Leave the cold behind and settle into a Keys winter filled with sunshine, bare feet, and time well spent at Key Lime Sailing Club and Cottages. Sail (for qualified sailors), or enjoy kayaking, paddle boarding, swimming, snorkeling, cycling, and fishing whenever the mood strikes.

Spot dolphins and manatees along the way, explore nearby sandbars, take sunset cruises, or wander through local marinas, tiki bars, seafood shacks, and waterfront restaurants.

Spend a day visiting state parks, coral reefs, historic sites, art galleries, and charming island towns throughout the Florida Keys, then come back to your cottage and slow everything down. This is the kind of winter getaway you will remember.

Reply to this email with your dates or any questions, or select a cottage and request to book here.

Slots are still open for this winter’s 8-day, 7-night coastal sailing passage from Key Largo to Key West, and it is built to turn “I know the basics” into real confidence on the water.

This is not a sightseeing trip. You are part of the crew from day one. Under experienced guidance, you rotate through real responsibility, including stepping up as Captain for the Day. You will plan routes, stand watch, make weather calls, handle the boat under sail, anchor, dock, and lead the way between classic Florida Keys stops in warm water and easygoing conditions.

By the end of the passage, you will have real offshore miles, stronger sail handling, better trim and reefing skills, and a true feel for navigation, weather, and cruising life. You can also complete ASA 104 along the way, with all required on-water skills covered. This trip is for sailors who want more than a resort vacation, beginners who are ready to jump in, and anyone curious about life under sail.

Winter start dates are flexible, but cabins are limited and tend to go fast. If you want your next season on the water to feel different from the last, this is where it starts.

View the full itinerary, dates, and certification details here.

Less than 24 hours left. The voting period for our photo contest is almost over.

Cast your vote now and help crown the winner of our Key Lime Sailing Club and Cottages photo contest! Our guests captured unforgettable moments during their stay, and you can help them win by visiting our Facebook page, viewing all the qualified entries, and clicking “Like” on your favorites.

You can like as many photos as you want and invite your friends to join the fun too. The photo with the most Facebook Likes by January 1, 2026 at 12:00 am EST will win a FREE three-night stay at Key Lime Sailing Club and Cottages, with winners of both the Photo Contest and Video Contest being announced on January 2, 2026 via Facebook and our email newsletter.

Thank you to all our amazing guests for sharing your beautiful memories in Key Largo. We are honored to be part of them and wish everyone the best of luck!