Maui Sunset Cruise: Open Bar, Pupus & Whale Watching

Summary

Front row sunset views, cocktails, whale sightings and barefoot on Ka’anapali Beach

You’ll board barefoot right on Ka’anapali Beach for a relaxed sunset cruise with open bar and heavy pupus—think crispy pork sliders and fried chicken—plus live music on select nights. Between drinks and laughter you might spot whales (in season) or just soak up those shifting Maui colors from the water. It’s casual, social, unexpectedly peaceful—a memory that lingers long after your shoes are back on.

What’s the experience like?

“Shoes off, folks — you’re on Maui time now,” our captain grinned as we shuffled barefoot across the sand at Ka’anapali Beach. I hesitated for a second — something about handing over my sneakers felt oddly intimate — but everyone else seemed game. The sand was still warm from the afternoon sun, and there was this salty breeze that made my hair stick to my face in a way I’d stopped caring about by day three. We clambered onto the catamaran, toes sandy, drinks already being poured somewhere behind us.

Our guide, Malia, pointed out Lana’i in the distance while someone handed me a crispy pork slider (honestly, better than I expected — sweet and smoky at once). There was pesto pasta salad too, which tasted like basil and ocean air if that makes sense. The open bar kept spirits high; Mai Tais seemed to multiply out of thin air. Every so often you’d hear someone laugh too loud or try to pronounce “pupus” correctly (I failed — Malia laughed but didn’t judge). From December to April they said we might spot whales. Sure enough, halfway through a mellow guitar set (live music on Thursdays), someone yelled “there!” and we all rushed to one side. Fins breaking the surface, just for a second. It’s strange how quiet everyone got.

The light went gold then pink then sort of lavender as we drifted further from shore. I remember leaning against the rail with sticky fingers from fried chicken and chili garlic aioli, just watching the sun slip away behind Moloka’i. People were talking softly or not at all. I didn’t expect to feel so peaceful out there — maybe it was the waves or maybe it was just being barefoot with strangers who felt like friends for an evening. We sailed back in near dark, shoes returned like some small ceremony. I still think about that view sometimes when things get noisy back home.

Step-by-step itinerary

Day 1 — Sunset cruise with open bar

• Board sunset cruise at Ka’anapali Beach
• Enjoy cocktails and pupus onboard
• Watch breathtaking Maui sunset
• Whale watching if between Dec 15 and Apr 15

Top questions

Is whale watching included in this Maui sunset cruise?

Yes, whale watching is included from December 15th to April 15th during the cruise.

Are drinks included on the Ka’anapali Beach sunset cruise?

Yes, unlimited alcoholic drinks are included with an open bar throughout the cruise.

What kind of food is served during the sunset cruise?

The cruise includes heavy appetizers such as crispy pork sliders, pesto pasta salad, Asian slaw, and fried chicken with chili garlic aioli.

Do I need to bring special shoes for this Maui catamaran tour?

No special shoes are needed; this is a barefoot sail—your shoes will be collected before boarding and returned after.

Is live music always available on this Maui sunset cruise?

Live music is available on Tuesdays and Thursdays only.

Where does this sunset cruise depart from?

The cruise departs directly from Ka’anapali Beach in Maui.

Is parking provided for this activity?

Validated parking is available for up to 4 hours for guests joining the tour.

Are dietary requirements accommodated?

You can advise specific dietary requirements at least 24 hours in advance of your trip.

What’s included

Your evening includes barefoot boarding at Ka’anapali Beach with all taxes and fees covered; unlimited open bar; heavy appetizers like pork sliders and fried chicken; non-alcoholic beverages; validated parking up to four hours; live music on select nights; plus seasonal whale watching—all wrapped up with your shoes safely returned at journey’s end.