Private Day Charter Classic Sailboat

Imagine spending a beautiful day aboard a 40-foot classic sailboat, gliding through the crystal-clear waters of St John, US Virgin Islands. For around $1,395 per group—up to six of you—you’ll enjoy a private, tailored day of sailing, snorkeling, and lounging. This tour, offered by Morningstar Sailing and Power Charters, is a perfect way to soak up the stunning scenery, warm breezes, and laid-back island vibe, all in a relaxed, personalized setting.

We particularly love that this experience includes gourmet lunch, an open bar with alcohol and soft drinks, and the chance to sail with a knowledgeable captain who genuinely cares about giving you a memorable day. It’s the kind of outing that feels both exclusive and authentic, away from the crowds.

One thing to keep in mind: the price and booking window might be a consideration for some, as it’s booked about 65 days in advance on average, and it’s not cheap. However, for those seeking a luxurious, private day on the water, this tour offers excellent value.

This trip suits travelers who want a personalized adventure, enjoy snorkeling and scenic sailing, and appreciate good food and drinks. It’s especially appealing for families, couples, or small groups looking for a memorable, all-inclusive experience in the Virgin Islands.

Key Points

• Private Custom Experience: Only your group sails, snorkels, and relaxes together.
• All-Inclusive Comfort: Lunch, drinks, snorkeling gear, WiFi, and restroom facilities included.
• Stunning Stops: Snorkel in clear waters and relax at Honeymoon Beach near Caneel Bay.
• Expert Crew: Captain Mike and his team are praised for their attentiveness and friendliness.
• Flexible Schedule: Usually booked 65 days in advance, with a 4-5 hour window.
• Great for Authenticity: Small group size ensures a more genuine, relaxed experience.

An In-Depth Look at the Private Day Sail

When we picture the ideal day on the water in St John, it’s this kind of experience—relaxed, intimate, and packed with natural beauty. The starting point at the Saint John Ferry Terminal in Cruz Bay makes logistical sense, especially if you’re already staying nearby or arriving by ferry. The convenience of pickup is offered, but it’s essential to confirm details beforehand.

The itinerary begins with a short ride in an inflatable tender that takes you from the shore to your sailboat. From there, your adventure unfolds over 4 to 5 hours, during which you’ll cruise along the coast, stopping twice for snorkel sessions and swimming. The first stop often takes you to the waters near Cruz Bay, offering calm, clear conditions perfect for marine life viewing.

The second stop at a secluded anchorage off Honeymoon Beach near Caneel Bay is a highlight. Here, the environment is tranquil—ideal for snorkeling, sunbathing, or just floating in the water. Many reviews mention how special it is to find a quiet spot away from the crowds, and the shallow waters make it perfect for all skill levels. We loved the way this stop balances activity with relaxation, giving you the chance to truly unwind.

What Makes This Experience Stand Out?

Snorkeling equipment is available to all passengers, making it easy to explore the underwater world without bringing your own gear. The Virgin Islands are famous for their visibility and marine diversity, so you’ll likely encounter colorful fish, coral, and maybe even a turtle or two.

The food and drinks are another high point. For lunch, you choose from nine gourmet deli sandwiches and five salads, all supplied by North Shore Deli—delicious, fresh, and satisfying after a morning of swimming. The all-day open bar is well-stocked with beer, soda, juice, water, and a variety of spirits, including vodka, rum, gin, tequila, and sparkling wine. Multiple guests have raved about Captain Mike’s bartending skills, noting how he keeps the drinks flowing and the atmosphere lively.

The onboard amenities include a fully functional restroom and shaded cockpit, essential for comfort on a sunny day. The WiFi on board means you can share your photos in real-time or check in with loved ones back home, adding a modern touch to this otherwise classic sailing adventure.

One review mentioned how Captain Mike even gave a sailing lesson, turning what could be a passive trip into an engaging, educational experience. That personal touch really elevates the trip beyond a mere boat ride—expect attentive service and genuine hospitality.

A Closer Look at the Stops and Activities

The first snorkel stop tends to be in calmer waters, perfect for everyone from novice to experienced snorkelers. The clarity of the Virgin Islands waters ensures vibrant marine life and gorgeous sea views, making it a favorite among guests. As one reviewer said, “Captain Mike is the best, thoughtful and attentive to ensure that we had a great time! He even gave my husband a sailing lesson.”

The second stop at Honeymoon Beach is often described as the highlight, especially because of its seclusion. It’s a peaceful bay with shallow, calm waters—ideal for swimming and sunbathing or simply soaking in the beautiful surroundings. Many guests comment on how rare it is to find such a quiet spot, which makes the experience feel exclusive.

The sailing itself offers excellent views of the Virgin Islands coastlines, and if the wind is right, you might get a chance to help sail or just enjoy the sensation of gliding across the water. Captain Mike’s expertise and friendly demeanor make the sailing part both safe and enjoyable.

Authentic Reviews: What Past Travelers Say

One guest described this as a “once in a lifetime experience,” noting that Captain Mike’s sailing lessons and the chance to swim with dolphins in Scotts Bay made it stand out. Others appreciated the friendly, knowledgeable crew and the way Captain Mike made everyone feel comfortable and included, even offering sailing lessons to interested guests.

Another reviewer called it their favorite activity of the vacation, emphasizing how much they enjoyed the smooth sailing, delicious food, and attentive service. The combination of natural beauty, good company, and excellent hospitality creates a well-rounded, highly memorable day.

Price & Value: Is It Worth It?

At $1,395 for a group of up to six, this experience is not the cheapest option out there. However, considering it’s private, all-inclusive, and lasts several hours, it offers quite good value. You’re paying for exclusive access to beautiful spots, the comfort of a fully equipped boat, gourmet food, and drinks, plus the personalized attention of a skilled captain.

For travelers seeking an intimate, tailored day that combines sailing, snorkeling, good food, and drinks, this trip provides a level of luxury and flexibility hard to match on larger, more generic tours.

Who Will Love This Tour?

This private sail is best suited for small groups, families, or couples who want an authentic, relaxed experience away from crowded boat excursions. If you enjoy snorkeling and swimming in calm waters, appreciate high-quality food and beverages, and prefer personalized service, you’ll find this trip hits the right notes.

It’s also ideal if you’re interested in learning about sailing or enjoying beautiful scenic views with a knowledgeable crew. Just be aware that it’s a premium experience, so budget accordingly.

The Sum Up: Why Choose This Private Sail?

This private day charter offers a luxurious yet authentic way to experience the Virgin Islands. From the friendly crew and sailing lessons to the secluded snorkeling spots and gourmet lunch, it’s designed to make your day on the water memorable and personalized. The all-inclusive drinks and comfort amenities mean you can focus solely on enjoying the moment.

If you’re looking for a small-group adventure that combines natural beauty, good food, and expert guidance, this trip is a standout choice. It’s perfect for anyone wanting to celebrate a special occasion or simply indulge in a carefree day on the water with loved ones.

For those who value authentic experiences, excellent hospitality, and scenic tranquility, this private sail checks all the boxes—and then some.

FAQ

How many people can participate in this tour?
Up to six people can join the private sail, making it ideal for small groups, families, or couples.

What is included in the price?
The cost covers the entire day on the sailboat, including snorkeling equipment, gourmet lunch, alcoholic beverages, soft drinks, WiFi, and restroom facilities.

Is transportation provided?
Not directly. You meet at the Saint John Ferry Terminal in Cruz Bay. Pickup can be arranged, but it’s best to confirm this when booking.

How long does the trip last?
The tour runs approximately 4 to 5 hours, giving enough time for sailing, snorkeling, relaxing, and enjoying lunch.

Are there any age restrictions?
Most travelers can participate, and service animals are allowed. Specific age restrictions aren’t listed, but the relaxed nature suggests it’s suitable for most ages.

Can I help sail or participate actively?
Yes, Captain Mike sometimes offers sailing lessons and encourages guests to get involved, making the experience more interactive.

What if the weather is poor?
The trip requires good weather. If canceled due to weather, you’ll be offered a different date or a full refund.

Is WiFi available on the boat?
Yes, WiFi is provided, allowing you to share your experience or check in online during your trip.

In sum, this private sailing adventure combines personalized service, stunning scenery, and all the comforts needed for a memorable day in the Virgin Islands. Whether celebrating, relaxing, or exploring, it promises a genuinely satisfying way to experience St John’s natural charm.