Sunset Sail Cruise in Key West

Experience a Unique Sunset Sail on the Jolly II Rover in Key West

For those seeking an authentic maritime adventure, the Sunset Sail Cruise in Key West offers a memorable journey aboard the square-rigged, topsail schooner Jolly II Rover. Priced at $95 per person, this 2-hour cruise departs from the historic Seaport at Greene and Elizabeth Streets and showcases some of the area’s most iconic sights. With a rating of 5.0 from 223 reviews, the tour is highly recommended by 98% of participants, making it a popular choice well in advance, typically booked 17 days ahead.

This cruise stands out because it takes travelers on a vintage vessel with striking red sails, offering a different perspective of Key West compared to smaller private boats or luxury yachts. The experience includes snacks, coolers with ice, bottled water, and cups, providing a comfortable and relaxed environment. While alcoholic beverages and soda are not included, the focus remains on enjoying the scenery, the sailing experience, and the lively atmosphere created by the crew.

Key Points

• Authentic square-rigged schooner with red sails offers a distinctive sailing experience
• Two-hour sunset cruise departing from the Key West Seaport
• Views include Man O War Harbor, Christmas Tree Island, Fort Taylor, and Sunset Key mansions
• Includes snacks, bottled water, and ice coolers, but no alcohol or soda
• Small group experience, with up to 41 guests, ideal for intimate outings
• Free cancellation available if canceled 24 hours in advance

The Unique Square-Rigged Schooner Jolly II Rover

The centerpiece of this tour is the Jolly II Rover, the only square-rigged, topsail schooner in the Key West area. Its vintage design and red sails immediately catch the eye as the vessel departs from the historic Seaport. This schooner provides an authentic sailing experience, allowing guests to feel the maritime history of the area while enjoying modern comforts.

The crew is known for being genuine and kind, ensuring guests feel welcomed from the moment they board. The owners and staff are praised in reviews for their friendly attitude, making the experience feel like a private gathering rather than a crowded tour. The small group size enhances the intimacy, providing plenty of opportunity to chat with the crew and learn about the ship’s history.

Departing from Key West’s Historic Seaport

The meeting point for this sunset cruise is at 631 Greene Street, right in the heart of the Key West Historic Seaport. This location is easy to access via public transportation, and the tour ends back at the same point, making logistics simple. The 2-hour sailing begins at a flexible time aligned with the sunset, so guests get to enjoy the changing colors of the sky during the cruise.

The boarding process is straightforward, and the mobile ticket system allows for contactless entry. Once on board, the crew provides a safety overview and prepares for a relaxing sail across the waters surrounding Key West.

Scenic Stops and Views Along the Route

During this cruise, you’ll see some of Key West’s most famous sights from the water. The vessel cruises into Man O War Harbor, giving an excellent vantage point of this busy maritime area. From the water, guests can also observe Christmas Tree Island, a small but picturesque island, and the mansions of Sunset Key, which provide a glimpse of the luxurious lifestyle of the area.

The Navy Mole and Civil War Fort Zachary Taylor are also visible from the boat, offering historical context and scenic beauty. The cruise continues past the state park area into the open Atlantic for a breathtaking view of the sunset. The crew often fires cannons, adding a lively and historic touch to the experience, as noted in many reviews praising this fun element.

The Sunset Experience and Additional Highlights

The prime time for this tour is, of course, the sunset. As the sun begins to dip below the horizon, vibrant colors fill the sky, reflected beautifully on the water. Many describe this moment as quiet and peaceful, perfect for family moments or romantic dates.

Along With the scenery, guests enjoy snacks served on board, with coolers of ice and bottled water available throughout. Although alcohol is not included, the relaxed vibe and spectacular views provide an ideal setting for unwinding. Some reviews mention the firing of cannons and spotting dolphins during the cruise, adding to the excitement and memorable nature of this sailing adventure.

The Crew and Onboard Atmosphere

The crew on the Jolly II Rover is often praised for being friendly, knowledgeable, and engaging. They take the time to explain the sailing process, share stories about the area, and answer questions. Many guests appreciate the small group setting, which fosters a more personalized experience and allows for more interaction with the crew.

The atmosphere onboard is described as laid-back and intimate, making it suitable for families, couples, and small groups. The cannon firing and occasional dolphin sightings contribute to a fun and lively environment that keeps guests entertained without feeling crowded or rushed.

Accessibility, Meeting Point, and Booking Tips

This tour is designed to be accessible for most travelers. Service animals are allowed, and the boarding location at Greene Street is close to public transportation options. The maximum number of travelers is 41, ensuring plenty of space and comfort.

Since the cruise is popular, it is advisable to book at least 17 days in advance to secure a spot. The free cancellation policy allows for full refunds if canceled at least 24 hours before the scheduled departure, giving peace of mind in case of weather changes or schedule conflicts.

Why This Sunset Sail Stands Out

What makes this tour distinctive is the vintage square-rigged schooner itself, offering an authentic sailing experience that many other tours lack. The scenic stops, combined with views of historic and natural sights, make this cruise a rich visual experience. The friendly crew and small group size create an atmosphere that feels more like a private sailing adventure than a typical tour.

The cost of $95 per person provides good value considering the scenery, the experience of sailing on a historic vessel, and the included snacks. The absence of alcohol might be a downside for some, but the lively cannon shots and dolphin sightings more than compensate for that.

Final Thoughts on the Sunset Sail Cruise in Key West

This sunset cruise aboard the Jolly II Rover offers a distinctive, relaxed, and scenic way to experience Key West from the water. Its vintage vessel, beautiful stops, and friendly crew make it an appealing choice for those interested in a less commercial, more authentic sailing experience.

While the tour is not suitable for those seeking lively nightlife or alcohol, it excels at providing peaceful vistas, fun moments like cannon firing, and opportunities for memorable photos. Perfect for families, couples, and small groups wanting a timeless sailing tradition combined with the beauty of a Key West sunset.

Frequently Asked Questions

What is the price of the sunset cruise?
The tour costs $95 per person.

How long does the cruise last?
It lasts approximately 2 hours, perfect for a short but scenic outing.

What are the highlights of the route?
Guests see Man O War Harbor, Christmas Tree Island, Fort Taylor, and the Sunset Key mansions, ending with the sunset over the Atlantic.

Where does the tour start and end?
Start and end at 631 Greene Street in the Key West Seaport.

Are snacks and drinks included?
Yes, snacks and bottled water are included, with coolers of ice available onboard.

Is this tour suitable for children?
Yes, many reviews mention the experience being great for families, especially with the casual, friendly crew.

Can service animals participate?
Yes, service animals are allowed onboard.

What is the cancellation policy?
You can cancel free of charge up to 24 hours before the cruise for a full refund.

Is there a limit on group size?
Yes, the maximum group size is 41 travelers, ensuring an intimate experience.

Is alcohol available during the cruise?
No, alcoholic beverages are not included or sold onboard.

Can I bring my own drinks?
The data does not specify, but since only snacks and bottled water are included, bringing your own drinks is likely allowed—it’s best to confirm at booking.

Who operates the tour?
The tour is operated by Schooner Jolly II Rover, with their contact available for questions.