Planning a trip to Hawaï in 2020

Old Nov 9th, 2018, 07:08 AM
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Planning a trip to Hawaï in 2020

Hello there, we are two senior couples, planning a trip to Hawaï for the first time , in the winter of 2020. We are coming from Ontario, Canada. We have at least two weeks or more if needed to visit. I’ve been told, to visit Kauai and Maui and the big island. We want to fly , first to Los Angeles to visit family for two days and get rid of some jet lag. We were thinking of doing Airbnb in Hawaï, when possible, cause we can split on cost. Any ideas on a itinerary would be so appreciated. One couple are great with a camera so it’s important to find great places to photograph and being close to the ocean would be awesome. Thank you in advance for any information.
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Old Nov 10th, 2018, 12:41 AM
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No shortage of beautiful places to photograph - everywhere!!

On vacation rentals - make sure the place you are renting is legal, especially on Oahu. Just because they are on Airbnb, doesn't make them legally operating. By 2020, it's possible there could be legislation or a crackdown on illegal rentals and you might, very suddenly, find yourself without lodging. Not to scare you because there are many legal short term rental owners and you'll have no problem finding one, but ask the owner to be sure.

We have a rental and we have a state of Hawaii Tax ID number and transient accommodation tax number plus our property is located in a resort zone. If the owner can provide you with the tax numbers and property is in community zoned for short term lodging, they are operating legally.

Last edited by TJM_70; Nov 10th, 2018 at 12:43 AM.
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Old Nov 10th, 2018, 04:04 AM
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Thanks so much for the info on Airbnb. I’ve been studying on where we should go. Do you think three islands is too much?
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Old Nov 10th, 2018, 09:33 AM
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With two weeks, I do think three islands is too much. Spend some time reading about the various islands so you can make a decision that is best for you. If you want to visit three islands, extend your vacation to three weeks.
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Old Nov 10th, 2018, 09:42 AM
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We've been to Hawaii many times (it's a really easy trip from California) and in many configurations. The first time we went (1978), we visited 4 islands in 2 weeks. The last time (last month), we stayed in two places on Maui over 9 days, and we've done everything in between! My advice is that moving is a shlep, especially when you have to fly to the new location, so you at least want to have plenty of time. I think 6 days per island (including arrival day) would be the minimum I'd want if I were going to fly off to another island. Each change of island takes at least 1/2 a day (packing up, checking out, driving to airport, airport rigamarole, flight, renting car, driving to new hotel, checking in, unpacking), but it isn't the time as much as it is the trouble.
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Old Nov 10th, 2018, 01:21 PM
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Having lives in Hawaii for three years I think a LOT depends on what YOU think is interesting and important to see and do in terms of how much time on ANY island is "right."

You say you have been "told" to visit certain islands but you do not say why, just that you apparently agree. It would be helpful if you were willing to tell people whether or not you have done any research about those three and if they seem different enough to warrant a visit to each one.

It is easy to stay VERY close to the ocean on some islands and perhaps more difficult on others. Will you rent a car because that will potentially make a HUGE difference.
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Old Nov 10th, 2018, 01:39 PM
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Having been to all 3 of those islands (on separate trips) I agree with sticking to two islands, at least 5 days for Maui and Kauai although a full week is better, and a minimum of 7 days for Big Island, but 10 is better.
Agree with TJM about making sure any vacation rental is legal, there are a not that are illegal and besides the possibility of the rental being shut down there is also the problem of possible "stink eye" from the locals who are probably tired of strangers traipsing through their residential neighborhood at all hours. Ask for a TVR number.
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Old Nov 10th, 2018, 07:42 PM
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DH and I live in New Zealand. In 2014 we did three islands in 16 days. Five on Oahu, five on the Big Island and 6 on Maui. It is certainly doable. We had a fantastic time visiting all three places. Did a lot of the tourist stops.
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Old Nov 11th, 2018, 05:22 AM
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Thank you for all the info, we have received so far. I am researching the different Islands. Wow, they are all so beautiful! Not sure now , what islands, we should visit. We will rent a car so we can be mobile.and we are thinking of three weeks.
We want to see Oahu for sure to visit Pearl Habor, Waikiki, Honolulu, Diamond head hicking...so a few days there but not sure where to stay but thinking a hotel on the beach for this Island.
As far as other islands go, this is what I am looking for..., great beaches to walk, snorkeling, see turtles, kayaking, Zodiac boat tour to view the island from the water, Scenic views from mountain tops, view waterfalls, maybe see whales, sunsets and sunrises, small villages with great restaurants, quaint shops. Experience great Hawaiian traditions, luau...
We thought renting a beachfront condo somewhere, so we could cook our own meals sometimes. We will rent a car. So can you tell me, which Island, we should choose?
Anxious to visit such a spectacular paradise. Thanks in advance.
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Old Nov 12th, 2018, 08:49 AM
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Each island offers just about all you are looking for so far as the experiences you want. Yet, they are each different. It's part of what is so amazing about Hawaii. If you are going for three weeks, consider Oahu, Maui and Big Island.

Oahu is big city life, country and most of the iconic historic and cultural sites of both Hawaiian and American history. Maui is crazy beautiful and has oceans that come up to the edge of the roads for miles and miles. Both of these islands are fairly small for us mainlanders.

Hawaii Island (Big Island) is aptly named - much larger, geographically diverse and very geologically young. Stunningly diverse and beautiful. You'd likely want to move at least once to keep your driving to a minimum - a few days leeward and a few windward. You'll find nice beaches here but not as many as Oahu, Kauai or Maui. But, you'll not find an active volcano anywhere else nor can you reach the summit of some of the earth's largest land masses. The volcanic coast is rugged and hypnotic.
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Old Nov 12th, 2018, 11:19 AM
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I’d just switch out Kauai (my favorite) for Maui in TJM’s post. I think Kauai is much more beautiful/lush than Maui.
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Old Nov 12th, 2018, 11:58 AM
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Thanks so much for your time. Well appreciated.
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Old Nov 12th, 2018, 12:03 PM
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If we stayed in Kauai, where would you stay, and should we do the luau on that Island?
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Old Nov 12th, 2018, 12:06 PM
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Thanks and which of the three Islands, would you stay the longest, cause we have to consider traveling time from east Canada.
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Old Nov 12th, 2018, 12:49 PM
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Since you are going in the winter, I would recommend that you stay in the Poipu area on Kauai. There are plenty of condos to rent in the immediate area. You will want to take e a catamaran to the Napili Coast. You may also want to do some whale watching. Cheryl did ana amazing whale watching tour from the Poipu area last year on a zodiac Photos at https://cherylmarlandphotography.smugmug.com Click on Kauai and you'll have access to many years of photos.

As afar as a luau is concerned, there are a number on the island. I'm not a fan of Luaus, so haven't gone to one on Kauai.
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Old Nov 12th, 2018, 12:54 PM
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I would visit Oahu in a concentrated few days - less than 7 full days (not counting your arrival day - we are from east coast US and it's a long trip for you, too) and then split the remaining time between Kauai and Hawaii...it's important to plan time for doing nothing other than sitting by the sea and soaking it in. Your travel days flying between islands are mostly wasted days.

Something like this -

Arrive Oahu
Days 2 - 5 Oahu
Day 6 travel to Kauai
Week in Kauai at resort on beach
Some sightseeing, mostly relaxing on the beautiful, ridiculous beaches there (some infrastructure is damaged from flooding this year...should be up and running by 2020)

Day 13 travel to Big Island - Hilo or Kona
Days 14 - 20 exploring Big Island (more active touring, less beach time...BI usually involves more driving. Consider staying a few days in Kailua Kona and a few either Hamakua, Hilo, Puna or Kau)
Day 21 depart for home
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Old Nov 13th, 2018, 11:10 AM
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That sound lovely, where would you stay , on the beach, in Kauai or Maui depending which Island, we choose? In Oahu, do you know of a good place to stay, Thinking of a hotel there but on the beach, do you have ideas any ideas. Thanks for the info!
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Old Nov 13th, 2018, 11:15 AM
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If it was me - and it isn't - I'd stay on Waikiki on Oahu. It's very lively, and there are a number of hotels that are beach front - walk out the door and onto the sand.

On Kauai, I'd stay on Poipu beach. There are number of beachfront hotels there as well.
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Old Nov 13th, 2018, 03:12 PM
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Thanks so much, Kathie and TJM 70 for your ideas. It’s overwhelming to try and choose when you’ve never been there.
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Old Nov 14th, 2018, 05:20 PM
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I have to agree about Waikiki - it's fun and it's really thrilling, at least on your first trip, to walk out the hotel door and onto the beach. Over the last 10 years or so, it's become very high end, though...not to our tastes...as far as shopping and dining. But, for first trip, a great choice.
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