My husband and I are going to Hawaii for the first time in March for our 20th anniversary. I have posted a couple of threads on hotels and got a lot of useful information. I have been looking at packages from expedia to fly from Chicago to Kona rent a car and stay 5 nights, then get to Maui on our own, rent a car in Maui and stay another 5 nights. The package price does seem to be cheaper than booking it by itself but not a huge difference. I looked at the hotels separately on expedia, the hotels websites, hotels.com and placestostay.com. Are there other websites that I am missing that could give me a better package price? Do other Fodorites prefer to book a package or do it all separate? Thanks!

Our trip to Maui was the only trip we've taken that we did not do a package. We wanted a specific hotel: Kaanapali Beach Hotel and then booked Delta Airlines. We did this seperate based on the recommendation of the travel agent we were using at the time. We received the worst flight times possible. From Midland a 4 hour lay over in Dallas, then another 4 hour lay over in LAX. It took us 15 hours to get there. And the same schedule coming back. The tickets were $1,553.00 for the 2 of us. When we returned, I found a new travel agent that I have used ever since with much better luck on flight accomendations.

We generally use Fun Jet or Southwest Airline pacakges for our vacations, and found that booking a package is much cheaper than booking hotel and air seperate. Fun Jet does go to Hawaii, but of course, Southwest Airlines doesn't. You might want to check Funjet's web-site for your dates and see what they have to offer. www.funjet.com

Thanks. Did try Funjet but don't think it is possible to do two islands. When I compared Maui alone to the prices on Expedia - Funjet was hiring and didn't even include the car.

Try www.pleasantholidays.com
or www.aavacations.com
or www.ata.com (discount airline).

I'm sure there's others. Good hunting.

We are going in May and I am going to try PRiceline for the first time. Check out biddingfortravel.com, they post an extensive list of what people are paying for the various hotels/resorts on the island. Substantial savings if you are willing to give it a try. However, I won't be using them for airline.

We did a 16 day trip a year ago and I used these guys: http://www.greathawaiivacations.com/. After doing a ton of research, Eric booked our 3 different condos, our interisland air and our car rentals on Maui and Kauai for a reasonable package price. So much easier than trying to book it all separately. (We used FF miles for our roundtrip from Chicago so didn't have to worry about that.)

I checked out pleasantholidays.com and the price came out about the same as expedia expect there was availability for a hotel in Maui that we were interested in that wasn't available on expedia.

Have people had good/bad experiences with Pleasant Holidays?

Pleasant Hawaiian Holidays (as it used to be called) has been around for a long time. They are a good company and they have locations all over the islands to help their travelers when they arrive on the islands. I remember my first trip to Hawaii, as a kid with my family, was in 1972 and was through PHH. I have used them since as an adult, most recently for part of our family's trip in the summer of 2004. I prefer booking everything separately myself (more flexibility in choice of properties, etc.) but if I were to book a package I'd definitely consider them first (comparing prices of course).

My folks took 9 people to Maui for an anniversary celebration thru Pleasant Holidays. It worked nicely for us.

Also try pleasantholidays pricing by phone, they are sometimes cheaper than the net. Then there's also www.classiccustomvacations.com which will generally beat pleasant by about $50 but you need a travel agent to book. Don't forget to make sure all taxes are added in the final price.

Husband and I have two preteen boys. We have used Pleasant 3 times since 2000. Twice as complete package (Air, Condo and Car)and Once with Air and Car package (fly and drive) and then I booked our favorite Condo thru VRBO.com. I have looked all 3 times and have never found cheaper anywhere else. We book a year in advance for best deal and you only pay a deposit until 90 days before and also have travel insurance included. For our trip in 2006 we have enough skymiles for two. Travel Agent suggested splitting miles for one adult and one child and other child and adult could still use a fly/drive package. This way both adults wouldn't be on skymile tickets in case something got changed. And an adult would be with a child when tickets were booked. We will still use VRBO.com for Condo again. Pleasant has website and I look for deals and then call my travel agent to arrange. She can usually get a little bit cheaper than even the website. Booking in advance is key to best deals. Start checking on website for package prices and the jump on deal when prices drops for your area.. Good luck with your arrangements.

I prefer to book everything separately simply for the flexibility unless the package price is substantially less. Packages can incur some hefty cancellation/change penalties whereas hotels have more liberal cancellation policies. And I can always use the air ticket funds to travel later for a change fee. My plans often change sometime between booking and actual travel.

I enjoy doing it myself but I'm weird that way. I know that the price at the Grand Wailea was MUCH cheaper by going to their own website than Expedia, Travelocity, etc. I'm talking $309 vs $485. I also found a great sale on Aloha for $370 pp Oakland to Maui. (that sale is over now) Planning the trip is half the fun for me. I guess I should've been a travel agent.