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Visiting Hawaii

sam_gordon

DIS Veteran
Joined
Jun 26, 2010
OK, thinking WAY ahead... summer of 2023. So for the sake of this planning, I'm going to assume all Covid restrictions have expired.

DW & I will be celebrating our 30th anniversary in June of '23. We have a tentative plan to fly to Vegas, spend a couple of days there (DW has never been and my aunt lives there), rent a car and drive to LA, spend a couple of days there (I've never been), then fly to Hawaii for a week before flying home. Here are my questions...

1) Do you stay in one hotel/resort/condo in Hawaii and travel to/from other islands, or "island hop" every day or so? Or just stay on one island?
2) Do you need to arrange inter island transportation far in advance, or something you can do day of or day before?
3) Is doing the "Pride of America" cruise around the islands the easiest?
4) Any island airport easier to get into from LAX or easier to get out of (probably to Atlanta, Detroit, or Minneapolis are the normal connection sites from our airport)? Maybe better to fly into one, then home on another?

Yes, we're in the very early planning stages, but I'm trying to come up with ideas.

TIA
 
If you've only got a week, I would stick to one island. We do like to plan our flights out, either to or from the primary island (we like Maui), to go through Oahu because I like part of a day to go to Pearl Harbor and Waikiki Beach. I'm personally not a huge fan of Oahu, so flying in the morning we go home and spending the day there before a red eye flight home usually works for us.

I have friends who have done the cruise and really liked it, but I prefer to spend the whole time on one island (two islands on one trip when we spent 12 days in Hawaii).
 
OK, thinking WAY ahead... summer of 2023. So for the sake of this planning, I'm going to assume all Covid restrictions have expired.

DW & I will be celebrating our 30th anniversary in June of '23. We have a tentative plan to fly to Vegas, spend a couple of days there (DW has never been and my aunt lives there), rent a car and drive to LA, spend a couple of days there (I've never been), then fly to Hawaii for a week before flying home. Here are my questions...

1) Do you stay in one hotel/resort/condo in Hawaii and travel to/from other islands, or "island hop" every day or so? Or just stay on one island?
2) Do you need to arrange inter island transportation far in advance, or something you can do day of or day before?
3) Is doing the "Pride of America" cruise around the islands the easiest?
4) Any island airport easier to get into from LAX or easier to get out of (probably to Atlanta, Detroit, or Minneapolis are the normal connection sites from our airport)? Maybe better to fly into one, then home on another?

Yes, we're in the very early planning stages, but I'm trying to come up with ideas.

TIA

If you fly from island to island, you waste a lot of time checking into/out of hotels and waiting around the airport. I would concentrate on one island but it's hard to choose.

We've done the Pride of America cruise and while it's nice to see several islands, the ship is run by American labor, and sorry, but the staff is lazy, and the food was lousy. worst cruise we've ever been on (out of 27 cruises.) We've also cruised Hawaii with Disney -- much better service, but it's sure pricey.
 
There is no such thing as "island hopping" in Hawaii. With checking in, TSA, flight, and picking up rental car, the whole process takes at least 3 hours for one flight. That's not counting driving to and from the airport or packing and checking in or out of accommodations if you are changing accommodations. Even in summer, the maximum amount of daylight that you have is about 13 hours.

Get a good guidebook, like Lonely Planet or Hawaii for Dummies. Do not get the "Revealed" series. You have time for one island only. Choose your island based on what you want to do. You can fly into any of the 4 major islands from LAX.

Do not wait until the day before to book interisland flights if you choose to fly interisland. Flight prices only go up, not down.
 


1) Do you stay in one hotel/resort/condo in Hawaii and travel to/from other islands, or "island hop" every day or so? Or just stay on one island?
For one week, I would pick one island. I recommend Oahu, and I'd spend half the week in Wakiki (highly recommend the Moana Surfrider) and half on the North Shore (Turtle Bay resort is wonderful, or there are a small number of legal AirBnBs to rent). Parking is expensive at resorts downtown; I'd only rent a car for the North Shore portion of the trip.
The area Aulani is in is beautiful but not worth going out of your way for to see, especially with only a week.

2) Do you need to arrange inter island transportation far in advance, or something you can do day of or day before?

Again, I wouldn't recommend visiting multiple islands with such a short period of time. Flights are cheapest when booked in advance, but depending on time of year, it's possible to book last-minute.

3) Is doing the "Pride of America" cruise around the islands the easiest?

I haven't heard great things about the ship itself and a mix of positive/negative about the experience itself.

4) Any island airport easier to get into from LAX or easier to get out of (probably to Atlanta, Detroit, or Minneapolis are the normal connection sites from our airport)? Maybe better to fly into one, then home on another?

Lots of flights from Delta (which I can see is your typical airline by your connection sites!) into and out of Oahu.
 
We are planning our third trip to Hawaii.

First trip to Hawaii was Oahu (I was there for work for 2 weeks) so we flew to BI for a weekend. Not a big deal at the time.

Second trip was 17 days over Christmas and New Year's. We did Maui, Kauai and finished in Oahu. Of course it took time to fly from island to island but we scheduled really early or really late flights so I really didn't think we missed out on too much Hawaii time.

This time we will be spending our entire 14 night vacation on Maui, but we will be flying to Molokai for 2 days and taking a day trip to Lanai.

I would never consider the interisland cruise unless it is a "taste of Hawai'i" kinda thing to plan for a future longer trip to a specific island or islands.

If I were you I'd look at what all of the islands have to offer and decide which most interests you and stay there. The islands are so different. Oahu is more city and urban. Kauai is a beautiful Garden island (with lots of chickens). Maui is a combo of Kauai and Oahu. No big city but more urban than Kauai. And the Big Island has a volcano! Since you have only one week I would not switch islands.

Personally, I'd skip the few days in Vegas and add more time to Hawaii so you could possibly see two islands.
 
Personally, I would not combine a Hawaii trip with a Vegas/drive to LA trip. There are way too many things to do and see in Hawaii that can't be done on the Mainland so I would just concentrate on the Hawaii part. It would probably also be cheaper just concentrating on Hawaii if you figure in money spent in Vegas alone plus car rental and airfare. Keep in mind rental car companies do charge a fee for different drop-off locations plus driving and dropping off in another state will increase the price.

1) Do you stay in one hotel/resort/condo in Hawaii and travel to/from other islands, or "island hop" every day or so? Or just stay on one island? I would not use one location to use as a base as I island hopped. Travel to and from the airport plus flight times would eat up a good portion of your day, even if you took the first and last flights of the day. On our honeymoon we did island hop, spending 3 nights at each Oahu, Kauai, and then Maui. We felt rushed travel days but it was nice to get a "taste" of each of these islands.
2) Do you need to arrange inter island transportation far in advance, or something you can do day of or day before? As you would be flying to each island, yes you do need to arrange airfare just as you would for any trip you fly on. Can you book the same day? Yes, but it will be more expensive and you won't get prime flight times.
3) Is doing the "Pride of America" cruise around the islands the easiest? Once again, you would only have a day on each island so you would only get a taste of what that island has to offer. Also, taking an excursion from a cruise ship really limits what you really see of the island in the amount of time you have each day.

4) Any island airport easier to get into from LAX or easier to get out of (probably to Atlanta, Detroit, or Minneapolis are the normal connection sites from our airport)? Maybe better to fly into one, then home on another? Depending on the time of year you go direct flights may not be an option, even in early summer. What we do is keep an eye out for historical flight information and plan around that. Kauai has a smaller airport and does not always offer direct flights. You almost always have to fly from Kauai to Oahu before flying back to the mainland.

We usually visit Hawaii every other year. We vary what islands we stay at. Sometimes we island hop, other times, like as I type this in Oahu, we don't. Each island is different in scenery, activities, and daily life.

If you have never been to Hawaii and this is a "once in a lifetime" trip, I would definitely spend a few nights in Oahu so you can see Pearl Harbor (don't forget visiting the Missouri next door!), Waikiki, and the North Shore. Stay in Waikiki and don't rent a car except maybe for a day for the North Shore and other sites as you drive there.

When we go to the Big Island we stay a few nights on the Hilo side so we can visit Volcano National Park. We then drive around the southside of the island to the Kona side for a week or so.

Kauai is very laid back, with the sidewalks rolling up in the evenings. Kauai and the Big Island are our favorite islands.

Like wvjules said, Maui is a combo of Oahu and Kauai. It's our favorite island to snorkel on.

All of this said, you can take a Vegas/LA trip anytime with great ease. Hawaii is different. I would separate these into two vacations and spend the entire time doing a few islands over a longer time period then just skipping through an island a day. To me this would be like skipping the TV show and only watching the commercials.
 


Where are you originating from? A week really isn’t enough to see Hawaii. Three would be awesome but not realistic for most people. If you can stretch it out, I would pick two islands and split the stay there. We loved Maui and Kauai.

I would totally skip Las Vegas and CA...can do another time.
 
Having never been to Hawaii we booked the cruise (Pride of America) to get a "taste" of each island. We're flying in and out of Honolulu and plan to stay on Oahu for a few days both pre and post cruise, so we'll be able to see/do more there.
 
OK, thinking WAY ahead... summer of 2023. So for the sake of this planning, I'm going to assume all Covid restrictions have expired.

DW & I will be celebrating our 30th anniversary in June of '23. We have a tentative plan to fly to Vegas, spend a couple of days there (DW has never been and my aunt lives there), rent a car and drive to LA, spend a couple of days there (I've never been), then fly to Hawaii for a week before flying home. Here are my questions...

1) Do you stay in one hotel/resort/condo in Hawaii and travel to/from other islands, or "island hop" every day or so? Or just stay on one island?
2) Do you need to arrange inter island transportation far in advance, or something you can do day of or day before?
3) Is doing the "Pride of America" cruise around the islands the easiest?
4) Any island airport easier to get into from LAX or easier to get out of (probably to Atlanta, Detroit, or Minneapolis are the normal connection sites from our airport)? Maybe better to fly into one, then home on another?

Yes, we're in the very early planning stages, but I'm trying to come up with ideas.

TIA
1) Do you stay in one hotel/resort/condo in Hawaii and travel to/from other islands, or "island hop" every day or so? Or just stay on one island?
If you're in Hawaii for just a week, don't island hop. Just stick to one island for the entire time.

2) Do you need to arrange inter island transportation far in advance, or something you can do day of or day before?
Yes, you have to arrange it in advance. It's plane travel. So if you book the day of or the day before, you're paying through the nose. Hawaiian Airlines and Southwest have inter-island flights. It's not like at WDW, where you can just hop on a bus and be at your destination in 30 min. There's the whole entire TSA check in, Hawaii agricultural check in, and airport nonsense to go through. It takes time.

3) Is doing the "Pride of America" cruise around the islands the easiest?
Honestly, you won't really get a great Hawaii vacation experience on that sort of cruise. Don't do the cruise. Go to one island, stay in a condo where you can walk to the beach, and you'll have a much better time.

4) Any island airport easier to get into from LAX or easier to get out of (probably to Atlanta, Detroit, or Minneapolis are the normal connection sites from our airport)? Maybe better to fly into one, then home on another?
Shop around with the airfare. You can definitely get 2 1-way tickets, which would allow you to fly to Hawaii out of one city and fly home into another city.
 
I can only speak to what DH and I did. We flew to Honolulu and stayed just off the beach for 3 nights. This allowed us to see Diamond Head, the Arizona and drive around the island. Then we took the Pride of America cruise to visit some of the other islands. We really enjoyed this because it allowed us to see multiple islands without the stress of finding lodging/transport on each island plus we had most of our meals covered. The cruise ship was smaller, a little older and nothing splashy (certainly not the Dream!) but the service and food were above expectation from what we expected based on reviews (we had friends do the same trip about 3 years ago and had the same opinion of the ship- better than expected and easy). We booked all of our tours via private operators to avoid the large bus crowds and that was the key that made the trip really excellent.

Of course, this trip (8 years ago) has given us the desire to return to Hawaii for a week without island hopping. Sadly our planned trip with the kids was cancelled due to Covid and I'm not certain when the stars will align to be able to organize another trip.
 
It has been several years since our last Hawaii trip, but most of the major airlines fly from their hubs to Hawaii. Most people don't realize Hawaii is SW of the USA, so places like Houston or Atlanta are about the same distance as LAX or SFO. Various airlines have merged in the past few years, so probably best to see who flies there now. From anywhere east of the Mississippi it takes 10+ hrs of flying time, so having a connection from one of the coastal airports helps to break up the flight. Partly depends on what you like to do in Hawaii, we liked the shopping/sightseeing and did some of the land tours offered. One week on an island seems about right. Islands are small enough where you can rent a car and decide to drive someplace different each day.

If your wife has never seen Vegas, stopping there for a few days is a good idea. Vegas is mostly about gambling, but even if not into that, there are lots of excellent places to eat along with touring the large hotels along the strip. Something you likely won't see most anywhere else.
 
I think you should consider a trip sort of like this:

1. Skip Las Vegas. There are cheap flights to Vegas all the time. Do that on another trip, like an extended weekend sort of thing.

2. Fly into LA. Or if you're going to visit Disneyland, fly into the Orange County airport (SNA). Do 2 days at Disneyland, 2 days to do the Hollywood sightseeing (Hollywood is not nearly as glamorous as most people think it is).

3. Fly from LAX to Oahu.

4. Spend 2 nights on Oahu in Honolulu. Visit Pearl Harbor.

5. Take an inter-island flight from Oahu to Maui.

6. Stay on Maui for 8 days, 7 nights, preferably in Kaanapali, Kahana, or Napili area (west side of the island). Napili has some wonderful, small little condo hotels where you basically step outside your unit and the beach is right there. It's pretty magical.

7. Maui has a wide range of stuff to do: great snorkeling, the Haleakala volcano crater (which you do NOT have to get up in the middle of the night to see at sunrise if you don't want to), eat at Mama's Fish House on the north side and watch all of the windsurfers, LOTS of great beaches everywhere to try out. Good hiking options. If you choose to drive the road to Hana, do your research beforehand and do NOT drive all the way around the island because it WILL violate your rental car agreement...if you get stuck, it could be thousands of dollars for you to be rescued and you WILL have to pay for that out of pocket.

Just remember in Hawaii: Don't leave ANY valuables in your car. Car break ins are common.
 
1) Do you stay in one hotel/resort/condo in Hawaii and travel to/from other islands, or "island hop" every day or so? Or just stay on one island?

We have done island hopping trips, never more than two islands, and single island trips.
It is less than ideal for island hopping trips to be less than three nights, preferable a minimum of four nights on each island.

2) Do you need to arrange inter island transportation far in advance, or something you can do day of or day before?

We have always had our inter island transportation arranged at the same time we booked the hotels and airfare to and from the mainland.

3) Is doing the "Pride of America" cruise around the islands the easiest?

While I love cruises I would not recommend the Pride of America as a way to see Hawaii. Hawaii is a very easy on your own place to navigate. No need to trade a loss in flexibility for the convenience of the all inclusive cruise experience. You will only get a very short exposure to each port instead of the indepth time you could spend if doing a land based trip. It's not like a Mediterranean cruise where you are in ports where driving rules are different and the language may be a barrier.

4) Any island airport easier to get into from LAX or easier to get out of (probably to Atlanta, Detroit, or Minneapolis are the normal connection sites from our airport)? Maybe better to fly into one, then home on another?

It all depends on which island you want to start and end your trip. Honolulu is a big city style airport. Much busier than any of the other islands airports but still extremely easy to navigate both arrivals and departures.

Maui and Kauai each only has one airport that commercial flights from the US would use.

The Big Island (Hawaii) has two airports, one in Hilo and the other in Kona. This is the only place where you have some decisions to make. You can end up driving A LOT on Hawaii going from the Kona side to the Hilo side and back and forth and back and forth. It can be as little as 80 miles to as much as 150 miles going side to side depending on start and end points. You really need to research what you want to see on Hawaii and where you want to stay to decide which airport to use.
 
Thanks guys.

Our plans aren't set in stone, the Vegas/LA came up because a) I'd like to make a longer vacation, so thought two weeks, and could encompass Vegas & LA, which I don't think would require a week each and b) my aunt has been trying to get me to bring DW to LV (I've gone 3-4 times for work) since she's moved out there.

I also thought it would be easier "body clock wise) to have an intermittent stop three hours away before going on to Hawaii.

I do anticipate this being a "once in a life time" trip to Hawaii. We'd also like to visit Australia and Europe/Israel in the future. Those might be 40th & 50th anniversaries though (assuming we live that long).

Keep the thoughts coming, they're much appreciated.
 
Thanks guys.

Our plans aren't set in stone, the Vegas/LA came up because a) I'd like to make a longer vacation, so thought two weeks, and could encompass Vegas & LA, which I don't think would require a week each and b) my aunt has been trying to get me to bring DW to LV (I've gone 3-4 times for work) since she's moved out there.

I also thought it would be easier "body clock wise) to have an intermittent stop three hours away before going on to Hawaii.

I do anticipate this being a "once in a life time" trip to Hawaii. We'd also like to visit Australia and Europe/Israel in the future. Those might be 40th & 50th anniversaries though (assuming we live that long).

Keep the thoughts coming, they're much appreciated.

Ok, if it's a "once in a lifetime" trip to Hawaii, then skip Las Vegas and LA entirely. Fly straight to Hawaii and spend 2 weeks there. One week on Maui and one week on the Big Island.
 
Ok, if it's a "once in a lifetime" trip to Hawaii, then skip Las Vegas and LA entirely. Fly straight to Hawaii and spend 2 weeks there. One week on Maui and one week on the Big Island.

If they're spending two weeks in Hawowii (not a typo as the real name of the state is Ha-WOW-ii), I would do at least two nights on Oahu so he can see Pearl Harbor and Waikiki. Then go to two other islands for 5-6 days each.
 
Island hopping is time-consuming. We've done that for a two-week stay, but not one week.
We've been to most of the islands and always rent a car. Car rentals are inexpensive there and roads are not complicated.
One fun thing we have done is split-stay on the same island. Different sides of the islands have different features, as do different resorts. This is a fun way to "mix it up" a bit. And maybe splurge on a couple days at a more expensive resort. You can store your bags and hit their pool/beach until check-in time, so there's no down time to the vacation.

Whatever you decide, you can't go wrong with Hawaii. Truly paradise!
 
We have been to Hawaii twice. The first was on our honeymoon where we stayed on Oahu for 3-4 days then took the inter island flight to Maui for 3-4 days and then an inter island flight to the Big Island for a few days. The second time we did the cruise on Pride of America. We had an amazing time! We flew in a day early and stayed over a day after it ended. We preferred the cruise. We saw so much and it was great to be able to unpack for the week. We found the food and staff wonderful.
 

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