Our Day sails offer a great way to see Key West from the water!  Experience the joy of setting sail and shutting off the engine as we sail you through the colorful waters that surround our beautiful Island, Sail through the internationally renowned live- aboard anchorage, past Mallory square and the old Customs House and out toward Fort Zachary Taylor.  Sail around Sunset Key and take a look at the Key West’s most fantastic National wildlife preserve.  We always have a chance to see dolphins, turtles and countless variety of sea birds. Sit back and relax or take a turn at sailing the boat, this truly is Your trip!

With over 15 years experience sailing and living in the Keys our captains and crew provide you with the local knowledge of  marine life, surrounding islands as well as stories of Key Wests rich and colorful history.  Come sail with us in comfort and style.

1 and a Half-hour Day Sail

On High Tide
1-6 guests, $295
7-10 guests, $495

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On Conch West
you and up to five guests
$395, charter only

On Free Spirit
you and up to five guests
$295, charter only

On Schooner When and If
up to 28 guests, $69/person
all day charter of boat, $3,800

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On our six-passenger boats (and ten-passenger High Tide), longer trips are available at $145.00 for each additional hour. Charters available aboard When and If, call for inquiries.

Public sails happen every afternoon on Schooner When and If. High Tide, Free Spirit and Conch West, our six passenger boats are available by charter only. High Tide departs daily from behind Schooner Wharf Bar in the heart of Old Town Key West. Schooner When and If departs every evening from Stock Island Marina Village.

Trip Includes: Cooler full of ice, soft drinks, water. Great views of Key West seen under sail!

You are welcome to bring any adult beverages of your choice.

Add Ons:
Fresh tropical fruit plate & snack — $25 (1-6 guests) / $35 (7-10 guests)

Call us to book: (305) 587-4488