Sunset Sail Cruise in Key West

If you’re looking for a way to soak up the beauty of Key West from the water without the fuss of high-end luxury or crowded boats, the Sunset Sail Cruise on the Jolly II Rover might just be your perfect match. This 2-hour voyage offers a slower-paced, genuine feel of the island’s coastline, with the added bonus of sailing aboard a vintage square-rigged schooner. It’s an experience that balances scenic views, a relaxed vibe, and a touch of nautical history.

What we love about this cruise is its intimate setting and the chance to really take in Key West’s stunning shoreline. The fact that it’s the only schooner in the area with this traditional rigging adds a dash of maritime character. Plus, the tour’s straightforward pricing and inclusive snacks make it accessible and easy to enjoy without worrying about hidden costs. One possible consideration is that the cruise doesn’t serve alcohol or sodas, so if you’re hoping for a full bar experience, you might want to look elsewhere.

This cruise is best suited for travelers who appreciate authentic boat experiences, enjoy scenic sunsets, and prefer a laid-back atmosphere. Families, couples, or small groups looking for a memorable way to end a day in Key West will find this trip particularly appealing. If you’re after a lively party or a large crowd on deck, this might not be the right fit—think of it more as a quiet, friendly escape.

Key Points

• A 2-hour sunset sailing on the vintage Jolly II Rover schooner
• Offers scenic views of Key West’s waterfront including Fort Taylor and Christmas Tree Island
• Smaller group size for an intimate, relaxed experience
• Includes tasty snacks, ice-cold water, and cups—no alcohol or soda
• Highly rated for authenticity, friendly crew, and beautiful scenery
• Easy booking, with most travelers reserving about two weeks in advance

An In-Depth Look at the Sunset Sail Cruise

This tour begins at the historic Seaport, located at Elizabeth and Greene streets—an area filled with the charm of old Key West. Boarding the Jolly II Rover, a vintage square-rigged schooner with striking red sails, immediately signals a step back into maritime tradition. Unlike modern speedboats or luxury yachts, this vessel invites you to slow down and enjoy the crew’s friendly, genuine hospitality.

The itinerary is designed to showcase some of Key West’s most iconic sights from the water. You’ll cruise past the bustling Man O War Harbor, where military and commercial ships come and go. The nearby Christmas Tree Island, a small, lush patch of land, offers a quiet contrast to the busy harbor. As the boat glides along, you’ll also pass by the historic mansions on Sunset Key, giving a glimpse of the island’s wealthier past, then view Mallory Square from a unique vantage point—an excellent photo opportunity.

The cruise continues past Fort Taylor, the Civil War-era fort that protected the waterfront, and the nearby state park. Once beyond the land, the schooner heads into the open Atlantic, where the true highlight awaits: the sunset itself. According to reviews, the timing and tranquility of this voyage reward you with a peaceful, picture-perfect moment when the sun slips below the horizon.

What’s included? Snacks and on-board coolers with ice, bottled water, and cups help you stay refreshed. The lack of alcohol or soda might be a slight disappointment for those expecting a festive toast, but in practice, the relaxed pace and scenic views more than compensate.

The crew earns high praise for their friendliness and knowledge. Several reviews mention the crew firing cannons and sharing stories, adding a fun, interactive element. Some guests even spotted dolphins putting on a show, a bonus that elevates the experience beyond just watching the sunset.

Group size is capped at around 41 travelers, but most reviews describe a small, intimate feel—often with fewer than 20 guests. This allows for better interaction with the crew and a more personal, relaxed atmosphere.

The Experience from Start to Finish

Departure and boarding are straightforward, with easy access from the historic seaport. Arriving a little early ensures you get a good spot and settle in comfortably. The boat’s vintage charm is immediately apparent as you step aboard; the red sails and traditional rig evoke a sense of maritime history that’s rare in the Caribbean scene.

Once underway, the crew’s storytelling and cannon firings become highlights. Many reviews note that the crew is engaging, sharing local lore, and making the cruise feel like a shared adventure. Plus, the optional extras—like firing cannons—add a sense of fun and history, making it more than just a sightseeing trip.

The scenery is the star of the show. As you glide past the shoreline landmarks, you’ll get a new perspective on familiar sights. The gentle motion of the boat, combined with the calming sea breeze and stunning sunset, creates an atmosphere perfect for unwinding.

Snacks and drinks are simple but sufficient. Pack a light sweater or jacket, especially if you tend to get chilly on the water in the evening. The coolers are stocked with plenty of water and cups, but if you want a more adult beverage experience, plan to bring your own, as alcohol isn’t included or sold on board.

The final moments of the cruise, as the sun dips into the ocean, deliver what many describe as a quiet, almost spiritual moment. Some reviewers mention the silence as the sun slips away, providing a peaceful break from the busier daytime activities in Key West.

Pricing and Value

At $95 per person, this cruise falls into the moderate price range for sunset sails in Key West. Considering it lasts about two hours and includes snacks, it offers good value—especially given the intimate setting on a vintage schooner. The reviews consistently mention the experience as worth the price, emphasizing the quality of the views and the friendliness of the crew.

Unlike larger, more commercial tours that can feel hurried or crowded, this trip’s smaller group size and relaxed pace make it feel more personal. The inclusion of snacks and water also simplifies the experience—no need to carry extra supplies.

Final Thoughts

If you’re after a laid-back, authentic way to enjoy a Key West sunset, this cruise is an excellent choice. The combination of a vintage schooner, scenic landmarks, and a friendly crew creates a memorable experience that’s both relaxing and visually stunning.

It’s particularly well-suited for small groups, couples, or families who appreciate history and quiet beauty. If you’re traveling solo, you’ll find a welcoming atmosphere—many reviews mention how friendly and genuine the staff are.

While it doesn’t include alcohol or music, the sense of space, the chance to chat with knowledgeable crew, and the beautiful views make this cruise a quietly enchanting part of a Key West visit. It’s a wonderful way to end a day, watching the sunset in a way that’s both scenic and heartwarming.

Frequently Asked Questions

How long is the cruise?
The cruise lasts approximately two hours, giving you plenty of time to relax and enjoy the scenery without feeling rushed.

Where does the tour start?
Boarding takes place at the historic Seaport at Greene and Elizabeth streets in Key West.

What is included in the price?
Your ticket includes the sunset sail, snacks, coolers with ice, bottled water, and cups. There are no alcoholic drinks or sodas included.

Is there a group size limit?
Yes, the maximum number of travelers is 41, but most reviews mention a smaller, more intimate group experience.

Can I cancel if I change my plans?
Yes, free cancellation is available up to 24 hours before the tour. Cancellations within 24 hours are not refunded.

Is the tour suitable for children?
Most travelers can participate, and service animals are allowed, but you may want to consider whether your children enjoy boat trips and outdoor sunset viewing.

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

In the end, this sunset sail on the Jolly II Rover offers a blend of history, scenery, and genuine friendliness—an authentic way to appreciate the natural beauty of Key West at day’s end. Whether you’re celebrating a special occasion or simply want a peaceful moment, it’s a modestly priced adventure that many find well worth the time and money.