Summer Itineraries in Hawaii

Long daylight hours and peak-season energy — plans built for the busiest, brightest stretch of the year.

20 itineraries

Windward Silence: Two Days on Molokai's Wild East Side

2 Days · Solo

Molokai (quiet, east side), Hawaii

Windward Silence: Two Days on Molokai's Wild East Side

4 stops

Salt Spray and Canyon Light: Two Days on Kauai's Wild South

2 Days · Solo

Kauai (non-Nāpali areas), Hawaii

Salt Spray and Canyon Light: Two Days on Kauai's Wild South

7 stops

Salt, Swell, and Sunlight: 2 Days Solo on Oahu

2 Days · Solo

Oahu (North Shore, Honolulu), Hawaii

Salt, Swell, and Sunlight: 2 Days Solo on Oahu

7 stops

Above the Clouds, Into the Valley: Two Days Beyond Maui's Resorts

2 Days · Solo

Maui (non-resort areas), Hawaii

Above the Clouds, Into the Valley: Two Days Beyond Maui's Resorts

7 stops

Turquoise Mornings: A Family Day on Waikīkī's Gentle Shore

1 Day · Young Families

Oahu (North Shore, Honolulu), Hawaii

Turquoise Mornings: A Family Day on Waikīkī's Gentle Shore

2 stops

Green Cathedral: A Gentle Day at Iao Valley for Little Explorers

1 Day · Young Families

Maui (non-resort areas), Hawaii

Green Cathedral: A Gentle Day at Iao Valley for Little Explorers

1 stops

Rust Canyons & Turquoise Shallows: Four Days in Kauai's Quieter South

4 Days · Couples

Kauai (non-Nāpali areas), Hawaii

Rust Canyons & Turquoise Shallows: Four Days in Kauai's Quieter South

12 stops

Salt, Sand & Shave Ice: 4 Days of Oahu with the Whole Crew

4 Days · Teen Families

Oahu (North Shore, Honolulu), Hawaii

Salt, Sand & Shave Ice: 4 Days of Oahu with the Whole Crew

11 stops

Tide Pools & Rust-Red Canyons: 5 Days in Kauai with Little Ones

5 Days · Young Families

Kauai (non-Nāpali areas), Hawaii

Tide Pools & Rust-Red Canyons: 5 Days in Kauai with Little Ones

9 stops

Red Dirt & Quiet Shores: 5 Days in Lanaʻi with the Kids

5 Days · Young Families

Lanaʻi (non-luxury), Hawaii

Red Dirt & Quiet Shores: 5 Days in Lanaʻi with the Kids

6 stops

Golden Sand & Gentle Swells: 5 Days in Oahu with the Kids

5 Days · Young Families

Oahu (North Shore, Honolulu), Hawaii

Golden Sand & Gentle Swells: 5 Days in Oahu with the Kids

9 stops

Beyond the Postcards: Four Days Along Maui's Wild Edge

4 Days · Couples

Maui (non-resort areas), Hawaii

Beyond the Postcards: Four Days Along Maui's Wild Edge

10 stops

Windward Silence: 4 Days on Molokai's Untamed East Side

4 Days · Couples

Molokai (quiet, east side), Hawaii

Windward Silence: 4 Days on Molokai's Untamed East Side

9 stops

Salt, Sun, and Slow Mornings: 4 Days in Oahu for Two

4 Days · Couples

Oahu (North Shore, Honolulu), Hawaii

Salt, Sun, and Slow Mornings: 4 Days in Oahu for Two

11 stops

Red Dust & Quiet Tides: 4 Days in Lanaʻi for Two

4 Days · Couples

Lanaʻi (non-luxury), Hawaii

Red Dust & Quiet Tides: 4 Days in Lanaʻi for Two

7 stops

Cliffs, Currents & Quiet Corners: 4 Days on Molokai's East Side

4 Days · Teen Families

Molokai (quiet, east side), Hawaii

Cliffs, Currents & Quiet Corners: 4 Days on Molokai's East Side

8 stops

Misty Mornings & Rainbow Chasing: 3 Days in Hilo with Little Ones

3 Days · Young Families

Hilo, Hawaii, Hawaii

Misty Mornings & Rainbow Chasing: 3 Days in Hilo with Little Ones

6 stops

Beyond the Postcard: 4 Days of Wild Maui for Families

4 Days · Teen Families

Maui (non-resort areas), Hawaii

Beyond the Postcard: 4 Days of Wild Maui for Families

10 stops

Cinder, Waterfall & Needle: 5 Days Beyond Maui's Resorts

5 Days · Young Families

Maui (non-resort areas), Hawaii

Cinder, Waterfall & Needle: 5 Days Beyond Maui's Resorts

8 stops

Canyon Rims & Turquoise Shallows: 4 Days in Kauai

4 Days · Teen Families

Kauai (non-Nāpali areas), Hawaii

Canyon Rims & Turquoise Shallows: 4 Days in Kauai

11 stops

Discover summer trips across Hawaii's diverse islands with 16 carefully curated itineraries spanning 1 to 5 days. Whether traveling with family, as a couple, or with young children, visitors can explore iconic destinations including Oahu's North Shore and Honolulu, Maui's non-resort areas, Kauai's quieter regions, Lanaʻi's natural beauty, Molokai's serene east side, and the unique landscapes of Hilo and Hawaii. From gentle shore days and family-friendly adventures to couples' getaways and waterfall chasing, these itineraries showcase both well-loved beaches and lesser-known corners of the Hawaiian islands.

Frequently Asked Questions

What types of trips are available on this page?

The page features 16 itineraries ranging from 1 to 5 days, designed for families with children, couples, and small groups. Options include destinations across six Hawaiian locations: Oahu, Maui, Kauai, Lanaʻi, Molokai, and Hilo/Hawaii.

Which islands are covered in the itineraries?

Trips cover Oahu (North Shore and Honolulu), Maui (non-resort areas), Kauai (non-Nāpali areas), Lanaʻi (non-luxury areas), Molokai (quiet east side), Hilo, and Hawaii.

Are there itineraries for families with young children?

Yes, several itineraries are specifically designed for families with little ones, including options in Waikīkī, Iao Valley, Kauai, Hilo, and Lanaʻi, with durations ranging from 1 to 5 days.

What length of trips can I find here?

Itineraries range from 1-day trips to 5-day journeys, allowing travelers to choose based on their available time and preferences.

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