Key West Historic Schooner When And If Sunset Cruise
Back at the ship by about 10:40 am, 4 h 50 min before all aboard. That keeps your 1 h safety margin with 3 h 50 min to spare.
Safety margin
- 8:00 amShip docks in Key West20 min to get off the ship and through the terminal
- 8:20 amLeave the pierAbout 10 min to the start point
- 8:30 amEarliest tour startTour runs 2 h. Latest sensible start: 12:20 pm.
- 10:30 amTour ends10 min back to the pier
- 10:40 amBack at the gangway4 h 50 min before all aboard
- 3:30 pmAll aboardGangway closes; the ship won't wait for independent tours
Estimates based on the tour's longest published duration, our researched travel times and typical pier queues. Confirm the departure time on the booking page and keep your watch on ship's time.
Our verdict
This tour fits a typical Key West call (8:00 am–3:30 pm). It runs 2 h; ashore by 8:20 am, you can start by 8:30 am and be back at the gangway around 10:40 am — 3 h 50 min to spare on top of a 1 h safety margin.
Rule of thumb: it keeps the safety margin as long as all aboard is 11:40 am or later. Even a short 7:00 am–2:00 pm call works.
The operator lists a meeting point in town rather than at the pier, but Key West is small: anywhere in the centre is within about 10 min of the ships on foot or by a short taxi ride, so we count 10 min each way.
Among the 350 Key West shore excursions we track, this is one of the shorter ones (the median runs 3 h); 85% of them fit a typical call.
Computed from the tour's published duration, the distance from the cruise pier to its start point and the typical Key West call. Adjust your ship's times above to recheck.
About this tour
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.
Max 28 per group
What's 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
Itinerary
- 1Stop 1Vessel 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.
- 2Florida Keys National Marine SanctuarySailing through the National Marine Sanctuary offers the unique opportunity to view marine wildlife. Sea turtles, bottle nose dolphin and marine birds.
- 3Mallory SquareWe sail past the famous sunset celebration at Mallory Square
- 4Opal Spa - Sunset Key CottagesSail past the offshore Key West Island of the rich and famous from the comfort of your seat aboard our majestic classic yacht
Meeting point and getting there
Start 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.
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.
From the cruise pier
About 10 min by taxi
Allow 20 min to get off the ship first. Taxi fares and pier details.
Returns
Back to the start point
Good to know
Free cancellation up to 24 hours before. For a full refund, cancel at least 24 hours before the scheduled departure time. If the operator cancels for bad weather, you can rebook or get a full refund.
- 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
Traveler reviews
Operated by Sunset Sail Key West. Prices, availability and tour details come from the booking partner and can change; the booking page is authoritative.
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