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      • Key West Bars & Lounges
      • Key West Entertainment
      • Key West Art & Culture
      • Key West Beaches & Places
      • Key West Shopping
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      • Key West Guided Tours
    • On the Water
      • Key West Sunset Cruises
      • Key West Sailing Trips
      • Key West Leisure Charters
      • Key West Snorkeling
      • Key West Dolphins
      • Key West Fishing
      • Key West Jet Skis
      • Key West Scuba Diving
    • Golf Carts & Rentals
    • Concierge Services
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  • On the Island
    • Key West Dining
    • Key West Bars & Lounges
    • Key West Entertainment
    • Key West Art & Culture
    • Key West Beaches & Places
    • Key West Shopping
    • Key West Spa & Wellness
    • Key West Guided Tours
  • On the Water
    • Key West Sunset Cruises
    • Key West Sailing Trips
    • Key West Leisure Charters
    • Key West Snorkeling
    • Key West Dolphins
    • Key West Fishing
    • Key West Jet Skis
    • Key West Scuba Diving
  • Golf Carts & Rentals
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Discover Key West

Sailing - Day Sails

 Day sailing in Key West moves at an easy, unhurried pace, shaped by open water and steady light. With the sun higher and the horizon wide in every direction, time feels less structured and more responsive to the wind.


The sails on this list are chosen for that sense of freedom, favoring open decks, consistent breezes, and a pace that encourages you to settle in rather than rush. It’s a way to experience the island from the water without a fixed agenda, guided more by sail than schedule.

Sailing

The Sunday Sail on Argo Navis

Spend your Sunday morning aboard Argo Navis, a luxury catamaran offering a relaxed brunch sail on the open water. Light brunch bites and adult beverages are included, all enjoyed at an easygoing, unhurried pace.

The Sunday Brunch Sail Details & Booking

Classic Day Sail on Schooner America 2.0

 Step aboard America 2.0 for a classic day sail that highlights traditional seamanship and the simple pleasure of moving under wind alone. With open decks and a relaxed pace, it’s an authentic way to experience Key West from the water. 

America 2.0 Day Sail details & Booking

Day Sail on When and If

 Sail aboard When & If, a classic schooner with a rich maritime history and a graceful, unhurried feel. This daytime sail is about wind, water, and tradition — a timeless way to experience Key West from the deck of a true sailing vessel. 

When and If Day Sail Details & Booking

 Some links on this site are affiliate links, which means I may receive a small commission at no extra cost to my guests. This is standard in the industry and never influences my recommendations — I only share experiences I genuinely trust to deliver a premium experience. 


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