St. Augustine, Florida

Sailing trips & boat tours

See historic St. Augustine on a guided hop-on hop-off trolley tour. Listen as your conductors narrate the tour with a fascinating and fun mix of trivia and stories. Find out about the oldest continuously inhabited settlement in the country at the St. Augustine History Museum. Enjoy a full 90-minute tour on the trolley or have the freedom to hop-on and hop-off at any of the 22 stops. Avoid getting through traffic or having to find and pay for parking. Let your conductor take care of navigating for you. Relive the story of the first settlement in North America as you see Castillo de San Marcos, the Spanish fort built in the 17th century. See the famous spring that Ponce de Leon which is deemed the Fountain of Youth, where you can actually sample the water. Explore the site of the first mass in America at the Mission of Nombre de Dios. Experience early St. Augustine as you tour Old St. Augustine Village, which features houses from the 18th and 19th centuries. Admire the Gonzalez-Alvarez House, the oldest documented colonial house in Florida which was lived in by British, Spanish, and American colonists. Immerse yourself in the 500 year history of the city as you view the exhibits at the St. Augustine History Museum.  There are 22 Stops conveniently located close to many places of interest in St. Augustine: 1) 167 San Marco Ave: Old Town Trolley Tours of St Augustine, The Old Jail, Oldest Store Museum Experience, St. Augustine History Museum, Gator Bob’s Trading Post, Spice & Tea Exchange 2) 10 W. Castillo Dr.: Visitor Information Center 3) 31 Orange Street: Potter’s Wax Museum, Old Drug Store, Tolomato Cemetery 4) 1 St. George Street: City Gates + St. George Street (historic walking mall), Oldest Wooden Schoolhouse 5) 20 S. Castillo Dr: Colonial Quarter, Pirate & Treasure Museum, Castillo de San Marcos 6) 6 Avenida Menendez: Bay View at the Best Western, Shipwreck Museum 7) 39 Hypolita Street: Hypolita Street and St. George Street, Columbia Restaurant 8) 38 Sevilla Street: Flagler Memorial Presbyterian Church + Grace United Methodist Church Ancient City Baptist Church 9) 81 King Street: Villa Zorayda Museum 10) 80 Cordova St: Lightner Museum, Flagler College 11) 112 Riberia Street: St. Augustine Distillery 12) 146 King Street: San Sebastian Winery 13) 139 King Street: Whetstone Chocolate Factory 14) 38 Cathedral Place: Plaza de la Constitucion, Government House, Cathedral Basilica of St. Augustine 15) 22 St. Francis Street: Oldest House, Fernandez Llambias House 16) 111 Avenida Menendez: St. Augustine Marina, Schooner Freedom, The Black Raven Pirate Cruise 17) 1 S. Castillo Dr.: Castillo de San Marcos National Monument 18) 19 San Marco Ave: Ripley’s Believe It or Not! 19) 27 San Marco Ave: Old Town Trolley Welcome Center 20) 101 San Marco Ave: Mission of Nombre de Dios, Shrine of Our Lady of La Leche 21) 137 San Marco Ave: The Old Senator + Villa 1565 22) 11 Magnolia Ave: The Fountain of Youth

Voted one of the “10 Best Holiday Lighting Displays in the World”, St. Augustine’s award-winning Nights of Lights is admired by a global audience and is celebrating its 28th year. With over 3 million sparkling white lights adorning every corner of the city and stretching for nearly 20 blocks, it creates an enchanted wonderland that will put a smile on your face and warm holiday memories in your heart. The open-air trolleys are perfect for sightseeing and taking pictures. Complimentary magical viewing glasses allow you to enjoy an enhanced, fully immersive Holiday Experience. Each year guests of the Old Town Trolley are asked to help choose the city’s Top 3 lighting displays. Winners of these prestigious awards will receive cash, prizes and one of the most sought-after trophies in the city! To provide guests with the safest and most comfortable sightseeing experience, only full rows for up to 4 people are available, to assure social distancing.

Join in on a 1.5-hour voyage which includes a first-rate, interactive show onboard a real pirate ship. The ship was designed and built for its purpose, to be a floating performance stage for live pirate shows. The goal is to provide a wide variety of dynamic and interactive entertainment programs that suit all ages. The crew's ambition is to deliver the best pirate show in Florida, regardless of the audience age group. The performance is rehearsed but not scripted, allowing the pirates to improvise and interact with the crowd. No other attraction can live up to this exhilarating and unique adventure.

When the Conductor howls “All Aboard!” – will you be there? Explore the darker side of the Nation’s Oldest City and let a Ghost Host be your guide. See the Old Jail, the site of countless documented paranormal experiences that's listed on the Florida and National Register of Haunted Places. Don’t miss this frightfully fun riding tour. You will hear stories of the haunted Huguenot & Tolomato Cemeteries. Listen as the Ghost Host details true stories of paranormal activity and tales of murder and mayhem in St. Augustine. You'll also experience a unique scary stop inside the Potter's Wax Museum. You won’t want to miss this Ghost Tour! It’s the only ghost tour that takes you inside two of the city’s most haunted buildings! Voted Best Ghost Tour of Best of St. Augustine

Explore St. Augustine's magical Nights of Lights from the comfort of an electric cart. Visit the most important landmarks in Florida's oldest city in a unique ride, full of Christmas spirit. More than 3 million white lights decorate the city of St. Augustine, in what has become a must for visitors looking for a scenic night in town. Starting your tour at the St. Augustine Waterfront, you will get a night time overview of the best sites and brightest decorations. This 45 minute tour will drive through the Plaza de la Constitucion, St. Augustine's city center, with its impressive Christmas tree and thousands of lights adorning the surrounding tress and foliage. Your ride will be complemented with Christmas songs, ideal for setting the mood to pass by several sites in city, like the Flagler College, the Lightner Building, among others.

Embark on your St. Augustine adventure aboard a spacious, state-of-the-art catamaran. As the sun sets, watch the city bathed in a warm, golden glow while leaving your worries behind. Savor complimentary beer, wine, margaritas, champagne, and light snacks, all while enjoying live performances by some of the city’s beloved musicians. Share the moment with someone special, letting the music and the magic of the evening carry you away. Create unforgettable memories as you sail through the tranquil waters of this historic city.

Fun for all ages! Come experience the laid-back island vibes of Black Raven’s Tropical Sunset Cruise, an afternoon trip inspired by the sights and sounds of the Caribbean! Feel the sea breeze in your hair as you sip on a delicious Bahama Mama cocktail, or any of your favorite drinks from our fully stocked bar. Enjoy the sounds of your favorite beach hits by Jimmy Buffet, Bob Marley, and more! Place your own song request with any of the pirates. Guests will be treated to a 2-hour sunset cruise on the Matanzas River sailing north past historic St. Augustine towards Vilano Beach. Experience views from a different perspective through the Bridge of Lions, past the Castillo de San Marcos, The Great Cross, Vilano Bridge and Pier, the St. Augustine Inlet, St, Augustine Lighthouse, and through Salt Run where pods of dolphins are out during feeding time. Keep an eye on the treeline for bald eagles! Take a pirate ship ride into paradise, only on the Black Raven!

Meet your crew and start your family-friendly boat tour from St. Augustine out onto Dolphin Bay. Head for the nation's oldest and most historic waterfront to take in its many sights at sunset while cruising on the St. Augustine Inlet. Make an eco-friendly, non-intrusive stop to see the area's most interesting residents – pods of Atlantic bottle-nosed dolphins. While they are not always on the bay and sometimes go out to sea, they are often seen on the cruise. Next, head under the famous Bridge of Lions and up close and near the downtown St. Augustine waterfront only yards away from the old Spanish fort, one of the most historic and important buildings in North America. Enjoy well-placed narrations about the local ecosystem and history, as you enjoy the many sights and sounds on your route from the comfort of a boat. NIGHTS OF LIGHTS (Nov 22rd - Jan 25th 2025 - 5:30pm, 6:45pm, 8:00pm, 9:15pm) The Holiday Lights of St Augustine - voted top ten must-see holiday sights, is especially suited to our unique travel back-in-time approach to boat tours. This peaceful cruise along the banks of this charming seaside community is an incredibly beautiful experience this time of year as the light-spectacular of St Augustine’s, Nights of Lights leaves you glowing. This celebration is a continuation of the century-old Spanish Holiday tradition right here in the early settlement of St Augustine.

Take a voyage on a pirate ship as you watch a live and interactive pirate show designed for adults. All of the material is suited for a more mature audience so this cruise isn't for the easily offended. Enjoy drinks from a fully licensed bar as you're entertained by a dynamic and interactive performance.  The crew’s ambition is to deliver the best pirate show in Florida regardless of the audience age group. The performance is rehearsed, but not scripted, allowing the pirates to improvise with the crowd. No other attraction can live up to this exhilarating and unique pirate adventure.

Get into the holiday spirit with a guided tour of the Night of Lights in St. Augustine. Glide through the city on a comfortable electric vehicle and see the city's historic landmarks illuminated by hundreds of thousands of holiday lights. Meet your guide and hop into your electric vehicle. Put on your complimentary magical glasses and watch as the lights transform into sparkling holiday-themed shapes. Sing along to classic Yuletide songs playing through the premium sound system. Cruise through the city and see the historic landmarks in downtown St. Augustine.