The Latitude & Leisure Way

Each Hawaiian island moves to its own rhythm — shaped by dramatic landscapes, microclimates, and cultural traditions that make every visit feel like stepping into a living story. At Latitude & Leisure, we know these islands beyond the surface. Years spent living, studying, and exploring here, paired with our formal training as Certified Hawai‘i Destination Experts, give us a rare depth of understanding and insider insight.

That local knowledge is woven into every itinerary we design — from hand-picked guides and boutique stays to thoughtfully timed island-hops and immersive cultural encounters. The result is a Hawai‘i journey that’s seamless, deeply connected, and unmistakably yours — elevated by true local perspective and crafted with intention,

O‘ahu – Iconic Hawai‘i, Effortlessly Within Reach

O‘ahu captures the essence of Hawai‘i — where surf culture, golden-sand beaches, and island energy flow together under the silhouette of Diamond Head. From the historic depth of Pearl Harbor to vibrant nights in Waikīkī and quiet escapes into lush valleys, this island offers a perfect balance of discovery and ease.



At Latitude & Leisure, we go beyond the highlights — pairing you with expert local guides, arranging private behind-the-scenes access to cultural sites, and timing your days to miss the crowds. Whether it’s a sunset sail along the coast, a chef’s table dinner in Honolulu, or a hidden waterfall hike, we craft an O‘ahu experience that’s as seamless as it is unforgettable.

Hawai‘i Island – Where Earth Comes Alive

The Big Island is a living laboratory — lava flows meet black-sand beaches, rainforests yield to alpine peaks, and the stargazing skies stretch endlessly overhead. Days here might include watching molten rock reshape the landscape, snorkeling with manta rays under the moonlight, or exploring ancient petroglyph fields that whisper stories of the past.



Our itineraries layer these iconic moments with details that make them extraordinary — like private astronomy sessions atop Maunakea, expert-led volcano hikes, or a farm-to-table dinner on a coffee estate. This is Hawai‘i at its most elemental, revealed with insider precision and thoughtful pacing.

Kaua‘i – Wild Beauty, Intentionally Unfolded

Kaua‘i is Hawai‘i in its rawest form — emerald valleys carved by waterfalls, the serrated drama of the Nāpali Coast, and rivers that meander through timeless landscapes. It’s a haven for those who seek serenity and cinematic beauty in equal measure.



Latitude & Leisure designs Kaua‘i journeys that move at the island’s slower, more soulful rhythm. Kayak hidden waterways, join a local naturalist to explore lush botanical gardens, or end your day with a private picnic overlooking Waimea Canyon. Every detail is timed to nature’s pace — and curated to make you feel like Kaua‘i is yours alone.

Maui Nui – Three Islands, Infinite Possibilities

Maui – Romance, Rhythm, and Refined Adventure

Maui is a study in contrasts — sunrise above the clouds on Haleakalā, the winding Road to Hāna, and evenings filled with fine dining and starry skies. It’s also a gateway to Maui Nui: three smaller islands, each with its own personality and possibilities.

With Latitude & Leisure, we turn this beloved destination into something extraordinary. We might plan a sunrise ceremony on a volcanic summit, reserve a private catamaran for a day of secluded snorkeling, or map out a farm-to-table tasting trail through Upcountry. Whether you crave soft adventure or refined relaxation, we design Maui around how you want to feel.

Lāna‘i – Intimate, Isolated, Incomparable

Lāna‘i whispers luxury in its quietest form — uncrowded beaches, rugged backroads, and two world-class resorts. It’s a place where privacy isn’t a perk; it’s the point.



We enhance that exclusivity with tailored touches — arranging a private 4x4 exploration of Polihua Beach, a marine biologist-led snorkeling session in Hulopo‘e Bay, or an after-hours stargazing experience from the island’s highest ridge. Every detail is designed to deepen your connection with this rare, remote paradise.

Moloka‘i – Culture at Its Core

Moloka‘i is Hawai‘i at its most authentic — sea cliffs towering above the Pacific, taro fields rooted in centuries of tradition, and a slower rhythm that still moves to the heartbeat of aloha.



Our approach here is deeply intentional: guided hikes through sacred valleys, immersive cultural workshops with local artisans, and storytelling experiences that reveal the island’s living history. It’s travel designed to connect you with place, not just pass through it.