Top St Augustine Seasonal & Special Occasions

Relax on a serene adults-only Sunset River Jazz Cruise along the historic St. Augustine bayfront. This two-hour journey features live jazz, artisanal charcuterie, and a complimentary glass of boutique wine while you watch the sunset over the water. Ideal for date nights or a calm evening with friends, this cruise offers comfortable seating and scenic views, perfect for conversation and unwinding. Enjoy the laid-back atmosphere as you take in the sights and sounds of the river, with wildlife like dolphins occasionally making an appearance. - 2-hour adults-only cruise starting at sunset - Live jazz band sets the mood for relaxation - Includes artisanal charcuterie and one complimentary glass of wine - Comfortable seating and scenic views, perfect for socializing

Sunset is one the most beautiful times of day and many people like to take cruises to see sights from the water when the sun goes down. Kick up the fun with this St. Augustine Sunset Booze Cruise that allows you to see the sights at sunset and enjoy some drinks on the water, too. This cruise has room for up to 24 passengers and takes place in a unique cycle boat.

A delicious tour of America’s Oldest City awaits you on this chauffeured food and wine tour through St. Augustine. This auto-adventure whisks you through the streets of St. Augustine’s historic district in an open-air electric vehicle, stopping at some of the guide’s favorite dining venues. Local cuisine paired with tasty wines await your taste buds. As you ride along the streets, pass Flagler College, the Huguenot Cemetery and other historical landmarks.

Sail along St. Augustine’s picturesque coastline—and indulge in a number of generous wine samples—during this two-in-one tour. Make your own way to the dock, hop aboard the pontoon boat, and get comfortable: as you set off, you’ll see landmarks like the Castillo de San Marcos, the Bridge of Lions, and more. You’ll also taste six different wines, and will have access to the on-board bar.

Want to eat out during your trip to St. Augustine, but not sure where to go? Get acquainted with the city’s wine and food scene during this St. Augustine Food, Wine, and Cocktail Tour. Go to some of the most unique spots in the city to grab a bite and an alcoholic beverage in the afternoon, one of the best times to explore, with a guide who knows the city’s history well.

See St. Augustine’s spectacular Nights Of Lights celebration from the water with this unique boat tour. This excellent way to see the city shine is available as a public tour consisting of as many as 32 people or you can book a smaller boat for an intimate, private tour for up to six. Float by the Bridge of Lions, see the Old Fort, and marvel at the Old City lit up with holiday cheer.

PLEASE NOTE: Booking 1 Traveler = 1 row that can seat up to 4 people. Book 2 travelers for groups of 5 - 8 people and you will get 2 rows! Get into the holiday spirit on a trolley tour of St. Augustine’s popular, annual Nights of Lights Festival! Traffic is heavy and crowds are thick for this high demand, often sold-out activity so book ahead to secure your preferred date and time and avoid disappointment! Hop on the trolley, sit back, pop on your 3-D glasses and enjoy a fully immersive holiday experience from more than 3 million lights along the city’s Historic District. After your trolley tour, enjoy a holiday cookie and a cup of hot apple cider.

The Creepy Crawl Haunted Pub Tour in St. Augustine invites guests to explore the city's most haunted pubs and historic sites while enjoying a night of ghost hunting and storytelling. Real EMF meters are provided for a hands-on paranormal investigation experience, with guidance from expert ghost hunters along the way. Participants visit off-the-beaten-path taverns, enjoy a complimentary welcome drink, and receive exclusive discounts at each pub stop. The tour lasts approximately two hours and includes stops at haunted venues, cemeteries, and other supernatural landmarks throughout the historic district. Designed for those who love a mix of history, spirits, and the supernatural, this haunted pub crawl offers a thrilling and authentic look into St. Augustine's ghostly past. Tours depart rain or shine from the Tour St. Augustine office, and all guests must be 21 or older to participate.

Combine a haunted tour with a pub crawl with this original haunted pub tour in St. Augustine. Follow your guide around to some of downtown St. Augustine’s most infamous and allegedly haunted watering holes, where you can grab drinks (own expense) while learning about the haunted history of the city.

Explore St. Augustine’s beautiful Intracoastal Waterway on your private floating tiki boat! This BYOB cruise is the perfect way to relax, take in scenic waterfront views, spot local dolphins, and enjoy good times with friends or family. Whether you’re seeking a romantic sunset cruise, a lively booze cruise, or a private charter, this fun and customizable experience is your ticket to the best of St. Augustine by water. What to Expect: Scenic boat cruise along St. Augustine’s Intracoastal Waterway and Matanzas Bay Floating tiki boat atmosphere BYOB booze cruise with cooler and ice provided Private or shared options available Dolphin watching and wildlife spotting opportunities Romantic sunset cruises and island-hopping options

St. Augustine’s Nights of Lights festival is among the historic city’s most celebrated events—but you can only get partial views while walking with the crowds on land. This evening boat tour makes the most of the scene, catching the lights and their twinkling reflections on the waterfront. And with a guide onboard, you’ll get fascinating insights you wouldn’t find on your own.

Experience the Nights of Lights in St. Augustine from the water on this festive catamaran cruise. Choose between a narrated sunset option with historical context or a non-narrated viewing cruise focused on the illuminated skyline. Passing landmarks such as Castillo de San Marcos, this experience offers a unique way to view the city’s renowned Christmas lights with clear vantage points along the bayfront.

The annual Night of Lights celebration is one of St. Augustine’s most popular events. Running from November through January, the Ancient City lights up with more than 3 million sparkling lights that dance along the centuries-old architecture. Explore Old Town and other historical areas illuminated by this joyous event during a private golf cart tour. No matter if you love holidays or history, this special experience is sure to leave a smile on your face.

Celebrate the magic of the holiday season by floating on the water, admiring the renowned Nights of Lights from a unique perspective. Glide along as you take in the stunning displays that illuminate the night sky, all while enjoying the tranquility of the water. This one-hour experience offers a memorable way to soak in the festive spirit, making it perfect for families, couples, and friends alike. Join us for a holiday adventure you'll cherish.

As the oldest continuously occupied colonial settlement in the United States, St. Augustine has a wealth of history within its city limits. See both historical sites and natural landscapes while on this shared sailing cruise. Climb aboard a luxury yacht and sail down the Tolomato River and Matanzas River. This small-group sailing tour passes by the St. Augustine Lighthouse and Bridge of Lions, as well as showcases spectacular sunset views.

Experience the historic charm of St. Augustine, Florida, in style with our luxury, 8-passenger including the guide, and golf cart tours. Discover the nation's oldest city from the comfort of your own personal golf cart, guided by knowledgeable local experts. Cruise through brick-lined streets, past centuries-old architecture, and along the scenic waterfront as you soak in the rich history and vibrant culture of this enchanting destination. During the holiday season, see one of the top ten holiday lights displays in the world on your own personal golf cart tour. Downtown St. Augustine glows with holiday magic as millions of tiny white lights that drape the city's unique Spanish Colonial architecture and glow from the downtown sidewalks to the rooftops, over the Bridge of Lions, along historic buildings, public spaces, hotels, restaurants, and approximately 20 blocks of the Nation's Oldest City's historic district. No long lines, no waiting, and a central pick-up location.

Experience the Nights of Lights in St. Augustine on a private electric golf cart tour. Travel through the historic streets with your group, viewing illuminated landmarks from a comfortable, open-air vehicle. The private format offers a more flexible and efficient way to see the lights compared to walking, with easy navigation through busy areas and space for up to seven guests.

Celebrate the magic of the season this year with Holly Jolly Hunt. Holly Jolly Hunt is an app based scavenger hunt that you can play anywhere of your choosing. Explore the city and look for holiday related items, both traditional and not so traditional. Take a photo through the app to score points for your scavenger hunt team. Perform fun, holiday challenges that will bring laughter to your team. See your score on the leaderboard compared to other teams from all over. Holly Jolly Hunt is guaranteed to provide lasting holiday memories. Whether you play with friends, family, or even co-workers, Holly Jolly will put a smile on your face for the rest of the year!

St. Augustine is no stranger to spirits, spectors, and somethings that go bump in the night. As the oldest continuously occupied colonial city in the United States, it has a bloody real-life history that’s inspired ghostly tales. Decide for yourself whether or not some of the Ancient City’s landmarks are resting places for the undead during this exciting pub crawl. You’ll visit bars and restaurants where the employees and patrons report ghostly encounters.

Join our Day Cruisin' Tour for day drinking, dancing & singing! Party with us while we cruise up and down the Matanzas River viewing Old Town St. Augustine. Expect drinking games, singalongs, and unforgettable moments! Our crew will play an upbeat playlist to start the party on our beautiful historic waterway! This tour is great for bachelorette & birthday parties! THIS IS A PARTY BOAT - EXPECT A PARTY! All tours are BYOB - Bring your own booze and food with you! AGE REQUIREMENT: 18 YEARS OR OLDER

St. Augustine Mobile Wine Tasting Tour: Sip, Savor & Explore Experience the charm of St. Augustine like never before with our exclusive Mobile Wine Tasting & Food Pairing Tour. Perfect for wine enthusiast and curious newcomers, this intimate, chauffeur-guided experience blends indulgence, education, and scenic exploration. What to Expect Glide through historic streets of St. Augustine in a quiet, eco-friendly vehicle while enjoying curated wine tastings, gourmet charcuterie pairings, and personalized service. Ideal for couples, friends, or small groups (up to 12). Call larger groups 877-4-WINETOUR Tour Highlights: •Downtown Parking for a hassle-free start. • Concierge-Style Guidance • Exclusive Tastings with charcuterie & dessert. • Scenic Views of St. Augustine’s landmarks. • Inspiring Atmosphere with soft music & great conversation. • History & Wine Education from expert guides. • Handpicked Stops at top local venues. Uncork an unforgettable journey in the Nation’s Oldest City!

In the charming city of St. Augustine, the annual "Nights of Lights" celebration transforms the historic streets into a dazzling spectacle from November through January. This captivating event features three million sparkling lights, creating stunning light displays that illuminate the city's rich architectural history. For an unforgettable experience, visitors can embark on a tour via a state-of-the-art golf cart, allowing them to comfortably explore the twinkling wonderland. This convenient and eco-friendly mode of transport enhances the magic of the event, providing a unique perspective on one of the most enchanting holiday traditions in Florida.

Stroll along St. Augustine's century-old streets in the company of a local—and sample the best of its craft beer offerings as you explore—on this immersive, two-in-one tour. In the afternoon, meet your guide at one of the city's beloved breweries, where you'll enjoy a tour and tasting. Then, set off on foot: you'll discover a number of top historical landmarks, will hear stories from your guide, and will enjoy more tasting sessions.