OAHU

The 5 Best Sailing Tours with an Open Bar in Oahu

5 sailing trips  ·  from $35 a head

The good sailing tours with an open bar in Oahu fill up weeks ahead and the small boats go first. Below: the 5 to book early, what each includes and how they differ.

Oahu's Waikiki Coast: Moana’s Sunset Cocktail Sail - Sunset views, city lights, and changing weather
Bay, Harbour and Coastal Sailing, Coastal Sailing Tours in the USA, Oahu Sailing Tours, Sailing Tours, Sailing Tours with an Open Bar, Sailing Tours with an Open Bar in Oahu, Sunset Sailing Cruises, Sunset Sailing Cruises in Oahu, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Oahu’s Waikiki Coast: Moana’s Sunset Cocktail Sail

Waikiki Sunset Cocktail Sail with Open Bar - The open bar and the value of the price
Oahu Sailing Tours, Sailing Tours, Sailing Tours with an Open Bar, Sailing Tours with an Open Bar in Oahu, Sunset Sailing Cruises, Sunset Sailing Cruises in Oahu, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Waikiki Sunset Cocktail Sail with Open Bar

2.Waikiki Sunset Cocktail Sail with Open Bar

★★★★★★★★★★4.5 · 554 reviews · 1 hour 30 minutes (approx.) · from $84

Review of Waikiki’s 1.5-hour sunset catamaran sail, with an open bar, Diamond Head views, barefoot boarding, pricing, tips, and drawbacks.

“I would definitely recommend thus to everyone, no matter the age! Our entire family loved it! The crew were all extremely friendly and the sunset was beautiful! Will definitely do this again the next time we come back!”

Check availability →Read our full review

Waikiki 3pm Tradewind Sail - Open Bar Included - The 3 PM route toward Diamond Head Lighthouse
Oahu Sailing Tours, Sailing Tours, Sailing Tours with an Open Bar, Sailing Tours with an Open Bar in Oahu, Tour Reviews, USA Sailing Tours

Waikiki 3pm Tradewind Sail – Open Bar Included

3.Waikiki 3pm Tradewind Sail – Open Bar Included

★★★★★★★★★★5.0 · 246 reviews · 1 hour 30 minutes (approx.) · from $53

Review of Holokai’s 3 PM Waikiki tradewind sail, with Diamond Head views, possible wildlife, drinks, practical tips, and honest value advice.

“This was nothing more than a booze cruise. The captain/driver was clearly not looking for whales. He was busy chatting. I understand that whales are fickle and that you cannot count on them. He clearly didn't care or make it look like he was trying. Don't bother with this group. They did honor the no what try again policy. Not Not Not worth the money.”

Check availability →Read our full review

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast - A catamaran ride with Waikiki behind you
Bay, Harbour and Coastal Sailing, Coastal Sailing Tours in the USA, Oahu Sailing Tours, Sailing Tours, Sailing Tours with an Open Bar, Sailing Tours with an Open Bar in Oahu, Swimming and Beach Sailing Trips, Tour Reviews, USA Sailing Tours

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

4.Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

★★★★★★★★★★5.0 · 236 reviews · 2 hours (approx.) · from $34Best value

Review of Moana’s Waikiki Swim’n’Sail, a two-hour catamaran trip with swimming, cocktails, Diamond Head views, and friendly crew.

“I was celebrating my birthday and always wanted to do anything like this. The crew was friendly and professional. It was an awesome experience. I'll definitely do it again.”

Check availability →Read our full review

Honolulu Sunset Sail from Kewalo Harbor Including Drinks - The ride from Kaka’ako to Waikiki
Bay, Harbour and Coastal Sailing, Coastal Sailing Tours in the USA, Oahu Sailing Tours, Sailing Tours, Sailing Tours with an Open Bar, Sailing Tours with an Open Bar in Oahu, Sunset Sailing Cruises, Sunset Sailing Cruises in Oahu, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

5.Honolulu Sunset Sail from Kewalo Harbor Including Drinks

★★★★★★★★★★5.0 · 169 reviews · 1 hour 30 minutes (approx.) · from $61

Review of Oahu’s 90-minute Honolulu sunset sail from Kewalo Harbor, with Diamond Head views, drinks, music, tips, and honest value advice.

“This is so much fun! The crew was fun, super energetic and kept the drinks flowing NONSTOP! The catamaran was clean, big and had such great spots to sit at! Small FYI, you have to remove your shoes before you get on the boat! Nice, clean feet is a must! lol”

Check availability →Read our full review

Scroll to Top

Every kind of day on the water

Pick a rig, a coast or an afternoon.