Explore Jacksonville

Tour St. Augustine by Land, Sea, Air and Palate

Discover a variety of ways to explore the Oldest City in America.

At nearly 13 square miles—just under 10 of them of them actually on land—St. Augustine is easy enough to explore by simply spending a day strolling the narrow, sight-filled streets. However, these 16 guided tours offer a much deeper look at America’s Oldest City. 

Horse drawn carriages in front of historic buildings
Horse-drawn carriage tours are a quaint way to see the city. (Courtesy FloridasHistoricCoast.com)

Land Tours

Old Town Trolley Tours depart every 15 minutes to take visitors past more than 100 points of interest. Conductors entertain guests with trivia and humorous stories as they point out St. George Street, St. Augustine Distillery, The Fountain of Youth and other popular attractions. Hop off at any one of the 23 trolley stops to explore on your own, then use your ticket for free admission to the St. Augustine History Museum.

Take a guided tour by bike or Segway. St. Augustine Bike Rentals offers four guided, two-hours tours per day (including training). Guides emphasize historic sites as well as favorite local hangouts that are often missed by tourists. A VIP tour can accommodate up to 10 passengers on a multi-passenger golf cart.

Not only was St. Augustine the first city in America, but it was also home to the first community of free ex-slaves—founded in 1738. Tour St. Augustine highlights historic sites that demonstrate the city’s role in black history and the Civil Rights Movement. Tours are $20 and are offered on the third Saturday of the month.

Pirates have a long history in St. Augustine, as the port city was a prime target for buccaneers in the 1500s. Today they’re more entertaining than terrifying. Take a trolley ride with Pirate Melee and be whisked away by pirates to an enchanting evening that includes dinner and a show. 

A sailboat passes the lighthouse.
Water tours offer a relaxing way to see St. Augustine by water. (©Mr.TinDC/Flickr, Creative Commons)

Water Tours

For a unique tour of the Old City, take a 3-hour catamaran adventure with Bluewater Adventures. These sporty, two-person boats come stocked with a cooler of water for guests to sip while following guides along a sightseeing tour of the waterways. Sunset tours are available.

Florida Water Tours operates a 45-foot pontoon that cruises the Intracoastal Waterway. Watch dolphins and other marine wildlife, take a happy hour scenic cruise or sail away on a full moon tour on the appropriate night. A ghost tour may be a little more spooky on the water, but that just makes taking the Ghost Boat more exciting. Some tours allow you to BYOB.

Native Sun Boat Tours offers a variety of leisurely pontoon boat tours of the Intracoastal Waterway and Matanzas Bay. Cruise by popular sites like Castillo de San Marco, the St. Augustine Lighthouse and the Bridge of Lions. Book a sunset tour and enjoy a complimentary beer, wine, soda or water as the setting sun changes the skyscape. Visit during the holidays and see the stunning Night of Lights by waterway—the entire downtown glows with white Christmas lights.

Rather than the usual sights, an ecologocial tour with Sea Serpent Tours explores the freshwater wildlife and vegetation in the rivers and creeks by airboat. Peddle the hydrobike for a more active tour experience, or explore the St. John's River by kayak or paddleboard.

What could be more relaxing than seeing St. Augustine while lying on a trampoline aboard a private sailboat? St. Augustine Eco Tours will allow guests to charter the boat with up to six friends for a whole afternoon, while a Coast Guard certified captain points out the wildlife and sights. A two-hour beachcombing tour gives guests an up-close look at the ocean's ecosystems and takes them on a search for fiddler crabs, oysters, sea grasses, marine worms, jellyfish, reptiles and other marine wildlife. Shutterbugs may enjoy a two-hour photography tour—choose where to photograph and wait as long as needed to get just the right shot.

Aerial view of Castillo de San Marcos
Aerial view of Castillo de San Marcos (©Ins1122/Flickr, Creative Commons)

Air Tours

The city looks incredible from the air. Old City Helicopters will take guests on a 30- to 60-minute tour, with packages starting at $39 per person (minimum of two guests) for a tour of North Beach. Want to tour an area that isn't covered by one of their usual routes, such as Ponte Vedra or Jacksonville? They'll customize a tour by request.

Add to the thrill of an air tour by taking flight in a fully restored 1935 Waco YOC biplane. St. Augustine Biplane Rides offers several tours starting with an introductory tour of the Intracoastal Waterway and Matanzas Bay for $65 (two passenger minimum). The custom plane can seat up to four passengers, making it a great option for families. A sunset tour can be added to most packages for an extra fee.

Old cemetery headstones in St. Augustine
The Ghost and Gravestones trolley tour takes guests through the spooky side of St. Augustine. (©Joe Penniston/Flickr, Creative Commons)

Ghost Tours

A city as old as St. Augustine is bound to have a few ghosts, and tour guides with Ghost Tours of St. Augustine are happy to tell you about them as they lead groups through the dark alleys by lantern light. A Haunted Pub Crawl mixes drinks and pub-lore with exploration using paranormal investigating equipment. Or take the Maritime Tales & Legends Tour—climb aboard the El Galeon and Nao Victoria in the moonlight to learn what eerie secrets these wooden replica Spanish ships hold. 

"Ghost Hosts" aboard a black trolley lead guests on a "frightseeing tour" through sites like the Huguenot Cemetery and the Old Jail, rumored to be one of the most haunted places in the city. Ghosts & Gravestones operates similar tours in Boston, Savannah, Key West and San Diego. 

Top-hatted storyteller Dion Moore leads guests through the streets of St. Augustine, spinning tales of the spirits and the history behind them. Secrets of St. Augustine Ghost Tours are conducted at 8 pm Monday through Friday, and 8 and 9:45 pm Saturday. 

Boy eating Cuban sandwich
Food tours explore how the other countries have influenced St. Augustine's cuisine. (©Rob Brisco/Flickr, Creative Commons)

Food Tours

You can tell a lot about a place by its cuisine. City Walks Food and Wine Tours takes guests through history by way of gastronomy. Explore five to six local restaurants and gourmet shops during the three-hour tour. Many dishes were created exclusively for the tour by local chefs. Guides explain how St. Augustine's cuisine has been influenced by countries around the world. After the tour, guests receive a gift that includes a Culinary Heritage Recipe Gift Card set. 

The Tasting Tours offers a variety of tours to suit any palate. The Vittles and Vino VIP Carriage Tour takes guests to four or five tasting venues via horse-drawn carriage, while the Wine & Dine Roadster Tour takes them there in a roadster-style golf cart. Lovers of suds can explore local brews on the Beer & Craft Brewery and Barrel & Kegs Tour. Schedules and prices vary and are available on the website.