BOOK 7+ DAYS IN ADVANCE AND RECEIVE AN ADDITIONAL 5% OFF YOUR ONLINE BOOKING. ENTER PROMO CODE EARLY AT CHECKOUT.

Windjammer Classic Day Sail

Wreckers Race at sea with Sebago Watersports while enjoying a scenic view

Windjammer Classic Day Sail

Windjammer Classic Day Sail

STARTS AT $49.95
DURATION: 2 Hours
DEPARTS DAILY: 1:30PM
WINDJAMMER CLASSIC DAY SAIL

Overview

Glide Back In Time with Sebago Watersports

Don’t miss a unique sailing adventure aboard the Appledore II, a luxurious 2-masted schooner that blends 19th-century charm with modern amenities. With a limited capacity of 49 passengers, this intimate experience offers hands-on sailing activities. As you sail from Key West’s Historic Seaport into the Atlantic, keep an eye out for marine life while enjoying complimentary beverages onboard.

Take Sail On The Appledore II

Wreckers Race at sea with Sebago Watersports while enjoying a scenic view

Your Tour Includes:

A daytime sail past Key West’s most iconic landmarks

The chance to hoist sails and steer the ship alongside our crew

Bottomless drink options, including champagne, homemade sangria, boutique wine, premium beer, cocktails, soft drinks, and filtered water

What To Bring

  • Hat
  • Sunglasses
  • Camera
  • Valid, government-issued photo ID (for alcoholic beverages)

Important Notes

Boarding starts one half hour before departure time. Spring and fall departure times vary based on when the sun goes down. Please check with us for exact departure times upon booking. Please bring a valid, government-issued photo ID. All prices do not include Florida sales tax.

Reviews

Windjammer Classic Day Sail

STARTS AT $49.95
DURATION: 2 Hours
DEPARTS DAILY: 1:30PM

Private Charter Requests

Discover Key West your way! Enter your information below and we will be in touch!

Custom Charter Options

  • Experience amazing Key West Sunsets with customized catering options
  • Morning or Afternoon Snorkels
  • All day adventures or eco-tours
  • Dolphin Watches
  • Parasailing

CONTACT COURTNEY TO CUSTOMIZE YOUR VERY OWN WORRY-FREE DAY ON THE WATER.

Give Us A Call

Contact Us

"*" indicates required fields

Name*
Trip Date*