Sunset Sail Cruise in Key West
Overview
Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's most photographed ship! The Schooner Jolly II Rover is the only squared rigged, topsail schooner in the Historic Seaport! It is Key West's famous "Red Sails in the Sunset" Tall Ship! There is no band playing or loud music. We go sailing! Plenty of room to get up and mingle with other guests. Help raise the sails! Steer the ship! Shoot the cannons! Or just sit back and relax!
What's Included
- Snacks
- Coolers of ice with cups and bottled water
- Sunset Sail
- Alcoholic beverages Alcoholic Beverages
- Carbonated beverages Soda/Pop
Meeting Location
631 Greene Street
Key West, FL 33040, USA
Detailed check-in instructions, including the exact address, are provided with your booking confirmation.
This activity ends back at the meeting point.
What To Expect
Book Online
Safe & secure Easy breezy Hassle‑free
Schooner Jolly II Rover
2 hours Admission Ticket Free
Additional Info
- Confirmation is instant and will be received at time of booking
- Service animals allowed
- Public transportation options are available nearby
- Suitable for all physical fitness levels
- Infants and small children can ride in a pram or stroller
- Infants are required to sit on an adult’s lap
- There is no wheelchair ramp but we will do out best to accommodate wheelchair passengers.
- This tour/activity will have a maximum of 41 travelers
Frequently Asked Questions (9)
Q: Will I get seasick on Sunset Sail Cruise in Key West?
Cancellation Policy
Still have questions?
We're here to help.
Activity code: C-103151P2
Traveler Photos
Reviews
Average 4.97 out of 5 stars based on 292 traveler reviews collected by City Sky Diving and partner sites such as Cool Destinations and TripAdvisor
Additional Info
Similar Tours & Activities
Dark Side of Key West Ghost Tour
Dare to walk the haunted heart of Key West—where the veil between the living and the dead is razor-thin. Your journey begins sweetly enough at...
$35
Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start with a Light...
$54
Go where other tours can’t. Enter historic Fort East Martello after dark, meet Robert the Doll, then stay behind for an extended paranormal investigation inside...
$99
This tour goes beyond the typical Key West history walk by connecting the island's people, cultures, architecture, plants & wildlife. Led by a passionate local...
$69
Dare to walk the haunted heart of Key West—where the veil between the living and the dead is razor-thin. Your journey begins sweetly enough at...
$35
Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start with a Light...
$54
Go where other tours can’t. Enter historic Fort East Martello after dark, meet Robert the Doll, then stay behind for an extended paranormal investigation inside...
$99
This tour goes beyond the typical Key West history walk by connecting the island's people, cultures, architecture, plants & wildlife. Led by a passionate local...
$69
Travelers Who Bought This Tour Also Bought
Key West 6 Seater EZGO Golf Cart Rental
Need a Key West golf cart rental that can get a group of six around the island in fun style? A 6-seater gas-engine EZGO Express...
$180
Key West 4 Seater EZGO Golf Cart Rental
Considering a golf cart rental in Key West? Four adults can zip around the island in style on a 4-seater gas-powered EZGO golf cart, and...
$99
Key West 4 Seater Electric Car Rental
Cruise Key West with family or friends! Four people can get around town in comfort and ease with the smooth, silent GEM 4-seater electric car...
$99
Key West 6 Seater Electric Car Rental
Our 6-seater GEM electric cars beat any regular rental car hands down when it comes to zipping around Key West with a party of 5...
$180
Need a Key West golf cart rental that can get a group of six around the island in fun style? A 6-seater gas-engine EZGO Express...
$180
Considering a golf cart rental in Key West? Four adults can zip around the island in style on a 4-seater gas-powered EZGO golf cart, and...
$99
Cruise Key West with family or friends! Four people can get around town in comfort and ease with the smooth, silent GEM 4-seater electric car...
$99
Our 6-seater GEM electric cars beat any regular rental car hands down when it comes to zipping around Key West with a party of 5...
$180
Frequently Asked Questions (9)
The answers provided below were previously given in response to questions from City Sky Diving customers.
Filter by:
If you have any doubts about becoming seasick on the water, we recommend taking a Dramamine® Motion Sickness Relief tablet the night before your trip. Some people recommend taking it the night before your cruise and then again that morning so you will not feel so drowsy.
Feb 2023- For a full refund, you must cancel at least 24 hours before the tour start time.
- If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.
- Any changes made less than 24 hours before the tour start time will not be accepted.
- Cut-off times are based on the tour local time (EST).
- This tour requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.
- Snacks.
- Coolers of ice with cups and bottled water.
- Sunset Sail.
- Alcoholic beverages. Alcoholic Beverages.
- Carbonated beverages. Soda/Pop.
This tour requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
Apr 2025There is no minimum age for this tour, so bring your wee one along for an adventure. This tour requires at least one adult to accompany children..
Apr 2025If a date or time is not listed on the calendar, it’s sold out or unavailable for another reason. Support cannot assist further if a date or time is not on the calendar.
If you find a date and time that works for you, book it NOW because things always sell out at this time of year.
Apr 2025Accessibility information for the Sunset Sail Cruise in Key West is as follows:
- Service animals allowed
- Public transportation options are available nearby
- Suitable for all physical fitness levels
Detailed check-in instructions – including meeting point address, Google map, and parking information – for Sunset Sail Cruise in Key West will be included in your confirmation email from City Sky Diving. Please be sure to double and triple check your email address is correct at checkout so this important email makes its way to you!
Mar 2024Once your refund is processed, it usually shows on your card statement within 5–10 business days. The exact timing depends on your bank or card issuer.
Want it sooner? When you cancel, choose Receive a refund to my wallet instead. The credit is in your Wallet straight away and is applied automatically at checkout on your next booking when you’re signed in with the same email. You can see your balance any time in My Wallet.
If you paid part of your booking with Wallet credit, that part always goes back to your Wallet. Trip protection isn’t refundable.
Oct 2026What's Included
- Snacks
- Coolers of ice with cups and bottled water
- Sunset Sail
- Alcoholic beveragesAlcoholic Beverages
- Carbonated beveragesSoda/Pop
Additional Info
- Confirmation is instant and will be received at time of booking
- Service animals allowed
- Public transportation options are available nearby
- Suitable for all physical fitness levels
- Infants and small children can ride in a pram or stroller
- Infants are required to sit on an adult’s lap
- There is no wheelchair ramp but we will do out best to accommodate wheelchair passengers.
- This tour/activity will have a maximum of 41 travelers
