St. Augustine, Florida, isn’t just the country’s oldest city; it’s a treasure trove of stories, scenic views, and fun activities. What makes it especially appealing for travelers are the variety of tours that reveal its charms from multiple angles—by land, water, and even in the dark. Whether you’re keen on exploring historic landmarks like the Castillo de San Marcos, eager to see the city sparkle during the Nights of Lights, or want a fun family adventure like a pirate treasure hunt, St. Augustine offers something for all. We’re particularly fond of the Hop-on Hop-off Trolley Tour because it makes seeing the city’s highlights relaxed and flexible, plus it includes a visit to the St. Augustine History Museum—a great way to learn about Florida’s oldest settlement without feeling rushed.
If you’re visiting during the holiday season, the Nights of Lights Trolley Tour is a must for its enchanting display of over 3 million lights decorating the historic district. And if marine scenery is your thing, the Sunset Boat Tour with Dolphin Spotting offers a relaxing way to enjoy the sunset, spot playful dolphins, and see the city from the water.
Quick Overview
This list covers a broad spectrum of tour types in St. Augustine, from historic trolley rides and scenic boat cruises to spooky ghost tours and sweet treat walks. You’ll find options for families, couples, and solo travelers alike, with prices ranging from $32 to $99. Many tours include special features like dolphin sightings, live music, or holiday light displays. For a full experience of what’s available, check out the detailed descriptions below.
1. St. Augustine: Hop-on Hop-off Trolley Tour with Museum Entry
At number 1, the Hop-on Hop-off Trolley Tour is perfect for travelers who want to see all the major sights at their own pace. For $38 per person, you can enjoy 1 or 2 days of unlimited hop-on hop-off rides, avoiding the hassle of parking and city traffic. The tour includes entry to the St. Augustine History Museum, clarifying the city’s fascinating timeline. Highlights include visiting the Castillo de San Marcos, where you can walk through the oldest masonry fort in the continental U.S., and tasting a drink from Ponce de Leon’s legendary Fountain of Youth. The flexibility lets you linger at spots or hop off for quick visits, making this a practical choice for families and history buffs alike. Guests praise the friendliness and knowledge of the guides, and with a 4.6/5 rating from 838 reviews, it’s a reliable way to get oriented in the city.
Bottom Line: A budget-friendly, flexible tour that covers everything from historic forts to famous fountains—ideal if you want to explore at your own pace.
2. St Augustine: Nights of Lights Trolley Tour
At number 2, the Nights of Lights Trolley Tour offers an intimate way to experience St. Augustine’s world-famous holiday display. For $81, up to 4 people can enjoy a cozy, private ride lasting just 40 minutes. The tour covers the entire historic district, where over 3 million lights transform the city into a winter wonderland—perfect for creating memorable holiday photos. The experience is sweetened with complimentary sugar cookies, warm apple cider, and magical viewing glasses that enhance the spectacle. This tour is best for those wanting a romantic or festive experience without the crowds, and reviews highlight how special the atmosphere feels, especially with the Christmas carols and friendly contest to pick the best lights.
Bottom Line: A delightful, festive ride that captures the magic of St. Augustine during the holidays, perfect for small groups or couples.
3. St. Augustine: Sunset Boat Tour with Dolphin Spotting
Number 3 on our list is the Sunset Boat Tour with Dolphin Spotting, which is a fantastic way to combine scenic beauty, wildlife, and history in just one hour. For $40 per person, this tour takes you under the iconic Bridge of Lions and along the A1A Scenic and Historic Coastal Byway, offering stunning sunset views. The chance to see bottle-nosed dolphins playing in the waters makes it especially family-friendly. The captain shares stories about local ecosystems, and the peaceful cruise is a calming activity after a day of sightseeing. Reviewers love the “breathtaking sunset and dolphin sightings,” making it a top pick for nature lovers.
Bottom Line: An excellent short cruise combining wildlife viewing and sunset scenery—great for families or anyone wanting a relaxing, scenic experience.
4. St. Augustine: Ghosts and Gravestones Old Town Trolley Tour
For those who enjoy a spooky twist, the Ghosts and Gravestones Old Town Trolley Tour is a fun 80-minute journey into the city’s darker corners. At $36, you’ll be led by a Ghost Host who shares tales of haunted buildings and cemeteries like Huguenot and Tolomato Cemeteries. The tour also visits the Old Jail, where you might catch a shadow or two. It’s a lively way to explore St. Augustine’s eerie past, especially around sunset or after dark. Visitors mention the stories being “chilling but enjoyable” and appreciate the lively narration that keeps the atmosphere fun rather than frightening.
Bottom Line: A spirited tour for those intrigued by ghost stories, suitable for families with older kids and horror fans alike.
5. St. Augustine: Sunset Cruise with Live Music and Drinks
Number 5, the Sunset Cruise with Live Music, combines relaxing scenery and entertainment aboard a spacious catamaran. For $69 per person, this 2-hour cruise offers views of the golden sunset over St. Augustine, accompanied by live music and complimentary drinks, ranging from beer and wine to champagne. Light snacks are also included. It’s perfect for couples or friends looking for a romantic or celebratory evening. Reviewers love how the music and atmosphere make the experience more memorable, describing it as a “beautiful way to unwind after a busy day.” The spacious deck is a bonus, allowing everyone room to relax and enjoy the view.
Bottom Line: A sophisticated, scenic sail with drinks and live music—ideal for a special night out.
6. St Augustine: Nights of Lights Tour by Electric Cart
Number 6, the Nights of Lights Tour by Electric Cart is a lively 45-minute ride through the illuminated streets. For $39 per person, you’ll explore the city’s dazzling light display on a cozy electric cart, singing along to Christmas tunes along the way. It’s perfect for families or small groups wanting a quick, festive overview of the millions of holiday lights. The reviews highlight how fun and easy it is to get into the holiday spirit, especially when riding with friends or children. The compact tour makes it an excellent choice for those short on time but eager for a holiday highlight.
Bottom Line: A short, cheerful way to see St. Augustine’s holiday lights with the added bonus of singalongs.
7. St. Augustine: Treasure Hunt Cruise with Onboard Show
Number 7 is the Treasure Hunt Cruise with Onboard Show. For $36, kids and adults can join a pirate-themed adventure aboard a pirate ship, complete with live sword fighting, cannon fire, and a treasure chest to take home. The interactive show makes it a hit with families, and the opportunity to spot dolphins during feeding time adds a wildlife twist. The lively pirate actors make this an energetic, fun-filled experience that feels genuinely immersive. Reviewers note that kids love the “pirate jokes and treasure,” while adults appreciate the lively atmosphere.
Bottom Line: Perfect for families and kids who love pirates, jokes, and a little swashbuckling action in a scenic setting.
8. St. Augustine: St. Johns River Airboat Safari with a Guide
At number 8, the St. Johns River Airboat Safari offers a 1.5-hour adventure for wildlife lovers. For $80 per person, you’ll ride an airboat through the Florida Wetlands, searching for alligators, turtles, snakes, and a variety of birds. The guide shares stories about the local ecosystem and folklore, making this both educational and exciting. The boat’s open design makes it easy to spot wildlife, and the natural scenery is stunning. Reviewers often mention the “thrill of skimming across shallow waters” and the chance to see dolphins, adding an extra thrill.
Bottom Line: A wildlife-rich, educational adventure suitable for active travelers and nature enthusiasts.
9. St. Augustine: Nights of Lights Sunset Sail with Live Music
Number 9, the Nights of Lights Sunset Sail with Live Music combines spectacular light displays, sunset views, and live entertainment. For $75, you’ll cruise on a spacious catamaran for 2 hours, enjoying complimentary drinks and light snacks. The live music adds a lively touch as the city’s lights begin to glow. It’s a romantic outing or a special treat for friends. Reviewers rave about how the views of the city and the music make this cruise stand out, and the relaxed atmosphere makes it an excellent way to unwind.
Bottom Line: An elegant way to experience the Nights of Lights from the water, especially with great drinks and live music onboard.
10. St. Augustine: Chocolate & Sweet Walking Tour with Tastings
Number 10, the Chocolate & Sweet Walking Tour is a treat for the sweet tooth. For $99, you’ll explore downtown with a guide, visiting local candy shops and bakeries. Starting with a coffee or iced tea, you’ll taste pralines, chocolates, and other confections, plus receive a goody bag to take home. This tour combines history, culture, and delicious treats, making it perfect for those who love sensory experiences. Reviewers call it “an absolute delight” and appreciate the small group size, which makes for a personalized experience.
Bottom Line: A delicious, indulgent way to learn about St. Augustine’s confectionery scene and history.
11. St. Augustine: Waterfront and Downtown Golf Cart Tour
Number 11 is the Waterfront and Downtown Golf Cart Tour. For $32, you can explore in comfort while a guide points out historic landmarks like the Old Jail and Hotel Ponce de Leon. The electric golf cart makes it easy to navigate narrow streets and discover the Spanish and British colonial architecture. The tour lasts 1 hour, making it a quick yet rundown for first-timers. Reviewers praise the friendly guide and the relaxed pace, which allows for plenty of photo stops.
Bottom Line: A quick, fun introduction to the city’s most important landmarks—ideal if you’re short on time but want to see a lot.
12. St. Augustine: Black Raven Tropical Sunset Cruise
The Black Raven Tropical Sunset Cruise ranks number 12 with its Caribbean-inspired vibe. For $32, you’ll cruise the Matanzas River on a relaxed 2-hour sail, enjoying music and dolphin sightings. The fully stocked bar ensures everyone can sip on a favorite drink while watching the sunset. Reviewers highlight the “laid-back atmosphere” and the stunning sunset views. It’s perfect for those wanting a relaxed, tropical experience without leaving Florida.
Bottom Line: A chill, tropical-style cruise with great drinks and dolphin sightings—ideal for unwinding after sightseeing.
13. St. Augustine: Guided History Walking Tour
Number 13, the Guided History Walking Tour offers an in-depth look at the Historic District. For $33, you’ll stroll through the streets with a knowledgeable guide who shares stories about the oldest stone fort, Castillo de San Marcos, and the city’s evolution through three empires. It’s an engaging way to learn about local landmarks and get personalized recommendations for eateries and shops. Reviewers emphasize the friendly, informative narration and the relaxed pace suitable for all ages.
Bottom Line: A solid, informative tour for history lovers and first-time visitors wanting a guided overview.
14. St. Augustine: Boat Cruise and Electric Golf Cart Tour
Number 14 is a combined Boat and Golf Cart Tour. For $85, this 2.5-hour experience includes a panoramic boat cruise through Matanzas Harbor and a golf cart ride passing iconic landmarks like Castillo de San Marcos and the Alcazar Hotel. This dual approach offers the best of land and sea for a comprehensive view of the city. Reviewers appreciate that it’s “less tiring than walking,” and the combination allows for varied perspectives on the city’s history and architecture.
Bottom Line: A well-rounded, relaxed way to see the city’s highlights from both water and land.
15. Saint Augustine: Bourbon History and Tasting Experience
Rounding out the list at number 15, the Bourbon History and Tasting is a must for spirit enthusiasts. For just $37, you explore the Saint Augustine Distillery and learn about the unique Florida bourbon scene. The guided 1-hour tour includes a tasting session where you can savor the distinct flavors of local spirits. Reviewers note it as an “intimate experience” and appreciate how knowledgeable the hosts are about bourbon’s history and craft.
Bottom Line: An educational and flavorful experience for those interested in spirits and local distillery craft.
16. St. Augustine: Dolphin and Manatee Paddle or Kayak Tour
Finally, number 16 offers a peaceful nature outing with the Dolphin and Manatee Paddle/Kayak Tour. For $65, you can paddle through the Anastasia State Park waterways, trying to spot dolphins, manatees, sea turtles, and crabs. It’s perfect for all skill levels, with the opportunity to enjoy quiet nature while observing marine wildlife. Reviewers call it “a wonderful activity for wildlife lovers,” highlighting the chance to see dolphins feeding in their natural habitat.
Bottom Line: A tranquil, wildlife-focused activity suited for outdoor enthusiasts and families.
How to Choose Your Perfect Tour
Picking the right tour depends on what you want to experience. For a comprehensive city overview, the Hop-on Hop-off Trolley offers flexibility and value. If holiday lights are your thing, Nights of Lights by electric cart or Nights of Lights Tour by Electric Cart are fun and festive options. For those interested in marine scenery and wildlife, the sunset and dolphin cruises (Sunset Boat and Sunset Sail with Live Music) provide memorable experiences.
History buffs should consider the guided walking or trolley tours that highlight historic landmarks, while families with kids will love the Pirate Treasure Hunt or wildlife adventures like the Airboat Safari. Budget travelers might prefer shorter, more focused outings like the Chocolate & Sweet Tour.
Final Thoughts
St. Augustine offers an impressive range of tours catering to different interests and energy levels. If you’re a history lover, the Guided History Walking Tour or the Hop-on Hop-off Trolley are excellent choices. For a romantic sunset or holiday lights experience, opt for the Sunset Cruises or the Nights of Lights. Families and wildlife enthusiasts should consider the Pirate Treasure Hunt or Airboat Safari.
No matter your style, booking early is wise—especially during peak seasons like holidays or spring break. With so many unique options, your time in St. Augustine will be filled with memorable moments and plenty of stories to tell.