Best results for Sailing

Sail Key West's clear waters, kayak mangrove islands, snorkel vibrant reefs, and refuel with a buffet lunch—all in one day.

Sail past Key West landmarks on a 105-ft schooner while enjoying complimentary soft drinks and expert crew narration.

Admire Alcatraz, the Golden Gate Bridge, and city skyline on a 1.5-hour family-friendly bay sail.

Glide past Alcatraz and beneath the Golden Gate Bridge as the city skyline glows in the setting sun.

Watch Hilton Head's vibrant sunset while relaxing or helping crew aboard the historic Stars & Stripes

Sail for three hours to spot marine life and enjoy San Diego’s historic waterfront.

Learn essential sailing skills in a personalized session guided by a USCG-certified captain.

Watch fiery skies and enjoy a complimentary champagne toast on a relaxed evening sail.

Sail the serene Lowcountry waterways aboard a 35' catamaran with champagne and space for up to six guests.

Savor coastal views and learn to handle the sails on an exclusive 2-hour voyage for up to six.

Sail a luxury catamaran along Palm Beach and savor a scenic two-hour sunset cruise.

Unwind as the sun sets over the Indian River and look for dolphins on a relaxing 2-hour catamaran cruise

Sip complimentary champagne as you watch a legendary Key West sunset aboard the elegant Schooner America 2.0.

Enjoy a customizable 6–8 hour luxury sail on Sarasota Bay with captain and mate included

Enjoy a customizable luxury sail with captain and mate aboard a spacious 42-ft catamaran.

Join the crew or relax on a 1.5-hour Hilton Head coastal sail aboard a historic America’s Cup yacht

Watch the sky blaze over Waikiki on a relaxing two-hour catamaran sail

Toast the day aboard a catamaran as you watch the sun sink beneath the Oahu horizon.

Relax on a one-hour catamaran sail and soak in Waikiki’s dazzling coastal scenery.

Watch Honolulu’s skyline glow as you relax aboard a catamaran during a spectacular sunset cruise.

Watch the Hawaiian sunset from a spacious 53-foot catamaran with complimentary cocktails and light appetizers.

Enjoy a swim-optional sunset sail along the Waikiki coastline with inside and outside seating

Soak in Honolulu and Diamond Head views on a 2-hour catamaran sail

See marine life and Waikiki views on a one-hour Diamond Head sail

Sail a stable catamaran toward Diamond Head and toast the sunset with included drinks

See Oahu’s top sights by van, then sail at sunset on a Polynesian canoe

See wild dolphins, snorkel with turtles, and enjoy lunch on a 3-hour West Oahu sail

Set sail off Waikīkī to snorkel with turtles, then enjoy a fresh lunch and drinks included

Unwind on a Waikiki sunset catamaran with views of Diamond Head, drinks and light bites included

Unwind on a West O‘ahu sunset cruise with panoramic views, drinks, and light bites included

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

Sail past historic St. Augustine landmarks with a friendly crew

Sail at sunset past St Augustine landmarks with a small group and professional crew

Sail a private 2-hour charter past St. Augustine's historic waterfront with USCG-licensed captains

Customize your Waikiki sail with a private crew for snorkeling, sightseeing, and flexible departures

Sail a modern 40' catamaran from Kewalo Basin with spacious lounges and snorkel gear

Sail Waikīkī at sunset with a swim stop on a spacious BYOB trimaran

Spot dolphins and coastal wildlife as you sail historic St. Augustine

Sail Oahu's North Shore at sunset on a private 3-hour charter for up to six.

Customize your island day and sail to Turtle Canyon to swim or snorkel with turtles

Sail a catamaran off Diamond Head and snorkel with tropical marine life

Sail off Waikiki at sunset with skyline views and a pupu platter on a comfortable catamaran.

Customize your private sail for snorkeling, sunset, or sightseeing with up to 35 guests

Enjoy a private day or sunset catamaran sail off Waikiki with up to 37 guests.

Sail Waikiki’s coast on a 1-hour BYOB cruise with Diamond Head views

Sail Bodega Bay for three hours and watch for sea lions, whales, and birds

Sail South Maui at golden hour with live music, open bar, and a sparkling wine toast

Sip island cocktails and savor appetizers as you sail at sunset aboard a Hawaiian-built catamaran

Sail Maalaea Bay to secluded reefs with guided snorkeling, light breakfast and deli lunch included

Sail Maalaea Bay with snorkel stops, guided in-water tour, and meals included

Sail Ma’alaea Bay at sunset with crew, light appetizers, and soft drinks on a private catamaran

Enjoy a private sunset sail with light appetizers and soft drinks