“Perfect sunset cruise! Great crew, good drinks, amazing views of the islands at sunset.”
Verified Review
This two-hour sunset sail is as easygoing as it gets. Departing from Kā‘anapali Beach, the cruise takes you along Maui’s leeward coast, where the silhouettes of the West Maui Mountains contrast beautifully with the open sky. While this tour accommodates a larger group, the atmosphere feels more like a relaxed cocktail hour than a guided expedition. Sip on mai tais, wine, or local brews from the open bar, nibble chef-prepared appetizers, and soak in the glow of a Maui sunset from one of the island’s most scenic vantage points—on the water. From December to April, you may even spot migrating humpback whales.
GUEST REQUIREMENTS
For ages 5+, group size limited to 16 guests.
ACTIVITY LEVEL
Relaxing sail
WHAT TO BRING
Light windbreaker, sun protection
CANCELLATION POLICY
Changes or cancellations must be made 48 hours prior.
WHAT GUESTS ARE SAYING
4.7★ from 2,600+ reviews on TripAdvisor
Guests say the sunset sail is one of the most effortless ways to spend an evening on Maui — laid-back, never crowded, and with a crew that feels more like old friends than staff. Reviews highlight the quality of the cocktails and appetizers, the spacious catamaran, and the smooth barefoot beach boarding. Many mention how beautiful it feels to watch the sun sink behind Lanai or Molokai while gliding quietly along the Kaanapali coastline. For many, it’s a simple mix of good company, ocean breeze, and soft island twilight.
Enjoy a relaxing evening on the water with Teralani’s Holo Holo Sunset Cocktail Sail!
Enjoy a relaxing evening on the water with a Sunset Cocktail Sail. This 2-hour tour takes you on a leisurely cruise along Maui’s west coast, where you can admire the stunning views of West Maui’s rugged mountains and tranquil leeward waters. Sip on your choice of beer, wine, champagne, mai tai or tropical cocktail from our open bar, and savor our chef’s selection of appetizers. Watch the sun dip below the horizon and paint the sky with vibrant colors. Experience the magic of Maui at sunset on this unforgettable sail.
Times and duration
- (Feb.1 - Apr 15 departure time is 4:30pm)
- (Apr.16 - Aug 31 departure time is 5:00pm)
- (Sept.1 - Sept 30 departure time is 4:30pm)
- (Oct. 1 - Jan 31 departure time is 4:00pm)
NOTE: From December 15 - April 15 this trip offers whale watching
What's included:
- A 2-hour sunset cocktail sail along Maui’s west coast with stunning views, an open bar offering beer, wine, champagne, and tropical cocktails, and a selection of chef-prepared appetizers.Teralani Sailing Adventures has been taking guests along Maui’s Kaanapali coast for decades. Known for its fleet of sleek catamarans and friendly, island-born crew, Teralani pairs local hospitality with a relaxed vibe that makes every sail feel like an easygoing backyard gathering — only at sea. The Holo Holo Sunset Cocktail Sail is all about savoring the end of the day with open bar drinks, light bites, and warm salt air, while Maui’s sunset and neighbor islands drift into view.
Location: Meet on the beach in front of Leilani’s on the Beach restaurant at Whalers Village, 2435 Kaanapali Parkway, Lahaina, HI 96761.
Check-In: Arrive 30 minutes before departure for a quick beachside check-in and barefoot boarding straight from the sand.48 hours cancellation notice is required or you will be charged in full. No cancellation or changes can be made within 48 hours of trip. Due to traffic and parking please allow enough driving time (From South minimum 1.5 hours, from North minimum 30 minutes).
FOLIO TRAVELOGUE
Sunset, Served With a Twist
There are sunset cruises, and then there’s this: toes-on-deck, drink-in-hand, wind-on-face kind of sailing. As the boat pulls away from Kā‘anapali Beach, the sky shifts through soft pastels, then bursts into amber and rose. You lean into the rail, drink sweating slightly in your hand, and breathe in the salt air. Somewhere behind you, the bartender is pouring another round, and the West Maui Mountains glow like a painting left out in the sun.
A floating bar with the best view on Maui.
This isn’t a quiet whisper-on-the-waves experience—it’s more like a floating happy hour with great lighting. People chat. Someone laughs too hard. A couple clinks glasses. It’s social, casual, beautiful. No gear, no guide talk, no coordination needed—just show up, step aboard, and let the evening unfold.
You catch a moment of silence as the sun touches the horizon. Then someone next to you raises their glass and says, “It doesn’t get better than this.” You nod. They’re not wrong.
