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Winter is here in New York, so our next trip to Hawaii has been on my brain. Last year we were fortunate enough to spend three weeks traveling to Maui and the Big Island. I’d say from the minute we flew back home, we have been mentally planning our next visit! Since I so often get asked about Hawaii trips, I am sharing with you how to plan a trip to Hawaii.
How to Plan a Trip To Hawaii
From New York, it takes longer to get to Hawaii than it does to Italy! Even from the west coast, its a long flight. So even though technically a domestic trip (no passports required, ZIKA free destination!) its a big trip and one that takes careful planning.
In Hawaii there is so much to see and do, and like a Disney trip, you won’t be able to do it all. Its important to plan and choose what is important to your family.
Probably the best thing you can do in planning your Hawaii trip is to click the banner below. I am a full-service travel agent with Paradise Travel. Our Denver based agency plans A TON of Hawaii trips and I have personally been three times (as a kid, as a couple with my then-boyfriend-now-husband, and with my own family). Our services are free, and you get all our expert planning knowledge and access to great package prices.
Which Hawaiian islands to visit?
This is the question I most often get, and a question you can LABOR over for years. Here are som key take aways about each, unique island.
Oahu – Honolulu is the capital of Oahu and the only airport you can fly direct to from the Eastt Coast. But Honolulu is very urban chic, with high rise buildings, hotels and a bustling downtown. More Miami Beach than Adventures of the South Pacific. On Oahu you can visit the historic Pearl Harbor site, and stay at Disney Aulani. I love Waikiki which has that urban, surfer feel. The North Shore of Oahu has lots to do with a more local feel and this is a surfers mecca. For more about Oahu, check out this 7 Day Oahu Itinerary.
We are hoping to get to Oahu as a family real soon. I have personally been twice, but pre-kids. I would love to stay at Aulani before my kids get too old (not sure you can ever really be too old for a tropical Disney resort, but needless to say it’s something we plan to do in the next year and a half. Thinking about staying at Aulani? Then read What to Expect When staying at Aulani and definitely reach out as I am a College of Disney Knowledge graduate and have all the Aulani training!
Maui is a great island for honeymooners, and families alike. Maui has lots of nature to explore, beautiful beaches for surfing and paddling, but gorgeous resorts and amazing restaurants.
The Big Island – The biggest island is named “Hawaii” but is also known as “The Big Island”. Most visitors stay on the west side, in the Kona area, but you can also stay on the east side, Hilo.
The Big Island is very black and volcanic, but there are beautiful big island beaches. Life on the big island takes on a slow pace, with lots of natural sight seeing, and no nightlife. There are fun things to do on the Big Island, a trip to Volcano National Park being a highlight of this island! I mean where else can you see active lava flow?
Kauai – Kauai is the one major island I have not been to – yet! This island is the smallest, and most remote. Kauai is great for adventure seekers, honeymooners and those looking to really just relax! Kauai has beautiful beaches and amazing hikes.
Accommodations in Hawaii: Condo vs. Hotel vs. Resort
Once you narrow down which island(s) you want to visit, you need to think about what type of accommodation makes sense for your stay. Hotels and resorts are popular, of course, but definitely consider booking a stay in one of these fabulous Hawaii vacation homes.
A vacation home is a popular Hawaii accommodation because most Hawaii trips are longer, and therefore you are more likely to crave the comforts of home. For us, staying in a vacation home allowed us to have more space, cook our own food, and do our own laundry. Eating out is expensive in Hawaii, especially eating at a resort, so being able to grocery shop and make some meals at home will allow you to splurge on amazing meals out! Staying in a rental helped us visit Hawaii on a budget.
However there are some amazing resorts on the Hawaiian Islands! On our 2016 trip, we stayed in Maui for 8 nights (in this one bedroom condo), the Big Island for 8 nights (in this 2-bedroom townhouse) and then moved on to 5 nights at the Waiakoloa Beach Marriott.
A split stay is a great option to balance condo amenities with resort luxury. Just remember to be sure (with all accommodations) that you are aware of any resort fees, parking fees, etc. Hawaii hotels and resorts are infamous for hefty resort fees.
Favorite Hawaii Resorts and Hotels
The Big Island:
Plan your Hawaii flights and itinerary
Once you sort out the islands you would like you visit, you need to book your flights, both to and from home, and within the islands as well. Based on personal experience, I would recommend visiting two islands in a 2-3 week trip. Recently a friend went for about 10 days and visited all four islands. Needless to say, all of the schlepping around overshadowed the fun she had!
From New York, you can fly direct to Honolulu only. From the west coast you can fly direct into Maui, The Big Island or Kauai. On our recent trip, since we wanted to bypass Oahu, we chose to layover in LA and proceed directly to Maui. Prices, schedules and availability might force your hand of where you want to start your Hawaiian adventure (and something to consider if you are trying to purchase a round trip ticket to and from the same island).
Travel between islands necessitates flying. On our recent trip, we moved from Maui to Kona via a 10 seater Cessna on Mokulele airlines. Using Google flights, I stumbled upon a flight that was significantly cheaper than those on Hawaiian Airlines. When we arrived at the airport to head to Kona, we found out we were on a commuter airline! This turned out to be a great way to save a little money and offered us a unique experience we will never forget!
Right now, there are two airlines that operate inter-island flights, Hawaiian (which also travels from the mainland and destinations in Asia/Australia) and Mokulele. These flights tend to be under an hour and under $70 each way. If you are a nervous flyer, I definitely recommend booking with Hawaiian, as their planes are larger and more like the commercial airlines you are used to flying.
What to bring to Hawaii? Check out this Hawaii Packing List for Female Travelers
Renting a Car in Hawaii
In 2005, when hubby and I first visited Hawaii, we flew into Kona (after spending a few days in Waikiki) and literally got off the plane, looked at each other and said, “I guess we should rent a car.” Unless you plan to stay only in Honolulu, you will need to rent a car to get around!
You can read my best Car Rental Tips, but I would recommend renting the smallest car that you need, if you have budget in mind. The car rental companies do not let you take the cars off paved roads, so you will not be 4×4’ing over rugged terrain. If you are interested in doing that, you can rent jeeps by the hour or day!
It is also worth noting that on the islands, traffic moves slowly. Clearly we are not talking LA at rush hour, but many main roads have only one lane, and the flow of traffic peaks around 40mph. So budget more time to drive places than you would on the mainland.
Planning what to do in Hawaii
After you get your flights and accommodations sorted, now its time to plan all the fun stuff to do in Hawaii! You don’t want to over plan each minute of your trip, but any big tours or luaus that you want to attend – be sure to make reservations ASAP. The best stuff will book up and you don’t want to be disappointed!
On our Hawaiian trip, a Molokini Crater snorkeling tour and a Luau were our big activities, and big expenses! I did book each of these well in advance. It’s hard to sort through all the options, but look for tours that have consistent good reviews. I used Pinterest to plan our Hawaii trip – I loved reading first hand experiences from families and travelers. I also, like with all things travel, checked for online discounts and Groupons for the things I wanted to book.
Once you plan some of the big activities, you can fill in the rest of your days with trips to the various national parks, and of course the best beaches in the world! Remember, beaches in Hawaii are either free or have a minimal charge to park. I’m also pretty confident there is no such thing as a bad Hawaiian beach.
See Hawaii By Cruise Ship
Another way to see all four major islands – on Norwegian Cruise Line’s Pride of America. This ship does a seven night, round trip, weekly sailing from Honolulu.
Taking this cruise allows you to see a lot in just seven days. Plus you sleep and eat on the ship, so can help keep your budget in check. We love sailing on Norwegian, the service is top and its a great vacation! Even though I’ve been to the Hawaiian Islands three times, I’d love to do the Pride one day!
And my best Hawaii planning tip – Don’t forget to make time in your plans to stop for a shave ice! Be sure to sit back, relax, and enjoy the magic of the Hawaiian Islands!
OTHER AWESOME HAWAII POSTS:
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