Best results for Jacksonville Beach FL

Cruise St. Augustine overnight in a 2-seat automatic Slingshot

Try a 1-hour automatic Slingshot ride for two

Paddle stable Kaku kayaks to fish rich St. Augustine waters with scenic wildlife and downtown views

Cruise Historic Matanzas Bay and see landmarks from the water

Relax at the Anastasia Island sandbar on a BYOB cruise with a small group

Cruise on the water at sunset near St. Augustine

Private 2-hour sunset sail past St. Augustine bayfront landmarks

Savor expertly paired wines and seasonal appetizers as you sail past St. Augustine’s scenic coastline at sunset.

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

Private sunset sail with a chef-prepared four-course dinner

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

Sail St. Augustine waters and learn about dolphins with your guide

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

Get married dockside on a luxury sailing yacht with up to 20 guests

Sail St. Augustine and swap book club notes over tea

Hold a dockside wedding ceremony with a sailing yacht backdrop for up to 30 guests