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Sunset Sailing

Sunset Sail On The Ali'i Nui

From quiet and upscale to lively and adventurous, we work with several partners in South Maui to deliver your ideal sunset sail experience.

What we love:

  • A premium open bar.
  • Enjoy a wide array of fresh and local pupus in a buffet-style bar.
  • There is a good chance of whale sightings during the winter season December to April.
  • Our partners’ staff are very charming and cater to your every need, leaving you to simply relax and enjoy the food, the drink and the setting sun.
Sunset Sail On The Ali'i Nui

From quiet and upscale to lively and adventurous, we work with several partners in South Maui to deliver your ideal sunset sail experience.

What we love:

  • A premium open bar.
  • Enjoy a wide array of fresh and local pupus in a buffet-style bar.
  • There is a good chance of whale sightings during the winter season December to April.
  • Our partners’ staff are very charming and cater to your every need, leaving you to simply relax and enjoy the food, the drink and the setting sun.

What to wear:

  • Casual attire is usual, however feel free to dress it up!
  • Short, flowy dresses are not recommended for ladies since it often is windy while sailing.
  • A light cover-up is recommended if you get chilly.

Know Before You Go:

  • Space is limited, so be sure to reserve in advance.
  • A camera is a must!

Schedule & Rates:

Starting at $279/person

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Welcome Back!

We are experiencing a strong Fall and Winter demand for our all-suite experience at Hotel Wailea. We encourage you to book early with renewed Winter demand.

We will contribute $100 for each booking made through September 30th, 2023 to West Maui relief efforts.

Mahalo for all the mālama you’ve shown Maui,
The Hotel Wailea Team
• All parties of 9 or more are REQUIRED to make a reservation at least 24 hours in advance by calling 808-879-2224. Reservations will be held with a credit card with a $25 per person charge for no-shows.  

• A maximum of 16 guests will be accommodated.  

• Large parties (9-16 guests) will be subject to an automatic 21% service charge.  The final bill may only be split a maximum of 2 ways.  

• Large group reservations availability will be handled on a first come-first served basis as we have limited space for large groups. 

• Large groups without reservations will only be accommodated by splitting groups up based on table availability. Tables and chairs may NOT be moved or added to accommodate.  We may not be able to accommodate large groups without a reservation.