Best results for Sailing

Sail from Navy Pier for Chicago skyline views and the fireworks show

Private sail for up to 6 guests beyond Marblehead Harbor

Private 4-hour sail from Marblehead Harbor for up to 6 guests

Sail from Sausalito and choose hands-on sailing or a relaxed cruise

Private 2-hour sunset sail with downtown St. Petersburg views

Sail a Key West schooner at sunset with drinks, appetizers, and cocktails included

Private daytime sail with dinghy access for island exploring

Sail into sunset on a 2-hour Big Island catamaran cruise with drinks and snacks

Relax on a 3-hour sail with a U.S. Coast Guard–licensed captain from downtown St. Pete

Adults-only Key West sunset sail with champagne and gourmet cheese

Rent a Merit 25 for active sailing in Mission Bay

Charter a 41-foot sailboat for a 3-hour small-group sail

Catch the Key West sunset on the historic schooner Malabar X

90-minute Waikiki sunset sail with complimentary drinks

Waikiki 90-minute sunset sail with complimentary drinks

Sail San Francisco Bay from Pier 39 with 2 drinks included

Private Key West harbor sail with time at the helm

Charter a 1939 wooden schooner for a sunset sail from Key West’s Historic Seaport

Sail Key West waters on a private 4-hour charter for up to six guests

Private 3-hour Key West sunset sail with time to snorkel

Spend a full day sailing from Key West with up to 6 guests

Book a 3-hour private group sail for 7–12 people

Catered 2.5-hour sunset sail for up to 6 guests

Private 2-hour harbor sail with snacks and non-alcoholic drinks