Trip Planning - Guest Services - Holiday Guide

Resources to Help you Plan a Successful Vacation Trip to Maui

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About Trip Planning - Guest Services

Travel Planning, Guest Services, & Maui Vacation Deals

We created this Trip Planner page to help our repeat renters, and new ones too, connect with some of the resources we believe can help you plan a successful vacation trip to Maui. We only present resources here that we have sampled ourselves.

Whether you are a couple, family, old or young, Maui offers something for everyone. This guide can help insure you get the most from your Maui holiday. Do you need to rent a car? Is Travel Insurance needed? What are the best groceries and meal delivery services on Maui? What stores are near me? These questions and more are answered here.

Highlights of Trip Planning - Guest Services

Travel Insurance

How to find a Property to Rent on

Our Traveler FAQ section and How to Book page have detailed info on how to use our website to find the perfect vacation rental for your time on Maui as well as how to book that property

Plan Ahead - Book Early

Many first time Maui visitors are shocked when they see how early Maui Vacation rentals book- especially in South Maui. We don't have lots of high rises here and the condos are usually larger than in other areas so they really are a limited resource and book out early. We are talking more than 1 year in advance if possible.

Insure your vacation and travel worry free!

AIG Travel Guard:

Travel to Maui is not inexpensive and these days can be more complicated than usual. Protect your trip against the unexpected. Check out Trip Cancellation Insurance options.

No one expects to break a leg, loose a job, be stranded for days because of weather delays or realize they are landing on an island when a hurricane is forecast but these things happen more often than we would wish.

Trip Insurance for a vacation rental costs only 7-11%, depending on the type you purchase and is well worth it. Travel Guard offers Standard and Cancel for any Reason plans at a reasonable cost. We have used them and were impressed with their service. Unfortunately they can only provide insurance for those living in the USA. Other options can be found by searching on-line or checking our Travel Insurance Page.

Things to do in Trip Planning - Guest Services

Activity Booking, Meal Services, Family Friendly Activities

Options on this page are geared to help you find those resources that can make your Maui holiday a special time.  Look for unexpected activities (including day camps) for the kids, delivery, meal, activity and concierge services 

Personal Concierge & Activity Services, 

Though we are providing direct links to many of the activities and resources below, booking through our Concierge can do more than save you money. Key tips on where to sit, when to whale watch, what to request on a helicopter ride, etc can enhance your experience. Check out the activities then contact our concierge and let them make the reservations for you.

See our Booking Activities on Maui for more specific information

Condo Pre-stocking Meals & Delivery Services would like to be sure your vacation is as care free as possible. In addition to our Personal Concierge & Activity Services, Vehicle Rental & Travel Insurance suggestions, we are pleased to recommend a very reliable value added Condo Grocery & Goodies Pre-Stocking & Delivery Service & Meal Services. We use them and love the services they provide.

Meal Services

Private Cooks are pretty expensive but they are available.  A licensed kitchen (or cooking in your home) is required to insure your safety.  Since Covid most restaurants now offer meal delivery. My favorite  delivery service is HOPPER MAUI - a very local company and very reliable. They have an app and a website and deliver for some of our favorite island spots including Coconuts, Manoli's and many more.  Costco has some classic ready to cook meals; we have suggestions for grilling fresh island fish, resources for home made quiches, toffee, breakfast breads and more. We even have a way to have all the above delivered to your door. Keep Reading.

Pre-Stocking & Delivery Services:

When on island many of us dread the trip to the grocery store - the thought of schlepping groceries, paper products and beverages while others are playing on the beach is not the best part of my vacation.

To make life easier, there are now several options for CONDO SUNDRY & GROCERY PRE-STOCKING SERVICES. Liquor can also be delivered now.  Use the link above for detailed info and links.

Kids Stuff

Activities & Resources for Children is pleased to offer local Maui resources our members have found that make traveling with children a joy. Links to great opportunities for activities, camps, classes and more that offer unique Hawaiian experiences for your kids. Click HERE for info and links to Family Friendly Activities on Maui.

Transportation for Trip Planning - Guest Services

Getting Around on Maui - Airport, Transportation and Driving Info for Maui



$2 per ride or monthly pass. It's getting more reliable, but it's not quite like the mainland, so be sure you're not on a tight schedule.


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1 Kahului Airport Road, Kahului, HI 96732-2395 | (808) 872-3830)

Kahului Airport has two terminals--a main terminal and a commuter terminal. Upon arriving on Maui at Kahului International Airport's main terminal (OGG), come on down the escalator to Baggage Claim. This is a real, island setting with tropical breezes wafting through. There is plenty of seating around planters and a Starbucks - great for the 20-30 minute wait you may have for luggage when flying in from outside the Hawaiian islands.

Traveler Information, Shuttles, Buses and Cabs have Kiosks here. Best to have your reservation pre reserved. There is a new Transportation Center. This is where Rental Car kiosks are. Head across the street and turn left across the tram tracks before you get to short term parking. The terminal is a 5 minute walk. The Tram (when working) runs every 10 minutes.

Baggage turnstiles 1-2 on the west side of the area are for "local flights" on Hawaiian Air. Bags here come very quickly. IF you had a long wait in Honolulu when changing plans - it's possible your bags arrived before you so look around the turnstile along the wall. Should you be missing a bag, the various airlines have helpful folks available for filing a claim. Check the perimeter of the area near the exits.

Bathrooms in the terminal are good, Carts to help with luggage are available for a fee.


For those who haven't been to Maui since Covid, and want to head to South Maui, the North Shore or UpCountry, you're in for a surprise. The "new" access road and at least 3 new shopping areas are now in place. The Sugar Cane Factory is gone! As are the cane fields. You can now avoid shopping traffic on Dairy Road and take the new bypass. Signage is good but if you want to stop at Whole Foods don't take the left on Aalele, just keep right thru the light and join Hana Hwy to Maui Mall. Bearing left at that light will put you on Dairy Road and a hard left at the light will also give you access to CostCo.

If you want to stop at CostCo on the way to your condo you can also do that by taking that left on Aalele and keeping Right on Aalele instead of straight for the Access Road. Turn right onto 36A at the stop sign. First Costco entrance on Left is to gas station; next is for the main building.

For those heading to Hana or Up Country, you have two options. Take the new access road to the Hana/ Hwy turn off or follow the signs to the left shortly after getting on the access road to wander thru the sugar cane fields near the heliport.

Sound confusing?Just put your destination in your phone map app, take a deep breath and relax - it's Maui!

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Rental Cars on Maui can be picked up at the airport (or near by in Kahului), at some hotels, at rental car offices in Kihei or West Maui. When renting at the airport you will pay an extra airport facility fee (11%). All rental cars on Maui are now subject to an $4.50 per day Highway Surcharge fee BUT if you pick up your car at the airport that fee goes to $7.50/day. Save those airport facility taxes, take a cab or shuttle to your condo or hotel and pick up the car locally.

Check our Maui Rental Car Deals page for discounted rate on AVIS and more tips.

Statistics about Trip Planning - Guest Services


Weather for Trip Planning - Guest Services

Weather on Maui Varies Depending on Where you are.

Maui is an island with many micro climates. Weather on Maui varies from beach to mountain & windward to leeward. If it rains by the beach you can usually move a few miles from under the cloud and find sun. Temperatures vary little through out the year.

Travelers escaping the cold, snow and ice prefer the winter months. A big side benefit -it's also Whale season. That said, the best times to visit Maui are April through May and September through November. These spring and fall shoulder seasons provide the pleasant weather Hawaii vacationers seek without the high rates and heavy crowds that accompany the summer and winter.

However, if you’re into surfing, you’ll want to travel in the winter for the best conditions – just book as early as possible to get a discounted rate. Meanwhile, if you’re traveling with kids, you may want to splurge for a summer trip as that’s when the waters are calmest.

What are Maui's Micro Climates?

If it is raining in Ka’anapali it might be sunny in Lahaina or Kihei. Driving 10-30 minutes to escape the rain cloud is worth checking out. Also when you see rain in a forecast, it is usually raining somewhere in the Iao valley or upcountry, not usually on the coast. It could also rain for 15 minutes and the forecast would still show rain. So if you see RAIN on the weather channel, don’t believe it's going to rain in the resort areas of Maui. Most websites use info gathered from the weather station in Kahului at the air port. It is on the windward side of the island.

It is generally drier on Maui’s leeward side where you’ll find the spectacular beaches and resorts of Kapalua, Kaanapali, Lahaina, Kihei and Wailea. On the wetter windward side you’ll find lush Iao Valley and the scenic road to Hana. It’s warmer along the coast than Upcountry Maui where temperatures are typically 8-10 degrees cooler. If you’re driving up to the 9,740-foot Haleakala Visitor Center atop Haleakala National Park, expect temperatures in the 40s or lower, so bring warm clothes.

Where is the best place to Check out Maui's Weather?

Checkout the Maui page for it is the most accurate weather we have found. It allows you to choose the area of Maui you are planning on being in. Glen’s Narrative is an important resource to see tracks, live weather maps, etc if a hurricane or tropical storm should threaten. Glen lives upcountry on Maui and is a true professional.

The graph below represents weather in Kihei on the South Shore. Wailea, Makena and even Ma'alaea Similar graphs for other parts of Maui can be found on those area's guide pages.

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