Wailea Hawaii

Wailea Hawaii

I invite you to follow along as I show you how my wife and I navigated a wonderful week away in Wailea Hawaii staying in a wonderful home (AirBnB) for 4 nights, and the Fairmont Kea Lani for 2 unforgettable nights in a two-bedroom Villa, steps from Polo Beach.

We swam with Sea Turtles, rode some waves, ran on the beach, played golf, met some amazing people, and thoroughly enjoyed every moment.

We celebrated my wife’s birthday in style watching a Luau and fireworks show while enjoying a steak dinner from the comfort of our patio.

See details and photos from our entire trip below:

What we paid approx.
as a percent of retail

How we did it

Go to Wailea Hawaii – it doesn’t have to be complicated or expensive! In this chapter of the Travel Game I thought I was crushing it with the airfare deal we coordinated, but I would later find out that the airfare was upstaged by the 2-bedroom Villa we stayed in for 3 days (2-nights) at the Fairmont Kea Lani for 10% of the retail price. In the end, I organized a hell-of-a-trip of 6 nights, 7 days to Maui.

Let me paint you a picture: My home in Boulder to our “home” in Wailea…

  1. Uber from home to bus stop = FREE = American Express monthly Uber credit.
  2. RTD Bus to the airport (uses toll road so no traffic) = FREE = RTD pass comes with our apartment living.
  3. DEN airport checked baggage can be done 10 steps from getting off bus = no line down there = awesome sauce (must be 90-min prior to departure).
  4. Security line at airport = 2 minutes = CLEAR + TSA Precheck – ask me about getting global entry and TSA Precheck for FREE for 5 years, and CLEAR FREE for 3 months – I can hook you up.
  5. On-time departure on United. 7.5hr direct flight to Maui = watched 3 Oscar nominated feature length films…kidding…I watched 2 + “Gold” (Come on Mcconaughey…you said it was going to be great).
  6. Rental car = Hertz Gold Plus allows us to bypass lines and head straight to our car. This comes free with many credit cards – ask me. This is VALUABLE in Maui as most flights arrive each day at similar times and rental car shops are packed! P.S. just don’t do dollar/thrifty…it’s not worth the headache.
  7. Stop off at Whole Foods for a grocery run for the week then drive the 30-min to Wailea.
  8. Check-in to our AirBnB for 4 nights in Ekahi Village in Wailea. One can use Amex membership points and/or referral bonuses to pay for this via AirBnB. We paid full price for this (ouch I know – it goes against everything I believe in).
  9. After 4 amazing days and nights, we head down the road for 2-nights at the Fairmont. See details below.
  10. The rest is history/can be seen in our pictures and details below. I hope this inspires you to travel more, pay less, and consult with me if you have questions.


  • Summary: We coordinated a $2,000 round-trip flight for 2 on United Airlines from Denver, CO – Maui, HI for a net $22
  • Breakdown: We transferred American Express points –> Singapore Airlines KrisFlyer Miles –> Fly on United Airlines. See all the details HERE.


  • Summary: We stayed four nights at a wonderful AirBnB in Ekahi Village, Wailea Hawaii followed by two nights at the Fairmont Kea Lani in a 2-bedroom Villa in Wailea Hawaii.
  • Breakdown: We paid full retail price for the AirBnB and 10% of retail for the 2-bedroom Villa. If you’re interested in going the AirBnB route and not paying full retail price, talk to me, and I’ll show you how to use American Express Membership Rewards points and/or referral bonuses to help cover expenses. We used the Chase Fairmont credit card to get 2 free nights at any Fairmont worldwide. This credit card has since been discontinued so you can’t copy our strategy. Sorry! Talk to me about many other new and amazing strategies to stay at 5-star and 5-diamond resorts around the world for free and/or 1-50% of retail price.

Rental Car

  • Summary: We rented a Nissan Pathfinder from Hertz for the duration of our stay in Maui. We used the American Express Platinum card discount code to get over 50% off, not have to wait in line, and receive an upgrade. One must be a cardholder for this to work.
  • Breakdown: We paid $220 for the week plus $25 for gas. Retail was $470, so we saved $250 by being a Platinum cardholder and using that rate. The last time we went to Wailea Hawaii we rented from Dollar and we waited in line for about an hour before finally getting our rental. It seems that most flights arrive in Maui around the same time – mid afternoon and thus the lines for rental cars are extremely long. So, using Hertz Gold Plus Rewards was very helpful this time around.


  • Summary: I played 5 rounds of golf at Wailea Golf Club in three days! I switched between the Gold and the Emerald courses. I had the first tee time of 6:36am each of the three days, and played a 2nd round 2/3 days. I met some great people and even made two new friends. I had the opportunity to play with two of the marshalls and their advice around the greens was invaluable. Even if you would bet your life that the putt was downhill toward the middle of the island…the ball would roll toward the ocean. It was crazy.
  • Breakdown: So, in full disclosure – most of my golf trips lately have been nearly 100% free (using a variety of great options out there to take advantage of). I really wanted to play the courses at this golf club as it was a hop, skip, and a jump from our accommodations, and it comes so highly recommended. I couldn’t find a way to get it paid for. I ended up paying $555 for 5 rounds and they gave me Taylor Made M2 clubs for each round so I didn’t need to fly my own clubs over there. Cart and driving range and water/coffee and all that jazz was included. It was still the most expensive golf I’ve ever played!
  • Entrepreneurial note: I planned to take some amazing sunrise and sunset photos while playing and then packaging them up and offering them to the golf shop in exchange for free golf. Their website and photos are DECENT, relatively speaking to other top-notch courses so I thought I had a shot. However, I didn’t end up playing a sunset round, and I didn’t get my act together before we left to strike a deal. NEXT TIME!

Food& Drink

  • We had $100 in resort dollars that we used to eat at KO which has a sugarcane plantation era inspired cuisine. It was nice!
  • Included in the Villa package at the Fairmont, were 4 Buffet tickets per day to eat at the Kea Lani restaurant. So, we took advantage of that too.
  • This trip was especially nice because between the AirBnB’s full kitchen and grill, and the full kitchen and grill at the Fairmont Villa, we were able to grocery shop and cook our own meals for the most part.