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Hawaii Wedding - Help with Itinerary

Old Mar 29th, 2016, 11:25 AM
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Hawaii Wedding - Help with Itinerary

My wife and I will be heading to Hawaii in mid-October for a wedding and we figure we'd stay there for a vacation too. We're not too sure how much time to take off yet or what to see at all and wanted to get your guys' feedback.

Few notes:
1. We're early 30's
2. We like to do outdoorsy stuff, while relaxing on the beach is nice, we'd like to see cool things
3. We're not foodies, but we like good food but don't want to spend too much on food either
4. Excluding airfare, we were thinking $3-5k in budget, we'll probably use AirBNB for lodging.
5. Wedding is in Maui, so we'll be there for the first part

I honestly have no idea about what to do in Hawaii. The only thing I heard is that we should try to visit 2-3 islands depending length of trip.

Few questions:
1. What's a good itinerary and length of visit range? (Anywhere from 7-14 is okay)
We're probably going to book using Frequent Flyer miles, so should we do different airports arriving/departing?
2. Does Hawaii have any "Must do's?"
3. In terms of stuff to do, is Hawaii anything like New Zealand?
4. Any other tips/notes

Thanks in advance!
cadd is offline  
Old Mar 29th, 2016, 07:03 PM
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Wow. You are asking for a lot, with only a few words.
Many books and travel guides have been written on all this, as well as there being a wealth of internet info, and I think you are going to have to research some of the basics, before you can get the most value from Fodorites, when fine tuning things.
But I'll offer a bit of advice.
With you being first timers to Hawaii, and going to Maui, I'd also take in Oahu. Lots of history and culture there, and great scenery, too. And you are going to have a bit of a struggle, I suggest, keeping to your budget, but there are lots of ways to keep the costs down. Going to no more than 2 islands will help. For example, fly from home to one island, and back home from the other, saves one connecting flight.
For food, you will probably have to stay out of hotels, and eat where the locals eat. Unless you can get a good deal on a hotel that offers free buffet breakfasts.
Must do's are quite subjective, given that there is so much variety. For me, this would include a good luau, a few hikes, a whale watch ride, and soak in some of the history and culture.
And spend some time away from fellow tourists, sharing the aloha spirit with local people!
In my view, it's pretty hard to go wrong, vacationing in Hawaii.
kanunu is offline  
Old Mar 30th, 2016, 07:37 AM
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I would split the trip into a week on each island: Maui and then another.
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Old Mar 30th, 2016, 09:39 AM
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I don't know who told you to visit 2-3 islands. I've ever only gone to one, each trip.

Airbnb is NOT the way to go in Hawaii.

Yes each island has a list of "must dos" if you mean interesting things to see.

Hawaii is tricky to plan a first trip exactly because of the different islands, each one unique. I highly recommend getting a couple hard-copy guidebooks from the library and reading about each one (as far as you having no idea what to do).

For 7 days, I would just stay in Maui after the wedding. If you choose 10-14 days I would add ONE other island... Oahu, Kauai, or Big Island.
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Old Mar 30th, 2016, 10:56 AM
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Can you elaborate more on AirBNB and Hawaii and why it's not the way to go?
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Old Mar 30th, 2016, 11:32 AM
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Good question. I usually use vrbo and then vet the name of the property, owner and management company. I'm personally not a fan of Airbnb, but that is because of their corporate and legal handling of local laws and dismissing their responsibility of advertising illegal rentals in some areas of the world. VRBO has also taken a dark turn so their days are numbered other then as a search engine.
And why would suze recommend two islands she has not been to? I'm sure she means well.
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Old Mar 30th, 2016, 11:44 AM
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If you only have a week, stick to Maui, if 14 days then you could go to another island, depends which one you want to go to.
Hawaii has a huge problem with unlicensed vacation rentals which is why AirBnB is not a good idea. A legal rental should have a TVR number (not to be confused with a Tax ID). Hawaii is starting to crack down, and for example recently shut down a number of illegal rentals in Kailua on Oahu for example. It would be a shame to arrive to a prepaid rental only to find it is closed and you have to scramble to find a new place to stay at likely high rates. Book directly with either an owner or a reputable property management company if booking a condo.
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Old Mar 30th, 2016, 12:19 PM
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Hawaii is in the tropics, whereas New Zealand isn't, so IMO not really comparable in terms of things to do.

The only "must dos" on our first tropical island vacation was to lay on a beach, do some snorkeling, and have some drinks with little umbrellas in them. Although we've been on about 20 tropical island vacations since, that list hasn't changed. YMMV.

With your budget, I'd suggest 10 nights: 7 on Maui, and 3 on Oahu. Choose a condo for Maui - we usually book thru VRBO - and a Waikiki hotel for Oahu. Don't forget to factor in that you'll need a car the entire time on Maui.
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Old Mar 30th, 2016, 12:31 PM
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<Can you elaborate more on AirBNB and Hawaii and why it's not the way to go?>

You need to do some research on illegal rentals in Hawaii.
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Old Mar 30th, 2016, 12:37 PM
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<And why would suze recommend two islands she has not been to? I'm sure she means well.>

Because they are wonderful places to visit?

Because I would never suggest people should only go to the places I have been myself?

I named every major island as one to be considered, why is that a problem?
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Old Mar 30th, 2016, 04:30 PM
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Personally, you will most likely fly through Oahu, so I would spend a few nights there. Being young, there is nightlife and history and other things to do. Then, fly to Maui for the week. I have never used Air bandB, but I like hotels. I am sure you can get condos for the weekly rate in Maui, and hotel it on Oahu.
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Old Mar 30th, 2016, 04:37 PM
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I also recommend getting a book on the different islands to see which ones appeal to you the most. If you are traveling from the east coast, spend two weeks and see two islands.
Oahu has Honolulu which is a city on a beach but also lots of great things to do and see both in and out of Honolulu. Kauai is a beautiful place with more dramatic scenery. The Big island has7 different climates and was such a unique looking place to us.
Maui, I haven't been to in years, but it had everything from golf, beach, mountains, etc.. All the islands have their
own unique style. So, get a book, but I recommend if you are coming from the east, take a minimum of 10 days!!
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Old Mar 30th, 2016, 05:38 PM
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Agree. Take at least 10 days.
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Old Mar 30th, 2016, 11:49 PM
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Especially for first-time visitors, I recommend reading some travel guides ("Hawaii Revealed" etc) to get an overview of activities available on each island, and let that decide both where and how long you stay. Your post doesn't give much specific info, so you're basically asking other people to make your interest list for you.

From what you wrote, imo either Maui or Kauai would be my first choices, with the second of those taking priority if scenery is more important than infrastructure (restaurants, shopping etc). Your budget numbers are right in line with what we've been paying for two-week trips to Hawaii for the last 35 years: $4K-5K out the door for two people, if hotel, air etc fares are adequately shopped, and $5K-6K if they're not. This is with an upper-end hotel and flying from CA, your hotel and airfares may be substantially different.
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Old Apr 1st, 2016, 08:53 AM
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I agree with the others that if you are only going for seven days, then I'd probably just stick to Maui. If 10 days, you HAVE to do two islands. If 14 days, three islands is definitely not too much (I've done that)...but it will be more of a logistical challenge (connecting flights, car rentals). My first pick other than Maui would be Kauai. Squeezing in the Big Island would be worth it on a longer trip.

Maui: West and south for beaches/resorts. Lahaina is cute but touristy...you'll get tired of it quickly. Paia is a great little town (we loved staying at the Paia Inn); Mama's Fish House is great (very expensive but a once in a lifetime dining experience); The Road to Hana (and the stops along the way)....highly recommended but will take an entire day.

Kauai (my favorite island): I like the north shore best (Hanalei and Ha'ena are special places)....but lodging here is tougher to find than in Poipu. Princeville is condo vanilla but has the most hotels. If you can swing it....you HAVE to stay at (http://www.halemakaicottages.com)...cabin 3 first, then cabin 2 next. In Hanalei....have an early dinner at the Hanalei Dolphin then head over to Ke'e Beach to watch the sunset; Kalalua Trail is a must (you have to apply for a permit months in advance if you want to do the whole trail)...but the hike to the top of the hill overlooking Ke'e is quick and easy if you can't get a permit. On south shore....DEFINITELY take Captain Andy's sunset cruise along the Napali Coast (need to book months in advance and not sure if/when they shut down for the season)....will be the highlight of your entire vacation. The Grand Hyatt in Poipu (can be very expensive but rates vary wildly throughout the year) is highly recommended. The view from the lobby is one of the most amazing things I've ever seen....and their pools/lagoons are awesome. My brother enjoyed his stay at the Sheraton (cheaper) in Poipu. Waimea Canyon is also pretty cool. I've heard that Waimea Plantation Cottages (much cheaper) are cool...but they are out there. Avoid Lihue (ugly but has shopping essentials). Kapaa is a cool/funky town on windward side....worth a quick stop and might be a good central place to stay and/or find a hotel if you are on a budget.

Big Island: Love the Big Island. Has a completely different look and feel than the other islands. Don't be put off by the stark landscape when you first land. It's a special place. Kona has a Key West vibe imo. Loved Da Poke Shack for quick/awesome eats. Best beaches on the island are north of the Kona airport (esp. Kohala). I love Hilo but it's probably not worth the time to visit on a time-constrained vacation (although I could easily live over there). You HAVE to visit Volcano National Park....and is the one thing that you just can't do on any of the other islands.

Oahu: I wouldn't pick Oahu over the above three for a vacation. It has nice beaches (windward side) but the whole Oahu experience just doesn't feel "special" to me. But it's worth it just to say you've been to Waikiki and Pearl Harbor. If you stay in Waikiki...we LOVED the Rainbow tower at Hilton Hawaiian Village (see if you can get one of the corner rooms with a double lanai that looks toward Diamond Head) You can thank me later on that one. North shore surf town of Haleiwa is cool. Matsumoto Shave Ice is very touristy but they do have great t-shirts. Personally, I wouldn't spend the time driving to the north shore unless the big waves are rolling....super fun to watch.

Have fun! You'll have a blast no matter where you go.
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Old Apr 1st, 2016, 10:07 AM
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You didn't say where you are coming from. We travel to hawaii from Ny so we always stay 2 weeks. 14 days and 2 islands. Love Oahu for food and activities. Love the BI for kick back time and adventures.
Oahu- Sounds like you would love climbing Diamond Head, traveling to the North Shore for beaches and shrimp plate lunches. Snorkeling Hanauma Bay, walking through Waimea Valley. and a catamaran ride at Waikiki Beach.
BI- Volcanoes National Park, Mauna Kea summit drive.

Ps- Waikiki Beach is my all time favorite beach but it is not a laid back, low key place. It is busy with activity but the most beautiful view of Diamond Head is all yours. Soft rolling waves, lots of ocean to play in.
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Old Apr 1st, 2016, 11:39 AM
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Actually Captain Andy's and the other boats that leave from the west shore of Kauai do not shut down for the season, it is the tours that go out of the North Shore which are seasonal, usually from sometime in October until April, or occasionally in March. They do cancel from time to time in winter if the seas are too rough but that is a day to day thing.
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