With so much to do in Hawaii, planning a trip can be a bit daunting. Full of exotic landscape and extensive coastlines, luxurious fun in the sun is a must. However, there are also endless opportunities for active boomer travel adventures as well.
To help you plan your next Hawaiian adventure, take a look at our recommendations for creating a great trip! We’re sharing our handpicked travel resources for your next trip to the islands!
What you'll find in this Hawaii Travel Planner
- Plan your trip to Hawaii
- Online Hawaii travel resources
- Hawaiian travel books and guides
- Hawaii travel gear
Boomer Travel Tip
Come back often as we continue to update and verify our recommended online resources and products for you. Or subscribe to the My Itchy Travel Feet Weekly Broadcast to be the first to know!
Plan your trip to Hawaii
Booking flights: When looking for flights to Hawaii, Alan and I start here Kayak. After determining the best price, we click on over to the airline site to book.
You’ll find the best prices, and non stop flights, from major cities on the West coast. Booking a separate ticket to and from the gateway city, then a non-stop flight to Hawaii from that gateway city may save you money.
Rent a car: Unless you are planning to spend all of your time at a large resort property that has several restaurants, you’ll probably want to rent a car. Kayak is a good site to compare quotes.
Where to stay: Although we have favorite places to stay in Hawaii, it’s smart to check for current prices and specials, too. We start our search here at Kayak and follow that up reading the reviews on TripAdvisor.
Booking tours: Hawaii can be a busy destination. Booking tours in advance is a smart idea. There are so many adventures to experience. Start at Viator to see what’s available. Looking through the tours at Get Your Guide is another good option.
Online Hawaii travel resources
Whether you’re planning a Hawaiian land adventure or researching cruise excursions in Hawaii, online travel resources equal instant information at your fingertips. But we’ve found that too much information complicates research rather than speeding it up.
That’s why we’ve whittled it down to the best online Hawaii Travel Planning Resources. Bookmark our favorites for your next trip to Maui, Hawaii, Oahu, Kaui, Lanai or Molokai. We’ve also included our favorite Hawaiian travel apps.
The My Itchy Travel Feet Hawaii Destination Guide publishes first-person travel articles based upon our travel experiences, or those of guest writers. The guide covers the major islands in Hawaii, including Oahu, Maui, Kauai, Hawaii, Lanai and Moloka’i. It’s your free, one-stop resource for researching a trip to Hawaii from a boomer perspective.
As the official State of Hawaii tourism site, you’ll be able to find a ton of useful info such as accommodation suggestions, restaurants, sightseeing musts, and local events at Go Hawaii . The site breaks down travel ideas into themes such as foodies, outdoor adventures, romance seekers and more. There’s even a page for first-timers to Hawaii.
We’ve cruised through the Hawaiian Islands on many of our South Pacific Cruises. At Cruise Excursions in Hawaii, our collection of first-person Hawaiian cruise articles continues to grow, so check back often. Of course these Hawaiian travel ideas make great land adventures, too.
Six Spectacular Hawaiian Road Trips offers a great guide to road tripping through Hawaii’s most stunning landscapes. These scenic drives make a great break from relaxing on the beach.
National Park Service Hawaii Park Information: A trip to Hawaii wouldn’t be complete without exploring some of its amazingly scenic natural parks and historical destinations. Eight national park sites are spread throughout Hawaii including two national parks, an historical trail, two national monuments, three historical parks and an historical site. Of course the National Park Service official website for Hawaii is the place to go for up-to-date information on hours, fees, location and travel alerts for the parks.
Go Visit Hawaii is an informative site with detailed information on all of Hawaii’s many charms, both known and some great off-the-beaten-path recommendations. We especially like the deals section of Go Visit Hawaii.
Hawaiian travel books and guides
Online research is convenient, but there are times when we want to hold a book in our hands. And, of course, these days, we also download travel guides and books to Alan’s Kindle Fire or my very basic Kindle Paperwhite, when we want to travel light. With so many travel books on Hawaii, how do you choose which one is right for you? Follow our recommendations:
Hawaii, the Big Island Revealed – Hawaii’s big island is big on sights, so make sure to see the best of the best with this guide chock full of helpful information, especially for going-off-the-beaten-path. Many of our Hawaiian travels have been inspired by this book, or the versions for Maui, Kauai or Oahu. However, be aware, that some of the recommendations in the book encourage you to take chances on trails that trespass on private land or have dangerous elements to them. Don’t do that! But the books still are valuable as an overall resource, introducing you to sleepy towns, hole-in-the-wall restaurants and unique places to stay.
Backroads and Byways of Hawaii – if you’re planning on road tripping around Hawaii, you’ll want this Hawaii road guide that takes you to all of the spectacular sights. You do know about the gorgeous scenic drives in Hawaii, right? They make a wonderful break from all that sunning on the beach.
Fodor’s Maui Guide – Of course, Maui is Hawaii’s gem of an island. To make the most of a visit to this paradise, take Fodor’s guide with you wherever you go!
Hawaii Off the Beaten Path – Want to avoid all the tourists and the traps that go along with them? Use this off-the-beaten-path guide to learn about the island’s most exclusive and hidden spots!
Hawaii travel gear
You don’t need to bring much on a trip to Hawaii. Unless you’re staying for an extended period of time, a carryon and personal item bag should hold all you need. But a few essentials make the experience an even better one.
You don’t need a lot of clothes for a trip to Hawaii. Pack a carryon with beach apparel, a couple of nighttime outfits, and active wear for daytime adventures, one pair of sandals or flip flops, one pair of nicer sandals for going out to dinner (wear tennis/hiking shoes on the flight), and you’re done.
Boomer Travel Tip
If you’re looking for a more comprehensive list, my tropical cruise gear list works for Hawaii, too!
Don’t forget sun protection. Pack a hat, long-sleeve SPF treated shirts to wear in the water and SPF lip balm. Purchase sunscreen once you arrive. Carry it all in the Travel Smart All Purpose Microfiber Tote Bag, for a conveniently-sized personal bag on the plane or a day bag for the beach. Durable and comfortable, this bag does double duty for the stylish adventuress!
And bring an underwater camera—we use the Olympus TG-4—for taking photos on snorkeling or other water excursions.
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