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Hawaii Itineraries

Day-by-day guides crafted by people who live and breathe Hawaii — pick your island, pick your pace.

Looking to plan your dream vacation in Hawaiʻi? Our expert-curated Hawaiʻi itineraries help you plan your trip to any island. From 3-day escapes to 10-day adventures, we give you detailed day-by-day guides tailored to every traveler type — food lovers, adventure seekers, honeymooners, families and first-timers.

Three Days at 1 Hotel Hanalei Bay on Kauaʻi
Kauaʻi3 days

Three Days at 1 Hotel Hanalei Bay on Kauaʻi

Easy

What to expect from a stay at 1 Hotel Hanalei Bay — from the resort itself to the beaches, farms, restaurants and coffee shops just beyond its doors.

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Chef Ippy Aiona's Weekend in Waimea
Hawaiʻi Island3 days

Chef Ippy Aiona's Weekend in Waimea

Easy

For this itinerary, we are featuring the voice of local chef and restaurateur Ippy Aiona. Here, he shares what Waimea means to him and recommends his favorite spots for the best Waimea experience.

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Four Days in Kukuiʻula on Kauaʻi's South Shore
Kauaʻi4 days

Four Days in Kukuiʻula on Kauaʻi's South Shore

Easy

The community of Kukuiʻula spans over 1000 acres of coastal land in Kōloa. Here, you and your family can have your own home and everything that comes along with a prestigious Lodge at Kukuiʻula club membership without joining the club.

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Three Days in Kapaʻa on Kauaʻi's East Side
Kauaʻi3 days

Three Days in Kapaʻa on Kauaʻi's East Side

Challenging

Ride bikes along the coast, kayak the Wailua River, hike to a waterfall, tour a chocolate farm and visit local shops and restaurants on this 3-day Kapa'a itinerary.

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3-Day Lāhainā Getaway
Maui3 days

3-Day Lāhainā Getaway

Moderate

While still recovering from the 2023 wildfires, many of Lāhainā's businesses have reopened and are welcoming visitors. If you're traveling to Maui, consider spending a few days here to support its community.

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3-Day Solo Travel in Hilo
Hawaiʻi Island3 days

3-Day Solo Travel in Hilo

Easy

Hilo is perfect for solo travel. You can go where you want, when you want, at your own pace, and open the possibility of meeting people you would not have encountered if traveling with a companion. Here’s how to get a taste of Hilo Town while on your own.

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24 Hours on Lānaʻi
Lānaʻi1 day

24 Hours on Lānaʻi

Moderate

This Lānaʻi itinerary is best for couples, friends or solo travelers on Maui looking for a fun day trip.

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Maui Staycation on a Budget
Maui3 days

Maui Staycation on a Budget

Moderate

Maui is known for its opulent resorts, but you can still find reasonably priced hotels and create your own high-end experience without taking out a loan. This three-day Maui itinerary offers a glamorous vacation for a fraction of the price.

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This is the Most Transformative Wellness Retreat in Hawaiʻi
Lānaʻi4 days

This is the Most Transformative Wellness Retreat in Hawaiʻi

Moderate

Immersed in an optimal environment for healing, a week at this Lānaʻi resort will change your perspective of health forever.

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Hawaiʻi Island: Two Days, Three Unique Culinary Experiences
Hawaiʻi Island2 days

Hawaiʻi Island: Two Days, Three Unique Culinary Experiences

Moderate

A Hawai’i Island travel writer shares her recommendations for a quick trip to the island's west side to learn about locally-grown tea, freshly-harvested sea salt and the only sake made in Hawaiʻi.

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Itineraries: One Day on Maui
Maui1 day

Itineraries: One Day on Maui

On an island with so much to do as Maui, there’s no easy way to experience it all in one day. But if you just have a day, here's what you should do!

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Itineraries: One Week on Kaua'i
Kauaʻi7 days

Itineraries: One Week on Kaua'i

One week on Kauai is a vacation dream come true. You won’t want to miss out on all the sights this pretty paradise has to offer, but you’ll also want to indulge in some serious R&R.

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Itineraries: One Week on Hawai‘i Island
Hawaiʻi Island7 days

Itineraries: One Week on Hawai‘i Island

If you’re lucky enough to have a full week in this beautiful and diverse tropical paradise, there’s a few things you won’t want to miss. Here they are!

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Itineraries: Kauai Travel Guide
Kauaʻi7 days

Itineraries: Kauai Travel Guide

Whether you’ve got one day or one week, it’s easy to make the most of your time on the Garden Isle.

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Itineraries: Hawaii Island Travel Guide
Hawaiʻi Island7 days

Itineraries: Hawaii Island Travel Guide

There’s so much to see and do on the beautiful Island of Hawaii. Whether you have one day or an entire week, make the most of your time visiting the state’s largest and most diverse island.

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An Epic 3-Day Big Island Road Trip: Steal this Itinerary
Hawaiʻi Island3 days

An Epic 3-Day Big Island Road Trip: Steal this Itinerary

At over 4,000 square miles, it’s easy to see how the Big Island got its nickname. And the best way to explore? Circumnavigating it by car.

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A Maui Honeymoon Itinerary from Maui Coast Hotel’s Ellie Erickson
Maui5 days

A Maui Honeymoon Itinerary from Maui Coast Hotel’s Ellie Erickson

If you’re planning a Maui honeymoon, there’s no better person to get advice from than Ellie Erickson, Maui Coast Hotel’s senior sales manager.

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Halepuna Waikiki’s Jay Kitashima Shares His Ideal Three-Day Itinerary
Oʻahu3 days

Halepuna Waikiki’s Jay Kitashima Shares His Ideal Three-Day Itinerary

Halepuna Waikiki by Halekulani is a serene escape designed for travelers seeking luxury and award-winning hospitality.

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A Three-Day Oʻahu Itinerary From Halekulani Chef Concierge David Nakamura
Oʻahu3 days

A Three-Day Oʻahu Itinerary From Halekulani Chef Concierge David Nakamura

At the heart of every remarkable hotel experience is someone working behind the scenes to make the impossible possible.

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A 3-Day Itinerary for Families at Prince Waikiki
Oʻahu3 days

A 3-Day Itinerary for Families at Prince Waikiki

Prince Waikiki is the gateway to Waikīkī. Here's how to spend 3 days with the hotel as your hub.

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A 5-Night Culinary Tour of Oʻahu
Oʻahu6 days

A 5-Night Culinary Tour of Oʻahu

This itinerary is for serious cooks and eaters visiting Hawaiʻi to explore the island’s diverse food culture. Designed as a self-led culinary tour of Oʻahu, you’ll sample everything from Hawaiian lau lau to local-style Portuguese bean soup to ʻulu noodles.

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A 5-Day Hilo Itinerary From SCP Hilo GM Breeani Kobayashi-Kualiʻi
Hawaiʻi Island5 days

A 5-Day Hilo Itinerary From SCP Hilo GM Breeani Kobayashi-Kualiʻi

At SCP Hilo — the acronym stands for Soul Community Planet — the warm and grounded spirit of the hotel is a reflection of its general manager, Breeani Kobayashi-Kualiʻi.

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A 3-Day Golfing Getaway Itinerary at Royal Sonesta Kauai Resort
Kauaʻi3 days

A 3-Day Golfing Getaway Itinerary at Royal Sonesta Kauai Resort

General Manager Jim Pedone feels fortunate to lead the team at Royal Sonesta Kauai Resort – a beachfront property especially ideal for golfers. If this sounds like your idea of the perfect vacation, Pedone’s itinerary is for you.

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First-Time Travel to Lānaʻi: 4-Day Itinerary
Lānaʻi4 days

First-Time Travel to Lānaʻi: 4-Day Itinerary

There are many reasons to travel to Lānaʻi: world-class golf and scuba diving, epic hunting and fishing opportunities, and pristine beaches with crystal-clear water, to name a few.

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How To Master The Art of Bleisure on O’ahu
Oʻahu2 days

How To Master The Art of Bleisure on O’ahu

Have a business trip to Oʻahu coming up? Consider turning it into a “bizcation” by adding a few days of bleisure.

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A 5-Day Maui Itinerary for Solo Travel
Maui5 days

A 5-Day Maui Itinerary for Solo Travel

Best known for saying “e komo mai” to honeymooners and families, Maui can also be that rare spot to reclaim solo travel when you don’t have a significant other.

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Kona Adventure Travel: Weekend Itinerary
Hawaiʻi Island2 days

Kona Adventure Travel: Weekend Itinerary

The district of Kona, on the west side of Hawaiʻi Island, is rich in cultural history and offers plenty of adventure travel.

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