Christmas Cove and Pizza Pi Happy Hour Sail Tour

A personal, laid-back cruise combining stunning views, good food, and a relaxed vibe—this is the Christmas Cove and Pizza Pi Happy Hour Sail Tour in St. Thomas. For just $185 per person, you get about three hours of sailing, swimming, and sunset magic, all led by friendly guides in a small group of no more than six travelers. Departing from Red Hook, this trip offers a chance to unwind, enjoy some of the clearest waters in the Virgin Islands, and indulge in what might be the most unique pizza experience afloat.

What we particularly love about this tour is its blend of simplicity and charm. First, the personalized atmosphere created by the small group size means you’re not just one in a crowd, but part of a close-knit adventure. Second, the highlight of ordering pizza from the one-and-only floating pizza restaurant, Pizza Pi, is as fun as it sounds—imagine enjoying hot, delicious pizza while bobbing in calm, turquoise waters.

A possible consideration? The timing is quite specific—3:30 PM departure—and if you’re not an early riser or planning a leisurely day, it might feel a tad rushed to some. Also, since the tour is weather-dependent, rain might alter plans or cloud the sunset, but the crew’s flexibility and refund policy help ease that concern.

This trip is ideal for travelers who appreciate authentic, laid-back experiences—those who want to combine sailing with swimming and a good meal, all in a small-group setting. It’s particularly suited to first-timers, couples, or anyone eager to see stunning sunset views while enjoying a relaxed, social atmosphere.

Key Points

• Small group size creates a more personal experience.
• Swim in crystal-clear waters at Christmas Cove.
• Enjoy fresh pizza from the Virgin Islands’ floating pizza restaurant.
• Sail during sunset for picturesque views and a memorable atmosphere.
• All drinks included—beer, Caribbean Rum Punch, soft drinks, and water.
• Flexible cancellations up to 24 hours in advance.
• Departure from Red Hook makes it convenient for cruise passengers or those staying nearby.
• Expert guides, like Captain Eric and First Mate Casey, make the experience engaging and attentive.

What to Expect on the Christmas Cove and Pizza Pi Happy Hour Sail Tour

If you’ve ever dreamed of a leisurely afternoon filled with sailing, swimming, and sunset views, this tour ticks all those boxes. The experience begins at American Yacht Harbor in Red Hook, where a small, cozy boat awaits. With a maximum of six travelers, you’re not just a face in the crowd but part of an intimate adventure.

The Itinerary in Detail

Departure at 3:30 PM sets the tone for a relaxed afternoon. The captain, along with first mate Casey, makes sure everyone is comfortable right from the start. As you sail away from the harbor, you’ll immediately notice the calm, clear waters of St. Thomas, perfect for unwinding and absorbing the scenery.

The first highlight is arriving at Christmas Cove, a favorite stop thanks to its renowned visibility and tranquil environment. Once anchored, you’ll have plenty of time to swim in the pristine waters—a highlight for many guests. The water quality and ease of access make it perfect for both novice swimmers and seasoned snorkelers.

While anchored, you’ll have the chance to order pizza from Pizza Pi, the Virgin Islands’ only floating pizza restaurant. As noted in reviews, the pizza is delicious and adds a fun, quirky element to the trip. Captain Eric is known for going the extra mile—reviewers mention he even took the dinghy to fetch the pizza, ensuring it arrives hot and fresh.

Drinks and Snacks

The ticket price includes a variety of refreshing drinks—soft drinks, bottled water, beer, and Caribbean Rum Punch—making this a true happy hour on the water. The bar is fully stocked, so whether you prefer a cold beer or a rum cocktail, you’ll find something to suit your taste. The inclusion of drinks adds great value, especially considering the beauty of sipping a cocktail as the sun begins to set.

The Sunset Sail

After enjoying your swim and pizza, the crew will lift the anchor and start heading back to Red Hook. As the boat gently rocks along the shoreline, you’ll be treated to a spectacular sunset. Many reviews mention how beautiful and peaceful this part of the trip is—be sure to have your camera ready.

In the rare event of rain or cloud cover, the trip can still be fun, as one reviewer pointed out that a rainstorm made the experience even more memorable. The crew’s flexibility and attention ensure that even if the sunset isn’t visible, the trip remains enjoyable.

Return Journey

The return sail at sunset brings the tour full circle. With lights twinkling on shore and the quiet hum of the boat under your feet, it’s a perfect ending to a relaxing afternoon. You’ll arrive back at the dock by approximately 6:30 PM, which makes it suitable for those with evening plans or just a desire to wind down.

Why This Tour Is Worth It

When you compare the price to what’s included—sailing, swimming, drinks, and pizza—it offers an excellent value for a memorable experience. The small group setting means you’ll get personalized attention from guides like Captain Eric and Casey, who are praised for their friendliness and attentiveness.

The stunning views during sunset, combined with the chance to swim in clear waters and indulge in delicious pizza, create a balance of relaxation and fun. Reviewers frequently mention how much they enjoyed the casual, fun atmosphere, making it clear this isn’t a formal, over-structured tour, but rather a laid-back experience perfect for those wanting to enjoy the simple pleasures of sailing, swimming, and good company.

Who Should Consider This Tour?

This sail is ideal for travelers seeking a laid-back, intimate experience rather than large cruise ship excursions. It’s perfect for couples, small groups of friends, or solo travelers eager to meet others in a relaxed setting. If you love stunning sunsets, swimming in beautiful waters, and good food in a fun environment, this tour will suit you well.

It’s also a great choice if you want a more authentic taste of Virgin Islands life—a floating pizza, friendly guides, and a peaceful sailing adventure. If you’re short on time but want a well-rounded, enjoyable outing, this three-hour trip hits the sweet spot.

FAQ

How long is the tour?
It lasts approximately 3 hours, from 3:30 PM departure to roughly 6:30 PM return, making it a perfect late afternoon escape.

What’s included in the price?
Your ticket covers alcoholic beverages (beer, Rum Punch), soft drinks, bottled water, and pizza from Pizza Pi. The experience is all about relaxation and fun.

Is there swimming involved?
Yes, you’ll have time to swim in Christmas Cove’s clear waters after anchoring, which many guests find to be a highlight.

What’s the group size?
The tour is limited to a maximum of 6 travelers, ensuring a personalized and relaxed experience.

Can I cancel if my plans change?
Yes, you can cancel free of charge up to 24 hours before the trip, offering flexibility if your schedule shifts.

What if the weather is bad?
The tour requires good weather. If canceled due to weather, you’ll be offered a different date or a full refund. Rain might even add an unexpected layer of fun.

Where does the tour start and end?
It departs from American Yacht Harbor in Red Hook and returns there at the end of the trip.

Is this suitable for non-swimmers?
Yes, since swimming is optional, and the waters in Christmas Cove are calm and easy to access, it’s suitable for most.

Is this a good experience for families?
While designed for small groups, the tour’s relaxed pace and focus on swimming and sunset views make it enjoyable for families with older children.

Final Thoughts

This happy hour sail to Christmas Cove with Pizza Pi is a straightforward yet delightful way to experience St. Thomas from the water, especially if you appreciate a personalized, relaxed atmosphere. You’ll love the beautiful waters, the fun of floating pizza, and the stunning sunset views—perfect ingredients for a memorable afternoon.

The small-group setup allows for genuine interaction with the crew and fellow travelers, which many reviews highlight as a major plus. Whether you’re celebrating a special occasion, seeking a fun family activity, or just want a different perspective on the Virgin Islands, this tour offers a refreshing blend of sailing, swimming, and socializing.

If you’re after a laid-back, intimate experience that combines authentic local flavors with breathtaking scenery, this trip is hard to beat. Just remember to book in advance, as it’s popular—and with good reason.