Private Charter Sailing In Key West

Private Sunset Sails, Private Daysails, Private Snorkel Trips. Do you dream of the wind in your hair, the sky above, and the sea below? We get it. And we’ve got you.

Private Sunset Sail - It's Our Thing!

Key West sunsets are known for their beauty, but from on the water, they will take your breath away. A private sunset sail is a fun end-of-day treat for the family or a memorable, romantic trip to share with your sweetheart.

Book your exclusive sunset sail on a vintage vessel!
Perfect Keys sunset sailing
Three beautiful classic boats
Up to 32 guests
Customize your trip with catering, music, photography. The sky's the limit!

Private Day Sails

From sunbathing on deck to snorkeling beneath the waves, a private day sail is the perfect way to explore Key West with friends, family, or loved one.

Celebrate a special event or simply experience the joy of sailing with an experienced crew.

Book a sun-soaked private day sail today!
Choose from Harbor Day Sails or all day Snorkel & Sail trips
Three beautiful classic boats
Parties of up to 32 guests
Customize your trip with catering, music, photography. The sky's the limit!

Something Extra Special

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.
Great for Proposals, Weddings, and Anniversaries
Three beautiful classic boats
Enjoy with up to 32 people
Customize your trip with catering, music, photography. The sky's the limit!

Things To Know Before You Go:

Day Sails

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.

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.
Ready to begin?

Choose Your Trip

Day Privates

Book a sun-drenched private day sail today

Book Now

Sunset Privates

Book your exclusive sunset sail on a vintage vessel

Book Now
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