Sailing

Shape your own sailing adventure, from taking the helm to relaxing on the water

Classic schooner sailing with open-deck Gulf views

Watch the Gulf sunset aboard a traditional schooner

Sail Boca Ciega Bay on a private schooner with drinks and a restroom aboard

Private evening sailing with sunset views on Boca Ciega Bay and the Gulf of Mexico

Sail Boca Ciega Bay and the Gulf while watching for dolphins

Sail a private 3-hour sunset cruise on a 40-foot catamaran

Private catamaran sailing with tubing and hands-on helm time

Sail Key Largo on a private 40-foot catamaran for up to 6 guests

Sail Key Largo at sunset on a private 40-foot catamaran for up to 6 guests

Private Charleston harbor sailing with swim-ready water hammocks

Sail Charleston Harbor at sunset with views of Fort Sumter

Book a private sail and choose your own snorkeling or sunset plan

Relax on the water with Waikiki and Diamond Head views

Friday fireworks sail with front-row views from the water

Sail Waikīkī’s Gold Coast at sunset with optional swim time

Get on the water with equipment sized and set up for you

Take your celebration out on the water

Sail the Middle River and Chesapeake aboard a private luxury catamaran

See Pepin’s waterfront from the calm waters of Lake Pepin

Set sail on a 2022 Beneteau with cabins for coastal cruising or a Catalina trip

Sail the coast or reach Catalina aboard a modern two-cabin cruiser

Sail the coast, Catalina Island, or the Channel Islands on your own itinerary

Sail the coast or reach Catalina aboard a 3-cabin 2025 Beneteau