Cruise Port Guide · 19 cruises visit Kailua →
The bucket-list things to do — and the private, expert-led way to do each.
Here’s the bucket list for your day ashore: the most extraordinary thing to do at each stop, and the private, small-group, or expert-led way to make it yours — your own pace, real access, none of the crowd.
Paddle across the turquoise waters of Kailua Bay to the Mokulua Islands — twin seabird sanctuaries off Lanikai — on a guided small-group eco-kayak tour. A true bucket-list immersion in Oahu's most pristine coastal wilderness.
Ascend the iconic red-dirt Lanikai Pillbox Trail at sunrise for a panoramic ridge-top reward — twin WWII bunkers framing Lanikai Beach, the Mokulua Islands, and the emerald Ko'olau Range in one breathtaking sweep.
Explore Windward Oahu's two most ethereally beautiful cultural landmarks — the replica Byodo-In Temple mirrored in a koi pond beneath soaring cliffs, and the 400-acre Ho'omaluhia Botanical Garden — on a seamless private guided tour.
Trek through dense Hawaiian rainforest to the secluded Maunawili Falls — a stunning cascade plunging into a jade swimming hole — guided by a local expert who keeps the experience intimate, safe, and richly narrated.
Dive into the flavors of windward Oahu at the beloved Kailua Farmers Market, sampling rare Hawaiian fruit, local honey, poi, and artisan goods — then extend into Kailua's celebrated food scene with stops at Mānoa Chocolate and local legends.
Set sail from Kailua on a private catamaran charter to the Mokulua Islands, snorkeling with Hawaiian green sea turtles in crystalline waters before anchoring off Lanikai — consistently rated one of the world's top beaches.
⚓ Your bucket-list concierge
Tell us your sailing and we'll send the bucket list for every port — the most extraordinary thing to do at each, and the private, expert-led way to make it yours.
No spam. The honest plan, even when it says skip the ship’s tour.