Maui: Sunset Dinner Cruise & Whale Watching with 4-Course Meal

Summary

Whale watching from Ma'alaea Harbor with dinner cruise and sunset views

You’ll board at Ma'alaea Harbor for an evening of whale watching off Maui’s coast with local guides who know every story behind those migrating tails. Savor a full 4-course dinner as sunset colors hit the water, sip included drinks (the Mai Tais are generous), and listen for those sudden shouts when someone spots a whale breaching nearby.

What’s the experience like?

I didn’t expect to feel so giddy before we even left Ma'alaea Harbor. There’s something about the way the air smells here — a little salty, warm, kind of sweet — that makes you want to just breathe in deeper. Our guide, Kaleo, greeted everyone by name (how does he remember?) and made sure we were settled before we pushed off. The boat was smaller than I pictured — not cramped, just… cozy. You could actually hear people laugh over the engine.

The first time someone shouted “whale!” I nearly dropped my drink. It’s wild how everyone suddenly hushes, scanning the water like kids on an Easter egg hunt. We saw two tails flick up near Lana‘i — honestly, I’m still not sure if I blinked or if it really happened that fast. Kaleo explained how these humpbacks migrate here every year, and you could tell he wasn’t just reciting facts; he’d point out little details about their behavior between sips of his coffee. The sun started dipping lower and turned everything gold — even the napkins looked fancy for a second.

Dinner came out in courses (I lost count after dessert), and there was this moment when I was trying to eat salad one-handed because I didn’t want to miss anything outside. Someone at our table tried to pronounce “Moloka‘i” right — Li laughed when I tried too; pretty sure I butchered it. The Mai Tais were strong enough that nobody cared much anyway. And then there was just this quiet stretch where everyone watched the horizon, plates empty, no one saying much except for maybe a sigh or two. That part stuck with me more than I thought it would.

Step-by-step itinerary

Day 1 — Sunset dinner cruise and whale watch

• Start journey at Maalaea Harbor
• Spot McGregor Point Lighthouse
• Enjoy 4-course dinner on cruise
• Watch migrating whales
• Sip included Mai Tais and beverages
• View Pacific, Lana‘i, and Moloka‘i

Top questions

Is dinner included on the Maui sunset dinner cruise?

Yes, a 4-course meal is served during the cruise.

Are alcoholic drinks included on this whale watching tour?

Yes, Mai Tais and other beverages are included in your booking.

Where does the Maui whale watch cruise depart from?

The cruise departs from historic Ma'alaea Harbor between Kihei and Lahaina.

Is this sunset dinner cruise suitable for kids?

Yes, children are welcome and those under 4 ride free but must be booked in advance.

Are service animals allowed on board?

Yes, service animals are allowed on this tour.

Can wheelchairs be accommodated on this Maui cruise?

Collapsible wheelchairs may be accommodated if passengers can walk or be assisted onto the vessel.

How early should I check in for my whale watch tour?

Please check in 45 minutes prior to your departure time.

What’s included

Your evening includes all taxes and fees covered up front, a full 4-course dinner served as you sail past Lana‘i and Moloka‘i, unlimited Mai Tais or other drinks if you prefer something else, live commentary from marine naturalists who actually make it fun to learn about whales (not just facts), plus fuel surcharges so there aren’t any surprise costs later on.