Are you planning a vacation to a Hawaiian Island? I’ve been researching last-minute vacation packages to Maui – the Aston Maui Kaanapali Villas – because my closest friend has recently been diagnosed with breast cancer. She wants to soak up the sun before chemotherapy starts…and what choice do I have but to go with her?

Here are ten tips for booking cheap vacation packages to Hawaii. I’ve spent hours researching flights, hotels, and things to do in the Hawaiian Islands, and I want to share what I learned!

Don’t forget to pack your reading material – I’ve already picked up Fodor’s Maui 2010: with Moloka’i and Lana’i. Click the book for more info, and read on for a few tips for booking a holiday in Maui…

10 Tips for Booking Cheap Vacations to Hawaii

If you’re traveling solo, you might find Women Traveling Alone – Fighting Homesickness helpful.

1. Go further than Expedia.com. I was told that Expedia is the best way to get a cheap vacation package to Oahu – but it’s not. I found Red Tag.ca and West Jet Vacations far less expensive. Of course, booking the cheapest flight depends in part on where you live. The best thing to do is search for “cheap vacation packages to Maui”, and compare days, flights, hotels, and prices.

2. Be prepared for sudden price differences. It’s frustrating, but you need to accept that you’ll see a “$1,499” vacation package to Hawaii – and it’ll turn out to cost twice as much. The $1,499 price is based on the number of people in the hotel room, hotel availability, flight availability, and taxes. The price isn’t always what it first appears to be.

3. Clear your cached cookies often. Your computer might remember prices, days, and flight options – and that may not work in your favor. When you’re searching for vacation packages to Maui, make sure you delete your cookies so you can get the freshest, most recent deals.

4. Search for travel deals at different times of the day. I found Saturday afternoon to have the highest prices on even the cheapest online booking Web sites. First thing Monday morning, the prices had come down. I don’t know the exact best times to book, but I suggest searching for vacation packages at different times of the day and night.

5. If you call the online vacation package Web site, don’t expect miracles. I called the travel agents at Red Tag.ca, West Jet Vacations, Air Canada Vacations, and Expedia.com, and they all said the same thing: our search engines are the same, so they can’t get a better flight and hotel price to the Aston Maui Kaanapali Villas than I could. If you call a travel representative, don’t expect to get a better deal.

6. Consider booking a hotel and flight separately. Most vacation packages – such as all-inclusive resort vacations – that contain airfare and hotel accommodations are cheaper than booking flights and hotels separately. But, it depends on the hotel. I’ve learned that calling the hotel directly and talking to the in-house reservations department can help you book a less expensive room.

7. Don’t forget about transportation from the hotel to the airport! One of the vacation travel package websites I used for my vacation package to Maui provided a hotel shuttle option. It’s an extra fee, of course, but there’s nothing worse than getting of the airplane after a long flight, and having to figure out how to get to the hotel!

8. Call the hotel directly for prices and availability. I’m hoping the Aston Maui Kaanapali Villas will be willing to give me a better price than what I could get through Red Tag or West Jet Vacation! Don’t hesitate to call the hotel of your choice directly; they might be able to give you a break on your vacation package.

9. Make sure the travel vacation Web site is secure before you book. When you get to the “book and pay for your vacation package” page, make sure it’s a secure site. Secure Web sites have a [https://] beginning (not just [http://]), and are often in green. Don’t pay for a vacation package unless you know it’s secure.

10. Consider a budget youth hostel. When we went to Europe last year, my husband and I stayed in a youth hostel. It was fabulous — and I know Hawaii has them, too! Read Tips for Couples Staying at Youth Hostels for more info. It’s a whole different world than an all-inclusive resort, and it can help you see Maui and your fellow travelers in a whole new way.

When was the last time you went on holidays? Did you book a vacation package, or find a hotel when you arrived at your destination? I welcome your tips below!

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