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Best way to book multi-island trip??

Alexandria, Virginia
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Best way to book multi-island trip??

Want to go to Oahu, Maui and Kaui next year. Wondering what the best way (cost effective/other benefits) for booking hotels & airfare.

Should I do this myself, each individually? Go with the airlines or a particular hotel chain? Look for a travel agent?

Would love to hear from folks who've done multi-island trips.

Elk Rapids, Michigan
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for Lanai
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1. Re: Best way to book multi-island trip??

First time we went we used Pleasant Hawaain (now Pleasant Holiday). They can set up as much or as little as you want from total packages to any portion of flights, rental cars and hotels. They have a web site you can go to to do a check of what it will cost but we found their prices to be resonable.

California
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2. Re: Best way to book multi-island trip??

This all depends on how comfortable you are with making your own arrangements. If you are not familiar with Hawaii or booking travel on-line -- I highly recommend using a travel agent. Yes, "Pleasant" is a reliable company with lots of options. You can go on their website and play around - then go see an agent. Have a good idea of what you want before you go to the agent. He/She can help you decide ... I guess I'm saying is - know what you want vs. being sold something you don't. For example, there is extensive discussion of hotels and airlines on the TA site ... mosey through the hotel websites, too.

Packages can be very economical but -- here I am trying to be diplomatic again -- you might not personally like all the hotels they offer. That's where the homework comes in.

So -- drop by your local travel agent and pick up a "Pleasant" brochure and any others they have. There are several companies. Make a pot of coffee (OK, kinda hot in VA for coffee) ... pour yourself a big glass of iced tea and dig in.

Chicago
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3. Re: Best way to book multi-island trip??

I would do the work on my own, but I enjoy planning my travel and like to keep costs down. Airfare between islands is really easy to buy. There's 4 airlines (Go, Aloha, Hawaiian & Island Air) and all have frequent daily trips between the islands for very little money. All of the airlines have websites. Island Air flies smaller prop planes, so they restrict luggage weight and number of bags. Aloha and Hawaiian fly larger jets. I'm not sure about Go because it's a fairly new discount airline (associated with Mesa Air I think). Inter-island airfare doesn't need to be purchased very far in advance, especially if you're somewhat flexible about what airline you want to use and the time you fly. The best deals are usually available shortly before the flight time (a few weeks or month at most for most of the best deals).

Another good option for inter-island airfare is using frequent flier miles from a program that you have just a few miles in. Flights run about 5,000 miles, but I think that might be a good use of miles if you've got some random miles on an airline you don't normally use (ie you normally fly American but have some United miles from a business trip or two that you're never going to use because you don't normally fly united). Most of the inter-island airlines have partner airlines that would let you use miles from a major airline. However, I would only use this strategy if you're looking to use up some spare miles or have a ton in the bank. Inter-island airfares are really cheap ($30-$60 one way most of the time, but sometimes less than that), so if you're saving your miles for a big trip, don't waste them on an inter-island flight (not a particularly effective dollar/mile benefit).

As for hotels, there's lots of advice on these forums about people's preferred locations once you've narrowed down which areas of each island you might want to stay. Do some research on what you want to do on each island and what area you might want to stay, and then search through the forums for advice on people's hotel preferences. There's a lot of good info in here to be found.

New Hampshire
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4. Re: Best way to book multi-island trip??

LCWombat-

I'm also planning for a trip next year, and have done quite a lot of poking around so far, both in terms of purchasing each piece myself as well as looking for total travel packages.

The packages that I've found, when compared to pricing out each component myself, have been a bit more expensive. Not outrageous, but meaningful. For the package prices I've found, I can make the arrangements myself and either add an extra day or two, or book myself into nicer accommodations (caveat: part of this may be location-specific - there are probably more options, and the potential for more savings, if one is coming from the west coast than from my New Hampshire location).

I actually like doing all this planning, so this works out best for me. My last step before I actually book will be to take a spreadsheet with all the costs and see whether a travel agent can save me money on any portion of the trip. If they can, then I'll let them book that for me - otherwise, I'll just do it myself.

Chris

NYC
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5. Re: Best way to book multi-island trip??

We just returned from Oahu, Maui, Kaui & the big Island. We stayed for 4 days at the Ocean Tower Hotel in Waikiki Beach & took a 7 day NCL cruise on the Pride of Aloha. We were disappointed with the quality of the cruise & the service but the itinerary was awesome. This was our first trip to Hawaii & hopefully not our last. Good luck! Andrea

Elk Rapids, Michigan
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6. Re: Best way to book multi-island trip??

One of the pluses of using say Pleasant Holidays is you have someone available 24x7 if run into any problems. You book it all on your own you are...on your own.

Pleasant also offers a short indoctrination to the island you stay on, sort of a overview of the things to see and do.

As a disclaimer no I don't work for Pleasanr however I did find them to be very professional the one time we used them.

Chicagoland
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7. Re: Best way to book multi-island trip??

How long will you be in Hawaii? Sometimes people try to squeeze too many islands into one trip and spend too much time sitting at airports, renting cars, finding and checking in to the next lodgings. While air time is brief, each "hop" eats the better part of a day. Just about everyone who visits Hawaii comes back, so don't think you have to "see everything" in one trip.

DH and I have been visiting the islands for 25+ years. Early on we split a two week vacation between two islands; later, a month between two. Now we own in South Maui.

For us, condos are the best. We like having more than just a single hotel room with one bath. A resort condo has everything a hotel has except room service and you have more space, two baths, a kitchen, a private lanai or balcony. If you book through an agency, THEY decide which unit to assign you. If you book direct from an owner via a website like vrbo.com YOU know in advance exactly what you are getting -- and it usually costs less because there's no middleman getting a commission.

In our area of Maui the value season runs from May to the middle of December; next highest rates are for the months of January and March. Highest rates are the month of February and Christmas/New Years. You will get a better rate if you stay in one place a full week. Some additional bargaining is possible for September and Thanksgiving and the first half of December. Travel will be less crowded when mainland children are in school. Airfares may go down somewhat then, too. Weather can be a factor at higher elevations and over the northern parts of Kauai and Oahu in the winter/spring. Early autumn can be quite hot -- worst on Big Island.

Cruises are a very inexpensive way to get a glimpse of several islands. Nobody claims these are deluxe cruises, so you have to be prepared for very average food and service. If you do a cruise, you can skip the expensive ship's excursions and just rent a car to do your own touring on each island.

California
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for Oahu
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8. Re: Best way to book multi-island trip??

I think that it can be very difficult to plan a trip to a place you have never been. OK, I've done it several times, but like some of the posters above, it's a bit of a game for me and I have had travel agent training (although I have a completely different career - budget analyst). My sister on the other hand ... much better to have someone else do the planning.

LCWombat, there is no right or wrong way. If you are hesitant to make your travel plans on-line yourself -- do find a travel agent. I would hate for you to have a bad experience in Hawaii! On your SECOND trip -- you might want to do the planning yourself. There is so much hype about saving money on-line, etc -- it's a turkey shoot. Bottom line, I think the prices are close to the same -- as everyone is offered the same deals and they change constantly. You can make yourself crazy chasing stuff down.

A travel agent would be able to answer your questions and should be there for you if you run into a problem. That's what they get paid for. Do your homework on what YOU might like first.

Alexandria, Virginia
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9. Re: Best way to book multi-island trip??

Thanks everyone.

Here's some data:

- I am not interested in a cruise - did the NCL cruise and was extermemly disappointed.

- This trip is about taking our daughter (21) and possibly god-son (17) to hawaii to see highlights. Sort of graduation present

- We are very comfortable making our own arrangements w/in the US

- Just looking for a "good deal". With 2 grown kids in tow, it's almost the same to get a roll away in 1 room as it is for 2 rooms.

- Looking for insight into more cost effective alternatives. Wondering if booking with all Sheraton prpoerties and using points to pay for a couple nights, or other such discount program.

California
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for Oahu
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10. Re: Best way to book multi-island trip??

Most Sheratons offer a free night with 5 -- or fifth night free. Of course, this policy changes with the seasons and the individual hotels -- but we have used it several times.

Using points is a good idea and the hotels often are generous with your upgrades.

I guess you need to weigh the advantages of Starwood vs the cost-effectiveness of the packages.