We're here to help
    Book online or call (650) 414-7338
    1. Local experiences/
    2. Lahaina, HI/
    3. Vehicle Rentals/
    4. Motorcycle Rentals/
    5. Harley Davidson Heritage Softail Classic Rental in Maui
    Why travelers choose Greetwell
    Curated by our team

    Every experience is selected and approved for quality and safety

    Personal concierge

    Real humans available to help before, during, and after your booking

    Intimate & authentic

    Including unique in-home experiences you won't find anywhere else

    Easy booking

    Reserve in minutes with flexible cancellation on most experiences

    Greetwell

    Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

    About

    • Our Story
    • For Experience Providers
    • For Hospitality Partners

    Concierge Support

    • Help Center
    • (650) 414-7338
    • Contact our team

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Product image 1
    Gallery image

    Harley Davidson Heritage Softail Classic Rental in Maui

    Ride Maui's scenic roads on a classic Harley with gear included and flexible rental options.

    From$159/ motorcycle

    Duration

    4 hrs to 7 days

    Includes

    Helmets, Unlimited miles

    Highlights

    Discover Maui aboard the iconic Heritage Softail, blending timeless style with modern performance. Feel warm breezes and take in coastal views as you explore hidden beaches, waterfalls, and vibrant towns at your own pace.

    • Ride a Heritage Softail with classic style and smooth performance
    • Cruise Maui's coastline with tropical breezes and sweeping ocean views
    • Explore the Road to Hana with waterfalls and lush scenery
    • Climb to Haleakala for volcanic vistas above the clouds
    • Enjoy route recommendations for memorable rides
    • Choose flexible rentals from 4 hours to 7 days

    What's Included

    • Vehicle (One Driver, One Passenger)
    • Backrest
    • Unlimited Miles
    • Half Shell Helmets
    • Route Recommendations

    Things to know

    Rear passengers must be at least 7 years old. No off-road riding or the back side of Hana. A damage deposit and liability waiver are required at pickup.

    FAQs

    What types of motorcycles are available for rent?
    We offer Harley-Davidson touring bikes, Indian Motorcycles, sportbikes, adventure motorcycles, and lightweight cruisers from brands like Honda, Kawasaki, Suzuki, and Yamaha.

    What are the age and license requirements?
    Renters must be at least 21 with a valid motorcycle endorsement for motorcycles over 50cc. For 49cc mopeds, renters must be at least 18 with a regular driver's license.

    Is safety gear provided?
    Yes, required safety gear including helmets and goggles is provided free of charge.

    Can I rent for multiple days?
    Yes, rental periods range from 4 hours to 7 days.

    Are tours available?
    Yes, self-guided Navigation Tours are available with GPS-equipped motorcycles.

    What is the cancellation policy?
    For 1–2 units up to 2 days, cancel at least 24 hours prior and only the 10% deposit is forfeited; within 24 hours the full amount is due. For 3+ days or 3+ units, cancel at least 120 hours prior and only the 50% deposit is forfeited; within 120 hours the full amount is due.

    Do you offer insurance options?
    Optional damage waivers are available to limit financial responsibility in case of damage.

    Can I ride with a passenger?
    Yes, many motorcycles can accommodate passengers. Both rider and passenger must wear provided safety gear and comply with rental policies.

    Cancellation policy

    For 1–2 units up to 2 days: cancel at least 24 hours before start and forfeit the 10% deposit; within 24 hours, full amount is due. For 3+ days or 3+ units: cancel at least 120 hours before start and forfeit the 50% deposit; within 120 hours, full amount is due. Rebookings inside these windows are not refundable.

    Experience provided by AMS Motorcycle Kihei
    Experience provided by AMS Motorcycle Kihei

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text (650) 414-7338

    Reference #4Z76NC

    Four Hour Rental

    $159

    0

    Eight Hour Rental

    $179

    0

    24 Hour Rental

    $199

    0

    Two Day Rental

    $398

    0

    Three Day Rental

    $537

    0

    Four Day Rental

    $716

    0

    Five Day Rental

    $895

    0

    Six Day Rental

    $1,074

    0

    Seven Day Rental

    $1,113

    0

    Why book through Greetwell?

    • Greetwell Approved

      This experience meets our quality and safety standards

    • Includes Concierge Support

      Our team is here to help with questions, timing, or special requests

    • Flexible Cancellation

      Plans change? Most experiences offer flexible cancellation

    Search all experiences

    Discover what we've curated for you

    Meeting location

    1975 S Kihei Road. Kihei, HI 96753

    4.7 stars• 102 reviews

    Review summary

    4.7
    Excellent
    102 reviews•Google Maps

    The staff here absolutely makes the experience. AT, Denny, and Steven get called out by name repeatedly for being genuinely friendly, knowledgeable, and going the extra mile to help customers plan their adventures. One reviewer appreciated how understanding they were when a moped rental wasn't working out, quickly swapping them into a Slingshot instead. People consistently describe interactions as welcoming and pressure-free, with that authentic aloha spirit that makes you want to rent even if you hadn't planned on it. The Polaris Slingshot seems to be the star attraction and gets rave reviews for exploring Maui's scenic roads, especially the Road to Hana. Reviewers love how it combines motorcycle handling with car-like comfort, perfect for those curvy island roads while still being able to chat and take photos. The rental process is described as fast and simple, with staff offering helpful route suggestions. They also carry a solid selection of motorcycles and mopeds. Just note that the Slingshot is open-air, so checking the weather forecast is smart before heading out.

    What people are saying

    Review 1 of 4
    5/5

    Denny is hands down the best in business! We had a great experience working with him! Made everything fast and simple! We ended up renting 4 slingshots from him for 24 hrs! My family and I Had a blast on them!!! Created an lifetime’s memory in Maui with them!

    Photo of KB Yang

    KB Yang

    December 29, 2025

    Review 1 of 1
    5/5

    Denny is hands down the best in business! We had a great experience working with him! Made everything fast and simple! We ended up renting 4 slingshots from him for 24 hrs! My family and I Had a blast on them!!! Created an lifetime’s memory in Maui with them!

    Photo of KB Yang

    KB Yang

    December 29, 2025

    Nearby activities

    Thumbnail

    Harley Davidson Street Glide Rental on Maui

    From$179/ bike
    Thumbnail

    Haleakala Summit Sunrise or Sunset Navigation-Guided Slingshot Tour

    $450/ slingshot
    Thumbnail

    North Loop Coast Slingshot Adventure – Navigation Guided

    $350/ slingshot
    Thumbnail

    Polaris Slingshot R Rental in Lahaina, Maui

    From$149/ slingshot
    Thumbnail

    Maui Genuine 50cc Scooter Rental

    From$39/ scooter
    Thumbnail

    Myths of Maui Luau at Royal Lahaina Resort & Bungalows

    From$208/ person