Top St Augustine Holidays

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.

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.

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.

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.

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.

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.

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.

Join us for the jolliest Nights of Lights Joy Ride in St. Augustine, a fun-filled holiday tradition! Experience the magic of our stunning holiday lights from the comfort of an eco-friendly electric golf cart—cheer included! This private Joy Ride accommodates up to 7 people. Please note: We do not enter any buildings, and some seats may not face forward.

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.

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.

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!

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.

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.

Grabbing drinks in a new city can sometimes be overwhelming finding your own way from place to place. This Toast of St. Augustine Walking Pub Crawl takes the stress out of asking for directions with an experience led by a guide. You’ll visit historic pubs in St. Augustine while enjoying alcoholic beverages and learning about the city’s past.

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

Step into the shadows and raise a glass to the spirits—both kinds—on our St. Augustine Haunted Pub Crawl. This adults-only adventure blends the thrill of the paranormal with the buzz of the city’s vibrant nightlife, creating an unforgettable night out you won’t find anywhere else. You’ll journey through St. Augustine’s most infamous pubs, bars, and historic taverns—places where the drinks flow freely and the ghost stories linger long after last call. Along the way, uncover chilling tales, haunted hotspots, and eerie legends that give this city its spine-tingling reputation. Whether you’re out with friends or flying solo, this experience is all about connection, laughter, and a little mischief. Meet fellow thrill-seekers, share a toast with new faces, and soak in the electric energy of a night that’s equal parts spooky and social.

Celebrate the magic of Nights of Lights aboard our comfortable power catamaran with two festive options: Nights of Lights Sunset Tour (Narrated) Enjoy a beautiful sunset cruise followed by St. Augustine’s dazzling holiday lights. This tour includes engaging narration covering the city’s history and landmarks like the Castillo de San Marcos and the St. Augustine Lighthouse. Watch the skyline glow as thousands of white lights illuminate the bayfront. Nights of Lights Viewing Cruise (Non-Narrated) A lights-only experience with no narration and no sunset portion. Relax and take in uninterrupted views of the sparkling waterfront and historic landmarks from the water.

Combine your love of ghost stories with your spirited attitude on a 2.5-hour haunted bar crawl of St. Augustine. Together with your guide, visit four venues and enjoy a free drink and exclusive discounts at each. Between sips, listen to metaphysical and supernatural stories surrounding the city. Along the way, get to know some of St. Augustine's most popular neighborhoods, including the Flagler district and Old Spanish area.

Discover the enchanting Nights of Lights in St. Augustine from the comfort of a private electric golf cart. Perfect for groups of up to 12, this eco-friendly adventure takes you through the city to marvel at the dazzling holiday displays. Each tour features two separate golf carts driven by licensed guides who share the rich history and festive spirit of the area. Enjoy a unique and personalized experience as you glide through the twinkling streets of this historic city. - Private tour for groups of up to 12 with two eco-friendly golf carts - Licensed guides provide insights into St. Augustine's history and lights - Enjoy a leisurely ride through the stunning holiday displays - Perfect for families, friends, or festive gatherings during the holiday season Please note we do not enter any buildings and not all seats face forward.

What sets St Augustine Sailing apart from other Nights of Lights boat tours is the elevated experience aboard a luxury sailing yacht. While many tours offer a simple ride, St Augustine Sailing provides an intimate, serene setting that allows guests to fully immerse in the beauty of the holiday lights without the crowds or noise of typical boat tours. Our yachts offer a more personalized, relaxed atmosphere with comfortable seating, and the option to book private charters. You’ll also be guided by experienced USCG captains who know the waters and the best vantage points to view the city’s spectacular light display. Whether you’re celebrating a special occasion or seeking a peaceful, romantic evening, our tailored sailing experience ensures you enjoy the Nights of Lights in comfort and style.

Are you looking for the Elf on the Shelf? We think we saw him in St. Augustine on our Pinkmas Tour – and he had friends! See if you can spot him with us on this fun-filled family day time holiday tour during the Nights of Lights season in St. Augustine. This tour runs Nov 1st through Jan 11th. Join an enchanting journey through the charming streets of St. Augustine on the Holiday Pinkmas Elf Tour. This pinktastic daytime ride invites families to search for the mischievous Pinkmas Elves hidden in local shop windows while sipping hot cocoa. Led by a knowledgeable guide, discover the festive decorations and history of America's oldest city. Ideal for families looking to enjoy holiday cheer without the late-night crowds, this tour promises memorable moments and unique local finds. - Family-friendly tour perfect for all ages - Enjoy hot cocoa and interactive elf-hunting fun - Learn about St. Augustine's festive history from your guide - Daytime tour lasts approximately 45 minutes

Our "Rhythm of the Night" tour offers a lively evening experience on the water, combining music, dancing, and stunning views of the city’s skyline. As the boat cruises along the waterfront, as our crew sets the mood with an upbeat playlist, creating an unforgettable party vibe. It’s a perfect way to celebrate with friends or enjoy a unique night out in St. Augustine! Great for Bachelorette parties, birthday parties, special occasions or a wild night out! #1 PARTY BOAT IN ST. AUGUSTINE, FL THIS IS A PARTY BOAT - EXPECT A PARTY! BYOB Booze Cruise - must be 18+