THINGS TO DO IN ST AUGUSTINE
St. Augustine, the nation’s oldest city, is packed with history, charm, and stunning coastal beauty. Whether you’re here for a romantic getaway, a family vacation, or an adventure on the water, there’s no shortage of things to do in St. Augustine. But if you truly want to experience the city in the best way possible—without the crowds or the heat of the bustling streets—there’s no better option than exploring by sail.
At St. Augustine Sailing, we offer unforgettable experiences on the water, from private and shared charters to educational and romantic excursions. Sailing provides a peaceful and unique perspective of the city’s most famous landmarks, allowing you to soak in the sights while enjoying the refreshing ocean breeze. Read on to discover why a sailing adventure should be at the top of your list, along with other must-do activities in St. Augustine!
Explore St. Augustine
When it comes to things to do in St. Augustine, sightseeing is a must—but why fight the crowds when you can take in the city’s beauty from the water? Sailing offers a stress-free, panoramic view of St. Augustine’s most iconic landmarks, all while you relax on a luxurious yacht.
Sailing Experiences with St Augustine Sailing
We offer a variety of sailing adventures tailored to different interest and group sizes:
Private & Shared Charters
Enjoy a relaxing trip along the Intracoastal Waterway, taking in stunning views of St. Augustine’s historic skyline. See famous landmarks like:
- The Castillo de San Marcos, an impressive 17th-century fortress.
- The Bridge of Lions, a beautiful historic bridge best admired from the water.
- The St. Augustine Lighthouse, a picturesque landmark standing tall over the Matanzas River.
No Crowds, No Walking—Just Relaxing! Unlike traditional sightseeing, sailing allows you to experience the city’s beauty without the hassle of walking, traffic, or crowded tourist areas.
Sailing in St. Augustine is not just about the views—it’s about creating unforgettable moments on the water. Whether you’re looking for a peaceful escape, a family-friendly outing, or a romantic evening, our sailing experiences are the perfect way to explore the city.
Science and Sailing?
Looking for family-friendly things to do in St. Augustine? Our Sail Science Adventures combines hands-on learning with the thrill of being on the water, making it the perfect adventure for kids and curious minds alike.
What Kids Will Learn
- Marine Life and Ecosystems – Discover the diverse aquatic creatures that call St. Augustine’s waters home.
- Basic Navigation and Sailing Techniques – Learn how wind, water currents, and sails work together to propel a boat.
- Hands-On Science Experiments – Engaging, STEM-based activities that bring oceanography and environmental science to life.
This experience is ideal for families who want to mix fun with education, giving kids an unforgettable and interactive way to explore St. Augustine’s coastal environment. It’s one of the best ways to make learning an adventure while enjoying a unique view of the city!
Learn To Sail In St Augustine
Why just ride on a boat when you can learn to sail one? St. Augustine Sailing offers lessons for beginners and those looking to enhance their skills, making it one of the most exciting and rewarding things to do in St. Augustine.
Sailing Lessons for Every Skill Level
Beginner Sailing Lessons – Ideal for those with little to no experience, our beginner lessons provide both dockside and on-the-water training. Choose from:
- Basic Keelboat Prep – A foundational course covering essential sailing skills and terminology.
- Intro to Sailing – Experience sailing firsthand aboard a day sailor, learning key techniques in a hands-on setting.
- Learn the Ropes – Take your skills to the next level on a 35-foot sailboat, gaining confidence with larger vessels.
Each of these courses ranges from 2 to 3 hours, allowing you to get a taste of sailing or build a strong foundation at your own pace.
Want to dive deeper? If you’re planning to be in town longer and want a more immersive experience, we offer the full range of ASA Sailing Courses. From a single full-day course to multi-day certifications, you can advance your sailing skills at your own pace.
Learn to Sail Like a Pro – Just Add Water!
Private Sailing Instruction – Get one-on-one coaching tailored to your specific goals, whether you’re sailing for leisure or working toward certification. Our expert USCG-licensed instructors customize each session to focus on the skills you want to master.
Learning to sail is more than just a skill—it’s a lifelong adventure. Whether you’re visiting for a weekend or staying longer, taking a sailing lesson in St. Augustine is a unique way to connect with the water and gain confidence at the helm.
The Perfect Date Night
St. Augustine is often considered one of the most romantic cities in Florida, and there’s no better way to celebrate love than with a Sweetheart Sail. Whether you’re planning a proposal, celebrating an anniversary, or just looking for a unique date night, a sailing experience offers an intimate and unforgettable escape.
Why A Sweetheart Sail
- Sunset on the Water – Watch the sky transform into breathtaking hues of pink and orange as you sail into the evening.
- Champagne and Stunning Views – Toast to your love while enjoying the serene beauty of St. Augustine’s coastline.
- Peaceful and Private – A sailing experience is the perfect way to disconnect from the hustle of daily life and focus on each other.
Why the Sunset Tasting Cruise
- A Sunset Tasting Like No Other – Set sail into the evening and watch as the sky transforms into breathtaking hues of pink and orange, creating the perfect backdrop for an unforgettable night.
- Wine, Bites, and Coastal Beauty – Savor five exquisite wines, each perfectly paired with a gourmet appetizer, while taking in the stunning views of St. Augustine’s coastline.
- An Exclusive and Enriching Experience – A knowledgeable sommelier will guide you through each tasting, sharing insights on the wine selection as you relax and indulge in this elegant culinary journey.
Few things compare to the magic of gliding over the water with the one you love. If you’re looking for romantic things to do in St. Augustine, this experience is simply unmatched.
More Things to do in St Augustine
(When You're Not on the Water)
While sailing is undoubtedly one of the best ways to explore St. Augustine, there’s plenty to see and do once you’re back on land. After your time on the water, check out these must-visit spots:
Historic Landmarks and Attractions
Here are 8 landmarks and attractions you don’t want to miss:
- Castillo de San Marcos – The oldest masonry fort in the U.S., offering stunning views of Matanzas Bay and immersive historical reenactments.
- St. George Street – A lively pedestrian street lined with historic buildings, unique shops, and museums.
- Flagler College – A masterpiece of Spanish Renaissance architecture, once the luxurious Ponce de León Hotel. Guided tours showcase its stunning design and history.
- The St. Augustine Lighthouse and Maritime Museum – Climb 219 steps to the top for breathtaking views and learn about the city’s maritime heritage.
- The Fountain of Youth Archaeological Park – Explore the legendary site where Ponce de León is said to have searched for the Fountain of Youth. Walk the scenic grounds, enjoy historical exhibits, and taste the famous spring water.
- The Old Jail – A fascinating and slightly eerie look at St. Augustine’s past, complete with costumed guides and tales of its former inmates.
- Lightner Museum – Housed in Henry Flagler’s former Alcazar Hotel, this museum showcases fine art, Victorian-era artifacts, and unique collections from the Gilded Age.
Beaches and Outdoor Activities
St. Augustine has some beautiful beaches and plenty of outdoor activities for active families and groups. Here are a few favorites:
- Anastasia State Park – A beautiful beach and nature reserve perfect for hiking, kayaking, birdwatching, and picnicking.
- Vilano Beach – A quieter, more secluded stretch of sand with stunning views of the Atlantic Ocean and the St. Augustine Inlet.
- Fort Matanzas National Monument – A short ferry ride takes you to this well-preserved Spanish fort, offering insight into the city’s military history and stunning natural surroundings.
- St. Augustine Alligator Farm Zoological Park – Home to every living species of crocodilian, plus thrilling wildlife shows, a zip-line course, and exotic bird exhibits.
No matter how you choose to spend your time, one thing is certain—your visit to St. Augustine will be unforgettable.
Book your sailing adventure today and experience the magic of St. Augustine from the water!
For more information and to stay updated, visit www.sta-sail.com and follow them on social media @StAugustineSailing.
