How to Plan Your Hawaiian Dream Vacation

Sunset Sippin

Hawaii!  Just the thought of kicking back on a white sand beach, Mai Tai in hand, and listening to the waves roll in… mmm, what a dream.  This dream may be much more attainable than you have ever imagined!  No, you don’t have to have a trust fund, pinch pennies for years, or win a sweepstakes… You could be on your way to the islands sooner than you think.  Follow along with our ten tips to plan this amazing getaway now!


TIP #1: Follow our Guide to Fly Roundtrip to Hawaii for Only $33

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Impossible?  Not at all!  We show you how to use Chase Ultimate Rewards points to book a roundtrip ticket for only $33!  You can earn these points from the Chase Sapphire Preferred, Chase Ink+, or the Chase Freedom Card.  It only takes 25,000 UR points + $33 for a roundtrip ticket!

TIP #2: Island Hop

Many people will tell you to pick one island for your vacation.  When we planned our trip, quite a few people said we would need to spend two weeks on one island.  Maybe that works for some people, but we found island hopping to be the best way to go.  We got to experience three very different islands (Kauai, Oahu, and Maui), and we were never bored.

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American Airlines miles make it easy to fly from island to island.  Simply book award tickets on Hawaiian Airlines via AA.com for only 5,000 AA miles (4,500 if you have a Citi AA credit card) per segment + $5.  Award seat availability can be a bit spotty, so make sure these flights line up with the flight you plan to book from step 1.  If you cannot find award seats, these tickets are usually pretty cheap at $80-$100 per segment.

TIP #3: Book Big Adventures in Advance

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Kauai Helicopter Tour

Hawaii offers some awesome opportunities for one-in-a-lifetime experiences.  If you want to take a Helicopter Tour of Kauai, snorkel with sea turtles at the Molokini Crater, or dine at one of the world’s top restaurants, be sure to book in advance!!  These experiences are popular, and they will often sell out.  You don’t want to miss out because you waited too long to book.  Also, some tours offer advanced booking discounts… be sure to ask!

TIP #4: Do Not Over-Schedule

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This may seem to conflict with Step 2.  While you should see more than one island, you should not over-book yourself.  Between snorkeling, helicopter tours, and hiking the rocky coastline, make sure to leave time for relaxing on the beach or sipping Pina Coladas by the pool.  You’re on vacation after all, you should definitely kick your feet up and relax!

TIP #5: Pack Carry-on Bags Only

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Baggage Claim was CRAZY – Skip it!

I say it over and over again: DO NOT check bags.  Sure, you can lug more crap along if you pack a bigger bag; however, you will have to pay for the checked bag on each leg and waste time waiting at baggage claim.  With island hopping built into your itinerary, checked baggage fees can add up quickly!  With our carry-on bags, we were able to skip the lines at check-in, avoid fees, and breeze past the baggage claim mob.  Think about it… you’re traveling to the ISLANDS, so you do not need heavy clothing.  Keep it light and you will be grateful you did!

TIP #6: Bring Travel-Size Sunscreen and Bug Wipes

Since you will be packing carry-on bags, your liquids will be restricted to 3.4oz each.  Hotels provide most of what you need, but sunscreen and insect repellant are necessities in Hawaii.  To fit these into your carry-on bags, grab the following items:

  • Family Sized SPF-50 Sunscreen – Twelve ounces of high-SPF sunscreen to protect from the intense Hawaiian Sun.  This is much less expensive than buying actual travel-sized sunscreen.
  • Four Travel Sized 3.4oz Toiletry Bottles – Fill these bottles with sunscreen for easy packing in your carry-on.  Four mini bottles will hold a family-sized bottle of sunscreen perfectly.
  • Insect Repellant Wipes – These wipes work very well, and TSA won’t hassle you for trying to carry a full-sized can of bug spray.

TIP #7: Bring Athletic Shoes

Na Pali Coast cliffs
Hiking the Na Pali Coast

While most pictures of Hawaii feature beaches, do not make the mistake of only packing flip-flops.  Some of the most breathtaking memories from our visit came from our hiking adventures.  You will need good athletic shoes to hike the Kalalau Trail, Lanakai Pillboxes, and Diamondhead Crater!  To save room in your carry-on, just wear these shoes for the flights.

TIP #8: Pack Snorkeling Gear

Screen Shot 2015-11-13 at 2.57.54 AMThis may seem odd, but packing your own gear can save big money.  Resorts like to charge rental fees for snorkeling gear.  One resort we visited charged $9/hr or $40/day to rent a mask and snorkel!  This snorkel set from Amazon costs what you would pay for a 2-hour rental.  We brought along two of these sets, and they fit easily into our bags.

TIP #9: Buy Snacks/Beer/Liquor Upon Arrival

Another cost-saving tip is to buy your snacks and drinks at a local grocery store.  We stopped by a store on each island to buy a box of granola bars and a six-pack of local brew.  The granola bars were great for our early-morning hikes.  I probably don’t need to explain how expensive drinks are at resorts, so buying beer or liquor at a local store is a much better deal.  Mix a drink in your room before heading to the pool!

TIP #10: Consult our Guides and TripAdvisor 

We are putting together a guide to each island we visited.  You can find the list of posts here for Kauai, Oahu, and Maui.  We had a blast, and Brooke built some adventure-filled itineraries.  However, we obviously didn’t do everything on each island.  For a full list of all possible activities, be sure to check TripAdvisor.

Final Thoughts

Hawaii is incredible, and we hope that you have as much fun during your visit as we did.  Hopefully these tips help you plan an amazing and memorable vacation.  For those who have visited the islands, is there anything we missed?

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