Should I request help from a travel agent? (We have AAA)
How long should I plan the trip for? (1 or 2 weeks? 1 seems a bit short if I am gonna be hopping islands)
How much money would it cost total? I plan on buying tickets way in advance and staying away from peak summer season. Maybe fall or winter.
Should activities like parasailing, hiking, etc. be planned way in advance… or planned on the spot in Hawaii.
Or is an interisland trip even worth it? I’ve been to Oahu before and it was alright. It seems like a “partying” type of place and I don’t know if its worth going back for my honey moon.
Any ideas? Thanks in advance!

I suggest a 2-week trip to Hawaii, and avoiding Oahu since you have already been there. Don’t try to cover more than 3 islands in 2 weeks. I’d recommend 8 nights on Maui, 3 on Kauai, and 3 on the Big Island of Hawaii. (If you only have one week for your trip, I’d spend it all on Maui.) Remember that each time you move from one island to another, you waste a whole day of your vacation (packing up on the first island, drive to airport, return rental car, airport security, wait for flight, fly, get luggage, get new rental car, check in and unpack at new hotel).
You can plan it yourself with info from great websites like
But if you want to use a travel agent, be sure it is one who has been to Hawaii many times and really knows Hawaii, or one who lives in Hawaii.
Summer and winter are both high expensive seasons. Only spring and fall are cheaper off-seasons in Hawaii.
Activities can be planned after you arrive.
Cost varies tremendously, depending on how fancy hotels you pick and how fancy restaurants you eat at and how many paid activities you do.

3 Responses

  1. The big difference between Oahu and Maui, for example, is that Maui is slightly larger than Oahu in area and has about 1/7 the population. At the same time, Maui has just about as many things for tourists to do, with a much easier commute between places. Maui is the second largest island both in terms of area and population, so all of the other islands are more rural, with less retail, for example.
    Activities like hiking and zip lines are available on Maui year round. The humpback whales come to Maui waters beginning about December to breed, calve, nurse their young, and just hang out (they actually spend a good bit of their time here just floating still underwater). While they’re here, there are plenty of whale watching cruises to see them slap tails and fins and occasionally jump out of the water. However, during this time, parasailing doesn’t happen because it’s a danger to the whales. On the other hand, windsurfing and kite surfing activities continue.
    In the winter, monster waves may pound north facing shores, while the ocean will be “like glass” on south facing shores–good for snorkeling and swimming. In the summer, smaller waves will be on south facing shores, and snorkelers may head to north-facing beaches.
    Excellent advice from the other person about interisland trips. If you did go through a travel agency, Pleasant Island Holidays is one that many local folks use when they travel between islands. Most of the time, though, we just go to the websites of the airlines to buy our tickets.
    Many local folks avoid Go! because of the role that subsidiary of Mesa Airlines played in the bankruptcy and closing of local favorite Aloha Airlines. When we travel between islands, we use Hawaiian if we want to travel on big jets with many flights to choose from on any given day. For travel to Molokai and Lanai, we have to rely on Island Air with it’s Dash-8 turboprops the size of school buses, or smaller airlines that fly 9-seaters.
    The 9-seaters are really good for taking photographs (the windows are bigger and less scratched up, the planes fly closer to cities and mountains), but I’d advise you to wait until after you fly on one before eating a meal.
    The only ferry routes currently operating in Hawaii are between Lahaina, Maui and Kaunakakai, Molokai; Lahaina and Manele Bay, Lanai; and Maalaea, Maui and Manele Bay, Lanai. The ferry crossings to Lanai are smoother, cheaper, and faster, with better views for most seats. The one to Molokai may be two hours, with the middle hour in 16 foot swells in winter. It’s getting harder to get to Molokai. Jets quit flying there in 2004, and there’s only one hotel on the island now.

  2. Hiking does not need reservations, of course. You just drive to the trailhead and go. I don’t know about parasailing. If you have flexibility of a few days, I’d imagine you wouldn’t need reservations.
    If this is your honeymoon, I’d recommend getting all your accomodations and connecting flights in advance. You’ll have other things to do when you go, unless you two enjoy the excitement of adapting plans on the fly.
    Some things, such as biking down the volcano Haleakala, do not run every day, so it would be good to schedule that in advance.
    I’m originally from Hawaii, and we hike a lot when we go back. If you want suggestions, just email me and say which island.
    Any place away from Honolulu is going to be quieter, of course. Lahaina (Maui) and Kailua-Kona (on the Big Island) are also kind of built-up, in my opinion equal today to what Waikiki was a few decades ago.

  3. we just did that (in part at least). we only stayed 8 days– a second week would have been ideal.
    there are lots of similarities between islands and (respectful here) differences as well. they all are nice and worthy of your time.
    our solution was to island hop without changing hotels every two days. the solution? to stay on a cruise ship and changes ports every couple of days. check our Pride of America by NCL. we loved it. we got lots of shore excusing time and some on board relaxation as well.
    there are tons of things to do in H. adventure is your friend there. beaches are great; but we liked the jungle hikes even more. swimming in waterfalls, jumping from cliffs, eating fruit along the hiking trails. those were great experiences. the snorkeling was outstanding as well — especially near Kona.
    see the lava flow at night! we saw it from the water (on ship) and it was spectacular.
    we did a wonderful luau at Kauai and felt that we will stay there much longer on our next trip over. I liked the tourist things in Oahu; but enjoyed the drive to north shore and along the Eastern and southern coastline even more.
    the cost of the ship is altogether different than the cost of a nice hotel. I would recommend shopping for deals. I think you can negotiate well this year. enjoy. aloha.

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