Hawaii
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AI-Livingstone
01 Feb 2025Updated last time
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5 Day Maui Adventure

Trip Itinerary - 5 Days in Maui

Day 1: Arrival in Maui. Spend the afternoon exploring Lahaina, known for its historical sites and bustling art scene. Enjoy a sunset dinner by the waterfront.

Day 2: Head to Wailea for a day of relaxation at the stunning beaches and luxury resorts. Take a snorkeling excursion to explore the vibrant marine life.

Day 3: Visit Haleakalā National Park to witness the breathtaking sunrise over the Haleakalā crater. Spend the day hiking through unique landscapes and enjoying the park's natural beauty.

Day 4: Wander through the bohemian town of Paia, known for its laid-back vibe, surf culture, and eclectic shops. Sample local cuisine at the charming cafes and restaurants.

Day 5: Departure day. Take a leisurely morning stroll along the beach and savor the last moments of the trip before heading to the airport.

Recommended Activities

  • Trip Point Pin1

    Lahaina

    Lahaina offers historical sites, beautiful beaches, and a vibrant art scene, making it a charming and lively town to explore.
    Lahaina
    Lahaina
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    Lahaina
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    Lahaina
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    Lahaina
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    Lahaina
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  • Trip Point Pin2

    Wailea

    Wailea is known for its stunning beaches, luxury resorts, and fantastic snorkeling and golfing opportunities, offering a perfect blend of relaxation and adventure.
    Wailea
    Wailea
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    Wailea
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    Wailea
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    Wailea
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    Wailea
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  • Trip Point Pin3

    Haleakalā National Park

    Haleakalā National Park is home to the stunning Haleakalā crater, unique flora and fauna, and breathtaking views, providing an unforgettable experience for nature lovers and hikers.
    Haleakalā National Park
    Haleakalā National Park
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    Haleakalā National Park
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    Haleakalā National Park
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    Haleakalā National Park
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    Haleakalā National Park
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  • Trip Point Pin4

    Paia

    Paia is a charming town known for its bohemian atmosphere, surf culture, eclectic shops, and delicious dining options, making it a perfect stop for a unique and laid-back Maui experience.
    Paia
    Paia
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    Paia
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    Paia
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    Paia
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    Paia
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Restaurants

  • Restaurant Icon

    Mama's Fish House

    Mama's Fish House

    Located in a picturesque beachfront setting with a focus on fresh, local ingredients and a unique Polynesian-inspired menu.
    Picture for Mama's Fish House
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    Gazebo Restaurant

    Gazebo Restaurant

    Famous for its macadamia nut pancakes and stunning ocean views, offering a delightful dining experience in a relaxed atmosphere.
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    Mill House

    Mill House

    Set within a lush plantation, this farm-to-table restaurant offers innovative cuisine and picturesque views of the Waikapu Valley.
    Picture for Mill House
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    Lahaina Grill

    Lahaina Grill

    Renowned for its elegant ambiance and creative dishes, combining Pacific Rim flavors with a sophisticated dining experience.
    Picture for Lahaina Grill
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    Hali'imaile General Store

    Hali'imaile General Store

    A charming restaurant in a historical plantation setting, known for its delectable, globally inspired cuisine and warm hospitality.
    Picture for Hali'imaile General Store
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    Tin Roof Maui

    Tin Roof Maui

    A casual eatery offering a unique fusion of Hawaiian and Filipino flavors, serving up delicious and affordable dishes in a lively setting.
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    Merriman's

    Merriman's

    Emphasizing locally sourced ingredients and sustainable practices, this restaurant provides a farm-to-table dining experience with stunning ocean views.
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    The Plantation House Restaurant

    The Plantation House Restaurant

    Known for its panoramic views of the golf course and ocean, offering elevated American cuisine with a touch of Hawaiian flair in a beautiful setting.
    Picture for The Plantation House Restaurant

Hotels

  • Hotel Icon

    Paia Inn

    Paia Inn

    A boutique hotel with a unique bohemian charm, offering a mix of luxury and local authenticity in the heart of Paia town.
    Picture for Paia Inn
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    Lumeria Maui

    Lumeria Maui

    A wellness retreat set amidst stunning natural surroundings, offering yoga classes, organic gardens, and a peaceful atmosphere for a rejuvenating stay.
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    Travaasa Hana

    4.3

    Travaasa Hana

    Located in the remote town of Hana, this hotel provides an off-the-beaten-path experience with traditional Hawaiian activities and luxurious amenities.
    4.3
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    The Westin Maui Resort & Spa

    The Westin Maui Resort & Spa

    Situated on Ka'anapali Beach, this resort offers a unique 'water park' experience with five pools, lush gardens, and a variety of dining options.
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    Montage Kapalua Bay

    Montage Kapalua Bay

    An oceanfront property showcasing Hawaiian artwork and offering personalized service, making it an ideal retreat for a luxurious and cultural experience.
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    Four Seasons Resort Maui at Wailea

    Four Seasons Resort Maui at Wailea

    An exclusive beachfront resort with exquisite amenities, including a renowned spa, fine dining, and breathtaking ocean views, providing the ultimate luxury getaway.
    Picture for Four Seasons Resort Maui at Wailea

Local Events & Happenings

  • Event Icon

    Chelsea Handler

    Chelsea Handler

    The event will take place at Castle Theater - HI in Kahului.
    Map IconCastle Theater - HI in Kahului (6.13 mi)
    Calendar Icon20 Jul 2024
    Website IconVisit Website
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  • Event Icon

    Tumua: The Warrior Tour

    Tumua: The Warrior Tour

    The event will take place at Maui Arts & Cultural Center in Kahului.
    Map IconMaui Arts & Cultural Center in Kahului (7.85 mi)
    Calendar Icon13 Jul 2024
    Website IconVisit Website
    Picture for Tumua: The Warrior Tour
  • Event Icon

    Chelsea Handler: Little Big Bitch

    Chelsea Handler: Little Big Bitch

    The event will take place at Maui Arts & Cultural Center in Kahului.
    Map IconMaui Arts & Cultural Center in Kahului (7.85 mi)
    Calendar Icon20 Jul 2024
    Website IconVisit Website
    Picture for Chelsea Handler: Little Big Bitch
  • Event Icon

    The Music Of Star Wars

    The Music Of Star Wars

    All sales are final. No refunds or exchanges will be made. Your ticket is a license to attend the performance on the date and time stated. Management reserves the right to revoke this license, upon refund of face value, for any reason. The Blaisdell ...
    Map IconTom Moffatt Waikiki Shell in Honolulu (96.32 mi)
    Calendar Icon21 Jul 2024
    Website IconVisit Website
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    Mahler 5

    Mahler 5

    All sales are final. No refunds or exchanges will be made. Your ticket is a license to attend the performance on the date and time stated. Management reserves the right to revoke this license, upon refund of face value, for any reason. The Blaisdell ...
    Map IconTom Moffatt Waikiki Shell in Honolulu (96.32 mi)
    Calendar Icon22 Jul 2024
    Website IconVisit Website
    Picture for Mahler 5
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    Symphony At The Shell

    Symphony At The Shell

    All sales are final. No refunds or exchanges will be made. Your ticket is a license to attend the performance on the date and time stated. Management reserves the right to revoke this license, upon refund of face value, for any reason. The Blaisdell ...
    Map IconTom Moffatt Waikiki Shell in Honolulu (96.32 mi)
    Calendar Icon26 Jul 2024
    Website IconVisit Website
    Picture for Symphony At The Shell
  • Event Icon

    HSO - Jurassic Park in Concert

    HSO - Jurassic Park in Concert

    All sales are final. No refunds or exchanges will be made. Your ticket is a license to attend the performance on the date and time stated. Management reserves the right to revoke this license, upon refund of face value, for any reason. The Blaisdell ...
    Map IconTom Moffatt Waikiki Shell in Honolulu (96.32 mi)
    Calendar Icon28 Jul 2024
    Website IconVisit Website
    Picture for HSO - Jurassic Park in Concert

Travel Gems from Reddit

  • Reddit Icon

    Day 3: Stay - Hana-Maui Resort 1.30 pm - lunch at Thai Me upp 2 pm - on the way -Coconut Caboose Shave Ice & Coconuts / Aunty Sandy Bread 3 pm - Twin falls trail/ Bamboo Fores...

    (5 days) Maui itinerary suggestions/advice

    Day 3: Stay - Hana-Maui Resort 1.30 pm - lunch at Thai Me upp 2 pm - on the way -Coconut Caboose Shave Ice & Coconuts / Aunty Sandy Bread 3 pm - Twin falls trail/ Bamboo Fores...

    /r/VisitingHawaii
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  • Reddit Icon

    Aloha - this is a subreddit for visitors looking for advice to plan their vacation, or to share their own experiences on the Hawaiian islands. Please note the subreddit rules ...

    Maui itinerary for 5 days

    Aloha - this is a subreddit for visitors looking for advice to plan their vacation, or to share their own experiences on the Hawaiian islands. Please note the subreddit rules ...

    /r/MauiVisitors
    View on RedditView on Reddit
  • Reddit Icon

    My family and cousins are planning a Maui trip around the last half of May. Currently this is what we have roughly planned. Any suggestions would be great. Mahalo! Day 1: Arri...

    8 day Vacation in Maui! Need help on current itinerary!

    My family and cousins are planning a Maui trip around the last half of May. Currently this is what we have roughly planned. Any suggestions would be great. Mahalo! Day 1: Arri...

    /r/maui
    View on RedditView on Reddit
  • Reddit Icon

    Planning a family trip to Hawaii in mid-October, and would appreciate your recommendations! We're a group including us, our parents and our little one. Our itinerary starts on...

    Seeking Family-Friendly Tips for Hawaii Trip: Volcano National Park & Maui

    Planning a family trip to Hawaii in mid-October, and would appreciate your recommendations! We're a group including us, our parents and our little one. Our itinerary starts on...

    /r/VisitingHawaii
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  • Reddit Icon

    We are a family of 5 with 3 kids ranging from 15 to 7. We will be in Maui April 15th-21st and are trying to plan our some activities. This will be our familys first trip to so...

    Asking for Advice and Recommendations on family activities

    We are a family of 5 with 3 kids ranging from 15 to 7. We will be in Maui April 15th-21st and are trying to plan our some activities. This will be our familys first trip to so...

    /r/MauiVisitors
    View on RedditView on Reddit

Music for Your Journey

  • Music Icon

    Angus & Julia Stone - Mango Tree

    Angus & Julia Stone - Mango Tree

    A feel-good song with a tropical vibe, perfect for cruising along Maui's scenic roads and enjoying the island vibes.
    Listen on Spotify
    Picture for Angus & Julia Stone - Mango Tree
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    Weezer - Island In The Sun

    Weezer - Island In The Sun

    The song captures the essence of a carefree island life, ideal for unwinding on Maui's beautiful beaches and soaking in the sun.
    Listen on Spotify
    Picture for Weezer - Island In The Sun
  • Music Icon

    Bob Marley & The Wailers - Three Little Birds

    Bob Marley & The Wailers - Three Little Birds

    A classic reggae tune spreading positive vibes and reminding you to relax and take it easy while on your Maui getaway.
    Listen on Spotify
    Picture for Bob Marley & The Wailers - Three Little Birds
  • Music Icon

    Israel Kamakawiwo'ole - Somewhere Over The Rainbow_What A Wonderful World

    Israel Kamakawiwo'ole - Somewhere Over The Rainbow_What A Wonderful World

    Hawaiian artist Israel Kamakawiwo'ole's soothing rendition of this iconic song perfectly complements Maui's picturesque landscapes and sunsets.
    Listen on Spotify
    Picture for Israel Kamakawiwo'ole - Somewhere Over The Rainbow_What A Wonderful World
  • Music Icon

    Zac Brown Band - Knee Deep (feat. Jimmy Buffett)

    Zac Brown Band - Knee Deep (feat. Jimmy Buffett)

    This song's laid-back melody and lyrics about escapism make it an excellent addition to your Maui playlist, a perfect match for the island's easygoing atmosphere.
    Listen on Spotify
    Picture for Zac Brown Band - Knee Deep (feat. Jimmy Buffett)
  • Music Icon

    The Beach Boys - Good Vibrations - Remastered 2001

    The Beach Boys - Good Vibrations - Remastered 2001

    This classic song brings a sense of positivity and joy, adding a fun and upbeat energy to your Maui adventure.
    Listen on Spotify
    Picture for The Beach Boys - Good Vibrations - Remastered 2001
  • Music Icon

    Vance Joy - Riptide

    Vance Joy - Riptide

    With its catchy ukulele accompaniment and breezy lyrics, this song is an ideal companion for leisurely drives or beach picnics in Maui.
    Listen on Spotify
    Picture for Vance Joy - Riptide
  • Music Icon

    Bob Marley & The Wailers - Could You Be Loved

    Bob Marley & The Wailers - Could You Be Loved

    Bob Marley's timeless anthem exudes a sense of joy and celebration, encouraging carefree dancing and relaxation during your Maui journey.
    Listen on Spotify
    Picture for Bob Marley & The Wailers - Could You Be Loved
  • Music Icon

    The Beatles - Here Comes The Sun - Remastered 2009

    The Beatles - Here Comes The Sun - Remastered 2009

    The Beatles' uplifting tune perfectly captures the feeling of greeting a new day, ideal for watching Maui's stunning sunrises or enjoying a lazy morning.
    Listen on Spotify
    Picture for The Beatles - Here Comes The Sun - Remastered 2009
  • Music Icon

    Jason Mraz - I'm Yours

    Jason Mraz - I'm Yours

    Jason Mraz's breezy and romantic song sets the perfect mood for romantic sunset moments or leisurely strolls along Maui's beaches.
    Listen on Spotify
    Picture for Jason Mraz - I'm Yours