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Planning a Timeshare Trip to Hawaii

Maybe you’ve dreamed of going, but it seems to  be somewhat overwhelming, and you don’t know where to start--or when.  Having just done it for the fourth time, we thought we would put together some tips, timetables and ideas to help you plan your own personal trip to paradise.  And when you’re on the plane flying home after your dream vacation, as we are now, and someone asks you if it’s really worth it, you will answer with a resounding YES!

A short geography lesson to begin:  There are actually 8 major islands that comprise the state of Hawaii, as well as several smaller ones, but the four that are the most traveled to are Oahu, Maui, Kauai and the Big Island (also known as Hawaii).  The four islands have many things in common, but they are all very different.  Therefore, when you plan a trip, probably the first thing you want to do is decide (based on your research and interests) which islands hold the most appeal for you.  Here are some short descriptions, but please research these further before making your choices:

Oahu–generally considered the busiest island, because it houses the capital city, HonoluluWaikiki Beach is beautiful with much to offer, but Honolulu is pretty much like any major U.S. city, except that it has palm trees.  However, there are many quieter and very scenic areas on the island, to include the North Shore and Ko Olina coasts.  Much to see and do, including Pearl Harbor and the Polynesian Cultural Center.

Maui--the preferred island of many, as it has beautiful Ka’ anapaali beaches and resorts.  The Road to Hana is a popular, all-day drive with amazing twists and turns and glorious vegetation.  A visit to the Haleakala Volcano at sunrise is a memorable experience.

Kauai–known as “the Garden Isle,” is the oldest of the islands and home to Waimea Canyon, which many claim is more beautiful than the Grand Canyon.  Because of the lush rainforest, it rains more here, especially in the northern Princeville area.  However, one need only drive 45 minutes south to sunny Poipu and its beautiful beaches.

The Big Island--the largest of the four, can claim 9 temperate zones.  Kilauea is an active volcano, and you might even see lava spewing forth if you’re lucky.  There are gorgeous resorts along the Kona Coast and in the Waikoloa area, as well as several coffee plantations and beautiful waterfalls.

Now let’s talk about timing.  You probably know that Hawaii is one of the most desired timeshare locations–thus, the earlier you begin planning, the better.  Two years out is not too soon, although realistically, 1 to 1-1/2 years is probably about right.  Most timeshare systems and companies allow you to do an ongoing search, so it is best to give them some time parameters.  Try to be as flexible as possible, not only with times, but with islands, as well.

If the system in which you own has some Hawaiian resorts, then your chances for going to Hawaii are definitely good, provided you watch the booking windows and call or go online as soon as the window opens up to you.  From personal experience, we have found good availability in these systems:

Wyndham:  Kauai, Big Island, Oahu

Hilton:   Oahu, Big Island

Disney:  Oahu

Diamond:  Kauai, Maui, Big Island

You can check other resort systems to see what is available.  Generally, if you are trading through RCI, Maui is especially difficult to get.  If timeshare options do not work out, you may also want to explore rentals.

Once you have booked the week or weeks you want, then you need to begin to think about your air travel.  We suggest that you look at all possibilities such as flying direct to your island, or flying into Oahu and then hopping on an inter-island flight. You need to do the math and see what works for you.  A number of people from the east coast fly out to the west coast and spend a couple of days and then fly over.  This gives them a chance to break up that long flight, as well as it helps with the time change and jet lag.  Keep in mind that any stopover would involve additional cost for accommodations and moving to and from the airport. We have found that this is usually a more expensive option.

Knowing when to book a flight is always a hassle, and no matter what you do, the rates may go down after you book it.  We usually book somewhere in the 3-6 month window, after watching the rates for several months.  If we are going to be gone for several days, say 2-4 weeks, we might elect to fly from a smaller airport closer to our home.  That way family or friends can drop us at the airport and pick us up, thus saving airport parking fees.  If you live in or near a major large city, then this wouldn’t be an issue for you.  However, it never hurts to comparison shop!

Once your flight (s) are booked, you can book your inter-island flights if you are planning on traveling to more than one island.  We recommend that you do this early, also, because then all your flights will be set up, and you can book rental cars, if that is your choice.  There are 3 inter-island airlines to choose from:  Hawaiian, Go (formerly Mesa) and  Mokulele.  Check on-line for some reviews of the different airlines.

Rental car prices change almost by the minute, so once we know our flight arrival times, we reserve cars online.  Usually we check Dollar, Thrifty and Alamo, as we’ve found them to be the cheapest.  At 3 months out, they are usually pretty expensive, so we keep checking about once a week until the last 2 weeks–then we check daily.  When we find a cheaper car, we cancel the previous one, because they do not require a credit card to reserve the car. 

On our latest trip, we rented 3 cars on 3 different islands and we probably booked and canceled about 8 times–but we saved about $250 over our original bookings.  To learn more check out this post.

Depending on how long you are staying and your particular interests, you may not want to rent a car.  Many people feel that it’s a waste of money in Honolulu because resort parking fees are so expensive and they have a good transportation system.  However, keep in mind that taxis and shuttles can be expensive, as can resort transportation.  You are much more limited as to where you can go and what you can see if you don’t have a car, and you can lose a lot of time waiting around for rides.  Then again, if your goal is to relax at the resort, maybe you don’t need one.

We suggest you begin to do research on what to do on your trip.  We do a lot of internet work with “things to see and do”, “top ten lists”, etc.  We also check the library for some travel books.  A series of books which we found very helpful is “Maui Revealed”  The Big  “Island Revealed” and so on.  They are well-written and have a wealth of information in them.  Planning for a trip can be very exciting and fun.

 Over the next couple of months we will be writing 3 in-depth articles about the islands we visited on this trip, as well as four reviews of the resorts we stayed at.  Be sure to check them out and keep reading our blog.