Waikiki: Swim & Sail Cocktail Cruise with Diamond Head Views

Summary

Swim off Waikiki then sail past Diamond Head with cocktails

You’ll swim off Waikiki’s coast in clear water, relax on cushioned nets with a cold cocktail in hand, and sail past Diamond Head as local crew share stories and music. This cruise includes all fees and taxes plus onboard restrooms—expect laughter, salt air, and a view of Honolulu you’ll remember long after.

What’s the experience like?

I didn’t expect to feel so far from the city just by stepping onto a catamaran. The Waikiki coast was behind us almost instantly—one minute I’m dodging beach towels, the next I’m dangling my feet over the side, salt spray on my skin and that kind of hush you only get out on open water. Our captain, Kaleo, had this way of making everyone relax. He handed me a drink (pineapple something—cold and sweet) and grinned when I tried to pronounce “mahalo” right. Still not sure I nailed it.

We stopped for a swim, which I almost skipped because honestly, I thought it’d be freezing or too crowded. But the water was clear and warm enough that I just went for it. There’s this moment when you push off the boat and everything goes quiet except for distant music from the deck and your own breathing under water. A couple of us floated around, watching clouds drift over Diamond Head—the view is different from out here, bigger somehow. Someone spotted flying fish (Malolo, Kaleo called them), but they were gone before I could see.

After we climbed back in (I’ll admit it: not graceful), we sailed along the coast with drinks in hand. The netted lounge at the front was everyone’s favorite spot—even if you end up with wet shorts from the spray. No one seemed to care; there was laughter, music, some sunscreen smell mixed with ocean air. We passed right by Diamond Head Crater—everyone took photos but it’s hard to catch how wide-open it feels in real life. It’s not a snorkel trip (they’re strict about that), just swimming and sailing with time to let your brain quiet down for a bit.

Step-by-step itinerary

Day 1 — Swim and sail along Waikiki coast

• Swim off Waikiki beach
• Relax on catamaran seating
• Sip refreshments and enjoy music
• Sail past Diamond Head Crater
• Watch for dolphins and flying fish

Top questions

Is snorkeling included on this Waikiki cocktail cruise?

No, snorkeling is not permitted on this tour—swimming is allowed but no snorkel gear is provided or allowed.

Does this swim & sail cruise go past Diamond Head?

Yes, after swimming off Waikiki you’ll sail past Diamond Head Crater along the coast.

Are drinks included during the cruise?

The tour features cocktails available onboard while you relax during the sailing portion.

Is hotel pickup included for this tour?

No hotel pickup is mentioned; public transportation options are available nearby.

Are restrooms available on board?

Yes, there are restrooms available on board the catamaran for guest use.

How physically demanding is this cruise?

You should have at least moderate physical fitness; not recommended for travelers with poor cardiovascular health.

Can children join this Waikiki swim & sail cruise?

The tour does not specify age restrictions but check directly if traveling with young children.

Will we definitely see dolphins or flying fish?

Dolphin and flying fish sightings are possible but can’t be guaranteed—they depend on weather and luck.

What’s included

Your day includes all fees and taxes covered plus access to onboard restrooms; you’ll be guided by local crew as you swim off Waikiki Beach then enjoy cocktails while sailing past Diamond Head before returning to shore.