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Choose your Dates
You need to decide what time of year, month work best for you, your family, and your work schedule. ALSO, and just as important, you need to choose a time that fits your needs as far budget and weather. Off-season is usually around March May and September-November. At this time, you'll get cheaper tickets/rooms and there will be less people on the island (barring any holiday or Spring Break). Coming during the winter is attractive to those that live in colder, snowy climates, and in the summer for those that have incredible humidity where they live.

Where to Stay
Maui is made up of a diverse range of micro-climates and unique towns. You need to choose by area and by town. Keep in mind you'll likely want to fly into Kahului even if staying near the airport on the west side. Driving for an hour along the beautiful coast is usually better than spending a fortune flying into Kapalua.

South Maui - Kihei, Wailea, Makena.
This is your best chance of having sun 100% of the time. It's the desert side with some great beaches, restaurants, activities. Kihei is less expensive, but
only south Kihei is really nice (in our opinion.) South Kihei Road runs the entire length of both north and south Kihei, so don't be fooled. We like everything south of Kanani Road. Wailea and Makena have amazing resorts and condos on golf courses with great beaches, but you'll pay for it.

West Maui - Lahaina, Kaanapali, Kapalua, Napili
Also on the dry desert side, Lahaina Town is very concentrated and busy with great shopping and lot of restaurants on the water. Kaanapali and Kapalua are golf course towns on the water with big resorts. Napili is a more quiet village area with some pretty beaches too. Kahana is nestled between Kaanapali and Kapalua and has some nice beaches and good prices.

East Maui - Hana Town
Hana is generally what you think of when you imagine Hawaii. Lush rainforests that hug pure coastlines of lava rock, empty beaches, and slow living. This is where all the waterfalls are too. There aren't many choices on
where to stay, but you can rent a condo/house
Upcountry Maui - Makawao, Kula
Not many visitors stay Upcountry, but we recommend it to those that want a cooler experience with great views. These quiet villages are high on the slopes of Haleakala, so you won't have beaches, but you'll likely be able to
see them! The weather is much cooler and it feels like you're staying in the moors of Scotland. It's gorgeous with some beautiful landscapes.
Rent a Car - We will find the best deal.
Get a good price on a reliable car. Major considerations are getting a vehicle that
can hold all of your luggage and yourselves, gas mileage since you may be driving a
lot, and your preference of a convertible. If you want to surf and need a rack, make
sure it has one or buy a portable one. You'll most likely be flying into Kahului
Airport, so rent your car from here online beforehand.
Typically you will be booking a 1 bedroom condo with a pull out bed, allowing up to 4 guests.
You will have a kitchen where you will be able to prepare your own meals.
Fridge, Stove, Oven, Microwave, Coffee Maker,Toaset, etc.
There will be all the typical creature comforts - A/C, Washer/Dryer, Internet, TV, Parking, etc;
There may be an outdoor pool or hot tub.
If you need more than 1 bedroom  the cost will go up quite a bit.
Maui and Kauai Are Calling You!