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Sunset Sail Cruise on the Jolly II Rover in Key West
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Sunset Sail Cruise on the Jolly II Rover in Key West

by Schooner Jolly II Rover

2 hours
$85.50$95 on ViatorSave 10%/person
From
$85.50$95 on ViatorSave 10%per person

Choose from 1 available option

2 hours
Starting time
Friday 11 September 2026
Language
English
Free cancellation until 10 Sept 2026.
$171$190Save 10%
2 adults × $85.50
All taxes and fees included

How do you want to book?

Confirmation before Wed, 9 Sept - card's only charged if it's a yes. If it's a no, still time to book on Viator.

Book on Viator Confirmed right away, but you pay full price.$190

Overview

This two-hour sailing cruise takes place aboard the Jolly II Rover, a traditional topsail schooner with squared rigging and red sails, docked in Key West's Historic Seaport. You can help raise the sails, steer the ship, or fire the ship's cannons during the cruise. There is no loud music or live band, allowing you to enjoy the sailing experience fully. The route includes sailing past key landmarks such as Man O War Harbor, Christmas Tree Island, the mansions on Sunset Key, Mallory Square, the Navy Mole, and Fort Zachary Taylor. The boat then heads out into the Atlantic Ocean to watch the sunset. The cruise includes bottled water, cups, ice coolers, and snacks. Alcoholic and carbonated drinks are not provided. There is plenty of space to move around and interact with other guests. The operator tries to accommodate wheelchair users, although there is no wheelchair ramp on board.

Highlights

Two-hour sailing cruise on the Jolly II Rover
Sail past Historic Seaport landmarks in Key West
Opportunities to raise sails, steer, and fire cannons
Includes snacks, bottled water, and ice coolers
Views of Sunset Key mansions and Atlantic sunset

What's included

Ice coolers with cups and bottled water
Snacks provided during the sail
Sunset sailing cruise aboard the Jolly II Rover

What's not included

Alcoholic drinks are not included
Carbonated beverages are not included

Itinerary

1

Historic Seaport and Atlantic Sunset Sail

The cruise lasts two hours, sailing past Key West's Historic Seaport, entering Man O War Harbor, passing Christmas Tree Island, the mansions on Sunset Key, and Mallory Square from the water. It continues by the Navy Mole and Fort Zachary Taylor, then cruises past the State Park and into the open Atlantic Ocean to watch the day's sunset.

120 min

Meeting point

15 minutes before sailing time - In the Historic Seaport at the corner of Elizabeth and Greene streets. At the ticket booth on the dock along side the Conch Republic Seafood Company Restaurant.

End point

15 minutes before sailing time - In the Historic Seaport at the corner of Elizabeth and Greene streets. At the ticket booth on the dock along side the Conch Republic Seafood Company Restaurant.

Languages

English (guide)

Cancellation policy

  • Cancel at least 24 hours before start for a full refund.

Additional info

1–15 travelers per booking
Mobile ticket
Pushchair and stroller friendly
Service animals are welcome
Reachable by public transport
Infants travel on an adult's lap
Suitable for all fitness levels
There is no wheelchair ramp but the operator will try to accommodate wheelchair passengers.
Total
$171Save 10% vs Viator