When And If - Key West
Length:
80 Feet
Year Built:
1939
In Key West:
December through June
Capacity
32
Private Key West Harbor Day Sail
- 1.5 Hours
- From $424.62
- 202 William Street, Key West
Take the wheel or take in the sights as we sail you through a tour of Key West harbor, sail past the crowds at Mallory square and cross the line of the Gulf of Mexico into the Atlantic Ocean
Private Key West Harbor Sunset Sail
- 2 Hours
- From $693.38
- 202 William Street, Key West
At Sunset Sail Key West we bring you the perfect end to an island day; capture the magic of it all from the deck of your own private tropical sailboat.
Private Dolphin Watch/ Snorkel Sail
- 4 Hours
- From $908.38
- 202 William Street, Key West
Set Sail as we navigate under sail for a truly Eco friendly adventure! We will use our expertise to sail towards the Dolphin playground and then to our "backcountry" snorkeling destination.
Private Starlight Sail
- 1.5 Hours
- From $639.62
- 202 Williams Street, Key West
Relax as you sail out beyond the lights and sounds of Key West and get a clear view of the spectacular nighttime sky. Gaze into the night to spot the seasonal celestial highlights as we shut the engine off and take a peaceful sail through the starlight.
Private Snorkel Sunset Combo Sail
- 4 Hours
- From $1069.62
- 202 William Street, Key West
Enjoy the best of both worlds with a sail to a vibrant Florida Keys snorkeling spot, where you'll explore fascinating marine life and mangrove ecosystems. Afterward, dry off with a light snack platter and sail into the sunset, returning to the dock perfectly in time for dinner.
Private Chillout Lilypad Sail
- 3 Hours
- From $747.12
- 202 William Street, Key West
A short sail with Sunset Sail Key West brings us to a sheltered spot where we'll anchor in some shallow water and unroll the lily pad. This giant 6x12ft raft is the perfect watertoy, allowing you to lounge in the sun but stay cool in the sea!
About When And If
Marrying old-world elegance with racing performance, this classic 80-foot schooner is steeped in history and brimming with top-of-the-line detail.
You don’t have to be a history buff to fall in love with When and If, but it certainly helps. With her classic elegance and immaculate details, she turns heads wherever she sails. Although she is a champion racer, she can treat as many as 28 guests to more laid-back sailing as well. Having spent her life in private ownership, offering her as a charter vessel gives guests an exclusive opportunity to go back in time.
In 1939, the spectacular schooner was built for General George S. Patton. As WWII was beginning, he stated: “When the war is over, and If I return, Bea and I are going to sail her around the world.” Sadly, with Patton’s untimely death in 1945, it was not meant to be.
From the first time Captain Seth spotted When and If sailing off the coast of Maine, he was captivated by her beauty. He had the honor of overseeing her restoration in 2013 when she was 74 years old. When he had the opportunity to purchase her in 2015, he didn’t think twice — and in doing so ensured that she would remain in America, where she belongs.
When and If spends her winters in Key West, sailing these storied waters from December through June before heading north to Salem for the summer season. Departing from The Perry Marina, she offers an unmatched opportunity to experience one of the most historically significant vessels in American sailing history against the backdrop of one of the world’s great sailing destinations.
Things To Know Before You Go:
Sunset Sails
Options:
- Celebrate that special occasion on the water with a custom sailing trip to mark your birthday, engagement, proposal, wedding, anniversary…whatever the event!
- Let us help you create the perfect moment that will last a lifetime.
- With options for a photographer, music, or your favorite champagne, our the sky’s the limit on our custom charters. We’re here to make your dream sail come true.
Included:
- On When And If and Malabar X, complimentary iced bottled water and seltzer water, boutique wines and select beers are available on board.
- On High Tide, our cooler is stocked with ice, bottled water and soda with room for your own adult beverages.
- On snorkel trips, we provide snorkel gear and a fresh fruit platter.
What to bring:
- When And If and Malabar X: Please bring appropriate weatherwear and sunscreen for the day.
- High Tide: Appropriate weatherwear plus towels and bathing suits if you have booked a snorkel or lilypad sail. BYOB.
Departure Details:
- When And If and Malabar X depart from The Perry Marina.
- High Tide is docked right in Downtown Key West at Schooner Wharf Bar.
Sailing On When And If In Key West
Can I sail the boat?
Weather and traffic permitting, everyone who wants to will get a chance to man the helm and get a taste of what it’s like to sail.
Will I get a sunburn?
As it reflects off the water, the sun out on the water is brighter than on land. We highly recommend using some sunscreen– a minimum of 30 SPF or higher. Also, if you are prone to sunburn, you may want to wear protective clothing. And nothing reduces the glare off the water as well as polarized sunglasses.
What wildlife will I see?
Ocean wildlife, like wildlife everywhere, is diverse and unpredictable. Every trip will offer different species. Key West is filled with dolphins, manatees, tarpon, sharks, barracuda, turtles, and many species of birds. The reefs are brimming with exotic tropical fish and corals. Of course, we can not predict nor guarantee what you will see, our experienced crew will do their best to point out any interesting wildlife that you may encounter during your charter. Keep a camera handy.
Are children welcome?
Yes. Sunset Sail Key West is kid-friendly. However, all children must be supervised by an adult for the duration of the trip. Children 6 and under will be provided with a lifejacket they are required to wear on-board.