Hello. My wife and I are thinking about a possible trip to Hawaii for the first time.

I feel that if we are going to make the trip all the way out to Hawaii, we might as well see Pearl Harbor and the memorials due to their historical significance. However, all my research seems to indicate that O'ahu might not be the most scenic of the Hawaiian islands, and it definitely sounds like it is the most touristy. So, Pearl Harbor seems to be the only reason for us to go to O'ahu. Otherwise, one of the other three main islands sounds more appealing to me.

I was thinking about trying to go to O'ahu for a couple of days, then flying to another island like Kauai for 5 days after that. That seems like a good contrast to me. We would get to see the memorials and the touristy attractions in O'ahu, then we would be able to appreciate the scenery and the more laid back pace of Kauai.

Is two islands something that can be done on a trip that totals 7-8 days? It seems feasible to me, but I am hesitant to plan it in case it is too much of a hassle changing islands in the middle of our trip. I am wondering if sticking to one island is more advisable. Does anyone have any experience doing multiple islands within this timespan that can share their thoughts? Thanks!

Totally doable. We did three islands (Oahu, Maui, and Kauai) in I think 12 days.

Hawaiian Air has multiple flights every day to/from different islands that are relatively inexpensive. The airports are also close to the areas where you want to be, and if you want to pick up a rental car, that should be quick and easy, too. So not a lot of travel time.

Our second trip, we stayed on the Big Island the whole time, but I think it was a little shorter, and we had already visited the other islands anyway.

100% doable, I would recommend.

I would limit amount of time at O'ahu, the other islands had more appeal to me. PH was ok, boat out to the Arizona was closed bc of wind, so that was kind of a let down.

On my trip we flew into O'ahu spent 1 night, did Pearl Harbor and island hopped, and on last day got an early flight to big island spent a full day at volcanoes NP and caught a late night flight out that arrived at a decent time state side. Everything was laid back, never felt like an amazing race or rushed.

Watching. We are thinking about this in the summer and want to do 2 islands, one being Kauai. The other would be down to Big Island or Maui. Which of the 2 is best?

Absolutely doable. Pearl Harbor can be a pain to actually get a ticket to see(recommend using one of the travel services; there is a daily allotment of tickets and they typically snatch up nearly all tickets each day). The museum is ok, getting out of the tender to stand on the monument and straddle the USS Arizona is a transformative moment. Literal chills.

Highly recommend Kauai and Maui, with making a pond hopper stop in Oahu in the transit. HNL has lockers you can rent for a couple hours to store your luggage.

Wife and I love Kauai - recommend trying to break up the stay for some time on both the North and South shore of the island. Wildly different feels; the travel time to experience something on the other side of the island will eat half a day otherwise.

Kaanapali is the place(in our opinion) for Maui. Short drive from OGG, to Kapalua, restaurants, marinas, the road to hell, and the sunrise on the top of Haleakala is worth bringing a random sweater.

Recommend reaching out to @breezecustomtravel; she's very experienced planning trips to Hawaii. She can probably answer any questions you have.

Her email is lauren@breezecustomtravel.com

Awesome! Thank you all for your input. Sounds like a trip to multiple islands isn't as big of a hassle as I was thinking. This is exactly the feedback that I was looking for. I appreciate it!

I plan multi island vacations within this time frame for a lot of clients. Now on Oahu there are a lot of beautiful and tropical places to enjoy. I love the North shore.
Last year I visited 3 islands as being hosted by the Hawaii visitors bureau. Kauai being one of them. If you are looking for a travel advisor my contact info is in my Bio.

Thanks for the shoutout, ag-spirit!

Hawaii is a hot destination right nowI've already planned several multi-island trips this year, and it's always such a joy to put together!
You can absolutely do a two-island itinerary in 78 days, though most of my clients opt for 810 days for a more relaxed experience. Many first-time visitors who want to see Oahu and Pearl Harbor add it to the beginning or end of their trip for a night or two.

I highly recommend Maui or Kauai, though The Big Island has also been a favorite among some of my recent clients!

If you need help planning and booking, feel free to reach outI have plenty of recommendations to create your perfect itinerary!

If you're just picking two islands, I'd do Kauai and the big island.

Kauai is one of the most beautiful places on earth, particularly the Napali Coast and Waimea Canyon. It also has a very laid back, casual vibe, and is probably the least populated of the main islands.

The big island is fascinating with the volcanoes and the green and black sand beaches.

I'd fly into Oahu and see the USS Arizona, maybe take one picture of Diamond Head from Waikiki Beach, then get out of there and hop a plane and visit the two other islands.

Agreed. I love Maui, but I do think the Big Island and Kauai are the way to go for first timers (although it's hard to wrong with any island combo).

The Big Island has such diverse landscapes but it is also the best for snorkeling (Captain Cook and Two-step are great spots). And be sure to dive (or snorkel) with mantas at night. Ive done some pretty cool animal encounters in my life and this is in the top 3.

I think that if you hit the big island, then you should stay on the north side of Kauai. I love the south side, and you should definitely spend a day down there to see the canyon, but the south side is more known for it sunny beaches, and you'll get that on Hawaii. The north side of Kauai is more lush and mountainous, but also has great beaches. Be sure to hit Kee (get reservations) and Tunnels (best snorkeling on Kauai).

And you (the OP) say about 8 days…see if you can stretch that to 10-12. You're spending the time and money to get out there, you may as well stick around and enjoy it. And spend a day or two on a beach (I like Kee) doing nothing. It's awesome.

Did that trip several years ago. Stayed on Kauai about a week but flew over to Oahu for a day. Rented another car on Oahu and went to all the main tourist things then flew back that evening. Want to go back to the other islands.

Like others we have done Maui and Oahu together. It is kind of crazy to experience Honolulu after spending time on one of the quieter islands first; amazing that a major city exists in the middle of the Pacific.

And if you go I agree that PH is a bucket list item worth checking off.

We flew into Oahu at night, did Pearl Harbor next morning/afternoon and out that night. The Missouri tour and airplane museum were great.

No clue how mauis doing after the fire, but it's the second most touristy island and some of that is blah to us.

Kauai most scenic overall.

Big island most variety and local feel.

I easily did Waikiki Beach and Pearl Harbor in 4 hrs on a layover, so plan 6 hours from landing to takeoff and you will have plenty of time. Anything more than that and I would head to another island, or if you really want to stay on Oahu go to the North Shore.

kyledr04 said:

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Did that trip several years ago. Stayed on Kauai about a week but flew over to Oahu for a day. Rented another car on Oahu and went to all the main tourist things then flew back that evening. Want to go back to the other islands.

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Same thing. 7-8 day trip, with 5 days in Kauai broken by a full day hopping over to Honolulu and back. Only difference is that we used Uber in Honolulu.

Stayed on the east side of Kauai so we could drive anywhere on the island. If you're looking for a clean, budget option, we stayed at Hale Plantation in Kapaa. Booked it on Orbitz.

Kauai is a must. I'd rent a car here and up to Hanalei. Kauai is the most majestic IMHO. Enjoyed Maui. Oahu wasn't the best, used as a pit stop to island hop.

Me and the wife have only been to Hawaii once. We chose Maui and spent six days there with a rental convertible. I'm sure all the islands are amazing and have their own things that make them special. I would only say that we had the most amazing time on Maui and could have spent more time there. It's beautiful and the people are some of the nicest you'll meet. I golfed, we drove the road to Hana stopping multiple times for fruit drinks and side hikes all along the way, hit up the beach in Kihei, ate amazing food, and circumnavigated the whole island over the course of two days. The one thing we didn't do that I regret a great deal is that we didn't take in the sunrise on Haleakala. I always recommend Maui to anyone that asks, we will go back some day, it's magical.