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Planning stage of trip

New York, NY
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Planning stage of trip

Also posted on general Hawaii forum

I am in the planning stage of my trip to Hawaii. This is going to be a surprise for my wife for her B'day. Plan is to come to Hawaii for 10 days so basically try to visit 2 islands : Oahu & Kauai. Some basic facts that I know will help you guys make recommendations

Dates October 9th to October 19th

Arrive in HNL : 6:10 PM on the 9th

Depart from HNL : 7:50 PM on the 19th

Age : We're both 29 (no kids)

Interests : clubs, bars, relax on beach, spend time with each other

Islands I am thinking of: Oahu (4 nights) & Kauai (6 nights) (please offer suggestions as I am confused)

Budget : As low as possible, as we just bought a house, trying to squeeze in the trip

I see flights online approximately $550 p.p RT from EWR

So far I have managed to reserve the Westin Princeville Villas using a combination of SPG points and cash (4800 points + $90 per night) for the Kauai part. This can be cancelled.


1. Are these two islands good at the beginning of October?

2. Can you please suggest some itineraries? Idea is to party a little (25%), do some activities (zipline, snorkel 25%), and relax and spend time with each other a lot (50%, almost like a honeymoon)

Looking forward to hearing from you experts out there.

Also which is better:

- The Westin Princeville Ocean Resort Villas (North)


- Sheraton Kauai Resort (South)

New York, NY
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11. Re: Planning stage of trip

As there is such a big divide in the opinion, will it make sense to split my time between the north and the south.

My new itinerary could possibly be

Oct 9th to Oct 12 - 3 nights 2 full days in Oahu

Oct 12th to Oct 16th - 4 nights 3 full days at the Sheraton

Oct 16th to Oct 19th - 3 nights at the Westin Princeville

What do you experts think. Would 2 days in Oahu be sufficient? Any other suggestions?

Kauai, Hawaii
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for Kauai, Kapaa
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12. Re: Planning stage of trip

How long you stay on O`ahu should be based on how much clubbing you want to do. Waikiki is the place to be. Beyond that I'd suggest going to see Pearl Harbor and the Arizona Memorial.

I really like Anini Beach (north shore) for walking. The sand seems to pack harder than most, which makes for easier walking. It's a nice long beach, too.

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13. Re: Planning stage of trip


My husband and I are the same age and have similar vacation priorities. In the last three years, we've done Oahu once (stayed at the JW at Ko Olina but spent some time in Waikiki), Maui twice and I am now on Kauai.

I would personally suggest scrapping the Kauai/Oahu plan and try out Maui, especially if this is your first visit to Hawaii. It has (imo) a really nice mix of activities/beaches/natural beauty/bars and restaurants.

Oahu and Kauai are fabulous as well, but more on the extreme ends of busy and mellow.

I really like to settle in one spot as 10 days goes by FAST. In any case, I would definitely not do more than two spots.

Really, though, it's hard to go wrong with Hawaii.


Huntington Beach, CA
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14. Re: Planning stage of trip

Aloha Kar...NY :)

I like your plan of 3 nights on Oahu, and the rest of the time in ONE location on Kauai. I wouldn't split my time in two different locations on Kauai for just 6 or 7 nights. Kauai isn't that big.

I haven't stayed at the properties you're considering, but I can give my .02 on location. I went in October and the weather was starting to change. It rained a lot up north, not down south. Up north is beautiful and tropical, but if you want beach walking at night from your hotel, my guess is the Sheraton would be a better fit. Hanalei in the north IS beautiful though. You could have some fantastic beach walks there, too, but it won't be from your hotel.

If you're looking for 2nd Honeymoon ~ my opinion is that Kauai is the best choice. Others have mentioned Maui, and I LOVE Maui, but for the quiet honeymoon feeling ~ I'd definitely stick with Kauai. It is so lovely there, and in my opinion, probably the most romantic of the islands.

I love your plan to surprise your wife ~ it's awfully sweet :)


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15. Re: Planning stage of trip

If you are choosing the North side vs the South side based on nightlife you will be disappointed in both. As I mentioned Tahiti Nui in Hanalei Town is about as rowdy as it gets because the locals frequent this place. They have fun kareoke nights and good local bands play. It can get a bit wild at times after midnight. You know the stories. Guy goes to have a late night beer. Guy sees his girlfriend. Guy sees the hand of another friend on the behind of the girlfriend. Guy has that beer and then throws the empty glass at the guy with the hand on his girlfriend...... You get the picture. (this really happened to a friend of mine)

For beach walking my favorite is Hanalei Bay. All beaches are public so just park near the pier and take a stroll under the moonlight. You can do the same at the Sheraton. Either of your choices will be good ones. Read the reviews for both on the left side of this message box and read them all. You should get a feel for each.

Santa Rosa...
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16. Re: Planning stage of trip

GRAB THOSE FLIGHTS YOU FOUND. $550 out of Newark will not be beat.

Another option that I think would work for you......look into the Hyatt in Poipu. You'll have that second honeymoon feel, the dining, Stevenson Bar, the beach to walk along, the lagoon pool to romance by.

Anything else that strikes your fancy, including the short 1 hour drive to the northshore, just hop in the car and do it.

17. Re: Planning stage of trip

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