Weekend Getaways in Hawaii

Short trips with every day mapped out — verified attractions, realistic pacing, and food along the way across 7 destinations.

70 itineraries

Red Dust & Windswept Shores: Two Days on Lanaʻi

2 Days · Teen Families

Lanaʻi (non-luxury), Hawaii

Red Dust & Windswept Shores: Two Days on Lanaʻi

5 stops

Salt, Swell, and Golden Light: 3 Days Solo on Oahu

3 Days · Solo

Oahu (North Shore, Honolulu), Hawaii

Salt, Swell, and Golden Light: 3 Days Solo on Oahu

9 stops

Salt, Swell, and Shave Ice: 3 Days of Oahu for the Whole Family

3 Days · Teen Families

Oahu (North Shore, Honolulu), Hawaii

Salt, Swell, and Shave Ice: 3 Days of Oahu for the Whole Family

9 stops

Gentle Tides: Two Days of North Shore Soul and Honolulu Grace

2 Days · Active Retirees

Oahu (North Shore, Honolulu), Hawaii

Gentle Tides: Two Days of North Shore Soul and Honolulu Grace

4 stops

Red Dust and Quiet Shores: Two Slow Days on Lanaʻi

2 Days · Active Retirees

Lanaʻi (non-luxury), Hawaii

Red Dust and Quiet Shores: Two Slow Days on Lanaʻi

4 stops

Cliffs, Currents, and a Jungle at the Edge of the World: 3 Days on East Molokai

3 Days · Teen Families

Molokai (quiet, east side), Hawaii

Cliffs, Currents, and a Jungle at the Edge of the World: 3 Days on East Molokai

7 stops

Gentle Tides: Two Days Between North Shore Swells and Waikīkī Light

2 Days · Active Retirees

Oahu (North Shore, Honolulu), Hawaii

Gentle Tides: Two Days Between North Shore Swells and Waikīkī Light

5 stops

Windward Silence: Two Quiet Days on Molokai's Wild East End

2 Days · Active Retirees

Molokai (quiet, east side), Hawaii

Windward Silence: Two Quiet Days on Molokai's Wild East End

4 stops

Windward Silence: Three Days on Molokai's Untamed East End

3 Days · Solo

Molokai (quiet, east side), Hawaii

Windward Silence: Three Days on Molokai's Untamed East End

7 stops

Salt, Sun, and Shave Ice: 3 Days Across Oahu's Shores

3 Days · Teen Families

Oahu (North Shore, Honolulu), Hawaii

Salt, Sun, and Shave Ice: 3 Days Across Oahu's Shores

9 stops

Above the Clouds, Beside the Falls: Two Slow Days Beyond Maui's Resorts

2 Days · Active Retirees

Maui (non-resort areas), Hawaii

Above the Clouds, Beside the Falls: Two Slow Days Beyond Maui's Resorts

5 stops

Beyond the Resorts: Crater Light, Jungle Falls, and the Needle's Shadow

3 Days · Teen Families

Maui (non-resort areas), Hawaii

Beyond the Resorts: Crater Light, Jungle Falls, and the Needle's Shadow

7 stops

Above the Clouds, Into the Valley: 3 Days Beyond Maui's Resorts

3 Days · Solo

Maui (non-resort areas), Hawaii

Above the Clouds, Into the Valley: 3 Days Beyond Maui's Resorts

9 stops

Canyon Red, Ocean Blue: 3 Days on Kauai's Sun-Soaked South Side

3 Days · Teen Families

Kauai (non-Nāpali areas), Hawaii

Canyon Red, Ocean Blue: 3 Days on Kauai's Sun-Soaked South Side

9 stops

Turquoise Shallows & Canyon Light: Two Easy Days on Kauai's Quiet Side

2 Days · Active Retirees

Kauai (non-Nāpali areas), Hawaii

Turquoise Shallows & Canyon Light: Two Easy Days on Kauai's Quiet Side

5 stops

Canyon Light & Coastal Spray: 3 Days Solo on Kauai's Quiet Side

3 Days · Solo

Kauai (non-Nāpali areas), Hawaii

Canyon Light & Coastal Spray: 3 Days Solo on Kauai's Quiet Side

9 stops

Golden Sand & Gentle Waves: 2 Days in Oahu with Little Ones

2 Days · Young Families

Oahu (North Shore, Honolulu), Hawaii

Golden Sand & Gentle Waves: 2 Days in Oahu with Little Ones

4 stops

Clouds, Crater, and Coastline: Two Days Beyond Maui's Resorts

2 Days · Couples

Maui (non-resort areas), Hawaii

Clouds, Crater, and Coastline: Two Days Beyond Maui's Resorts

6 stops

Windward Quiet: A Family Weekend on Molokai's East Side

2 Days · Young Families

Molokai (quiet, east side), Hawaii

Windward Quiet: A Family Weekend on Molokai's East Side

4 stops

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

2 Days · Young Families

Kauai (non-Nāpali areas), Hawaii

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

4 stops

Waterfalls, Needles, and Little Feet: 2 Days Beyond Maui's Resorts

2 Days · Young Families

Maui (non-resort areas), Hawaii

Waterfalls, Needles, and Little Feet: 2 Days Beyond Maui's Resorts

3 stops

Salt, Swell, and Sunset Light: 2 Days on Oahu

2 Days · Couples

Oahu (North Shore, Honolulu), Hawaii

Salt, Swell, and Sunset Light: 2 Days on Oahu

6 stops

Cliffs, Blooms, and Sacred Water: Two Days on Molokai's Quiet East End

2 Days · Couples

Molokai (quiet, east side), Hawaii

Cliffs, Blooms, and Sacred Water: Two Days on Molokai's Quiet East End

4 stops

Turquoise Mornings: Two Easy Days of Oahu with the Kids

2 Days · Young Families

Oahu (North Shore, Honolulu), Hawaii

Turquoise Mornings: Two Easy Days of Oahu with the Kids

4 stops

Above the Clouds, Below the Falls: Three Easy Days in Wild Maui

3 Days · Active Retirees

Maui (non-resort areas), Hawaii

Above the Clouds, Below the Falls: Three Easy Days in Wild Maui

6 stops

Windward Silence: Two Days Along Molokai's Untamed East End

2 Days · Couples

Molokai (quiet, east side), Hawaii

Windward Silence: Two Days Along Molokai's Untamed East End

4 stops

Golden Light & Gentle Tides: 3 Days on Oahu

3 Days · Active Retirees

Oahu (North Shore, Honolulu), Hawaii

Golden Light & Gentle Tides: 3 Days on Oahu

6 stops

Red Dust & Quiet Shores: Two Days of Lanaʻi for Lovers

2 Days · Couples

Lanaʻi (non-luxury), Hawaii

Red Dust & Quiet Shores: Two Days of Lanaʻi for Lovers

4 stops

Slow Tides & Sacred Valleys: Two Days on Molokai's East Side

2 Days · Young Families

Molokai (quiet, east side), Hawaii

Slow Tides & Sacred Valleys: Two Days on Molokai's East Side

4 stops

Above the Clouds, Into the Valley: Two Days in Wild Maui

2 Days · Couples

Maui (non-resort areas), Hawaii

Above the Clouds, Into the Valley: Two Days in Wild Maui

6 stops

Lava Shores & Canyon Light: Two Days of Kauai's Quiet Side

2 Days · Couples

Kauai (non-Nāpali areas), Hawaii

Lava Shores & Canyon Light: Two Days of Kauai's Quiet Side

6 stops

Tide Pools & Toddler Time: Two Easy Days on Kauai's Sunny South Shore

2 Days · Young Families

Kauai (non-Nāpali areas), Hawaii

Tide Pools & Toddler Time: Two Easy Days on Kauai's Sunny South Shore

3 stops

Salt Air & Golden Light: Two Days of Oahu's Wild North and Storied South

2 Days · Couples

Oahu (North Shore, Honolulu), Hawaii

Salt Air & Golden Light: Two Days of Oahu's Wild North and Storied South

6 stops

Waterfalls, Needles & Easy Mornings: Two Slow Days in Wild Maui

2 Days · Young Families

Maui (non-resort areas), Hawaii

Waterfalls, Needles & Easy Mornings: Two Slow Days in Wild Maui

3 stops

Windward Quiet: Three Days on Molokai's Untamed East End

3 Days · Active Retirees

Molokai (quiet, east side), Hawaii

Windward Quiet: Three Days on Molokai's Untamed East End

4 stops

Lava Rock & Canyon Light: Two Days on Kauai's Quiet Side

2 Days · Couples

Kauai (non-Nāpali areas), Hawaii

Lava Rock & Canyon Light: Two Days on Kauai's Quiet Side

7 stops

Canyon Light, Coastal Calm: 3 Unhurried Days on Kauai's South Side

3 Days · Active Retirees

Kauai (non-Nāpali areas), Hawaii

Canyon Light, Coastal Calm: 3 Unhurried Days on Kauai's South Side

8 stops

Red Dust & Quiet Shores: 3 Days in Lanaʻi with the Kids

3 Days · Young Families

Lanaʻi (non-luxury), Hawaii

Red Dust & Quiet Shores: 3 Days in Lanaʻi with the Kids

6 stops

Slow Tides & Sacred Valleys: 3 Days on Molokai's Wild East Side

3 Days · Young Families

Molokai (quiet, east side), Hawaii

Slow Tides & Sacred Valleys: 3 Days on Molokai's Wild East Side

4 stops

Above the Clouds, Beyond the Road: 3 Days Off Maui's Resort Coast

3 Days · Couples

Maui (non-resort areas), Hawaii

Above the Clouds, Beyond the Road: 3 Days Off Maui's Resort Coast

6 stops

Waterfalls, Wildflowers & Little Explorers: 3 Days Beyond Maui's Resorts

3 Days · Young Families

Maui (non-resort areas), Hawaii

Waterfalls, Wildflowers & Little Explorers: 3 Days Beyond Maui's Resorts

6 stops

Salt Air & Slow Mornings: 3 Days of Oahu for Two

3 Days · Couples

Oahu (North Shore, Honolulu), Hawaii

Salt Air & Slow Mornings: 3 Days of Oahu for Two

9 stops

Windward Silence: 3 Days on Molokai's Wild East Side

3 Days · Couples

Molokai (quiet, east side), Hawaii

Windward Silence: 3 Days on Molokai's Wild East Side

6 stops

Windward Silence: Three Days on Molokai's Untamed East End

3 Days · Couples

Molokai (quiet, east side), Hawaii

Windward Silence: Three Days on Molokai's Untamed East End

6 stops

Red Dust and Distant Shores: 3 Days in Lanaʻi

3 Days · Couples

Lanaʻi (non-luxury), Hawaii

Red Dust and Distant Shores: 3 Days in Lanaʻi

6 stops

Above the Clouds, Beyond the Road: 3 Days in Wild Maui

3 Days · Couples

Maui (non-resort areas), Hawaii

Above the Clouds, Beyond the Road: 3 Days in Wild Maui

7 stops

Slow Tides and Sea Cliffs: 3 Days on Molokai's Quiet East Side

3 Days · Young Families

Molokai (quiet, east side), Hawaii

Slow Tides and Sea Cliffs: 3 Days on Molokai's Quiet East Side

5 stops

Tide Pools, Toddler Steps & Rust-Red Canyons: 3 Days in Kauai with Little Ones

3 Days · Young Families

Kauai (non-Nāpali areas), Hawaii

Tide Pools, Toddler Steps & Rust-Red Canyons: 3 Days in Kauai with Little Ones

6 stops

Canyon Mist & Coastal Fire: 3 Days in Kauai's Quieter South and West

3 Days · Couples

Kauai (non-Nāpali areas), Hawaii

Canyon Mist & Coastal Fire: 3 Days in Kauai's Quieter South and West

9 stops

Salt, Sand & Golden Light: 3 Days of Oahu for Two

3 Days · Couples

Oahu (North Shore, Honolulu), Hawaii

Salt, Sand & Golden Light: 3 Days of Oahu for Two

9 stops

Tide Pools & Rust Canyons: Kauai's Gentle South Shore for Little Explorers

3 Days · Young Families

Kauai (non-Nāpali areas), Hawaii

Tide Pools & Rust Canyons: Kauai's Gentle South Shore for Little Explorers

7 stops

Canyon Shadows & Turquoise Shallows: 3 Days in Kauai

3 Days · Couples

Kauai (non-Nāpali areas), Hawaii

Canyon Shadows & Turquoise Shallows: 3 Days in Kauai

10 stops

Mist, Bay & Fire: Three Days in Hilo

3 Days · Couples

Hilo, Hawaii, Hawaii

Mist, Bay & Fire: Three Days in Hilo

6 stops

Misty Falls & Market Mornings: 3 Days in Hilo with Little Ones

3 Days · Young Families

Hilo, Hawaii, Hawaii

Misty Falls & Market Mornings: 3 Days in Hilo with Little Ones

7 stops

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

Showing 60 of 70 — explore all of Hawaii.

More Collections

We use cookies to improve your experience and analyze site usage. Essential cookies are always active. You can customize your preferences or accept all cookies. Cookie Policy