Sailing

Choose your boat and learn to sail with a private instructor in Key West

Set sail on a private charter with room for your own food and drinks

An evening sailing charter with space for your own food and drinks

Enjoy a daytime sail and time on the water

Savor brunch and drinks aboard a Lowcountry catamaran

Sail into sunset with room for your group and your own refreshments

Learn at your own pace with private instruction on the water

Learn sailing fundamentals aboard Hobie Wave catamarans

Private sunset sailing with music, snacks, and coastal views

Sail Puget Sound as Seattle’s skyline glows at sunset

Private sail to a shallow-water anchorage with time to lounge on a Lilypad float

Private 2-hour Key West sunset sail with captain and mate

Sail a 1939 wooden schooner and take a turn at the helm

Private Key West harbor sail with time at the helm

Sail Key West aboard a 1939 wooden schooner with captain and crew

Sail Key West’s Atlantic coast at sunset aboard a historic schooner

Explore the coast aboard a canoe inspired by ancient Hawaiian design

Sail past Key West landmarks and relax on a private catamaran cruise at sunset

Sail Key West waters your way with snorkeling, kayaking, fishing, and time to unwind

Sail beyond Key West for snorkeling, kayaking, fishing and lunch

Private daytime sail with dinghy access for island exploring

Private evening sailing with sunset views across Tampa Bay

Sail aboard Lady Grace with an open bar and Caribbean sunset views

Sail aboard Lady Grace with live saxophone music and an open bar