F
Fun afternoon sail on classic schooner
A very pleasant and relaxed 2 hour afternoon sail on When and If. Tyler and the crew were competent, safe and hospitable and I was allowed to drive.
Key West Historic Schooner When And If Sunset Cruise
+8 photos
At a glance
- Duration
- 2 hours
- Price from
- $117 / person
- Rating
- 4.8 / 5 · 144 reviews
- Group
- Small group, up to 28
- Cancellation
- Free cancellation
- Meeting point
- We are docked at the end of "E" dock. E dock is on the waterfront boardwalk in front of the Waterfront Brewery. Check in happens at the vessel. Please arrive 15-30 minutes before the start of the sail to ensure plenty of time to find the boat.
- Confirmation
- Instant
Prices checked on Sep 11, 2026Things to do in Key West
Description
Historic Schooner. Champagne Sunset Toast. Elegant and Exclusive. Step aboard the historic schooner When And If, commissioned by General George Patton in the late 1930s, and sail into a breathtaking Key West sunset. Raise a champagne glass as the sun dips below the horizon, while your experienced crew handles the sails — or try your hand at steering this classic wooden schooner yourself. Glide along turquoise waters, spot playful dolphins and local wildlife, and enjoy an unforgettable evening that blends history, luxury, and adventure. Highlights: Historic schooner experience aboard the When And If, commissioned by General George Patton in 1939. Champagne sunset toast included Elegant and exclusive cruise - Avoid the crowds Hands-on sailing opportunity: take the wheel under guidance from your experienced crew. Spot dolphins, sea birds, and local marine wildlife. Perfect for romantic evenings, family adventures, or history enthusiasts — children sail at a discounted fare.
Tour Options
Itinerary
Vessel is docked at the Key West Historic Seaport at the end of E dock which is in front of the Waterfront Brewery. Look for the E sign on the dock piling and walk down to the end of that long pier. The schooner has varnished wooden masts with flags at the top of each mast. Check in and boarding happens directly at the boat and begins 15 minutes prior to departure.
Sailing through the National Marine Sanctuary offers the unique opportunity to view marine wildlife. Sea turtles, bottle nose dolphin and marine birds.
We sail past the famous sunset celebration at Mallory Square
Sail past the offshore Key West Island of the rich and famous from the comfort of your seat aboard our majestic classic yacht
Highlights
Soda/Pop
Bottled water
Select Beer and Wine Included. Sunset Champagne Toast and Bottle Service Upgrade Available
Experienced Captain and Crew
Restroom on board
Opportunity to Take the Wheel and Help Raise Sail
What's included
Included
Soda/Pop
Bottled water
Select Beer and Wine Included. Sunset Champagne Toast and Bottle Service Upgrade Available
Experienced Captain and Crew
Restroom on board
Opportunity to Take the Wheel and Help Raise Sail
Not included
Gratuities
Transportation to and From Vessel
Ships Souvenirs Available for Purchase Onboard
Traveller Ratings
4.8
144 reviews
Important Information
- Service animals allowed
- Public transportation options are available nearby
- Infants are required to sit on an adult’s lap
- Suitable for all physical fitness levels
- Children must be accompanied by an adult
Frequently asked questions
How long does Key West Historic Schooner When And If Sunset Cruise take?
Key West Historic Schooner When And If Sunset Cruise lasts about 2 hours. The itinerary has 4 stops.
How much does Key West Historic Schooner When And If Sunset Cruise cost?
Prices start at $117 per person for this Key West experience, booked through Viator with the price shown before checkout. There is 1 booking option, so the final price depends on the option you choose.
Can I cancel Key West Historic Schooner When And If Sunset Cruise for free?
Yes. Cancel at least 1 day before the start for a full refund. Later cancellations are non-refundable.
Where does the tour start?
The meeting point is We are docked at the end of "E" dock. E dock is on the waterfront boardwalk in front of the Waterfront Brewery. Check in happens at the vessel. Please arrive 15-30 minutes before the start of the sail to ensure plenty of time to find the boat. . Hotel pickup is not part of this experience.
Is this a private or a group tour?
It is a small-group experience with a maximum of 28 participants.
Is the tour suitable for children?
Infants are required to sit on an adult’s lap Children must be accompanied by an adult
Will my booking be confirmed immediately?
Yes, bookings are confirmed instantly.
Is Key West Historic Schooner When And If Sunset Cruise worth it?
Travellers rate it 4.8 out of 5 across 144 verified reviews; it is run by Sunset Sail Key West. Most-mentioned highlights: Soda/Pop; Bottled water; Select Beer and Wine Included. Sunset Champagne Toast and Bottle Service Upgrade Available.
Reviews(144)
C
Historical Sunset Cruise
Beautiful experience. If you are looking for a historical sunset cruise that is not crowded or noisy, this is fantastic. Champagne toast at sunset and drinks during the sail. Crew is professional and great communication. You even get to hoist the sails if you want. Highly recommend this!
1 people found this helpful
C
Sunset Sail
Fantastic crew. They provided tremendous insight into the history of the ship, sailing, the keys and other great facts
D
What an experience!!
This sunset cruise was one of the best outings that we did while we were in Key West! It was pretty cloudy so we weren't sure if we were going to be able to see the sun setting, but the sky glowed a beautiful pinkish color at sundown! There were also a few dolphins that followed the boat for a while which was a fun bonus! Captain Tyler and his crew were awesome! Highly recommend this experience...you won't be disappointed!
T
Sublime Sunset Sail!
What a wonderful experience with Captain Zachary, Koss and Cameron! They were very professional and very cordial. They welcomed passengers to help hoist the sails and kept everything flowing smoothly and safely. We could tell they love what they do and are passionate about it. Compared to the other boats we saw leaving the harbor for sunset sail, this one felt the most relaxed and uncrowded, which was exactly what we were looking for. And their "Schooner Red" wine was wonderful! I'd encourage everyone to support this small business. One note, there was some confusion about where the boat was docked -- some sites may say Perry Marina but the correct site is the downtown Key West Marina.
K
Devastatingly Disappointed
We arrived to the dock at 6:15, 15 minutes prior to departure to find an already empty slip. I called at 6:20 to learn that there had been a dock change for that evening, but no effort had been made to contact us by the Tour Operator because we booked through Trip Advisor. I was told that it was because personal contact info was not passed thru from Trip Advisor to the Tour Operator. If this is true, then this Tour Operator should not be bookable on this channel. Clearly they can’t manage their business if they can’t communicate important information like dock charges to customers. Interestingly enough, I did receive an email informing me of the dock change, 5 minutes after my call. Something stinks! We were refunded our money which in no way made up for missing the beautiful sunset sail.
W
Fantastic Sunset Sailing
A truly amazing experience The crew were fantastic, attentive and friendly Got to help hoist the sails and the trip was a real sailing experience, not a sailing using the motor Sunset was beautiful Would highly recommend this outing for anyone who specifically wants a real sailing experience
M
Sporty seas, but a great crew!
We had a great time, however there were a number of folks who would have benefited knowing that the sail will be sporty😆. Captain and crew were amazing, took good care of us as guests, and our family had a great time!
X
wonderful!
Great boat and great crew. Perfect way to see the sunset from this historic and gorgeous boat.
2
Favorite activity in Key West!
This was our second or third trip on the When & if (first sunset cruise). Can beat the combination of classic yacht, Key West waters and awesome hosts / crew. We had a really great evening!
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