Watch holiday-decorated boats parade across Matanzas Bay after dark
2 hours
2-hour cruise, hot cocoa
Set out on a holiday cruise during St. Augustine's annual Regatta of Lights, when decorated sailboats, trawlers, yachts, and shrimp boats parade along the bayfront. Take in the waterfront light displays between the Bridge of Lions and Castillo de San Marcos.
Cancel at least 48 hours before your scheduled tour for a full refund. No refunds for cancellations within 48 hours or no-shows. Rescheduling within 48 hours incurs a 50% fee. Full refund if the operator cancels due to weather or minimum passenger numbers are not met.
Product ID: JG83SP
Do not bring alcohol aboard Osprey or Great Blue Heron; drinks are available for purchase on Osprey. On Island Breeze, you may bring your own adult beverages.
Dress for the weather and bring a jacket or sweater for the evening. Do not wear heels or flip-flops.
Florida Water Tours, 107 Yacht Club Dr., St. Augustine, FL 32084
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.
Captain Kevin, and Abigail were awesome!
Bill Mears
August 31, 2026
Captain Kevin, and Abigail were awesome!
Bill Mears
August 31, 2026
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