Private 2-hour sunset sail past St. Augustine bayfront landmarks
Kayak the Matanzas River Estuary with a naturalist-trained guide
Paddle a guided sunset eco tour with a lighted firefly kayak
Rent a single kayak with delivery around St. Augustine
Tandem kayak rental with delivery in St. Augustine
See historic forts and a lighthouse from the water aboard a nimble catamaran.
Rent a kayak at Marineland Marina and explore the GTM Reserve at your own pace
Charter a powerful airboat for a private ride tailored to your group
Enjoy an 8-hour pontoon rental for groups of 8 or 10 in St Augustine
Paddle 5+ miles as your guide selects the best route based on tides and time
Cruise Historic Matanzas Bay and see landmarks from the water
Adults-only pirate comedy cruise with explicit skits, songs, and jokes
See St. Augustine by boat and golf cart, with free photos

Savor family-style brunch and bottomless mimosas on a private catamaran with views of St. Augustine
Savor mimosas and a boxed brunch while sailing St. Augustine with a captain and crew
Savor mimosas or seasonal wines while sailing St. Augustine’s scenic waterways with a captain
Private 2-hour sunset sail for up to 6 in St. Augustine
Sail past St Augustine landmarks on a 2-hour small-group charter
Sail into sunset views of St Augustine landmarks on a small-group charter
Sail a private 2-hour charter past St. Augustine's historic waterfront with USCG-licensed captains
Cruise St. Augustine at sunset on a 21+ boat with a cash beer and wine bar
Sail St. Augustine waters and learn about dolphins with your guide
Paddle from downtown St. Augustine into quiet salt marshes on a guided kayak tour
Cruise St. Augustine at sunset on a private captained boat
Enjoy a 90-minute private boat ride to St. Augustine's holiday lights with BYOB and your music for up to 11
Enjoy sunset views with live music, drinks, and snacks aboard a spacious catamaran
Cruise St. Augustine’s Intracoastal on a private captained sunset boat
Cruise St. Augustine on a private open-air party boat with your own captain
Cruise Matanzas Bay on a private captained sunset boat ride
Cruise St. Augustine with an easy-to-drive boat that seats up to six for hassle-free fun
Paddle stable Kaku kayaks to fish rich St. Augustine waters with scenic wildlife and downtown views
Private 90-minute sunset boat ride for up to 8 in St. Augustine
Adults-only sunset jazz cruise with St. Augustine waterfront views
Cruise St. Augustine’s waterways with narrated landmark views
Paddle Durbin Creek with a guide, with rental or bring-your-own kayak options
Paddle a clear kayak at sunset with LED lights near the St. Augustine Lighthouse
Paddle St. Augustine in a clear kayak with LED lights at dusk
Private bachelorette cruise in St. Augustine with a giant floating mat
Cruise St. Augustine’s historic waterfront with a private captain
Cruise the Matanzas River on a private 8 AM eco tour with Captain Adam
Celebrate on a private catamaran with a licensed captain and crew
Learn sailing basics with classroom and dockside instruction
Learn sailing basics in a small group of 2–4 people
Build sailing confidence with a beginner-friendly 2-hour coaching sail
Sail St. Augustine and swap book club notes over tea
Build coastal navigation skills with a self-paced ASA 105 online course
Train as crew on Sunday sails with a USCG captain or ASA sailing instructor
Learn to skipper a keelboat in a two-day ASA 102 course
Practice coastal navigation theory in a four-day ASA course
Train to skipper a 30–50 ft sailboat on a 4-day ASA 106 course
Join a women’s sailing race team and practice on Zephyr
Parasail above St. Augustine for panoramic views in an 8-minute flight
Relax with your favorite drinks and enjoy a scenic St. Augustine sunset from the water.
Spot dolphins and birds with a naturalist captain on a small-group eco cruise