The Best Annual Events in St. Augustine
The nation’s oldest city is a vibrant hub of history, culture, and unforgettable St. Augustine events that attract visitors year-round. From lively festivals to exhilarating sailing races, the city offers a diverse array of experiences for locals and tourists alike. At St. Augustine Sailing, we elevate these events by offering a unique perspective from the water. Our private and shared charters provide luxurious comfort, stunning views, and memories that linger long after you leave the dock.
In this guide, we unveil the best St. Augustine events and show how sailing with us makes them even more extraordinary.
St. Augustine’s Best Annual Events
St. Augustine’s event lineup spans every season, offering something for every interest. Below, we highlight our favorite annual St. Augustine events:
Spring: Culture, Competition, & Community
Spring in St. Augustine bursts with energy, bringing St. Augustine events that celebrate culture, competition, and community. The Celtic Music & Heritage Festival in March transforms Francis Field into a lively celebration of Irish and Scottish traditions. Expect bagpipes, kilts, traditional dance, and hearty cuisine that honor the city’s diverse roots. A sailing charter along the Matanzas River also complements this festive atmosphere, offering a serene escape with stunning views of the historic coastline.
The Ladybug Race, hosted by St. Augustine Sailing in between March and early May, is a must-attend for sailing enthusiasts. This exhilarating event celebrates the local sailing community with a weekend of competitive class races along the Tolomato River. Open to sailors of all skill levels, the event kicks off with an in-water boat show featuring vendors, workshops, and seminars and held Friday and Saturday. While the main regatta, held on Sunday afternoon, challenges captains and crews to navigate wind and tides with precision and teamwork.
Don’t own a boat? Join our Crew Program or Women on the Water (WOW) program to race on one of our vessels. Proceeds from the Ladybug Race support the WOW program, empowering women of all ages to build confidence and skills through hands-on sailing training. Spectators can enjoy VIP views from the committee boat or book an on-the-water viewing packages.
The Rhythm & Ribs Festival in April, also held at Francis Field, combines mouthwatering BBQ, live music from local bands, and family-friendly activities. Foodies and music lovers flock to this feast for the senses, savoring savory dishes and lively performances. Pair this event with a sunset sail to cap off a perfect spring day with coastal breezes and scenic views.
The Forts and Fairways Golf Tournament each spring blends sport and scenery at St. Augustine’s premier golf courses. Golfers compete amidst lush fairways and historic surroundings, drawing enthusiasts and spectators alike. After a day on the greens, unwind with a Sunset Dinner Cruise, where the gentle waves and stunning bayfront views provide a relaxing contrast to the competitive spirit.
The St. Augustine Food + Wine Festival in May is a culinary delight, showcasing gourmet tastings, chef demonstrations, and wine pairings at various venues across the city. Foodies indulge in local flavors and innovative dishes, celebrating St. Augustine’s vibrant dining scene. Finally, The Sunset Tasting Cruise along the Matanzas River enhances this experience, offering a refreshing escape with panoramic views of the historic coastline to end your day.
Summer: Music, History, & Coastal Vibes
Summer in St. Augustine brings a wave of events that highlight the city’s musical and cultural heritage.
On August 2nd, St Augustine Sailing celebrates their Anniversary, and as a heartfelt thank you to both their loyal guests and new friends, they generally run a special offer for sails that occur only on that day.
But the celebration doesn’t stop there! Throughout the month of September, local St. John’s County residents can enjoy an exclusive discount on multiple experiences throughout St Johns County.
The Sing Out Loud Festival in September is Florida’s largest free music festival, featuring local and national acts across genres like rock, folk, and indie. Performances at venues like the St. Augustine Amphitheatre create an electric atmosphere. A sailing charter offers a refreshing escape from the summer heat, letting you enjoy the music-filled shoreline from the water.
The Fort Mose Jazz & Blues Series, held through the summer at Fort Mose Historic State Park, celebrates African American history with soulful concerts. As the site of the first legally sanctioned free Black community in the U.S., Fort Mose adds profound historical context to the experience. Sail to the park’s waterfront for a unique perspective on this cultural gem.
The Spanish Wine Festival in September honors St. Augustine’s Spanish heritage with wine tastings, tapas, and live entertainment. This festive event draws crowds to the historic district, celebrating the city’s deep-rooted connections to Spain. Pair it with a sunset sail, sipping your favorite beverage while cruising past the iconic bayfront.
Fall: Culinary Arts & Local Flavors
Autumn in St. Augustine is a delight for foodies and art lovers, with events that showcase local creativity and flavors. The St. Augustine Greek Festival in October fills Holy Trinity Greek Orthodox Church with the aromas of souvlaki, baklava, and live Greek music. Visitors dance, dine, and immerse themselves in Mediterranean culture, creating a lively atmosphere. Unwind afterward with a sailing charter along the scenic Matanzas River, soaking in the cool autumn breeze.
The Datil Pepper Festival celebrates St. Augustine’s signature spicy datil pepper with tastings, cooking demos, and fiery competitions. Crowds gather to sample datil-infused dishes, from sauces to desserts, embracing the city’s unique culinary heritage. A sailing adventure provides a refreshing contrast to the pepper’s heat, with stunning views of the historic coastline.
The St. Augustine Art & Craft Festival in showcases handmade works by local artisans, perfect for holiday shopping. Stroll through rows of unique creations, from pottery to jewelry, in the crisp fall air. A relaxing sail afterward lets you reflect on your finds while cruising along the Matanzas River, with the city’s skyline as your backdrop.
Winter: Festive Lights & Maritime Magic
Winter sparkles with St. Augustine events that bring festive cheer. The Nights of Lights, running from mid-November to mid-January, is a world-renowned holiday spectacle, named one of the top light displays by National Geographic. Millions of twinkling lights adorn the historic district, creating a magical ambiance best viewed from the water on a St. Augustine Sailing Nights of Lights charters.
The St. Augustine Christmas Parade in December fills downtown with floats, bands, and Santa himself, spreading holiday joy to spectators lining the streets. This festive event captures the warmth of the season, and a sailing charter offers a cozy way to extend the celebration with bayfront views.
The Regatta of Lights, a December boat parade, illuminates the bayfront with decorated vessels gliding through the water. Our charters provide prime viewing spots for this dazzling maritime display, ensuring you enjoy the spectacle in comfort and style.
The St. Augustine Film Festival in January attracts movie buffs with independent films screened at venues across the city. This cultural event showcases diverse stories and cinematic talent, offering a cozy indoor experience during the cooler months. Pair it with a sailing charter to enjoy the winter waterfront, where the crisp air and serene views create a perfect balance.
Your Front-Row Seat Awaits
St. Augustine events are spectacular, but experiencing them from the water with St. Augustine Sailing takes them to new heights. Our luxury yachts offer unmatched views of events like the Ladybug Race, Nights of Lights, and Regatta of Lights, letting you skip the crowds while enjoying comfort and style. From gourmet dining to cozy blankets, our charters provide personalized service that makes every moment special. Whether you’re planning a romantic private sail or a shared tour with friends, we craft experiences that linger in your memory.
Don’t miss your chance to make lasting memories—book your private or shared charter today at St. Augustine Sailing and discover why St. Augustine events are best enjoyed from the water.
For more information and to stay updated, visit www.sta-sail.com and follow them on social media @StAugustineSailing.
