A multi-day sailing adventure combining passagemaking skills with leisurely stops to fish, snorkel, swim, and shore excursions.
A multi-day sailing adventure combining passagemaking skills with leisurely stops to fish, snorkel, swim, and shore excursions.
Join us this winter for an unforgettable 8 day/7-night Coastal Sailing Adventure in the beautiful Florida Keys!
For many of us, a sailing passage is the ultimate sailing experience where you put to use all that you have learned plus learn more than you ever thought possible. Under the guidance of Captain Jason Cox, ASA Outstanding Instructor of the Year, each crew member will take turns being a “Captain for the Day.” You will set the watch schedules, divide up the duties, plan the navigation route, monitor the weather, and guide the vessel safely to its next destination.
Each leg is carefully thought out to give you the practical experience needed while affording time for relaxation and fun. There will be plenty of time to swim, snorkel, fish, relax on secluded beaches, and more! You’ll likely spot an abundance of wildlife including dolphins, manatees, rays, turtles, reef fish, birds, and a host of other fascinating creatures! How about enjoying a fine dinner each night at a beautiful anchorage watching the breathtaking sunsets that happen nightly?
Do you want to add an ASA 104 during the journey? This trip is tailored for completing all the on-water skills needed for that certification.
Captain Jason has a wealth of teaching experience, delivery experience, and personal adventures sailing with his family. Tap into the wealth of his knowledge with a trip that promotes active learning. There is so much that goes into getting a boat ready for a passage, and then making the passage go smoothly. Take part in this one of a kind of opportunity that combines learning with adventure and fun!
Who's invited
- Current Sailor. Improve knowledge and skills.
- Adventure Seeker. Find it on the ocean.
- Sailing Vacation. Spend the week with us.
- Lifestyle Change. Learn about traveling by sailboat.
- Retirement Planning. Explore before committing.
- Sailing Spouse, Come for the memories.
- No Sailing Certifications. Hop Aboard.
Although there are a few physical requirements to be met, we welcome just about anyone on our trips.
Learn or Improve Sailing Skills
- Adhering to a proper watch schedule
- Steering/Helming
- Trimming sails
- Navigation
- Monitoring weather
- Recording logbook info
- Cooking/Meal Prep
- Cleaning
- Anchoring/docking
- Boat Handling
- Leadership
Florida Keys Sailing Adventure Itinerary
8 Days of Sun, Snorkeling, and Smooth Sailing
Arrive by 9:00am and settle into your floating home for the week. After stowing gear, provisioning, and getting familiar with the boat + safety gear, the anticipation builds.
Aim to cast off by 3:00pm for a short and easy shakedown sail.
Drop anchor at Cowpens Anchorage or another calm, nearby anchorage—perfect for your first sunset afloat.
Sails up! Journey down the shimmering Keys coastline, stopping to snorkel the lively corals at Hens & Chickens Reef.
Continue to Long Key, where you’ll anchor for the night under a sky full of stars.
Enjoy a smooth day on the water as you make your way to Bahia Honda—a favorite for its beautiful beaches, clear water, and serene anchorage.
Drop the hook and unwind.
Start the morning with beach time—walk the sand, swim, or just sip coffee with your toes in the water.
Depart in the late morning and sail toward the colorful, carefree world of Key West.
Pull into the marina and indulge in a well-earned evening ashore.
A full day to explore Key West—wandering historic streets, watching roosters strut, or enjoying sunset celebrations at Mallory Square.
Return to the marina for another comfy night on shore-power.
Wave goodbye to Key West and log some excellent sailing miles as you head back up the Keys.
Anchor for the night in one of the peaceful spots near Sister Rock Bay, Vaca Key Bight, or Fat Deer Key—quiet, protected, and perfect for relaxing after a long and satisfying sail.
Sail toward Islamorada with a snorkel stop at Cheeca Rocks, a coral hot-spot bursting with color and marine life.
Arrive at Lorelei, known for its sunset magic and laid-back vibes. Enjoy dinner at the restaurant before returning to your anchorage for the night.
Leave early for a gentle morning sail back toward Key Lime, aiming to arrive by midday.
Pack up, step ashore, and bid farewell to a week of sunshine, salt air, and unforgettable sailing memories.
Dates/Pricing
As we embark this Winter on our newest sailing package offering, our Captain has agreed to remain flexible regarding dates. We are likely looking at sailing 2-3 weeks this Winter with another possible trip in early March. We will select final dates based on accommodating the greatest number of people.