Sail Historic Waters: Day Sailing Adventure on the 1939 Schooner When And If in Key West
Difficulty
easy
Duration
2 hours
Fitness Level
Suitable for most fitness levels; no strenuous activity required but basic mobility helpful for moving around the boat
Overview
Experience Key West like never before aboard the 1939 schooner When And If, where history meets hands-on sailing along the Atlantic coast. Raise the sails, steer the helm, or simply relax with a drink as you glide through captivating seascapes.
Day Sail on When And If
2hrs Afternoon Yachting
Select participants and date
Adventure Photos
About This Adventure
Embark on a memorable sailing adventure aboard a stunning 1939 wooden schooner, once envisioned by General George S. Patton. Experience the thrill of raising sails, steering the helm, or simply relaxing while enjoying boutique wines and beers. Set against the beautiful Atlantic coast, this journey offers a unique glimpse into American maritime history.
Sail away on the gorgeous 1939 wooden schooner yacht built for General George S. Patton
"When the war is over, and if I live through it, Bea and I are going to sail her around the world." When And If is the peacetime dream of an American war hero with her greatest destiny as yet unfulfilled. Come be part of the story of this gorgeous vessel as you help raise sail, take a turn at the helm or simply relax and enjoy this unique and timeless experience. Set sail on a beautiful piece of American history and enjoy the true blue-water sailing we offer on the Atlantic coast out of the lovely brand new Stock Island Marina.
What's Included
- A two hour trip with a captain and two crew on a shared sailing excursion
- Two boutique wines made in honour of the yacht, and select beers
- Bottled water and seltzer water
*** 8 Person Minimum required to Sail. If you would like to guarantee your sail you may book for all 8 and we will issue a refund for any additional guests that sign up***
!Description of image
Adventure Tips
Arrive Early for Check-In
Plan to arrive at least 15 minutes before departure to get settled and enjoy a safety briefing.
Dress in Layers
Key West’s coastal breeze can shift; bring a light jacket or sweater to stay comfortable.
Bring Sun Protection
Wear sunscreen and a hat to guard against strong afternoon sun while sailing.
Stay Hydrated
Drink plenty of water before and during the trip to avoid dehydration on the open water.
Local Insights
Wildlife
- Brown pelicans gliding above the reef
- Bottlenose dolphins occasionally spotted alongside the schooner
History
Key West’s maritime history is rich with stories of naval legends and early American explorers, embodied by vessels like When And If, designed by General George S. Patton himself.
Conservation
The crew practices eco-friendly sailing to minimize impact on the delicate reef systems and marine life around Key West.
Select participants and date
Adventure Hotspots in Key West
Frequently Asked Questions
Recommended Gear
Sunglasses
Protects eyes from glare reflecting off the water during your sail.
summer specific
Light Jacket
Keeps you warm in cool breezes prevalent during spring sailing.
spring specific
Non-Slip Footwear
Ensures safe footing on wet and potentially slippery deck surfaces.
Reusable Water Bottle
Helps you stay hydrated throughout your trip in the sun and wind.