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Planning a Trip to Hawaii? 7 Things to Keep in Mind!

Updated: 3 days ago

A lot of thought and care needs to be put into planning a trip to Hawaii.  Of course, that is why I recommend using a travel advisor (me)!  I have 7 things to keep in mind as you go into the planning process.  Let’s dive in. . . .

Adventure travel in Hawaii

Determine if you want to stay on one island or island hop?  

As you’d imagine there are pros for each. 

Single island itineraries are easier to plan and can be less hectic, and since all of your time will be spent in one place it will allow for full immersion into all the island has to offer.  You also won’t have to deal with inter-island flights which can be expensive and take time from your vacation schedule. 

On the flip side, island hopping can help if you’d like to experience as much of the state as possible in one trip, allowing you to compare the offerings and vibes on each island.  A great choice for island hopping is a cruise.  You may choose from a more traditional ocean cruise or an exciting expedition cruise around this island paradise.  Both cruise types eliminate some of the more common hassles associated with island hopping.

Hawaiian Plumeria

Decide which island fits your style.

There are eight major islands that make up Hawaii with the most frequently visited being Oahu, Maui, the Big Island of Hawaii, and Kauai.  

Each island has a unique culture, history, landscape, vibe, and things to do and see. 

Choose Oahu if you are looking for an island with a city vibe that’s near/on a beach. (Honolulu/Waikiki)!  Think lively clubs, bars, nightlife, shopping, and dining. 

Maui is for those who want a tropical paradise with a little of everything – beach, hikes, volcanoes, rainforests, resorts, and nightlife. 

The Big Island is known for its multiple climates and abundance of natural attractions, including Volcanoes National Park. 

Kauai is known as “the Garden Isle” and for good reason.  Its lush landscapes make it a perfect escape for those looking for a more outdoor and active vibe. 

Hawaii Sea Turtle

Have a budget. 

Your trip will likely have a lot of components – air, hotel, transportation, activities, and food. 

Hawaii offers a wide range of options in both style and price point for accommodations, activities and food.  

I recommend you try to come into the planning process with a budget range in mind. 

A budget range will help you set expectations in the recommendation process and facilitates my creation of an itinerary that meets your specific needs.

Hawaii coastline perfect for an expedition cruise visit

Book well in advance. 

The most critical components of a trip to Hawaii (or anywhere, actually) are flight and hotel. 

Pricing for both is subject to change at any time and is usually based on supply and demand. 

So, typically, the earlier you book the better. 

Once your dates are solidified and options selected, place a deposit, or complete the booking! 

If you’re considering travel during a peak time this is even MORE important.

Plan activities in advance. 

Do NOT wait until you’re in destination to book tours and excursions. 

Put together your must-do list and purchase. 

Again, the sooner the better, since space on some activities is limited and can sell out quickly. 

It will also help in sticking to your budget.

USS Arizona Memorial Pearl Harbor Hawaii

Know what to pack

Thinking about your trip and what it involves can help in determining what to pack. 

For the most part, the vibe in Hawaii is relaxed, but if you have more active things planned (hikes, biking, etc.) you want to pack for that. 

I am sure that if you have a strenuous hike planned, you don’t want to forget your boots. 

Flip flops at all other times are perfect, but I am sure you don’t want to hike in them. 


Likely a rental car will be recommended, but at the end of the day, it is your call. 

If the thoughts of driving in an unknown place, heavy traffic (especially on Oahu) and sometimes expensive parking (even at hotels) don’t appeal to you, we can work around it. 

Transfers and ride share options can always be discussed. 

Adventure travel in Hawaii

Hopefully these 7 things to keep in mind for Hawaii, will help you as you plan your travel.

I’ll help keep these things top of mind as we go into the planning process and certainly as you’re getting ready for the most exciting part – the trip itself! 

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At Milestones & Mondays Travel, I transform wanderlust into adventures & unforgettable experiences for active travelers looking to get away from the crowds and deeper into the destination with expedition cruises, small ship cruising, small group active vacations and solo travels for those seeking experiences beyond the ordinary.

When clients turn their travel planning over to me, they receive a custom itinerary for their trip based on their travel style, desires and budget as well as a trusted advocate in their corner. I help them navigate the vast options and challenges in planning trips that are off the beaten track, with unique and immersive experiences, and I am there to provide support as needed before, during and after travel.

Along with my premium travel planning services, many of my clients receive additional amenities and benefits when booking with me and my preferred luxury travel suppliers.

I invite you to browse my website and encourage you to subscribe to my email list to receive travel inspiration and the latest travel opportunities delivered to your inbox each week.


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