Have the sea to yourself with a private charter

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!
Choose from a Sunset or Starlight Sail
Conch West and High Tide available year-round
Enjoy with up to 12 people
Custom charters are limited only by your imagination!

Private Day Sails

From sunbathing above deck to snorkeling beneath the waves, a private day sail is the perfect way to explore Key West with friends, family, or your significant other.

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

Book a sun-drenched private day sail today!
Choose from Harbor Day Sails or all day Snorkel & Sail trips
Conch West and High Tide available year-round
Enjoy with up to 12 people
All trips are customizable

Something Extra Special

Celebrate that special occasion on the water with our engagement, anniversary, Chillout Lilypad Sail and other special occasion sails.

Let us help you create the perfect moment that will last a lifetime.

With options for a photographer, guitarist, or your favorite champagne, our custom charters are limited only by your imagination!
Great for Proposals, Weddings, and Anniversaries
Conch West and High Tide available year-round
Enjoy with up to 12 people
All trips are customizable

Things To Know Before You Go:

Day Sails

Included:

Coolers stocked with ice and soft drinks are provided on-board. You are more than welcome to bring your own food or beverages. On 4-hour snorkeling trips, we provide a fresh fruit platter. Snorkeling equipment provided on snorkeling sails.

What to bring:

We welcome you to bring food and drinks of your choice. We’ve got plenty of room in our coolers for mixers and “adult drinks.” We suggest you bring a hat, towels, and sunscreen. Check ahead of time with us to see what the sailing conditions look like–If you are prone to motion sickness, you may want to take something in advance or try wearing anti-motion sickness wrist bands.

Departure Details:

Conch West and When and If depart from the Stock Island Marina Village, while High Tide is docked right in Downtown Key West at Schooner Wharf.

Sunset Sails

Options:

Conch West and High Tide are available year-round for sails, and When and If sails Key West from Thanksgiving to Memorial Day.

Ask about our engagement, anniversary, and other special occasion sunset sails. Custom Charters are limited only by your imagination! Create your own sailing trip to satisfy your personal preferences.

Included:

Coolers stocked with ice and non-alcoholic drinks are provided on-board. You are more than welcome to bring your own food, mixers, and adult beverages along for the ride.

What to bring:

As the sun sets and we sail away from the shore, it can get a little chilly. We provide blankets, but you may want to bring a jacket. Check ahead of time with us to see what the sailing conditions look like–If you are prone to motion sickness, you may want to take something in advance or try wearing anti-motion sickness wrist bands.

Departure Details:

Conch West and When and If depart from the Stock Island Marina Village, while High Tide is docked right in Downtown Key West at Schooner Wharf.
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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