guests, making it an economical choice per person.
• Highly Booked in Advance: On average, booked 65 days ahead, so plan early.

👉 See our pick of the 11 Best Tours In St John

Why Choose the Private Day Charter Classic Sailboat?

This tour offers more than just sailing; it’s about crafted moments on the water. Past guests raved about Captain Mike’s thoughtful service and his knack for making everyone feel at ease. His relaxed approach combined with his sailing skills creates a safe, fun environment — whether you’re trying sailing for the first time or just want a peaceful day floating and soaking up the sun.

What makes this experience stand out is the personalized touch. With only your party on board, you get tailored attention and the freedom to customize your day. Whether that means lingering longer at the snorkeling spots or enjoying extra time sunbathing on deck, this trip adapts to your mood.

The Itinerary Explained

Starting Point and Transport:
Your adventure begins at the Saint John Ferry Terminal in Cruz Bay, a convenient location easily accessible by ferry or private transport. From there, you’ll be taken out to the sailboat via an inflatable tender — a fun, close-up prelude to your day on the water.

Sailing to Cruz Bay:
Once aboard the 40-foot sailboat, you’ll set sail toward Cruz Bay, enjoying the breeze and panoramic views of the Virgin Islands. The boat features a shaded cockpit and a fully functional restroom, ensuring comfort throughout the trip.

First Snorkel Stop:
Your first snorkeling spot offers a chance to explore the vibrant marine life of the Virgin Islands. All snorkeling equipment is provided, so even beginners can enjoy the clear waters. Past guests have appreciated the quality of the gear and the ease of access to these prime spots.

Honeymoon Beach Anchorage:
The second stop is a secluded anchorage near Caneel Bay, known for its pristine shoreline and calm waters. Here, you’ll have time to snorkel some more, swim, or just relax on deck. Multiple reviews highlight how this spot offers a peaceful, less crowded environment to unwind.

Return and Reflection:
After a few hours of sailing, snorkeling, and sunbathing, you’ll head back to Cruz Bay, with the option to relax with a beverage or take photos of the stunning scenery. The experience usually lasts about 4 to 5 hours—just enough time to enjoy everything without feeling rushed.

Food, Drinks, and Extras

Gourmet Lunch:
A standout feature of this tour is the included lunch, featuring nine gourmet deli sandwiches and five salads, all from North Shore Deli. Guests love the quality and variety, making it a satisfying break during your day at sea.

Open Bar:
The “Very Open Bar” includes beer, soda, juice, water, and a selection of spirits like vodka, rum, gin, and tequila. Guests frequently mention the relaxed, friendly atmosphere created by the crew’s bartending skills and the impressive drink selection, which elevates the whole experience.

Snorkeling Equipment & WiFi:
All snorkeling gear is provided and easy to use. Plus, free WiFi on board lets you share your adventures in real-time or check in with loved ones.

Comfort & Convenience:
The boat’s shaded cockpit and restroom facilities ensure comfort, especially in the Caribbean sun. The crew’s attentive service helps ensure everyone’s needs are met, whether it’s a quick drink or some extra snorkel time.

Authentic Experiences & Guest Insights

Guests consistently mention Captain Mike’s thoughtful approach — from giving a sailing lesson to sharing local knowledge. Diane_I noted that Captain Mike was “thoughtful and attentive,” making their trip memorable. Andrew_M appreciated how the crew took them to snorkeling spots they couldn’t access on their own, adding a sense of discovery.

Another reviewer, Thomas_H, described the experience as “once in a lifetime,” especially mentioning swimming with dolphins in Scotts Bay, which showcases how flexible and personalized the trip can be. Past guests also love that the trip is private, making it ideal for families, couples, or small groups celebrating special occasions.

Pricing & Value

At $1,395 for up to 6 guests, this private charter breaks down to roughly $232 per person — an excellent value considering the exclusivity, gourmet lunch, open bar, and all snorkeling equipment included. Plus, with the trip lasting around four to five hours, you’re getting a significant amount of quality time on the water.

Compared to larger, more generic tours, the private aspect means you control your schedule and destinations, making it worth the premium price for many travelers. The positive reviews consistently highlight the high standard of service and the memorable moments created.

Who Would Love This Tour?

This experience is ideal for those seeking a luxurious, private day out with friends or family in St John. It’s perfect for celebrating special occasions, such as honeymoons, anniversaries, or simply a desire for a calm, personalized escape. Travelers who value good food, quality drinks, and the chance to snorkel in less crowded spots will find this tour hits the mark.

It’s also suited for first-time sailors thanks to Captain Mike’s friendly teaching style. But if you’re after a lively party atmosphere or large group experience, this might not be the best fit.

Final Thoughts

The Private Day Charter Classic Sailboat in St John offers a beautifully curated day on the water, blending relaxation, adventure, and personalized service. The combination of gourmet food, excellent drinks, and scenic snorkeling stops makes it a standout choice for travelers who want to make the most of their Caribbean time without feeling rushed or crowded.

The focus on comfort, quality, and a flexible itinerary ensures you’ll leave with fantastic memories. Whether celebrating a special occasion or simply looking for a peaceful day on the sea, this tour delivers a memorable, tailored experience that genuinely feels worth the investment.

FAQs

Is transportation included?
No, private transportation to the meeting point at Saint John Ferry Terminal is not included, but the terminal is accessible via public transit or taxi.

What is the group size?
The private charter accommodates up to 6 guests, making it ideal for small groups, families, or couples wanting exclusivity.

How long does the trip last?
The experience runs approximately 4 to 5 hours, giving plenty of time for sailing, snorkeling, and relaxing.

Is snorkeling equipment provided?
Yes, snorkeling gear is included and ready for use at each snorkeling stop.

Can I bring my own drinks or food?
The tour provides a gourmet lunch and an open bar, so bringing additional food or beverages isn’t necessary. However, check with the provider if you have specific needs.

Is this tour suitable for children?
Most travelers can participate, and kids who enjoy water activities will love the snorkeling and sailing.

What if the weather is bad?
The experience is weather-dependent, and if canceled due to poor conditions, you’ll be offered a different date or a full refund.

Are service animals allowed?
Yes, service animals are permitted on board.

How far in advance should I book?
On average, this tour is booked about 65 days ahead, so planning early is recommended to secure your preferred date.

In essence, if you’re after a private, laid-back sailing day with excellent food, drinks, and snorkeling, this charter in St John might just be your perfect Caribbean escape.