Setting Sail: Explore St. Augustine’s Waters with Luxury, Brunch, and Adventure

From out here, it’s not hard to imagine what Ponce de Leon and Don Pedro Menendez de Aviles saw from their wooden boats all those centuries ago. St. Augustine still draws sailors and explorers from around the world. And whether it’s a sunset sail with your best friends, a family brunch on the water or learning the ropes of sailing, St. Augustine Sailing is ready to make it happen.

Brunch, anyone? The Brunch Sail has become one of the most popular sailing experiences. A chilled mimosa greets you as you board a world-class sailboat for a shared brunch. Or choose to have a chef prepare your brunch of Eggs Benedict and bottomless mimosas on board with a private brunch for 4 to 10 people. This is luxury.

The Sunset Tasting Cruise redefines dining with a seasonal tasting menu that showcases the finest flavors of the region. Prepared fresh by an onboard chef, each of the five single-serving dishes is crafted to delight your palate and perfectly paired with three ounces of premium wine for each course, hand selected by the staff sommelier. This 2-hour luxury experience, served on a spacious and elegant catamaran, is dining at its finest – on the water, in the glow of a St. Augustine sunset.

The thrill of sailboat racing comes to life with the second annual Ladybug Race Event taking place May 3- 4, 2025 on the Tolomato River. Don’t miss the In-Water Boat Show kicking off at
10 a.m. In addition to the excitement of the competition, there will be seminars, immersive workshops and a chance to be part of a vibrant sailing culture. Best of all, proceeds will go toward supporting St. Augustine Sailing’s Women on the Water (WOW), aimed at empowering women through education and support.

How about some high tea on the high seas with your favorite women in the world? A High Tea Adventure in May is a mother-daughter experience that will create unforgettable memories as you sail on a luxury yacht around the Nation’s Oldest City. Enjoy fresh baked scones, finger sandwiches and delicious pastries paired with a selection of fine teas. As a keepsake of this wonderful day on the water, each will receive a commemorative gift box including teacup, saucer, stirring spoon and napkin so you can relive the special day together for years to come. There are many other tea adventures on the water to choose from.

Of course, one of the best ways to see the Ancient City is from the waters that surround it. Be sure to ask about the Sail Science Adventures that let you explore local wildlife up close in their natural habitat, from Manatee Magic, Dolphin Delight and Turtle Trivia, to Ancient Rocks and Birds by the Bay, all lead by experts in the field. There are also Romantic Adventures customized to your needs and desires--from popping the question to wedding ceremonies. You ask, St. Augustine Sailing says “yes”!

Chances are, you’ve always dreamed of sailing your own boat. Why not try it out with some lessons? From learning the ropes and ASA to practicing more advanced skills and private instruction, you’ll be taught by USCG licensed captains and instructors.

No matter what experience you’re looking for on the water you’ll appreciate the top-of-the-line luxury yachts, catamarans and sailboats helmed by an elite crew of seasoned captains with over 100 years of experience sailing the world. If you’re a foodie, check out culinary sailing experiences including Sip ‘N Sail sunset cruises, 4-course dinner cruises, and a selection of 2-hour Land and Sea Adventures to satisfy all kinds of tastes.