We'll be taking our first ever trip to Hawaii in June 2025, for a family wedding in Oahu. The plan is to stay for 4 nights in Oahu, at the resort where everyone is staying, and then so some exploring on our own.

We're interested in some hiking (nothing too technical), beaches and some historical and cultural sightseeing. The catch is that we love privacy and would prefer to find a nice rental property that is NOT a resort or condo community. We hear great things about Kauai and the Big Island.................Love to try new foods and great restaurants, but are equally comfortable putting together meals 'at home' in a nice rental property.

Any suggestions? we'd prefer to choose just one other island to visit, rather than spending time traveling between spots.

There is more "historic and cultural sightseeing" on Oahu than any other island. Pearl Harbor, Iolani Palace, Bishop Museum, ShangriLa Estate, Honolulu Museum of Art, Byodo-In Temple, Foster Botanical Garden and the Kuan Yin temple there, Mission Houses, Queen Emma Summer Palace, Plantation Village (just a few off the top of my head).

How many days is your trip total? If it is less than 10 days I would suggest staying on Oahu but finding different lodging than whatever resort that first 4 days is. I've been a half-dozen times and never stayed at a "resort or condo community" myself.

All the islands are beautiful and each has pros and cons for a visitor depending your interest and amount of time.

aloha suze

I have been to all four major islands, multiple times over 40 yeas, including three visits since the lockdown was lifted. If your wedding party is at the Ritz Carlton (Turtle Bay) resort it's a lovely property with a fun "sundowner" bar. Recommend a visit to Kahuku Farms for lunch if you have any time to explore.

While both Kauai and Big Island are great, you may have a hard time finding the desired type of accommodation in June. Most places to stay ARE in the big resort developments, and you have to be careful with illegal AirBnbs.

If you can find something in Hanalei in June, I would be surprised, but that's where I'd start. As a backup, try the south side of Kauai west of Poipu (Lawai or Kalaheo/Waimea). Bear in mind that all beaches in Hawaii are public.

On the BI, maybe the Mauna Lani area.

Good luck. If you want to ask on the TripAdvisor forums, C_n_H_Pure usually has good advice and vacations on Kauai regularly.


An unusually clear day on Kauai in October (Kalalau Lookout)

An important detail is missing -- how many days in total on the island(s) do you have? As suze says, if less than 9 or 10 days you're probably best served staying on Oahu. Also are your flights already booked R-T in/out of Honolulu?

I don't agree that you shouldn't experience another island. Kauai has the advantage of being about half an hour away by plane and has an easy to navigate airport. Four nights is a good amount of added time.

If someone has never been to either Kauai or the Big Island, they may not be aware of the wealth of historic and cultural sights there. Of course, anyone's definition of what that is varies as does their interest in things such as WWII history or ancient Hawaiian sites.

One historic site on Oahu that I prefer to Pearl Harbor, for example, is the "Punchbowl" Cemetery which is a bit of a three-fer (historic cemetery, visit inside a volcanic crater, and viewpoints.) Tours are not permitted to stop there, so the only realistic way to visit is via rental car. While in that area, you can also tour the Heiau up near Tantalus Lookout at the "Puʻu ʻUalakaʻa State Wayside Park".

Many of the hiking trails on Oahu (as well as in Kokee/Waimea State Park in Kauai) can be exposed, or slippery with root hazards when it has been raining. Better-maintained trails would be in the National Parks and monuments on the Big Island. There are also some coastal walks in Kauai that are fine as is the walk along the closed road between the Kalalau and Puu O Kila overlooks.

The gohawaii.com website does a good job of listing attractions. Just as an example, here are the ones for the Big Island
https://www.gohawaii.com/islands/haw...istoric-places

We need to know how many days total for the trip. After the 4 days already planned for Oahu, how many more? If you have at least another week, sure add another island. If only 2-3 more (one week total) then the idea to stay on Oahu.

If you do change islands try to fly home from the second one, so you don't have to backtrack thru HNL

I don't "NEED" to know. You have my recommendation for a good number of nights for Kauai. For the Big Island, four would also be fine if you flew into KOA, or add a few more nights and fly from HNL to Hilo (less than an hour to the National Park) then do 3 or 4 nights on the west side of the Big Island, whatever your budget and work schedule allow. See if a one-way car rental works. Note that Hilo is mostly short hops from Honolulu on Hawaiian, but KOA has several nonstop routes to the mainland.

You can also use a connecting short hop and layover and fly nonstop HNL to your home airport. Now that Alaska and Hawaiian Airlines are going to be one airline, check the flight sales on Hawaiian Airlines, both cash fares and a double-miles bonus which can be transferred free to Alaska Airlines.

thanks for all the response so far -- very helpful!

we haven't figured out the flights yet, but we would definitely aim for open-jaw if w decide to visit another island. we are thinking close to 2-weeks for the total trip, starting in Oahu for the wedding week, and then branching out from there. it's a pretty laid-back group and we'll be staying at Paradise Bay Resort, not the Ritz :~). Also, the wedding is at the end of June, so we'll be crossing over into July for the rest of our time.

originally, we thought about going to Japan or South Korea after the wedding, but remembering how beastly hot and humid it was in Taiwan in July when we were there for a wedding many years ago, decided to put those plans on hold.

another option, of course, would be to stay an extra few days in Oahu and then spend a week on the West Coast (maybe even British Columbia) before heading home...............

Many options of course but my favorite island is the Big Island of Hawaii, primarily because it offers so many different types of environments and experiences. Oahu does offer much to see and do with Pearl Harbor, in my mind, the most interesting to visit. Very well done museum and film and the memorial itself is very moving.

Two weeks is enough time for two islands. Nice location for Oahu but you might like a few more days there to visit Waikiki and see a few places in downtown Honolulu as where you are staying is a bit out of the way for the usual things people enjoy.

Since I live on the west coast (Seattle) for me that sounds nowhere near as exciting as pretty much anywhere in Hawaii

Two weeks helps a lot - and really opens up options. Two Islands is the obvious one. Vancouver/Seattle would be a bit difficult in July because it is prime cruise season so hotels can be really expensive.

There is so much to see on the Big Island that it could easily take up the rest of your time. If you want a fun low-key and affordable place to stay for a few nights on the Hilo side (with a full kitchen), check out the Dolphin Bay Hotel. East side weather can be wet although I've been lucky both times since the lockdown lifted. At least it's warmer than staying up in Volcano and there are a few things to see closer to Hilo. To me, Hilo feels the most Hawaiian, not a cookie cutter planned golf course development or high rise tropical beach resort.

For Hawaii Volcanoes NP, there are some big construction projects about to start, contracts pending. We were lucky to be there last month, before they close the Sulfur Banks boardwalk for refurbishment.

I am a fan of the Bishop Museum in Oahu where one could easily spend the entire day. A little pricey though. Check their website and see if it interests.


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