Cruise St. Augustine at sunset on a 21+ boat with a cash beer and wine bar
1.5 Hours
Free parking, Expert guides
See St. Augustine from the water on a 1.5-hour adults-only sunset cruise aboard the Great Blue Heron. Cruise past key landmarks and enjoy drinks for purchase from the onboard cash beer and wine bar.
Ages 21+ only. Gratuity is not included; clarify the recommended amount with Greetwell before booking. Arrive at least 15 minutes before departure.
Cancel at least 48 hours before your scheduled tour for a full refund. No refunds within 48 hours or for no-shows. Rescheduling within 48 hours has a 50% fee. Full refund if cancelled by the operator due to unfavorable or unsafe weather.
Yes. You must be 21 or older to join this sunset cruise.
You can buy beer and wine from the onboard cash bar.
Bring your ID if you plan to drink alcohol, cash for gratuity, and weather-appropriate attire.
Castillo de San Marcos National Monument stands as the silent sentinel of St. Augustine's waterfront, its weathered coquina walls glowing amber as the sun dips low over Matanzas Bay. Built by the Spanish in the late 1600s, this star-shaped fortress is the oldest masonry fort in the continental United States, and there is no better vantage point to admire it than from the water. As your sunset dolphin cruise glides past, you will see the Castillo de San Marcos National Monument from an angle few visitors ever experience, framed by golden light, swaying palms, and the gentle wake of your boat.
The cruise traces the historic Matanzas Bay shoreline, where dolphins often surface in small pods, arcing through the calm evening water. From the deck, the fortress reveals its full silhouette: the diamond-shaped bastions, the high curtain walls, and the sentry boxes that once watched for approaching ships. Your captain shares stories of pirates, sieges, and the Spanish soldiers who defended this coastline for centuries, weaving the natural beauty of the bay together with the deep history of Castillo de San Marcos National Monument. As the sky shifts through shades of rose and violet, the fort takes on an almost cinematic quality, and the salt breeze carries the scent of the Atlantic just beyond the inlet.
This experience is perfect for couples seeking a romantic evening, families wanting a relaxed introduction to St. Augustine's heritage, and photographers chasing that perfect golden hour shot. History lovers will appreciate seeing Castillo de San Marcos National Monument from the same waters that Spanish galleons once sailed, while wildlife enthusiasts will delight in the dolphins playing alongside the boat. Whether you are a first-time visitor or a returning explorer, watching the sun set behind Castillo de San Marcos National Monument from the bay is a memory that lingers long after you step back onto the dock.
St. Augustine looks absolutely magical from the water, and this tour company clearly knows how to show it off. Travelers consistently rave about spotting dolphins (some even mention "Tippy," apparently a local celebrity!), catching spectacular sunsets over historic sites like the Castillo, and cruising past the city's iconic bridges and lighthouse. The crew gets tons of love by name, with Captain Kevin, Katrina, Paul the astronomer, Rose, and others mentioned for being knowledgeable, friendly, and genuinely enthusiastic about sharing local history and wildlife facts. People appreciate that the narration hits just the right balance without being overbearing. What makes this stand out is how many people say they're already planning their next trip or bringing visitors back. Groups of all sizes seem to have great experiences, from couples to large parties of 19, and even an 86-year-old guest thoroughly enjoyed herself. The different tour options get equal praise, whether it's the 90-minute dolphin watching, sunset cruises, or stargazing adventures. Beyond dolphins, guests spot ospreys, eagles, and various bird species. The only thing close to criticism is one four-star review with no comment, but otherwise it's wall-to-wall enthusiasm. If you want a relaxing way to experience St. Augustine's natural beauty and history while actually learning something, this seems like a solid bet.
We had a wonderful ride on the Osprey with Jeremy and Marceles. We were celebrating my parents 55th wedding anniversary this weekend. They both are older with some mobility issues and the guys were so helpful with the boarding and exit from boat. We saw a lot of dolphins 🐬 and loved the education and history we learned. Thanks so much for a great time!
Renae Hawkins
May 24, 2026
We had a wonderful ride on the Osprey with Jeremy and Marceles. We were celebrating my parents 55th wedding anniversary this weekend. They both are older with some mobility issues and the guys were so helpful with the boarding and exit from boat. We saw a lot of dolphins 🐬 and loved the education and history we learned. Thanks so much for a great time!
Renae Hawkins
May 24, 2026