Maui: Ka'anapali Luxury Sunset Dinner Sail

About This Experience

This is the longest and most filling of Teralani’s three Kāʻanapali sails. It is a 2.5-hour sunset sail with a full dinner and an open bar. The morning trip is the whale watch, and the 2-hour cocktail sail serves appetizers only. Here the crew serves an assisted buffet on board a sailing catamaran that loads straight from the beach by the Outrigger Kāʻanapali Beach Resort.

The listed menu is more than finger food. It starts with caprese skewers, teriyaki meatballs and a Greek-style salad. Mains are curry-marinated fresh Hawaiian fish and a truffle-teriyaki braised short rib, with miso tofu for vegetarians on request. Sides are coconut-whipped Molokaʻi sweet potatoes and kimchi wok-fried green beans, and dessert is a coconut-crusted brownie pop. The open bar pours premium Hawaiian beer, wine, sparkling rosé, mai tais, vodka and rum with mixers. To drink, you must be 21 or older and bring a valid picture ID.

The listing sells it for sunset views, the West Maui Mountains and wildlife, not for whales. In winter you may see humpbacks from the deck, but this is not a whale watch, and nothing about whales is promised. If whales are your priority, Teralani’s morning whale-watch sail is the better pick, with a naturalist and a hydrophone on board; see our review.

Recent reviews from June to October 2026 praise attentive crew, a clean boat, strong drinks and a musician on board. The food draws the mixed comments. One 3-star review in September 2026 found it unimpressive, and older reviews say the menu changed or the dishes were dry. In 2024 one guest found the check-in spot about half a mile from where they expected, so read your voucher carefully. Children have joined past sailings, so it is not an adults-only evening.

It rates 4.8 from 165 reviews, from $169 per person, with free cancellation up to 2 days before. Boarding is from the sand, and the listing says it is not suitable for wheelchair users. For a lighter evening, compare Teralani’s cocktail sail; for a bigger boat with live music on set nights, see Sea Maui’s dinner cruise in our review.

Highlights

• Fresh Hawaiian fish or braised short rib, with a vegetarian option on request
• The longest of Teralani's three Kāʻanapali sails, at about 2.5 hours
• Views of the West Maui Mountains as the sun goes down
• An onboard musician on some sailings, per a recent review
• Boarding by the Outrigger Kāʻanapali Beach Resort, with no harbor drive

What's Included

• ✓ Assisted buffet dinner with appetizers, mains and sides
• ✓ Coconut-crusted brownie pop for dessert
• ✓ Open bar with Hawaiian beer, wine, sparkling rosé, mai tais, vodka and rum
• ✓ Cane-sugar sodas, tropical juices and filtered water
• ✓ About 2.5 hours of sailing at sunset

Not Included

• Gratuities for the crew
• Hotel pickup and drop-off
• Whale watching; this is a dinner sail

What to Bring

• A valid picture ID if you plan to drink
• Clothes you can wade in for beach boarding
• A light layer for the evening breeze
• A dry bag or zip bag for your phone
• Cash or a card for crew tips

Good to Know & Caveats

• This is a dinner sail. The listing does not include whale watching, so any whales you see in winter are a bonus.
• Boarding is from the sand at Kāʻanapali Beach. Not suitable for wheelchair users.
• Alcohol is served only to guests 21 and over with a valid picture ID.
• Vegetarians can ask for miso tofu in place of the meat main. Request it when you book.
• Reviews on the food are mixed. Recent guests praise it, while a September 2026 review and some older ones found it disappointing.
• A 2024 reviewer found the check-in spot about half a mile from where they expected. Allow time to find the Outrigger beach front.
• Free cancellation only up to 2 days before.

Meeting Point

On Kāʻanapali Beach at the Outrigger Kāʻanapali Beach Resort, where the catamaran loads from the sand; your voucher gives the exact check-in spot and time.