Choose Between Two Options
$347 for private sunset cruise or evening cruise in Coconut Grove for up to six, valid Friday–Sunday ($695 value)
$320 for private sunset cruise or evening cruise in Coconut Grove for up to six, valid Monday–Thursday ($645 value)
Classic Sail Charters
Handicap Accessible: No
Staff Size: 1 person
Parking: Parking lot
Most popular offering: Half-Day and Sunset Sailing
Pro Tip: Bring sunscreen, hats, and a smile
Q&A with Tony Ireland, Captain
What inspired you to start or run this business?
Before starting Classic Sail Charters, I volunteered with a community sailing organization that exposed people to sailing who had never sailed before. Most of the participants in the program realized the special calm joy that comes after casting off lines and raising sail. Gliding quietly through the water under sail seems to wash the stress away, and it was apparent in their eyes and faces. After 25 years working in corporate offices, I decided this was for me.
What’s your favorite part about your job?
Helping people get away from it, and watching the faces light up.
Is there anything else you want to add that we didn't cover?
Sailing yachts is a sporty activity that requires some mental concentration, as well as some physical strength. When the wind is up and the boat pitches and rolls a bit, it is not the best or safest activity for children under 7, nor is it much fun for the parents.
What is the best reaction you’ve ever gotten from a customer?
"Thank you, that was wonderful."