Wayne’s 2019 10 Day Ultimate Waikiki Itinerary


Welcome to Wayne’s 10 Day Ultimate Waikiki Vacation Guide. As a frequent visitor to Waikiki, I thought I would share the planning and our travel experience that went into the making of this Waikiki vacation.  For the record, the average stay in Waikiki is 8 days so hopefully, you can use our tips accordingly.

Trip Preplanning

Buying Plane Tickets To Honolulu

Flying to Hawaii can be expensive. Almost exclusively we fly Hawaiian airlines into Honolulu. Because we can start our trip any day of the week, I like using Hawaiian Airlines monthly price calendar to decide when we leave. Pro tip: January to April is the most expensive time of year to fly to Hawaii. Optimizing our travel dates around the Hawaiian monthly price calendar makes for the cheapest fares possible.

Daylight Savings Time:

Hawaii and Arizona are the only two states that don’t observe Daylight Savings Time, so depending on the time of year you visit Hawaii, you may inherit an additional hour of jet lag. 

Where To Stay:

As with everything, it depends. Waikiki Beach is broken down into 9 sections, with some being much more crowded than others. 

Waikiki’s 9 Beaches (East to West):

  1. Outriggers Canoe Club Beach
  2. Kaimana Beach
  3. Queens Beach
  4. Kapiolani Beach
  5. Kuhio Beach
  6. Royal Moana Beach
  7. Gray’s Beach
  8. Fort Derussy Beach
  9. Kahanamoku Beach (In front of Hilton Hawaiian Village)

If you are looking to be “part of the action”, restaurants and shopping the eastern part of Waikiki Beach is what you’re looking for, but it’s definitely more crowded. If you are looking for fewer crowds, then the western part of Waikiki will fit the bill. Personally, we like being with arms reach of good food and shopping but stay away from the bigger crowds on the west side near Fort Derussy/Kahanamoku beaches.

If you are vacationing with a larger party, an Airbnb will probably be your best option. If you are vacationing in a smaller party then a hotel might be your better choice. See our article on what a Waikiki vacation will cost. 

Dinner Reservations:

Waikiki can be very busy, so I like to use Open Table to make dinner reservations about a month out. When making dinner reservations, I’d recommend planning around the beautiful sunsets Hawaii has to offer. A quick internet search will give you the sunset time for when you are visiting. Also, don’t forget to check out and plan around the fireworks every Friday at the Hilton Hawaiian Village (see our video), which starts around 7:45. 

Primetime in Waikiki for dinner starts around 6:30 pm, so if you are like us and you’ll be using Uber or Lyft, you’ll start seeing fares increase around that time. On our latest trip, Uber fares seemed to consistently beat Lyft’s fares by $2 or $3 dollars. Keep in mind you can pretty much get from one end of Waikiki to the other for around $10. Don’t mess with the rental car or parking hassle.

Where Did We Eat In Waikiki 

We like to mix up where we eat with old favorites and new discoveries that we can share with you! So here is our 10-day dinner plan and I’ll give you our overall recommendations below:

My top 14 Waikiki Restaurants are:

Breakfast:

Locals Restaurants:

Coffee Shops:

High End Dining:

  • Azure (The tasting menu is fabulous)
  • Roy’s Waikiki (While a restaurant chain, it’s a go to when in Waikiki)

Pre Waikiki Shopping:

After many trips to Hawaii, I’ve revised the travel essentials that I make sure I pack or get an order in to Amazon before I leave. You can see my list of travel essentials here!

Hawaiian Airlines Bidding For First Class:

Hawaiian Airlines along with 17 other airlines now offer “upgrade bidding”. The minimum time spent flying to Hawaii is going to be at least 5 hours, so if you are looking for more amenities, this could be the option for you!

Around a week prior, Hawaiian will send an email offering to participate in the upgrade bidding. When you go to the website they will have a required minimum bid. Usually, the day prior you’ll receive an email if your offer was accepted or not. I typically bid the bare minimum and we’ve had a 66% success rate (your mileage may vary). Hawaiian’s couch seating is pretty comfortable, so I typically keep my “upgrade” bids to a minimum.

Tips for Successful Bids:

Look how full the airplane is. Visit the airline’s site to make a “dummy” booking for first-class This will give you insight as to how many open seats there are and you can adjust your bid accordingly. Even though I place the minimum bid, it’s probably a better strategy to go slightly above minimum. Don’t fall for the email from the airline trying to get you to increase your bid. 

Airlines offering “upgrade bidding”

Transportation To and From Honolulu to Waikiki

We use to rent a car at the airport but we’ve given up that practice for a few years now. It’s cheaper for us to use Uber or Lyft to get to Waikiki. A typical trip using a larger vehicle (for our luggage) is around $38 each way.

We’ll rent a car for a few days on the trip but not the whole time. It cost more in taxes to rent from the airport and if you factor in hotel parking fee per night, I believe it’s better to just rent a car for the days you know you want to explore the island and use Uber/Lyft for all other short trips within Waikiki. There are many rental companies in Waikiki and usually at least one in each hotel.

Hawaii Relaxation Plan

Admittedly,  the average stay in Waikiki is 8 days, however, I typically stay ten. My recipe for escaping stress is fairly simple. Days 1-4 you don’t do anything other than relax on the beach or poolside. Have some beverages and naps and enjoy Waikiki’s beach and pools. Following day 4 every other day spend half a day exploring the island and the other half beach or poolside. Reserve a couple of full days for longer excursion such as North Shore or Waimea Falls. See our article on the Top 20 Best Days Trips From Waikiki.

Wayne’s Top 12 Waikiki Things To Do

We’ve been to Waikiki enough that our adventuring out isn’t as much as a priority as enjoying the fabulous views and weather, but we have some favorites that we love. 

My top 12 Activities In Waikiki Are:

I hope you found my travel tips helpful. Checkout (and subscribe) to our YouTube Channel as we start to grow our video content. Mahalo, and I hope you have the best Waikiki vacation ever!

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