SPECIAL – (Up to 4 Passengers) All Inclusive Day Sail

A Private Day Sail in St. John: Relaxing, Authentic, and Well-Arranged

Imagine spending a peaceful five hours on the calm waters surrounding St. John in the US Virgin Islands. For up to four passengers, this all-inclusive private sail offers a chance to explore stunning cays, snorkel with sea turtles, and enjoy a gourmet lunch—all in a relaxed, intimate setting. The price is $1,346.67 for your group, which includes everything from fuel to drinks, making it a straightforward and stress-free experience.

What we love most about this trip is the personalized attention provided by the crew—you’re not just another seat on a crowded boat, but part of a small, friendly group. Second, the freedom to choose your stops and the chance to sail on a 40-foot vessel with the opportunity to take the helm are rare delights for sailing enthusiasts or curious first-timers.

One aspect to consider is that towels are not included, so bringing your own might make your day more comfortable. Also, since this is a private tour, it’s best suited for those who value exclusivity and personalized service over larger, more generic group outings. This experience suits travelers who appreciate authentic, laid-back days at sea, especially those keen on snorkeling and enjoying pristine shorelines.

Key Points

• Private Experience: Up to four people, personalized service, no crowds.
• All-Inclusive: Fuel, drinks, lunch, snorkeling gear included—no hidden costs.
• Flexible Itinerary: Stops at protected bays and beaches, with options for snorkeling and swimming.
• Authentic Sailing: Opportunity to sail a 40-foot boat and even take the helm.
• Ideal for Relaxation: Peaceful waters, sunbathing, and stunning scenery.
• Great for Snorkelers: Daily sea turtle sightings and suitable gear for all skill levels.

Discover the Charm of a True Private Sailing Adventure

This all-inclusive day sail from Cruz Bay is designed for those craving a genuine, laid-back experience on the water. With a mere four passengers, the crew can tailor the day to your preferences, whether that involves relaxing in a quiet bay or actively snorkeling among vibrant sea life. The itinerary is thoughtfully optimized so you get a taste of multiple spots, yet leave plenty of time to soak up the sun or try your hand at sailing.

Starting from Cruz Bay allows for easy access to the calm, protected western shoreline of St. John, which is ideal for a gentle, scenic day on the water. The boat, a comfortable 40-foot sailboat, provides a perfect platform for both relaxing and active pursuits. We loved the way the crew carefully balanced the schedule: no rushing, plenty of time for swimming, sunbathing, or just drifting with the breeze.

The Stopovers: Beautiful Bays and Beaches

The first stop usually takes you to a secluded bay on a nearby cay—an ideal spot for snorkeling, swimming, and relaxing. The crew provides all necessary gear and offers instruction if needed, making it accessible whether you’re a seasoned snorkeler or trying it for the first time. One review notes, “Captain Mike was very accommodating and willing to teach the fundamentals of sailing,” which hints at the personalized, friendly environment.

The second stop often involves exploring white sandy beaches—some of the most incredible shoreline you’ll find in the Caribbean. Here, you can enjoy more snorkeling or simply unwind on pristine sands. The experience of swimming with sea turtles daily, as mentioned in reviews, makes snorkeling here particularly memorable. Expect to see vibrant marine life and enjoy the crystal-clear waters.

Gourmet Lunch and Refreshments

The full deli lunch menu, which you select beforehand, is a highlight, offering a gourmet touch to your day at sea. Accompanying this are snacks, soda, juices, and a surprisingly open bar filled with island cocktails and mocktails—perfect for celebrating your day or just cooling down. Bottled water and soda are also included, making hydration easy in the warm Caribbean sun.

The Sailing Experience: More Than Just a Boat Trip

One of the unique features of this tour is the chance for guests to sail the boat themselves—a rare opportunity that adds a touch of adventure and authenticity. Whether you want to steer the vessel or simply enjoy the ride, this feature appeals both to sailing enthusiasts and curious travelers. The crew’s focus on teaching sailing basics, as reflected in reviews, means you might come away with new skills or simply a greater appreciation for this classic sailing craft.

The Experience in Detail: What to Expect and Why It Matters

Ease of Access and Convenience

The pickup option offered helps streamline your day, while the mobile ticket ensures no hassle upon arrival. The activity ends back at the same point, making logistics simple and straightforward. Since it stays within USVI waters, there are no additional customs or immigration fees, which simplifies the day even further.

The Itinerary: A Well-Optimized Schedule

The flexible itinerary ensures you maximize your time on the water without feeling rushed. Starting from Cruz Bay offers excellent opportunities for multiple destinations, including protected bays and pristine beaches. The boat is well suited for calm waters, making snorkeling and swimming more enjoyable, especially for less experienced swimmers.

Authentic, Small-Group Atmosphere

The reviews emphasize the personalized service—Captain Mike and Bridget are praised for their friendliness and local knowledge. The small group size means that your experience is tailored, and you won’t feel lost in a crowd. This setting is perfect for people who value a more intimate connection with their guides and fellow travelers.

Why Travelers Rave About It

One reviewer called it an “experience to remember,” highlighting the captain’s accommodating nature and the chance to see sea turtles while snorkeling. Others appreciated the local expert knowledge and the effort made to ensure everyone had a good time. The attention to detail—like providing snorkeling gear, gourmet lunch, and an open bar—creates an all-around premium experience.

Considerations and Tips

Since towels are not included, pack your own if you plan on spending lots of time in the water. The non-refundable policy means you should confirm weather conditions, but the company offers rescheduling or refunds if cancellations are due to poor weather. Given the small size and private nature, this tour is best suited for those wanting a peaceful, exclusive day rather than a boisterous party cruise.

Why This Tour Offers Real Value

At just over $1,300 for four people—roughly $330 each—this private sail offers remarkable value when considering the inclusions: all fuel, drinks, lunch, snorkeling gear, and personalized service. Compared to larger group tours, the intimacy and flexibility make it worth the investment, especially if you’re celebrating a special occasion or simply prefer a quieter, more authentic day at sea.

The fact that reviews consistently praise the friendly crew, stunning scenery, and delicious food supports the notion that you’re paying for quality, genuine experiences rather than just a boat ride. It’s a chance to enjoy unspoiled nature, learn a bit about sailing, and create memories that feel personal and special.

Who Should Book This Tour?

This sail is ideal for small groups or couples seeking a private, relaxed day on the water. If you enjoy snorkeling, love the idea of a gourmet lunch, or want the chance to try sailing yourself, this is a perfect fit. It’s also suited for travelers who appreciate authentic experiences and want to avoid the crowds typical of larger tours.

Those new to sailing will appreciate the friendly instruction, while seasoned sailors will enjoy the opportunity to take the helm. It’s less suitable for travelers looking for a lively party vibe or those on a strict budget, but for anyone wanting a peaceful, scenic, and well-organized day in the Virgin Islands, this trip delivers.

Frequently Asked Questions

What is included in the price?
All fees, taxes, fuel, alcoholic drinks, bottled water, snacks, and a full gourmet lunch are covered. The use of snorkeling equipment is also included.

Are there any hidden fees?
No, everything listed—fuel, drinks, lunch, taxes—is included in the all-inclusive price. However, gratuities are not included and are at your discretion.

How many people will be on the boat?
Up to four passengers per booking, making it a very intimate experience.

Where does the tour start and end?
It begins at the Saint John Ferry Terminal in Cruz Bay and returns there at the end of the cruise.

Is transportation to the meeting point provided?
Pickup is offered, making it convenient to get to the start point.

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

Can I bring my own towels?
Towels are not provided, so bringing your own is recommended for comfort.

Is this activity suitable for children?
Most travelers can participate; service animals are allowed, and the small group setting is generally family-friendly.

How far in advance should I book?
Since it’s a private tour with limited spots, booking well ahead is advisable to secure your preferred date.

Final Thoughts

This private, all-inclusive sailing adventure in St. John offers a seamless blend of authentic sailing, beautiful scenery, and gourmet highlights like fresh lunch and island cocktails. It’s perfect for those wanting a peaceful day with plenty of snorkeling, a chance to learn sailing, and personalized attention.

The experience is especially suited for travelers valuing small-group intimacy and authenticity over large, touristy cruises. If you’re looking to relax, explore, and enjoy the crystalline waters of the US Virgin Islands in comfort and style, this day sail might just be your perfect match.

Whether celebrating a special occasion or simply escaping the crowds for a day, you’ll leave with a deeper appreciation of the sea, some new skills, and unforgettable views. Just be sure to pack your towel, bring your sense of adventure, and enjoy a day that’s truly tailored to you.