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Dear Val – I’d like to take my mom and dad (69 and 70, reasonable health) to Hawaii and I’m somewhat overwhelmed! There are so many books and resources, but I’m having a hard time figuring out what would work for my elderly parents and me. Where should I begin? I’m planning my trip for 2nd week of June. Thanks in advance!

June is a great time to visit Hawaii, Ksenya. Actually anytime is great, but mid-April to mid-June is considered low season as most folks tend to visit the islands when the weather is bad in their home states (usually during December – February.)

As your planning your tropical vacation, keep in mind each island has a leeward side (the side sheltered by the wind) and a windward side (I’m guessing you can figure out what that means!). The windward side is typically east and north and is generally cooler and moist while the protected leeward side is west and south and usually hot and dry. At 83, my mom is cold all the time so we typically stayed near the hot and dry portion of each island when we visited in 2008.

Most major US carriers fly into Honolulu International Airport (on the island of Oahu) although some have direct flights to Maui, Kauai, and the Big Island. For planning purposes, it’s best to assume a connection through Oahu to get to the neighboring islands. But making a stopover on Oahu is not a bad thing. In fact, I suggest staying a night or two before venturing to another island. Not only will this help everyone catch their breath from the long flight but you’ll have the opportunity to visit the USS Arizona Memorial at Pearl Harbor. It’s seriously a sight to behold. Sad, but an important part of US history (and one I wouldn’t recommend missing).

Because we were on the island for so little time, I arranged a day tour with a local driver to see the sites. We saw sea turtles basking in the sun, the Dole pineapple plantation and the ridiculously stunning seascape as we circumnavigated the entire island. This is a great option as it lets someone else do all the thinking (and driving!) and they know where to go. A great place for sunset cocktails is House Without a Key at the Halekulani Hotel:


Happy hour at House Without a Key at the Halekulani Hotel, Oahu.

When it comes to venturing beyond Oahu, I recommend asking your parents what they think of when they think of Hawaii. I would ask the same question of you, Ksenya. What you (and your parents) have heard about Hawaii can help dictate and determine which islands you should explore. For mom and me, the #1 thing on our list was seeing volcanoes via helicopter. Other sites on our list: driving the road the Hana (I didn’t even know what this was, but had to do it,) visiting Waikiki (following in the footsteps of the Brady Bunch) and Maui (mom saw Oprah take her staff there.) We also went whale watching but I would not say that was mom’s favorite activity:

Mom is clearly enthralled with whale watching.....

Mom is clearly enthralled with whale watching…..

Our answers to “What pops into your head when you think of Hawaii” dictated our route. There was definitely a lot of island hopping during our ten-day vacation, but don’t worry, we also did a lot of relaxing poolside and on the beach. We basically spent two nights on Honolulu and then split the rest of the time between the Big Island of Hawaii (for volcanoes) and Maui (road to Hana and Wailea area where Oprah visited). If your parents don’t have any particular ideas in mind, check out Hawaii’s Official Tourism site to help decide which islands to explore when visiting Hawaii. I must say, I found the big island to be totally enthralling. If I had the money I would snap up a property in South Kona in a heartbeat.

On each island, I rented a car since I knew we’d be doing lots of driving to see the coast line and other sites around the island. I’m not sure I needed a car the whole time since the resorts can book tours (including getting us there and back); however, I like to drive so it worked for us. If you’re planning on just chilling out and occasionally going out and about, a car may not be necessary. And if you change your mind, some hotels have a car rental office located onsite.

I used Hawaiian Airlines to travel between islands. There are other airlines, but Hawaiian has a stellar reputation and that matters to me (even if it cost more money).

When it comes to hotel rooms, I am a bit old school: I buy the Frommer’s Guide to whatever region I’m visiting. Between the book, searching reviews on TripAdvisor and Expedia (my preferred travel aggregator) and consulting friends, I booked hotel rooms on the leeward side of each island which fit my budget. If you’re planning on sharing a room, I suggest getting a room with a separate sitting area. Having a bit of room helps so we’re not on top of one another and can have a place where either of us can have a quiet moment to read. One other suggestion, if possible, pick a hotel room that faces the ocean. It’s part of the draw of going to Hawaii so take advantage if possible. Having a hotel room with an ocean view can also give you some amazing sunsets:


This sunset was so overwhelmingly beautiful it almost looked fake! And yes, mom did turn around to watch the sun disappear over the horizon.

Two other recommendations: arrange for a lei-greeter meet you as you deplane. It was magical, even after a 13-hour direct flight from New York. I used Greeters of Hawaii but if you Google it, you’ll find several options (I only did it upon arrival at Honolulu but you can arrange for greeters to meet you at every airport).


Even with the leis, mom and I look a little rough after our 13-hour flight from JFK in New York to Honolulu International Airport.

And don’t skip a luau. We did one on Maui which was arranged through our hotel. Yes, it felt a little touristy, but mom and I loved it!

Although we never did see the volcano from a helicopter (bad weather), visiting Hawaii was an outstanding trip. It’s impossible to have a bad time when the weather is so stunning, the smells from all the tropical plants are so intoxicating and the landscape so breathtaking. Hope this is helpful, Ksenya, and feel free to ask additional specific questions if you have them! Delighted to help!

Stay tuned next week when I answer Lee Ann Hadley’s question about how to overcome the inertia of getting her mom moving vs. putting off vacation time and again.