Oahu Sailing

choose your activity below
oahu sailing tours hawaii nautical
Maitaʻi Catamaran sunset sail card image with guests enjoying an evening Waikiki cruise and tropical drinks onboard

Sit back and enjoy Hawaii's beauty as you experience a Hawaiian sunset. Complimentary beverages include Mai Tais, beer, wine, champagne, juices and soft drinks.

hourglass_top 1.5 hours
Maitaʻi Tradewinds sail card image showing a daytime Waikiki catamaran cruise with ocean breezes and scenic coastline

Hop on board the Maita'i, a state-of-the-art catamaran for a fun sail along the Waikiki coastline.

hourglass_top 1.5 hours
Maitaʻi Catamaran fireworks sail card image with guests enjoying a nighttime Waikiki cruise and fireworks overhead

Enjoy a sail along Waikiki Beach after sunset, just in time for the weekly Aloha Friday fireworks show. Great photo opportunities!

hourglass_top 1.5 hours
North Shore summer sunset sail card image featuring a catamaran cruise with warm light and coastal views

Enjoy a sail along Oahu's North Shore aboard the Ho'o Nanea. Relax in the warm evening sun and watch the spectacular scenery as the sun sets.

hourglass_top 2 hours
Hawaii Nautical Waikiki Sunset Cocktail sailing

Come aboard the Ko Nau Lani and enjoy a romantic sunset cocktail sail along Oahu's beautiful west shore. This is the perfect Oahu sunset cruise if you are staying in the Ko Olina resort area.

hourglass_top 2 hours
Sunset Cocktail Cruise

Enjoy a romantic sunset sail along the Waikiki shoreline. There is nothing like a Hawaiian sunset, and nothing beats watching one at sea. This scenic sunset sail takes you south toward Diamond Head.

hourglass_top 1.5 hours
Activity must have a file with Key=Card to satisfy this template. If image is present but this message is displayed then the Title for that image is missing.

Enjoy an afternoon sail off Waikiki Beach. Relax in the Makani Catamaran's semi-enclosed cabin or lie down on the sunbathing net and enjoy the sun.

hourglass_top 2 hours
Makani Catamaran - Sunset Sail

View the setting sun from the Makani Catamaran in Waikiki. Sit back and relax on this fun Oahu south shore sail.

hourglass_top 2 hours
Aloha Friday Fireworks

Enjoy a unique vantage point of the Friday night fireworks in Waikiki. Come aboard the Makani Catamaran for an evening sail along Waikiki Beach. An island-style dinner and a drink is included!

hourglass_top 1 hour
Activity must have a file with Key=Card to satisfy this template. If image is present but this message is displayed then the Title for that image is missing.

Come aboard the Spirit of Aloha and enjoy a sailing adventure along the Waikiki coastline. Sail toward Diamond Head and enjoy the sights of Oahu's scenic south shore along the way.

hourglass_top 1 hour
Activity must have a file with Key=Card to satisfy this template. If image is present but this message is displayed then the Title for that image is missing.

Come aboard with Port Waikiki Cruises on this relaxing sunset cocktail cruise. This is a barefoot sailing excursion where you will enjoy the views of the ocean, sunset, and enjoy appetizers, snacks, and assorted beverages.

hourglass_top 1.5 hours
Maitai Catamaran Waikiki sailboat tour boat docked at Waikiki before departure

Set sail from Waikiki Beach and enjoy beautiful coastline views of Oahu's south shore, as well as our "delite"ful friends that we often encounter, such as dolphins, turtles, flying fish and whales (seasonal) to name a few.

hourglass_top 1.5 hours
Surf Scene Safari catamaran tour – scenic North Shore cruise on Oahu with ocean views and surf-spot watching

The Surf Scene Safari with North Shore Catamaran is a scenic cruise along Oahu's legendary North Shore. Sail aboard the Ho'o Nanea to see world-famous surf breaks, golden beaches, and ocean wildlife such as dolphins, sea turtles, and humpback whales in season.

hourglass_top 2 hours
Star of Honolulu – Mai Tai Sunset Cocktail Cruise

The Mai Tai Sunset Cocktail Cruise is a laid-back evening sail aboard the Star of Honolulu, offering panoramic sunset views of Waikiki and Diamond Head. Sip a Signature Star Mai Tai, enjoy light pupu snacks, and relax on spacious open decks as the sky glows and island music sets the mood. This smooth, social cruise is a simple, memorable way to experience Oahu's golden hour.

hourglass_top 2.5 hours