Waikiki: Sunset Catamaran Sail with Drinks & Diamond Head Views

Summary

Sunset sailing past Diamond Head sipping cocktails from Waikiki

You’ll sail barefoot from Waikiki as golden hour hits, sipping local cocktails while Diamond Head glows ahead. Watch for sea turtles or dolphins beside the boat, snack on pupu platters, and feel the hush as everyone waits for that fleeting green flash at sunset. It’s relaxed, salty-skinned fun you’ll remember long after your feet hit land again.

What’s the experience like?

I didn’t expect to leave my shoes at the pier — just handed them over and felt the wooden deck under my feet as we stepped onto the catamaran in Waikiki. The air was sticky-sweet, sunscreen and salt mixing with something floral I couldn’t place. Our captain, a guy named Keola, grinned and told us to watch for honu (sea turtles) as we pulled away from shore. I half-listened, half-stared at the skyline getting smaller behind us, thinking how different everything looks from out here.

We drifted toward Diamond Head — or Lēʻahi, like Keola called it — and someone handed me a cocktail that tasted like pineapple and rum (I probably drank it too fast). There was this moment when the sun started dropping behind the crater’s edge and everyone just went quiet, except for some kid giggling up front. The light did that thing where it turns gold then pink then almost green for a second — people say you can see a ‘green flash’ but I’m not sure if I imagined it. Anyway, I still think about that view sometimes.

The crew kept bringing out little bento boxes with poke and crunchy stuff I couldn’t name (Li laughed when I tried to say it in Mandarin — probably butchered it). Someone spotted dolphins off the port side and suddenly half of us were leaning over the rail, hoping for another glimpse. It all felt kind of loose and easy — drinks flowing, hair tangled by wind, toes drying out in the open air. We turned back as Waikiki started lighting up again; honestly, I didn’t want to get my shoes back yet.

Step-by-step itinerary

Day 1 — Sunset catamaran cruise near Diamond Head

• Depart from Waikiki
• Cruise along Waikiki coast
• Look for sea turtles and dolphins
• Reach Diamond Head volcanic cone
• Pause to enjoy sunset glow
• Watch for green flash on horizon
• Return to Waikiki with skyline views
• Enjoy complimentary drinks and appetizers

Top questions

Is hotel pickup included for this Waikiki sunset catamaran sail?

Pickup is only included with specific pricing options—be sure to select it during booking if needed.

Are drinks included on the Waikiki sunset cruise?

Yes, complimentary local beer, signature cocktails, wine, and unlimited nonalcoholic drinks are provided.

What food is served during the catamaran sail?

You’ll get an individualized light bite bento (pupu platter) with appetizers.

Can you see wildlife like turtles or dolphins on this tour?

Yes—Hawaiian Green Sea Turtles and Spinner Dolphins are often spotted along Oahu’s coast; whales may appear in season.

Is this cruise suitable for all ages?

The cruise is suitable for most fitness levels but alcohol is only served to guests 21+.

Do you need to remove your shoes before boarding?

Yes—this is a barefoot cruise; shoes are kept safely at the pier while you’re onboard.

Where does the catamaran depart from?

The boat departs directly from Waikiki Beach on Oahu’s south shore.

What happens if there’s bad weather?

If canceled due to poor weather conditions, you can choose an alternative date or receive a full refund.

What’s included

Your evening includes barefoot boarding at Waikiki Beach, complimentary local beer, signature cocktails or wine plus unlimited soft drinks throughout the sail, light bite bento appetizers (pupu platter), friendly crew service with cultural insights about Diamond Head (Lēʻahi), and optional shuttle pickup if selected during booking before returning to shore under city lights.