High/Low - Booking a Vacay in Maui

maui[trip style =  sun + beach]

Booking a vacation in Maui can be wildly expensive or moderately priced depending on: - when you book - how you book - who you book with - your penchant for luxury - whether you eat-in or go out - the number of activities you do while there

All these things considered, here's how to do Maui High, Med and Low: {do one or combine all three} High

  • Flight: fly business class with your preferred airline. Note that airlines carrying on to Australia, etc... will have a more luxurious offering than those just doing direct or one-stop runs back and forth to the islands.
  • Accommodation:
    • Ritz Carlton Kapalua
    • Four Seasons Wailea
    • Fairmont Kea Lani Wailea
  • Car: Avis and Hertz offer the best high-end car rentals at the Kahului Airport (OGG)
  • Eating out:
    • Mama's fish house (all fish is fresh and caught by some of the servers)
    • any restaurant at the Four Seasons Wailea
  • Activities:
    • charter a helicopter over the mountains and/or to Hana
    • luau at the Hyatt Ka'anapali [much better than the luau at the Wailea Marriott]
    • for more activities, see lists below


  • Flight: Alaska and Hawaiian Airlines offer friendly service in economy class, but many other airlines like Air Canada or West Jet fly direct to Maui. If you want to splurge a little, Hawaiian Airlines' business class has semi-reasonable prices, from around $550 each way (out of Seattle).
  • Accommodation: take an educated risk and book your hotel via hotwire or priceline. When you book in the "Resort Class" of properties for the Wailea/Makena or Ka'anapali areas, you end up with one of two hotels for the each area.  Prices can be as low as $120/night (not including taxes). *If you book through one of these websites, your hotel has to ask you whether or not you want to pay the resort fee, usually $25 extra per day.
  • Car: Get your car through priceline or hotwire and pick it up at the airport. 
  • Eating out:
    • Humu-humu at the Grand Wailea
    • Mala at the Marriott Wailea
    • Joe's at the Wailea Tennis Club
    • Roy's in Ka'anapali
    • Hula Grill in Ka'anapali
  • Activities: see high or low activity lists.


  • Flight: set up a Kayak Fare Alert for airports in your area and OGG, Maui's airport. Book when dates and prices appeal to you.
  • Accommodation: staying at a rental condo/home with a kitchen is an excellent way to control costs. Some best bets are: vrbo.com, ownerdirect.com
  • Car: if you want any flexibility while on Maui, renting a car is required, especially since grocery shopping and self-guided excursions will be a big part of your getaway. Bidding for a car on Priceline can be a cheap way to get a vehicle.
  • Eating out: take advantage of your kitchen and make some nice meals in your rental condo---most of which have BBQs in the common outdoor areas. If you're set on eating out, the Barefoot Bar at the Hula Grill in Ka'anapali has an excellent Happy Hour complete with live music. In Wailea, Cheeseburger Island Style has excellent prices and a great breakfast special.
  • Activities: There is so much to do in Maui that doesn't require a tour guide. Here's a sample:
    • drive to Hana
    • watch the windsurfers and kite-boarders at Hookipa beach
    • browse the shops in Paia
    • take advantage the beaches in front of any hotel --all beaches are public
    • snorkel at Black Rock in Ka'anapali or Ahihi Bay in Makena
    • stand-up paddleboard in Kihei
    • take surf lessons in Lahaina
    • drive to watch the sunrise at Haleakela (wear warm clothes, it's cold at 5.30am!)
    • walk the seawalk in Ka'anapali and/or Wailea
    • swim at Black Rock while the Sheraton's torch-lighting ceremony is taking place (watch for 'the dive' at the end)

[photo by @tripstyler]