Help Us Plan Our Trip to Hawaii

From the recent thread about beaches it looked like this might be a good place to ask for help planning our trip to Hawaii.
We are planning to go to Hawaii for 2 weeks this summer. We are starting in Oahu so we can visit Pearl Harbor, but we need to decide on a 2nd island for the next week.
I was thinking Kauai so we would have a contrast between a busy island and a less busy island, but some people have said Maui would be a better choice, esp for snorkeling.

A little about us: we like snorkeling, hiking, and adventure. We care less about fancy restaurants or spas. Our favorite beach day would be hiking a short distance to a low key, quiet beach and spending the day snorkeling and enjoying the water. The USVI was a great fit for us. We stayed near Red Hook and really enjoyed the little town for restaurants and groceries. It was a perfect size, it sure we would have enjoyed staying near Charlotte Amalie.

Since it looks like quite a few of you have been to both Hawaii and USVI, I would love some advice on what 2nd island to choose and what part of the island you would recommend.

I’m interested in this thread too! We are also planning a Hawaii vacation this summer (actually in May) and plan to go to Oahu for Pearl Harbor (3 days) and then Kauai for a week, although we haven’t finalized any plans yet. I was considering Big Island instead of Kauai, but I think our family will enjoy the lush beauty of Kauai more. I’m also interested in suggestions.

We like to rent a house on the North Shore of Oahu, near Sharks Cove. In the summer there are no waves and you often have the beach to yourself. The snorkeling at Sharks Cove is wonderful.

If you go to Maui, note that the road network is like a star, with popular destinations like Hana, Haleakala, and Lahaina / Kaanapali at the ends of the branches. If you stay at the end of a branch, it can be a long drive to anything on another branch.

Public transportation buses are usable on Oahu, but not so much on other islands.

I’d do Maui. Stay out by Lahaina / Kanapoli. Great snorkeling options – Take a trip to molokini crater. Also can go up to Haleakala. The trip to Hana is pretty cool. Good luck.

Kauai hands down. Hike Waimea Canyon. Peek at Kalalau trail… hike some to the point past where permits are needed. I recommend staying in Poipu (sunniest place in HI). Lots of condo options. There is a botanical garden (Allerton Gardens) that is not to be missed.

https://hawaiistateparks.org/parks/kauai/waimea-canyon-state-park/

https://www.huffpost.com/entry/kalalau-trail-kauai_n_57294fade4b096e9f08fad37

https://ntbg.org/gardens/allerton

We love Maui and Kauai, but from your description, I’ll vote for Kauai too.
In the summer both sides of the island would be fine, but Poipu is much closer to Waimea Canyon.
There is a cultural hike in Poipu that is nice - right along the beach - Maha’ulepu Heritage Trail.
There are many small beaches all over the island.
Eat some Lappert’s ice cream while you’re there.
There are restaurants from little dives to high end places to enjoy.
If you decide on Maui, we can make recommendations for there also.

The Kalalau Trail is closed at least through mid 2019 due to flooding. Other good choices on Kauai are

https://www.backpacker.com/trips/4-incredible-kauai-hikes

I have hiked Nounou Mountain Trail and Alaka’i Swamp Trail and enjoyed both. There are also shorter birding trails in Koke’e State Park that are very nice.

I adore the Big Island, as it encompasses all the terrain of the islands in one. That said, if I wanted a respite from O’ahu, I’d go to Maui and stay in Ma’alaea Bay - it’s far enough from Lahaina to avoid all that touristy stuff, on a beautiful beach that’s walkable (it’s about 2 miles long), there’s snorkeling with big green sea turtles there, and it’s a short drive to upcountry and Kehei for daily adventures if you like. There’s even a few restaurants at the harbor there and the Pacific Whale Foundation is in the harbor so you could even do some cool excursions with them.

We just went to Maui for the first time last July with our two teenagers. It was incredible! We stayed on Kaanapali side. Road to Hana was the highlight of the trip (diverse ecosystem, waterfalls, black rock beaches)! Lahaina is fun with lots of shops and restaurants. Good luck with your planning.

Many years ago, i spent a week on Molokai and while surely it can’t be as great as it was then, I still remember it as a magical time.

Another vote for the Kalalau trail on Kauia. Getting the state camping permits may be a problem, but check the website. If you can reserve the days, then build the rest of your trip around that. It’s a long hike in, so be sure to pack light. We were in Koke’e last summer. The Alaka’i Swamp trail was in disrepair, but that would make a great tune-up hike for Kalalau.

I loved Kauai and have plans to go back. It is a good contrast to the bustle of Oahu. Maui is also very busy and would not contrast as much.

If snorkeling is important to you, Molokai is the place. The best snorkeling spot of Oahu or Maui would just be average at Molokai. The whole island is surrounded by good spots. Hiking, though, is not nearly as good as Kauai.

Just got a Save the Date for the wedding of my cousin’s son, which will be in Maui. Lodging and such seems easy—lots of info on the wedding website. I would like to use Amex points for the flight if it works. Have never been to Hawaii—what’s the best way to fly to Maui from Boston? Fly to Honolulu and then Maui or another way?

Maui has an international airport. It’s crazy large.

That would work, @Bromfield2! Another possibility is to split the trip into two 5-ish hour legs and fly into one of the larger West Coast cities (Seattle, San Jose, Portland, etc.) and fly directly to Maui from there.

When we went to Maui a few years ago, we changed planes in either LA or San Francisco on United from NY but the very best thing we did was to leave Maui on a Friday afternoon and spend a weekend in San Francisco, always a favorite place to visit. It broke the trip up nicely and we lucked out with picture perfect weather in San Francisco and then had a morning flight back to NY. I have been to Hawaii several times and the trip back to the East Coast is not fun, so if I ever go again and I hope to revisit, I would definitely plan a stop on the way back.

Hopefully by the time you plan to go the government shutdown will be over and you can visit Pearl Harbor which is definitely worth visiting at least once in your life. Someone I know had planned a Hawaii vacation for the early fall after she retired from being a principal in an elementary school but unfortunately it fell during the last government shutdown and Pearl Harbor was closed.

14 - Lol. Kahului, even with the expansion, is not large by any means. Pales in comparison with Oahu's HNL.

@Bromfield2, consider weather potential in layover locations. Don’t fly through Chicago in the winter, for example.

Generally, West Coast airports are fine for HI travel layover. SFO and LAX can get busy though.