First-timer’s guide to Hawaii: 14 days, four islands, five flights, three rental cars and two missing hiking poles

Exploring Kauai

Spectacular Waimea Canyon on Kauai, one of the highlights of a 14-day tour of the state.Susan Glaser, Cleveland.com

HONOLULU, Hawaii – Fourteen days, four islands, five flights – a lot could go wrong, I feared, as I planned my first-ever trip to Hawaii.

I’m happy to report that almost nothing did.

I could attribute that to good planning, but I know it took a good bit of luck, too.

Before and after my trip, the Kona airport on the Big Island was shut down due to cracks in the runway; Kilauea Volcano, also on the Big Island, threatened to erupt, possibly upending my plans; and high-wind warnings were keeping visitors out of the ocean early during my stay.

I worried about all these things and more, mostly for naught.

The weather cooperated, no flights were delayed and I got to swim in the water everywhere I went.

This was one of the more complicated trips I’ve planned, and I admit to being a bit nervous -- starting with my 6 a.m. departure from Cleveland on a blustery Saturday in February.

I booked a flight to Honolulu on United Airlines with a scant 50-minute connection in San Francisco. Turns out, it was plenty of time.

The only glitch? Apparently you’re not supposed to pack hiking poles in your carry-on bag. But even then, Transportation Security Administration officers waited to enforce that rule until I was headed back to Cleveland – so I was able to use the poles during the whole trip before leaving them behind at Lihue Airport on Kauai.

Traveling with only a carry-on bag was important to me because I was booked on five flights – from and to Cleveland, plus three interisland hops. A carry-on bag is typically free on both United and Hawaiian airlines, but a checked bag would have cost as much as $40 per flight.

So I packed light (kind of) and kept the souvenirs to a minimum.

I started my tour on Oahu, where my husband and I spent a single night. Although I enjoyed the afternoon on Waikiki Beach, our main reason for starting here was to tour Pearl Harbor National Memorial. It’s a must-see for every American.

From Honolulu, we flew to Maui for three full days of touring, followed by five days on the Big Island and five days on Kauai.

I scheduled Kauai last because I figured it would be my favorite island, as well as the most relaxing. I figured correctly on both counts.

We flew home from Kauai on an overnight flight to Denver, where we connected to Cleveland.

Among the highlights:

* Hawaii Volcanoes National Park on the Big Island

* Supporting the businesses and chronicling the comeback of West Maui after devastating wildfires last summer

* The Road to Hana on Maui

* Hiking the Napali Coast on Kauai

* Snorkeling Kealakekua Bay on the Big Island

* Doors-off helicopter tour of Kauai

* Waimea Canyon on Kauai

There were certainly activities and attractions that we missed – notably stargazing atop Mauna Kea, the Big Island’s massive 13,796-foot-high volcano. Traveling from Cleveland in February, I wasn’t excited about donning full-winter gear for what typically is a cold, blustery tour. Still, I’m certain I missed something special.

Keeping costs down

No way around it – Hawaii is a very expensive destination, from hotel prices to rental cars to food. Though I considered this a bucket-list trip – and I wasn’t trying to keep to a strict budget -- I didn’t want to (completely) break the bank. I tried to keep overnight costs below $300 a night, and for the most part, I succeeded.

The helicopter tour was the single most expensive activity we did – $324 per person. But it was spectacular.

Food was expensive, too. We had access to a kitchen at most of the places we stayed and typically ate breakfast in our condo before heading out for the day. We could have made it cheaper by cooking dinner in our condo, but we opted to eat most dinners out.

Exploring Kauai

Mai Tais at Duke's Kauai on the final night of a two-week Hawaiian tour. Susan Glaser, Cleveland.com

A taste of Hawaii

We ate seafood every day, tried Spam, poke and lots of shave ice. Among the highlights:

* Many, many Mai Tais. I’m not sure I’d ever had one of these rum drinks before, but I made up for it on this trip. The traditional Tiki drink combines rum, curacao, orgeat syrup and lime juice. The best I had was at Nalu’s South Shore Grill in Kihei, Maui. The food at Nalu’s was terrific, too.

* Spam musubi, a traditional Hawaiian lunch that was popular with plantation workers. It combines a slice of Spam, rice and nori (seaweed). I wasn’t sure I would like it, but I did – enjoyed at the Pine Tree Café near the Kona airport.

* A smorgasbord of traditional Hawaiian fare at the Island Breeze Luau at the Courtyard by Marriott Kamehameha’s Kona Beach Hotel on the Big Island. Among the buffet items: poke, kalua pork, haupia, and poi – the bland, starchy paste that is made from the taro plant. It was the only Hawaiian food that I didn’t care for.

* Lots and lots of shave ice. I figured this was just a fancy snow cone, but I was wrong. The best shave ice I had combined delicate ice shavings atop ice cream, mochi, boba and a rainbow of flavors at a place called Aloha Icelabs in Waikiki.

Experiencing Hawaiian culture

I made an effort, too, to learn some Hawaiian history and experience culture during the trip.

Among our stops: Hulihee Palace, the summer house for King Kalakaua and Queen Kapiolani on Kailua-Kona; Kealakekua Bay State Historical Park, also on the Big Island, where the sacred Hikiau Heiau temple once stood; and Wailua River State Park on Kauai, where the remains of four major temples are part of the Wailua Heritage Trail.

Read more:

Touring Hawaii’s Pearl Harbor, a history lesson and memorial service all in one

Maui after the fires: Hawaiian island is open, welcoming and absolutely stunning

Exploring the Big Island (which isn’t all that big): From Hawaii Volcanoes National Park to the Kona coast

No, you don’t need four-wheel drive in Hawaii, and other car rental tips

Five days on Kauai: North Shore vs. South Shore, and the view from a doors-off helicopter tour

No, you can’t take hiking poles in your carry-on bag (and other TSA misadventures)

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