EcoTours. Amidst America's most enduring human history, EcoTours investigates St. Augustine's natural history. Scenic cruises, kayak tours, and catamaran excursions on Matanzas Bay offer a chance to see bottlenose dolphins, bird habitats, lakes, creeks, and saltwater marshes. Along the way are incredible photo ops of the city and the Castillo from the water. 111 Ave. Menendez, St. Augustine, FL, 32084. 904/377–7245. www.staugustineecotours.com.
The Pirate Ship Black Raven. Whether you prefer Captain Hook or Captain Jack Sparrow, it's a pirate's life for everyone aboard the Black Raven, even if you're only sailing on the Mantanzas River. This "floating performance theater" hosts live pirate shows that include sea chanties, black powder cannon firings, sword-fighting lessons for kids (with harmless foam blades), and treasure hunts on weekends. This is just entertainment, not historical education, so expect the jokes to be cheap and cheesy. However, the atmosphere's lively and the river's lovely. Kids can trade their "letters of marque" to get a share of the booty—if, that is, the crew and the kids can manage to get their treasure back from Blackbeard. There are also adults-only evening cruises—the ship includes a fully licensed bar, so grown-ups can live out the fantasy of "yo-ho-ho and a bottle of rum." Cruises can be cancelled for inclement weather, so call to check before making final travel plans. St. Augustine Municipal Marina, 111 Avenida Menendez, St. Augustine, FL, 32084. 904/826–0000 or 877/578–5050. www.blackravenadventures.com. $29.95.
Schooner Freedom. Cutting a sharp profile, this 72-foot replica of a 19th-century blockade-runner sails from the marina for excursions across Matanzas Bay. You can relax and savor the breeze, or you can help the crew prepare to set sail. There are two-hour day ($35 per person) and sunset ($45) sails as well as a 75-minute twilight/after dark sail ($35). Precise times vary by season. Reservations are advised. St. Augustine Municipal Marina, 111 Ave. Menendez, Slip 86, St. Augustine, FL, 32084. 904/810–1010. www.schoonerfreedom.com.