My Trip Planning Process: Where to Visit Next?

One of the most frequently asked questions is how I choose the destinations for my trips. In this post, we're going to look at a few trips I'm planning to take in the future with some of my hotel certificate nights that are expiring soon.

The first step is to inventory my "stock" of certificates:

Hyatt (expires Feb 2018)

  • Two free nights (any hotel)

Fairmont (expires Feb 2018)

  • One free night (any hotel)
  • One room upgrade certificates
  • One "3rd-night free" certificate (requires two paid nights)

IHG (expires in summer 2018)

  • One free night (any hotel)

Cathay (expires in 3 years)

  • 50,000 Cathay points

Two Player Mode

Since I'm traveling with a friend, they also have an inventory of free night certificates to use:

Hyatt (expires in summer 2018)

  • Two free nights (any hotel)

Ritz-Carlton (expires in Oct 2018)

  • Three free nights (Tier 1-4 hotel)

Potential Destinations

For each card, we have a few destinations in mind. 


  1. Park Hyatt Tokyo: We're big fans of Tokyo and read raving reviews about the view from the Park Hyatt Tokyo. 
  2. Park Hyatt Sydney: The hotel is located right next to the Sydney Opera House. Visiting Sydney is on our bucket list, so why not do it in style? The main thing deterring me from booking is that the rooms look plain. 
  3. Grand Hyatt Kauai: The Hyatt in Hawaii looks beautiful, but we're hesitant to book because the food is notoriously expensive. Sure, we can get flights and hotels for "free," but food on the island is typically 2x the prices in San Francisco.
  4. Park Hyatt Maldives Hadahaa: Dream location, but it's far to travel to, and the food and activities are also incredibly expensive.


For IHG nights, already I booked two nights in Bora Bora. Since the certificates aren't expiring until late 2018, I'm not as worried.


For Fairmont, I have three different certificates to redeem before February. I was thinking of taking a trip to Whistler, Canada for skiing. My strategy is to use the Citi Prestige to book four nights by phone, and use the certificates when I check-in. Here's the breakdown:

  • Booking the nights
    • Book the nights with the Citi Prestige for four nights
    • Make a separate booking for a single night (using the free night certificate)
  • Stay
    • At check-in, tell them that the single night is the same party
    • Apply 3rd-night free certificate at checkout
  • Final Results
    • Using the Citi Prestige, 3rd night free, and a free night
    • Pay for ~2 nights for a 5-night stay
    • The nightly rate is still $550/night since it's peak season
    • This comes out to paying $1,100 for $2,750 in value

Reading data points from Flyer Talk, you can use the 3rd-night free certificate when you arrive at the Fairmont and have them remove the amount when you arrive. 

The final thing I'm going to do is use the free night as well. This means I'm paying for two nights to get five nights. Alternatively, I could just use the free night in Vancouver. 


My Ritz-Carlton nights were supposed to expire in November, but I called the reservation line on the back of the card to get them extended for another year. I'm was looking to redeem my nights in April, and the agent was nice and extended my nights.

The three places we're considering are:

  1. Ritz-Carlton, Osaka: The case against Osaka is that it's a Tier 3 hotel, and the certificates work for Tier 1-4, so it's like losing value. 
  2. Ritz-Carlton, Okinawa: The Ritz-Carlton in Okinawa is a resort and hard to get to, but it's supposed to be an amazing experience. 
  3. Ritz-Carlton, Kapalua: The Ritz-Carlton in Hawaii is in an isolated part of the island. The cost of food and activities is another factor to consider. 

For all of these hotel nights, I'm still in the planning stage. A large factor is if I can find a good deal to fly to any of the destinations.