annaschummi

We have already been in Hawaii back in 2017 visiting Oahu, Maui and Big Island and felt absolutely in love with this paradise.
For 2019 we managed to get 2 award tickets from Rome to LAX and the question was "where should we go"? The answer was obvious, back to Hawaii, but before flying back to Rome, my husband would like to come back to San Francisco and drive a Mustang down Big Sur (boys remain boys)
So...the input is:
1) We will visit 2 islands only: Maui and Big Island are our choice
2) We need to buy tickets in economy from mainland to Hawaii: no status with no airline. Preferably non-stop. Which is a more reasonable combination: LAX-KOA and OGG-SFO or LAX-OGG and KOA-SFO? Early morning departure from LAX and red-eye to SFO would be great.
3) Flight from LAX will be Saturday 31st (Saturday of Labor day week-end, I know...), coming back to SFO will be September 11th.
4) We would like to stop 4 nights on Maui and 7 nights on Big Island. On Maui we have already done Road to Hana, missed completely Western Maui and would like to come back to Haleakala since it was cloudy when we went there last time. On Big Island we would like to see Black and Green sand beaches, come back to Volcanoes NP and dedicate more time to Kohala beaches. Another trip to Mauna Kea summit on a bright day. Perhaps star gazing?
5) We do not care about resort and pricey hotels, so a B&B or even a condo would be the best option. I do not trust airbnb since I had some of my reservations cancelled right before the trip, so what would be the best solution for us for a condo rent? We were thinking of Kihei for Maui and Kailua-Kona for Big Island.

Any thoughts above the above plans will be much appreciated!!

FlyinHawaiian

No real difference comes to mind; just book whatever flights work out for your price/points/timing-wise. Since you are planning on spending more nights on the Big Island, it might make sense to do LAX-KOA first and use the extra days to get over the jet lag. That being said, the jet lag could work in your favor if you want to do the early morning trek to see the sunrise from the summit of Haleakala.

You might want to take a look at Aston Hotels; many of their properties are condos. https://www.aquaaston.com You can also look to book a travel package with Pleasant Holidays that includes airfare and hotel/condo stays (and even rental cars): https://www.pleasantholidays.com/Hawaii-Travel

guv1976

OP: No interest in visiting Kauai on this trip?

Also, do you have frequent-flyer miles with any airline that you might be able to redeem on any of the several carriers that fly between California and Hawaii?

annaschummi

I will check out these sites, thank you.
How does it normally work with condo rentals? Are there agencies that have an overall view of what can be rented? Is it better to go through an agency or sites like vrbo or is it similar to airbnb? I have never rented condos in US before, therefore many questions on this part.
Some spot questions that come in mind:
1) Green Sand Beach - we will not be trying to drive there, even though I know people who did it, but I have read somewhere that locals give a ride for a reasobable fee? Is it right? Can it be a solution?
2) Black Sand Beach - can I arrive there by car?
3) I am still troubled by the fact of travelling on Saturday of Labor day week-end. What should I expect it terms of renting cars, air fares? I understand that it is the end of high period and after that there will be less people, but still we'll be travelling on this particular day...

Nope, no Kauai because it does not attract me as other islands do. Personal humble opinion. I would have come back to Oahu (we stayed in Kailua) to see North Shore better, but too much stress doing 3 islands in 11 days.

I have some more frequent flyer miles of Alitalia, but redemption flights on Delta are till April only and the miles expire in December. So by December if flying period is not extended till September, I will not be able to redeem them to a Delta flight.
For this reason I am ready to buy any ticket on any airline for a reasonable price.

FlyinHawaiian

If you book with companies like Aston or via a consolidator like Pleasant Holidays, it is the same experience as if you book a hotel room via major chain like Marriott, Hilton, etc. It just happens that the rooms offered are suites in condominium properties. There's a central reservations desk you go to at the property to check in, have your payment card registered, and given the keys to your room.

I would never advise using a service for transportation where the person transporting you may not have the proper credentials and insurance to ensure your safety and wellbeing.

annaschummi

I have tried Pleasant Holidays search for my dates and there apprear only 3 rooms available, while other 20 are not (I think anyways it is too early to book for September, so fine to wait). Are there any other consolidators like this one?

FlyinHawaiian

I don't normally need the services of a travel consolidator for Hawaii so cannot offer much advice other to say that I believe Pleasant still does the most bookings for Hawaii so I often use their pricing as a baseline. There's a number of other sites affiliated with US-based airlines like AA, DL, and UA; here's DL's: https://www.delta.com/content/www/en...vacations.html

tatterdema

I agree with Guv1976 about Kauai. Not sure why it would not attract you, as it is the most beautiful of all the Islands, not just my opinion, but most peoples. It is very quiet, but that is really the only difference between it and Maui besides the drop dead beauty. I was shocked at how much I enjoyed it compared to Maui. Hanalei is a place like no where I have ever seen on earth. Same with the drive up to the canyon. There is no place on Maui or the BI that is comparable. Plus I found Kauai much easier to navigate than Maui.

Only advice I can give on BI is to try and fly into Hilo and out of Kailua-Kona if at all possible. Just makes the best use of time usually. Also, I personally would not waste time with colored sand beaches. Way over rated, again, just my opinion. If you must see one, I liked Punaluu the best, but it really is a long jaunt to get to it, unless you take that route back from VNP, which is kind of a waste because there is not much to see on that route other than Punaluu. Lol, I thought that drive was one of the ugliest of all of my drives in Hawaii.

Traveliing on Saturday of Labor Day weekend should be a piece of cake. Most people do not travel on that day, they are already where they are heading. Often airfare is cheap on that day also. If you do not mind not having swimming beaches right at your doorstep, I do like Kailua-Kona now that there is no Vog. I normally wouldn't stay there because of the Vog, but keep in mind it can always come back. If you need beaches close by, then Waikoloa Village has a ton of condos for rent at varying prices. Really cannot go wrong with any of them.

annaschummi

If you were to choose from Alaska, Hawaian, AA and Delta to make a Hawaii - Mainland flight, what would you choose?
Flight in economy, no status, one bag to check in.

HNLbasedFlyer

With no status, and no chance for status in the future, I'd pick whatever airline has the most convenient schedule with the most direct routing.

When Southwest enters the market, presumably soon, unless policy changes, checked bags will be free - that can add up.

I did notice you didn't mention United above - they actually fly the most from the US mainland to Hawaii as another option.

annaschummi

I do not mention United since I have not had nice experience with them in the past.
I need to fly in SFO or OAK from KOA or OGG. I will have a hotel in Union Square then.
The cheapest today is KOA - SFO with a 1.30 layover in LAX with AA. But this makes me arrive around midnight.
Hawaian flies nonstop KOA-OAK and OGG-SFO, but they are slightly more expensive. Both of them leave in the first afternoon and arrive late.
Then there is a nonstop Alaska to OAK at the same price as Hawaian but leaves earlier and arrives earlier. I have already traveled with AS this year into LAX.
Then an evergreen red eye by Delta with a layover in LAX which makes me arrive in the early morning and does not make me lose a day of the vacation.
I understand that IFE does exist on Delta flights, Alaska rents them for a fee and HA makes you download an app. No reports found so far how AA flight is.

747FC

AS is a no-brainer for me: Nonstop has a huge advantage over stop, and an NS itinerary that is only a bit more expensive is worth it due to the lack of potential problems.

annaschummi

Any huge difference between flying into OAK rather than SFO?

KristenNix

I would also vote for Alaska Airlines (AS). We have flown into and out of both OAK and SFO to/from HI when we lived in San Fran. There isn't a huge difference. I would pick the least expensive non stop option.

ucdtim17

If your destination is Union Square, no. BART is 28 min SFO-Powell St, OAK is 35 min to Powell St