Your Hawai'i. Your Way.
Where aloha runs deep and the land tells its story — from sunlit shores to misty valleys, discover Hawaiʻi through journeys intentionally crafted for you.
Hawai‘i:
Where Land & Spirit Intertwine
Hawaiʻi isn’t just a destination — it’s an experience shaped by ancestral rhythm, living culture, and landscapes that shift from rainforest to lava field to shoreline. Across its islands, the spirit of aloha ʻāina — a deep love of the land — invites travelers to move slower, listen closer, and let the journey unfold.
Every island offers its own story — the pulse of Oʻahu, the serenity of Kauaʻi, the volcanic breath of Hawaiʻi Island, the soft luxury of Maui, and the quiet power of Lānaʻi and Molokaʻi. From black-sand beaches to emerald cliffs and crater peaks, Latitude & Leisure curates Hawaiʻi journeys designed for travelers who want more than a vacation — they want connection.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.
Plan Your Dream Hawai'i Journey
Not sure where to start? Begin with a free interactive Hawai'i Bucket List — a curated planning guide designed to help travelers dream big, stay organized, and build unforgettable itineraries.
Islands That Shape the Journey
Every island in Hawaiʻi holds its own story — these are the places that shape the journey.
Iconic Hawai‘i, Effortlessly Within Reach
Oʻahu captures the essence of Hawaiʻi — where golden-sand beaches meet surf culture, urban energy mingles with sacred valleys, and the island’s heartbeat flows under the watchful silhouette of Diamond Head. From the turquoise embrace of Hanauma Bay to the wild serenity of the North Shore, it’s a place of contrasts: vibrant Waikīkī nights, the quiet of Nuʻuanu’s lush trails, and a living history that spans from ancient heiau to Pearl Harbor’s somber shores. Oʻahu is both the gateway and the invitation — easy to access, yet endlessly layered.
Here, Latitude & Leisure moves beyond the postcard. We’ll time your visit to avoid the crowds, pair you with expert guides, and open doors that most travelers pass by. Whether it’s a sunset sail along the South Shore, a private cultural tour in Honolulu, or a waterfall hike tucked into the Ko‘olau, your O‘ahu journey is crafted to flow effortlessly — blending discovery with ease.
Island Highlights: Waikīkī’s iconic shoreline, Lēʻahi (Diamond Head) summit views, North Shore surf breaks, Pearl Harbor’s living history, and immersive cultural storytelling at the Polynesian Cultural Center.
Where Earth Comes Alive
Hawaiʻi Island is elemental — a living landscape where fire meets sea, snow crowns the mountains, and black-sand beaches trace the edges of an ever-shifting shoreline. Lava fields stretch toward lush valleys, while waterfalls plunge into misty ravines and night skies blaze with stars. From ancient petroglyphs to the breath of volcanoes, this island moves to its own primal rhythm.
At Latitude & Leisure, we reveal the Big Island’s grandeur with insider precision. Whether it’s a private astronomy session atop Maunakea, a guided volcano hike at twilight, or a farm-to-table dinner on a Kona coffee estate, every experience is timed and layered with intention. We design your days to feel both grounded and extraordinary — the island as it’s meant to be felt.
Island Highlights: Kīlauea’s lava landscapes, Waipi‘o Valley overlooks, Mauna Kea stargazing, Kona coffee country, manta ray night snorkels, and hidden black-sand coves.
Wild Beauty, Intentionally Unfolded
Kaua‘i is Hawaiʻi at its most untamed — a place where emerald cliffs tower above turquoise waters, rivers wind through timeless valleys, and mist lingers on the Nā Pali Coast like a soft veil. Known as the Garden Isle, it moves at a slower rhythm, inviting travelers to quiet their own pace to match its breath.
We craft journeys here that feel intimate and unhurried: private kayak adventures on the Wailua River, golden-hour picnics at Waimea Canyon, and immersive time with naturalists who reveal Kaua‘i’s living landscapes. Each day flows with a balance of wild wonder and thoughtful design, so your time here feels less like a visit — and more like a belonging.
Island Highlights: Nā Pali Coast by sea or sky, Waimea Canyon and Kōkeʻe hikes, Wailua River and Secret Falls, Hanalei Bay’s calm, botanical gardens steeped in story.
Romance, Rhythm, and Refined Adventure
Maui is a study in contrasts — the hush of dawn atop Haleakalā, the lush curves of the Hāna Highway, and sunsets that set the ocean aglow. Known as the Valley Isle, it marries soft adventure with sophistication, welcoming travelers who want to savor beauty in every sense.
Latitude & Leisure transforms Maui’s icons into unforgettable touchpoints: a sunrise ceremony above the clouds, a private catamaran to Molokini Crater, or a tasting trail through Upcountry’s farms and vineyards. We curate with intention, blending luxury and adventure so that each moment feels effortless and deeply personal.
Island Highlights: Haleakalā sunrise, Road to Hāna, Molokini snorkeling, Lahaina history and dining, Upcountry farms and waterfalls.
Intimate, Isolated, Incomparable
Lāna‘i whispers its magic. Just a short ferry or flight from Maui, this secluded island trades crowds for quiet luxury — golden sands, rugged backroads, and a sense of stillness that invites you to exhale. Its beauty lies not in spectacle but in space — room to breathe, roam, and truly arrive.
Our itineraries lean into that stillness: private 4x4 adventures to Polihua Beach, guided snorkeling in Hulopo‘e Bay with a marine biologist, or stargazing from the island’s highest ridge after the last ferry has left. Here, exclusivity isn’t a luxury add-on — it’s the default.
Island Highlights: Hulopo‘e Beach, Keahiakawelo (Garden of the Gods), Polihua’s golden sands, marine encounters, secluded sunsets.
Culture at Its Core
Moloka‘i is the heart of old Hawaiʻi — untouched cliffs, taro fields rooted in centuries of tradition, and communities where aloha is more than a word; it’s a way of life. Here, the pace slows, stories deepen, and the land holds its history with quiet strength.
Our approach to Moloka‘i is intentional and respectful. We work with cultural practitioners, guides, and artisans to offer travelers authentic connection — guided hikes through sacred valleys, hands-on workshops, and storytelling experiences that honor place rather than perform it. Moloka‘i isn’t a stop on an itinerary; it’s a conversation with the past and present.
Island Highlights: Kalaupapa National Historical Park, cultural workshops, sacred valley hikes, taro farms, sea cliffs, living history.
Signature Ways to Explore — Expertly Crafted Journeys
There’s no single way to experience Hawaiʻi — only the one that’s right for you. Whether it’s sunrise above volcanic peaks, slow days on golden beaches, or cultural encounters that linger long after you return home, every journey can be shaped to match your rhythm.
At Latitude & Leisure, we pair iconic moments with insider access, thoughtful timing, and a touch of effortless luxury to make each island experience truly unforgettable.
Island Hopping Odyssey
Oʻahu • Maui • Kauaʻi • Hawaiʻi
Seamless, multi-island journeys highlight Hawaiʻi’s diverse rhythms — from Oʻahu’s energy to Kauaʻi’s wild beauty and Hawaiʻi Island’s raw power. Every connection is thoughtfully arranged for an effortless flow.
Cultural Heritage Trail
Sacred Sites & Landscapes
Experience the islands through sacred landscapes and living traditions. Sunrise ceremonies, heiau visits, rainforest hikes, and marine encounters connect you deeply to Hawaiʻi’s culture and spirit.
Coastal Luxury Escape
Seaside Serenity & Indulgence
Ocean-view villas, spa rituals, chef’s table dining, and sunset sails define these elegant escapes on Maui, Lānaʻi, or Oʻahu — where luxury and tranquility meet.
Adventure Circuit
Volcano Peaks & Reefs
Hawaiʻi’s wilder side comes alive with Molokini snorkeling, volcanic hikes, Wailua River kayaking, and stargazing atop Maunakea — soft adventure with breathtaking views.
Seasonal Feature: Whale Season - From December through April, humpback whales return to Hawaiian waters. Watch from your lanai, sail alongside these gentle giants, or join marine naturalists for an intimate, unforgettable encounter with one of nature’s great migrations.
Best Time to Journey
Hawaiʻi isn’t just about where you go — it’s when you go that shapes the story. Each season offers its own rhythm, from winter whale songs to summer surf and endless golden sunsets. Whether you’re seeking the calm of shoulder season or the vibrant pulse of summer, the best time to visit depends on the experience you want most.
Peak Season
December–April
Whale season, warm tropical breezes, and picture-perfect days make this the most popular time to visit. Ocean conditions are ideal, and cultural events and festivals bring the islands to life.
Shoulder Season
May & September–October
A quieter rhythm with fewer crowds, warm weather, and lower rates. Ideal for travelers who want breathing room while still enjoying sunny skies and gentle trade winds.
Summer Highlights
June–August
Surf eases on the North Shore, snorkeling conditions shine, and long, sunny days make it perfect for beach escapes, family adventures, and road trips around the islands.
Festive Season
Late November–Early January
Holiday travel peaks — with lively events, hula performances, and warm winter getaways. It’s a vibrant time — best planned well in advance to secure prime stays and experiences.
Pro Tip: Signature experiences like whale watching, sunrise at Haleakalā, and prime snorkeling often book out months in advance. Reserve early to secure the best guides and viewing windows.
Insider Planning Tips
A little thoughtful planning goes a long way in Hawaiʻi. With its year-round warmth, shifting trade winds, and diverse islands, the magic often lies in the rhythm of how you travel. Plan just enough to ensure smooth transitions — but leave space for those moments that unfold naturally, island by island.
- Book marquee experiences early — sunrise at Haleakalā, prime snorkeling tours, cultural ceremonies, and whale watching often fill months in advance.
- Build your journey around 2–3 islands — popular pairings like Oʻahu + Maui or Kauaʻi + Hawaiʻi Island create a smooth flow without overpacking your itinerary.
- Pack light and smart — resort wear, breathable layers, a light rain shell, and comfortable footwear keep you ready for everything from luaus to ridge hikes.
- Savor the golden hours — sunrise sails, sunset beach walks, and late afternoon excursions offer some of the islands’ most memorable moments.
- Allow buffer days around flights or cruises — it’s the easiest way to ease into (or out of) island time without travel-day stress.
- Tailor the pacing to your style — Hawaiʻi can be indulgently slow or full of adventure. A little structure leaves room for spontaneous magic.
Your Hawai‘i Journey, Answered
Your questions are where the journey begins. Here’s what travelers ask most — and how Latitude & Leisure turns answers into effortless escapes.
Can I visit more than one island on my trip?
Yes — and it’s one of the best ways to experience Hawaiʻi. Most travelers combine two to three islands to balance variety with ease. A well-paced journey often begins on Oʻahu, then flows to Maui, Kauaʻi, or Hawaiʻi Island. Inter-island flights are short (30–45 minutes) and frequent, making connections seamless. To minimize travel fatigue, plan at least 3–4 nights per island. For a luxury experience, we can coordinate private transfers, tailored pacing, and carefully timed itineraries to maximize every moment.
What’s the best time of year to go?
Hawaiʻi is a year-round destination, but the ideal time depends on what you want to experience. December–April brings whale season, warm tropical weather, and lively festivals. May and September–October offer sunny days with fewer crowds. Summer months are perfect for snorkeling, beach days, and family adventures. If you’re traveling during holidays or whale season, book accommodations and key experiences 6–9 months ahead to secure the best options.
Is it worth visiting Haleakalā at sunrise?
Absolutely. Watching the sun rise above Haleakalā’s summit is one of Hawaiʻi’s most moving experiences. The colors shift from deep indigo to gold as clouds roll across the crater rim. Access requires a reservation, and temperatures at the summit can drop to the 40s °F, so warm layers are essential. Many travelers pair this with a guided descent or breakfast in Upcountry Maui. For the best experience, book early — reservations open 60 days in advance and sell out quickly.
Do I need to rent a car on each island?
For most travelers, yes. Public transportation is limited outside major resort areas, and many of Hawaiʻi’s most beautiful spots — waterfalls, scenic drives, farm-to-table restaurants — are best reached independently. Rental cars give you flexibility to explore at your own pace. If you prefer not to drive, we can arrange private transfers, guided tours, or luxury chauffeur services to keep your journey effortless.
Will it rain?
Yes — but usually only in passing showers. Rain is part of Hawaiʻi’s lush beauty, and it often clears within minutes, leaving behind vivid rainbows and refreshed landscapes. Leeward (south and west) coasts are generally sunnier and drier, while windward (north and east) sides receive more rainfall. Lightweight rain shells or travel umbrellas are recommended, especially on Kauaʻi or during winter months.
How far in advance should I plan my trip?
For peak travel periods (December–April and summer), planning 6–12 months in advance is ideal to secure preferred accommodations, inter-island flights, and signature experiences like sunrise at Haleakalā or prime whale-watching tours. Shoulder seasons offer more flexibility, but early planning still ensures the best pacing and flow between islands.
What about families or multigenerational groups?
Hawaiʻi is ideal for families and multigenerational travel. Many resorts offer spacious villas, private excursions, and activities that appeal to all ages — from snorkeling and sailing to cultural workshops and spa retreats. Inter-island itineraries can be paced to balance active adventure with relaxation. We specialize in tailoring journeys that keep everyone engaged without feeling over-scheduled.
If I’m traveling for a specific sport or passion, where should I go?
Surfing: Oʻahu’s North Shore, Maui, Kauaʻi.
Snorkeling & Scuba: Molokini Crater, Kona Coast, Hanauma Bay.
Golfing: Maui, Hawaiʻi Island (Big Island), Oʻahu.
Hiking: Nāpali Coast, Lēʻahi (Diamond Head), Haleakalā.
What are the key festivals or holidays in Hawaii, and how do they impact travelers?
Merrie Monarch Festival (April) – Hula competitions and cultural events. Book early as Hilo fills up quickly.
Lei Day (May 1) – Island-wide celebrations with live music and leis. No closures, just festive energy.
King Kamehameha Day (June 11) – Floral parades and cultural ceremonies. Some road closures near parade routes.
Aloha Festivals (September) – Parades and performances. Enhanced visitor experience, no closures.
Christmas & New Year’s – Holiday fireworks, peak season rates, and busy beaches.
Do I need special gear or clothing?
No mountaineering gear required — just smart, versatile packing. Lightweight layers, swimsuits, comfortable walking shoes or sandals, and a waterproof shell are key. For sunrise at Haleakalā or stargazing on Maunakea, bring a warm layer. Reef-safe sunscreen, hats, and reusable water bottles are essential. If you plan on snorkeling, most tours provide gear — though some travelers prefer to bring their own mask and snorkel for comfort.
Are cultural experiences available beyond luaus?
Yes — and they’re often the most memorable part of a journey. Beyond luaus, travelers can join guided visits to heiau (temples), take part in sunrise ceremonies, learn lei-making and hula from cultural practitioners, or explore historic sites like Puʻuhonua o Hōnaunau. We partner with trusted local guides who share authentic stories and traditions with deep respect for place.
Discover Hawai'i, Curated Your Way
Discover the art of travel, island style—lush, soulful, and effortlessly inspiring.
From volcanic peaks to golden shores, our curated journeys blend local connection with elevated comfort. Each itinerary celebrates the islands’ natural rhythm—whether you’re chasing waterfalls, sailing at sunset, or savoring farm-to-table flavors beneath the palms.
Isles of Discovery
Cruise Hawai‘i’s coastline—small-ship sailings, snorkeling reefs, and island-hopping in effortless style.
Heart of the Islands
Explore the heart of Hawai‘i—volcano summits, waterfall hikes, and stays rich with aloha spirit.
Rhythm of Relaxation
Surrender to island ease—oceanfront luxury, curated dining, and moments that flow as naturally as the tide.
