Available Adventures
Welcome to St Augustine Sailing
Whether you’re seeking adventure, relaxation, or a romantic getaway, we have the perfect sailing excursion for you. Our diverse booking options are designed to cater to every sailor’s dream.
Below you will find our sailing experiences divided by Featured & Seasonal first, then Shared, Private, Wedding Packages, Sailing Lessons, and Membership Packages.
No matter what adventure you are looking for, we are here to help make your time on the water unforgettable! Simply choose the experience that suits your needs, and let us take care of the rest! We look forward to welcoming you aboard!
40th Anniversary Celebration
Join us on Saturday, August 2nd as we celebrate four decades of unforgettable moments on the water! Since 1984, St. Augustine Sailing has been helping locals and visitors alike experience the beauty, freedom, and adventure of life under sail. This special day is packed with family-friendly fun—from pirate-themed Treasure Hunt Sails and interactive dockside games to our sunset BBQ celebration. Whether you’re setting sail or just soaking up the atmosphere, there’s something magical waiting for everyone. Come be part of the legacy—and the fun!
Featured & Seasonal Sails
Discover the best of St. Augustine with our Featured and Seasonal sailing trips. These exclusive excursions highlight special events, local festivals, and the natural beauty unique to each season. Don’t miss out on our sunset cruises, holiday specials, and wildlife spotting adventures.
Nights of Lights Packages
Glitter
Enjoy a private 3-Hour sail while our chefs go above and beyond to impress your inner foodie.
Prices starting at
Sparkle
Private 2–Hour Charter Experience will include an Upscale Perfect Pairing of Sweet & Savory Bites.
Prices starting at
Twinkle
Give the gift of memories and quality time with this special 75-minute Dessert Cruise.
Prices starting at
Shared Nights of Lights Tour
Experience festive cheer and over 3 million twinkling lights aboard a beautiful 35‘ sail boat for 1 – hour.
Prices starting at
Shared Sailing Experiences
Join fellow enthusiasts on a Shared sailing adventure. This option allows you to book a spot on a vessel alongside other guests, creating a lively and social atmosphere. Depending on the sailing experience and the vessel selected, group sizes can be for 4, 6, 8, 10, or 12 passengers. It’s an excellent way to meet new people but yet keep it small and intimate while enjoying the open sea.
“Our experience… could not have been better! Everyone we spoke with while booking was incredibly knowledgeable and helpful, as well as patient! We had a wonderful day on the Catamaran and Daniel was an excellent captain!
– Elizabeth Mayhew / Google Review
“Absolutely fantastic. The boat was in great shape a real beauty. The captain, Chris, was knowledgable and a pleasure to sail with. It was like a continuing education class with the beauty of sailing thrown in. I look forward to many more trips.”
– Chris Norris / Google Review
“Our experience… could not have been better! Everyone we spoke with while booking was incredibly knowledgeable and helpful, as well as patient! We had a wonderful day on the Catamaran and Daniel was an excellent captain!
– Elizabeth Mayhew / Google Review
“Absolutely fantastic. The boat was in great shape a real beauty. The captain, Chris, was knowledgable and a pleasure to sail with. It was like a continuing education class with the beauty of sailing thrown in. I look forward to many more trips.”
– Chris Norris / Google Review
sailing booking
Private Sailing Experiences
For a more personalized experience, opt for our Private sailing excursions. You’ll have the entire vessel exclusively for your party, allowing for a customized journey tailored to your preferences. Ideal for family outings, romantic escapes, or corporate events, private charters offer privacy and flexibility on the water.
Wedding & Elopement Packages
Make your special day unforgettable with our Wedding Packages. Exchange vows surrounded by the breathtaking backdrop of the ocean. We offer comprehensive packages that include everything from the ceremony setup to a celebratory sail afterward. Let us help you create a magical maritime wedding.
ASA Lessons
Set sail on a learning adventure with our Sailing Lessons. Our experienced instructors provide hands-on training for all skill levels, from novices to seasoned sailors looking to refine their techniques. Gain confidence and nautical knowledge while enjoying the thrill of sailing.
“Fantastic experience took 104 & 114, would highly recommend. Professional and friendly staff, got tons of hands on experience, intercoastal, docking, anchoring, ocean, etc.. I feel ready to bareboat charter now” – Omar Tarazi
Beginner / Non-ASA Lessons
Memberships
Become a part of the St. Augustine Sailing community with our Membership Packages. Members enjoy exclusive benefits such as discounted rates, priority booking, and access to member-only events and excursions. It’s the perfect way to make sailing a regular part of your lifestyle.
