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.

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.

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?

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.

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.

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.

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.

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.

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.

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.

I’d just switch out Kauai (my favorite) for Maui in TJM’s post. I think Kauai is much more beautiful/lush than Maui.

Thanks so much for your time. Well appreciated.

If we stayed in Kauai, where would you stay, and should we do the luau on that Island?

Thanks and which of the three Islands, would you stay the longest, cause we have to consider traveling time from east Canada.

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.

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 :-(

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!

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.

Thanks so much, Kathie and TJM 70 for your ideas. It’s overwhelming to try and choose when you’ve never been there.

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.

Thanks to all.Really appreciate your time given. I think I can put an amazing itinerary together now. Merry Christmas to all!

My DH and I have been 'wintering' in Hawaii for thirty years. We've stayed Poipu, Kauai; Waikiki on Oahu; the Kohala Coast of the Big Island of Hawaii; and now we stay in South Maui. Winter brings cool, wet, windy weather and rough ocean conditions to the northern parts of Kauai and Oahu. (World surfing championships are held north shore Oahu in winter.) You can stay south and tour north, choosing a 'best weather' day. With just two weeks, though, I would regretfully leave Kauai off the list for this trip. Winter IS a good time to stay where the whales are most numerous: Off Maui, and to a lesser extent, off Big Island.

Plan some nights Honolulu/Waikiki. You can skip a rental car within the city, hiring one for a day to drive around the coast. Do 'historic' and 'city' here.

One way to allocate time is to think what you want to see and do on each island. They all have some of the same 'typically tropical' scenery and beaches, but each has some unique parts -- or 'best of' something. Get maps. Discover how long it will take to accomplish your 'wish list', then locate a convenient lodging on each island from which to tour.

Oahu is very developed. Maui is a bit less less developed. Big Island is relatively undeveloped -- and much, much larger than all the others put together. Visitors usually stay NW on Big Island plus a night or two SE (Volcano and Hilo). Fly KOA and ITO to avoid crossing the island twice.

A hotel/condo combination is nice -- more economical as well as more relaxing over 14 nights away from home. YOU will have to select your islands, but we can help with suggestions once we know your needs and lodging budget. You need flights to/from Hawaii, interisland flights, rental cars, and lodging.

This may seem 'far away', but people do book a year in advance for winter, and you have some research to do. I like "Hawaii For Dummies" as a quick read about each island's personality. I do NOT recommend the touring advice on the following site (dangerous, sometimes illegal tips), but the lodging portion is useful: www.hawaiirevealed.com

You can enjoy two or three islands in two weeks, but not each needs the same amount of time. Day One is largely adjusting to the time change. Each transit between islands eats 4 - 5 daylight hours, door to door. All the islands have *traffic* today. Condos are generally 'best buys' for minimum one-week stays. We've seen more problems with airbnb than VRBO, but neither outfit vets for legal lodgings. There are also good rental agencies local to each island.

Thanks so much, I’ve been looking at flights from home to Honolulu...will spend at least 4 nights there on Oahu. Found a hotel in Waikiki that I like, next to a car rental, close to shopping, restaurants and beach for some down time. Want to hike to Diamond head, visit Pearl Harbor, snorkeling , take in a Luau ( maybe keep that for Maui. Fly to Maui for a week, not sure what area yet. Big Island sounds interesting also. Still doing research. Appreciate your help.

Here's where 'best of' comes in. You can 'do it all' on almost any island, but you don't have months in the state. You need to budget your time and activities. Just comparing Oahu and Maui:

Oahu has beaches and good sea life, but it's more crowded, with more traffic. Maui has many easy-access beaches with good sea life where you can walk up or park free to swim or snorkel. It has raft and cat expeditions to Lanai and Molokini -- and along its own shores. Waikiki Beach is packed with tourists. Sand erodes badly. Rain runoff creates 'brown water (other islands, too, but this is a 'city' beach).

The Mormon's Polynesian Cultural Center on Oahu has an excellent theatrical production. The luau on Maui are lower key. Two highly rated stand-alone luau are in Lahaina Town, and two Wailea hotels host popular luau. There's less hassle getting TO places on Maui. (Well, Kaanapali is pretty buzzy.)

Honolulu has Pearl Harbor exhibits, the Iolani Palace, the Bishop Museum, iconic Waikiki, and a wide variety of ethnic cuisine. It has shops and nightlife. I'm content to view Diamond Head, but yes, you can walk or take the bus there and climb up! (Morning is cool.)

You can drive the pretty coast of Oahu easily in a day. You'd want several different days to see *some* of Maui's major sights: Road to Hana, Haleakala and Upcountry, West Maui, South Maui -- a week is too short for everything -- too much 'windshield time'. Maui does not have much nightlife or as wide a range of 'man-made'. (Kauai and Big Island are slower still.)

Ok thanks , so I think we will only do Oahu and Maui so I’ve map out our trip in Oahu 4,
or 5 days...Got that done. Now, Maui ...where should we fly into and where do you suggest we stay, seeming it’s February . Want to rent a two bedroom condo , on the beach for a week and we will rent a car to get around. Any ideas would be so appreciated, thanks.

This is the official state visitors' site: https://www.gohawaii.com/

There is also a site for each island: https://www.gohawaii.com/islands/maui

There's also printed guides but not sure if they're available outside US.

Have a great trip:)

Looks like ten nights for Maui.

South Maui is more convenient to the rest of the island. OGG is in Kahului, which is also where you start for Haleakala and Upcountry, Road to Hana, Iao Valley, Paia Town. We drive South Kihei - Kahului in 25 minutes mid-day. Lahaina is 45 minutes north -- unless there's a problem on West Maui's sole access, a 2-lane road between Maalaea and Lahaina Town. Lahaina - Kahului is close to an hour; another 20 minutes from Kapalua.

You could move, exploring West Maui from within it. JHM is in Kapalua. It's more expensive to rent a car at one airport and return it to the other.

I wouldn't plan an overnight in windward Hana in winter. You can drive it in 12 hours, making most stops; there are tours.

Some more affordable condos on Maui are in Kihei and Maalaea in South Maui, and in Kahana and Honokowai in West Maui. These are outside of the three 'tourist destination developments' of Kaanapali, Kapalua and Wailea.

All Hawaiian beaches are open to the public. With a car, you can sample more than 'the one out front'. True *beachfront* is expensive; not every place 'on sand' has good swimming or snorkeling. You will want air conditioning. Because condos are owned by individuals -- and there are few new complexes on Maui -- you need to be selective. Ask who will help you with any 'surprises'. I prefer low-rise, low-density condo complexes, but there is a case for taller buildings during whale season. Budget will determine some of where you stay.

Thanks again, now the more I research, the more I would like to do Kauai also... we will have 20 days in all. I know that I want to spend 4 nights in Oahu... we will fly home from there also so maybe two nights there before visiting other islands and 2 nights at end of our trip to relax a little before the long trip home. I see that Kauai is north of Oahu and Maui, south and then there’s the big island ...
dont want to be flying steady . Will I regret not visiting the big island?

It's your decision, you could spend 20 days split between two islands, or visit Oahu for 4 nights and the balance between Maui and Kauai. Save Big Island for another trip, lovely as it is.
My personal inclination, since Oahu and Maui are the two "busiest" and most visited, would be to spend time in one busier island and one more laid back and less visited. Have a great trip.

I wouldn't split Oahu. Because that takes time and hassle checking in and out of hotels twice. IF you need to fly thru Honolulu both directions, I'd try to make it so one of those times I just stayed at the airport and transferred to the next island directly. Just a thought.

Will I regret not visiting the big island?

I haven't yet had that regret, but I've only been to Hawaii a half-dozen times (once to Maui the rest on Oahu).

Don't worry about which island is north or south or whatever, since you're going to the airport anyway, that part really doesn't matter.

I personally think 20 days will seem very short if you try to go to every one of the islands! And it will feel like "flying steady".

Stay Oahu *either* first or last. Do not trek away from HNL and back twice. You may want to stay Oahu first to avoid a very long travel day at the end of your trip. It can be nice to do the buzzy city first, then gear down on a slower island. (Maui is slow-ER; not as slow as the very spread out Big Island or Kauai.)

We've discussed Kauai in winter. The gorgeous north will be wet and overcast, with rough oceans. Tours on the ocean and in the air often cancel or are unpleasantly rough. The entire northernmost portion of the island still has road closures today due to LAST winter's floods. Poipu may have sun, but is not the lush (RAINY) part of Kauai.

You have to decide how much time you're comfortable wasting in interisland travel. You lose 4 - 5 daylight hours, door to door, each time.

Have you made your list of see/do for each island under consideration?

You say you have made some choices regarding Oahu. You might want to run those past us for comment.

IF you want Big Island, and IF you want to stay both sides, give it a week-plus and fly via both KOA and ITO. You cold give Maui one week (in one location) then short Honolulu/Waikiki -- at ONE end of the trip. This limits interisland flights to three.

What are your best flight options round trip Home to HNL?

Just got back from 12 days in Kauai and Maui. If you are going to visit Kauai in the winter, you may get rain. Less likely in Poipu.
Our only rain occurred in Kauai. But we stayed in Poipu and avoided most of the showers on the rest of the island. You might be able to check the forecast and take day trips up north.
For Maui, I am also a fan of keeping a base in Kihei. We like the southern beaches -- there seems to be enough to go around and we've found good snorkeling there, too. We drive to Lahaina for dinner and the strolling down Front Street. You can also take a day trip upcountry and visit Haleakela with a bit less driving than staying in west Maui. It's really just up to you.

Our flight from Ontario, Canada to Honolulu is cheaper priced if we include return flights.
Starting in Oahu
Arrive late afternoon at our hotel, one block from Waikiki beach, so that day is gone.
What we want to do in Oahu...
1.Some nightlife
2.Beach time for first day
3.Pearl Harbor
4.Diamond head hike
5.Polynesian culture centre for luau
6.Halona blowhole lookout
7.Iolani Palace
8.Bishop museum
9.Drive the coast.
Anything else that is a “must see” on Oahu?
How many nights on Oahu to visit those spots.
Seeing waterfalls to photograph?
Snorkeling and kayaking?
We wait for this on another island?
Will buy a Go Oahu card, 3 day pass?
Also a Hop on, hop off, 3 or 4 day bus pass?
That will bring us to those places I mentioned, so won’t need a car except for one day to drive the coast.

Next Island, Kauai
I have a good list to do, for this island.
Haven’t found a place to stay yet.
But thinking central...closer to Lihue.
Checked out condos in Poipu ...
Still looking...

Found a 2 bedroom beachfront condo in Maui that we really like, close to Lahaina.
Have a list to do, for this island also.
We will rent a car on both Maui and Kauai.
Thinking of a week on each island.
We will fly from Kauai to Maui , then back to Oahu to catch our plane home .��

Sounds like you have your plans well under control. I just want to add that you mentioned you are going in the winter. I would personally not go around the Christmas or New Years holiday (unless that is when you prefer to go) as all accommodations will be at best doubled what you'd pay in November for example.

Since you will have a car I'd drive to the North Shore of Oahu (Pipeline, Waimea Bay, Sunset Beach) which have the iconic, world famous surfing beaches. It is more rural and old school Hawaiian surfing culture. You probably dont want to swim in the 15 to 20 foot waves, but it is fun to watch the surfers.

If you guys like snorkeling I would also recommend Hanauma Bay in Oahu. But you may need advance reservations and go as early as possible. It is (I believe) a state park.

Thanks to everyone for all the info. We will definitely check out Hanauma Bay and surrounding areas.

Not Lihue or Kapaa. (Congested, urban; no swimming beaches). Not northern Kauai in winter. Floods there are annual events. Last winter's was just worse. Constant rescues of dumb tourists from flash floods and muddy trails.

I only know of one *beachfront* condo complex in Poipu, Kiahuhna Plantations -- a few units are beachfront; most stretch back to a road. Old construction. Since all Hawaiian beaches are *public places*, beachfront has some drawbacks, too.

Snorkel Maui over congested Oahu. Free, lots of easy-access beaches w/good sea life -- not AS good as Big Island, but easier access.

The Marriott Waiohai two doors down is configured similarly - there are actual beachfront units, but the buildings are around in a horseshoe shape. The property is very nice (the units are typical Marriott Hawaii condos, the hallways are a little clinical, but the grounds are gorgeous and the location is great). All the units are two bedroom.

While the majority of the east shore beaches are not swimmable, there are a few exceptions such as part of Kealia, Lydgate, and Kalapaki Beach in front of the Marriott. I am not a fan but the condos there are a lot cheaper than many in Poipu.
You can also normally get into the water at Anini Beach and Hanalei Beach on the North Shore and contrary to Sue's repeated belief, it does not rain all day every day up there (although the odds are a bit higher).

Thanks, it so helps when we have names of places to check out��