Top St Augustine Romantic Tours

See St. Augustine from a new perspective with this leisurely sunset cruise. Climb aboard a boat for a scenic cruise including views of Castillo de San Marcos National Monument, the Bridge of Lions, and the St. Augustine Lighthouse. Sip beer or wine from the on-board bar with the Osprey, 21 and older option, or select the Island Breeze option for a family-friendly experience.

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.

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.

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.

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.

Explore St. Augustine’s Bay Front from the water on this private 2-hour cruise aboard a luxury sailing yacht with space for up to six passengers. With a USCG-licensed captain at the helm, sail along the historic bay front. Look for wildlife, including dolphins, and admire the historic sites. Relax onboard, learn about sailing, or even take the helm.

See St. Augustine’s spectacular Nights Of Lights Christmas celebration from a different perspective with this fun boat tour. This is an excellent way to see the city shine without being confined in a small vehicle or needing to walk. Float by the Bridge of Lions, see the Old Fort, and marvel at the Old City lit up with holiday cheer.

There is no better way to enjoy the famous Nights of lights in St Augustine than from an electric cart. Unobstructed views for taking perfect pictures. Avoid traffic by navigating through smaller street not accessible to larger cars and buses. Easy to get in and out of and more importantly its far more fun!

Knowing where to grab food and wine in a new city takes a lot of time and effort researching. Skip the nitty gritty details of studying online reviews and take this St. Augustine Food Walking Tour instead. This tour takes you to many local restaurants, eateries, and even a wine store to learn about the city’s food culture and history—while enjoying some tastings, of course.

Experience the magic of St. Augustine's Nights of Lights with Old Town Party Boat! Glide along the scenic waterways of the nation's oldest city while surrounded by dazzling holiday lights with your favorite drink in hand! We will be partying, dancing, singing & making memories while cruising past historic landmarks, beautifully adorned with twinkling lights, creating a festive atmosphere. Don't forget your camera to capture the enchanting moments! 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