By Deal or Destination? How do you travel?

a room with a table and chairs
Park Hyatt Zanzibar Royal Residence for only 30K per night. Does it make sense to plan travel around a deal like this one?

When planning a vacation, do you decide your destination and then look for travel deals? Or, does the travel deal determine your destination?  This question has been on my mind lately as I’ve been scouring Hyatt hotels for the best premium suite deals.  For example, when I stumbled upon the fact that the Park Hyatt Zanzibar Royal Residence was bookable for only 30,000 points per night, I wondered if I could someday build a trip around this deal.  Is it crazy to let the deal lead your path?

As I thought about this, I realized that many times in the past I’ve let deals drive the destination.  And, as a result, I’ve had great experiences that I would never have stumbled upon if not for the deal.  On the other hand, I’ve also had great experiences on trips where the destination was the primary goal.  Deals, if any, were secondary.  I don’t think there’s a right or wrong path to take here.

I skimmed through the big vacation trips I’ve taken in the last 10+ years.  Was I more often driven by the destination or the deal?  In most cases, it was a combination: I had a destination in mind, but the deal made it real.  Still, I forced myself to categorize each trip by the primary driver: destination or deal?  The cool thing about reviewing these was seeing how often future trips were influenced by past ones.  Sometimes a deal driven trip led later to a destination driven trip, and vice versa.

Before counting up my trips, I thought that the majority were deal driven.  And I was right, but only barely.  I count 12 deal driven trips and 11 destination driven.

In the following sections I put either “deal” or “destination” in parentheses depending upon which was the primary driver of the trip.  In most cases both deals and destinations were involved, but I tried to identify the primary driver.

2008 Hawaii (destination: Maui)

a waterfall in a forest
The Pools at ‘Ohe’o (AKA the Seven Sacred Pools)

We had wanted to go to Hawaii for years and finally pulled the trigger.  We found that flight prices were cheaper when booked as a vacation package (flight + car rental), and we rented an ocean-side timeshare condo to keep lodging prices down.  This was one of my favorite trips ever.  We fell in love with Hawaii and vowed to return to try out the other major islands.

2009 Australia (deal: cheap flights)

people walking on a bridge over a cliff
Three Sisters rock formation in the Blue Mountains. We took a day trip from Sydney.

A month or two before this trip, I remember my wife saying that she read in the New York Times that there were amazing travel deals to Australia.  And it was true.  Cash rates were far lower than usual.  We only had a week free that summer to travel, but we booked it anyway.  Thanks to the long flights and time zone challenges, we only had 5 or 6 days in Sydney, but still we loved it.  We realized then that we can explore the world even if we have minimal vacation time available.

2010 Hawaii (destination: Big Island)

a walkway in a cave

Hawaii’s big island didn’t disappoint. To save money, we repeated our trick of booking a vacation package consisting of flights and a rental car (it was cheaper than booking flights separately), and we again rented a timeshare condo.

2011 Hawaii (destination: Kauai)

a sandy beach with people on it

Yep, another Hawaii trip.  We again booked a flight and rental car vacation package, but this time rented an apartment from an individual (rather than renting a timeshare as we had done before).  We were blown away by how beautiful this island is!

2012 Northern Michigan (deal: 44K Club Carlson promo)

a sign on a building

Northern Michigan is a great place to visit in the summer.  And so we did.  But we were at least partially motivated by the fact that Club Carlson (now named Radisson Rewards) was offering a huge number of points for checking into each one of their brands.  And Sault Sainte Marie, MI, was one of the few places in the United States with a Park Inn.  It was a dumpy hotel so we visited only to check in to two separate rooms (one for me and one for my wife) so that we could collect the promised 44,000 points each.  The rest of the trip was destination driven.  If memory serves, we had a great time visiting Tahquamenon Falls, Petoskey, Traverse City, and Glenn Arbor.

2012 Alaska (destination: Alaska cruise)

chairs on a deck overlooking a body of water
Celebrity Millennium cruise from Seward Alaska to Vancouver BC.

We had heard great things about Alaska cruises.  In the end, though, we didn’t love it.  We decided that we’re not cruise people.  But the train ride from Anchorage to Seward was incredible.


2013 Around the world (deal: use miles for first class)

a man sitting at a table with food on it
Enjoying a meal in Singapore Suites first class.

At this point I had been collecting points and miles for a couple of years and I wanted to experience some of that first class goodness that I had been reading so much about.  So, I flew Lufthansa first class from Detroit to Frankfurt.  Then, Thai first class to Bangkok.  I spent 4 days in Bangkok before flying Thai first class to Hong Kong and then Singapore Suites back to the United States.  Awesome trip.


2014 Paris & Switzerland (deals: Lufthansa 1st, Park Hyatt Vendome, Club Carlson 2 for 1)

a table with plates of food and drinks
Breakfast at the Park Hyatt Vendome

This awesome trip was driven by a combination of deals.  For one, Lufthansa first class awards were wide open and available far in advance (which is unusual) from Toronto.  Second, Hyatt used to offer a free status challenge.  This would give you temporary top tier status.  So, by timing it right, I was able to use points to book the ultra-lux Park Hyatt Vendome with points, and my temporary top-tier status ensured that we got an awesome upgrade and free room-service breakfast.  And then there was the Club Carlson (now Radisson Rewards) Visa which used to offer two award nights for the price of one.  My wife and I each had the card, so we booked two back to back two-night stays at the Radisson Blu, Lucerne in Switzerland.  Our favorite part of the trip, though, was destination driven: We spent a few nights at a wonderful little inn in a Swiss mountain village named Mürren.  We loved everything about it.


2015 China (deal: $400 mistake fare)

a long stone wall with a path leading to Great Wall of China

American Airlines had a mistake fare: Round-trip business class flights to China were pricing at around $400.  I jumped online and booked my tickets for the only time-slot I had available.  This had me departing on a Tuesday and returning the same week on Friday.  Of course, it takes a while to get there, so I arrived late Wednesday evening and departed Friday morning.  In other words, I had Thursday to see China.  I did my best to see it all :).

See: One day in Beijing. Fewer words, more photos)

2015 National Parks (destinations: Arches, Bryce, Grand Canyon, Zion, and the Hoover Dam)

a group of houses with a stone chimney

This was an awesome 2-family trip where we spent most of our time hiking through the incredible beauty of a number of national parks.

For full details about this trip, see: Arches, Bryce, Grand Canyon, Zion, and more via trains, planes, and automobiles.

2015 Chile (destination: visiting a friend)

a room with a table and chairs

The primary purpose of this trip was to get away and visit a friend in Santiago Chile.  Of course, we took advantage of deals to get there (we flew AA first class with miles) and for lodging (we stayed at the Grand Hyatt Santiago and we were upgraded to the Diplomatic Suite, shown above).  Unfortunately, this hotel is no longer a Hyatt.

For details, see: To and from Santiago Chile, my favorite Diamond upgrade ever, and a weird Centurion Lounge lost and found policy.

2016 Necker Island (deal: 1.2 million miles)

two men standing next to each other

A week on Necker Island now costs 1.5 million Virgin Atlantic miles, but at the time I went it cost “only” 1.2 million miles.  I know that doesn’t sound like a deal, but it was definitely this award opportunity that led us to the island.  This was a trip of a lifetime — totally worth it.

See: Is Necker Island really worth 1.2 million miles?

2016 Costa Rica (deal: Andaz Peninsula Papagayo Costa Rica)

Andaz Papagayo Room with a View

We like to vacation somewhere warm each winter to get away from the Michigan cold.  Often this means visiting my wife’s family in Florida, but this year we decided to go farther afield.  I had read great things about the Andaz Peninsula Papagayo hotel in Costa Rica.  At the time, the hotel cost only 15,000 points per night (now 20,000).  And at the time of year we wanted to go, they would have charged nearly $1500 cash per night after resort fees!  So, the 15,000 points per night was an absolute steal.  What an awesome trip!

Read about it here: Huge value from Hyatt: Andaz Peninsula Papagayo Costa Rica

2017 San Diego (deal: Fairmont free night certificates)

a pool and a building with trees and bushes

For this trip we knew we wanted to go somewhere relaxing and my family preferred staying within the US.  Well, I had to use up my Fairmont free night certificates, right?  So, away we went to the Fairmont Grand Del Mar.

Read about our trip here: Booking a luxury trip with points and deals.

2017 Italy (destination: Tuscany)

a man standing in front of a field of trees

To celebrate my 50th birthday, we booked a culinary tour of Tuscany.  Other than using miles to get there and back, and a deal on a hotel night in Florence, this trip wasn’t about saving money.  We absolutely fell in love with Tuscany.

I haven’t written about the culinary tour, but you can see my photos from Florence here: Florence! Fewer words, more photos

2018 Japan (deal: Delta One Suites)

a man sitting at a table with food on it
Greg’s son enjoying Udon Noodles in Kyoto

I booked the return ticket for this trip before booking anything else.  Delta One Suites were brand new and one of the first routes served was between Detroit (my home airport) and Tokyo.  I found that I was able to book Delta One Suite saver-level award seats near the end of schedule, so I booked them.  We spent half of our trip in Kyoto and half in Tokyo.

Unfortunately, I don’t think I ever wrote up our trip itself, but you can read about our flights here: Delta One Suite Review. Detroit to Tokyo Narita and Back.

2018 Germany & United Kingdom (deal: Wyndham 15K)

a group of people sitting at a table

The genesis of this trip was a Wyndham deal where we were briefly able to book any property for only 15,000 points per night.  With another family, we scoured the website for amazing properties and landed on this 8 bedroom Manor House in Dorset, United Kingdom.  Around this target, we wove a much broader trip that started in Germany (Cologne, Baden-Baden, Neuschwanstein Castle, Munich) and continued on to England (London, Highclere Castle, Bath, and Dorset).  Most of the individual stops were destination driven, but the overall trip wouldn’t have happened if not for the Wyndham deal.  And we’re very thankful for that because the trip was epic.

See: Seeking value, finding adventure for 15K Wyndham points per night

2019 Grand Cayman (destination: visit friends)

a group of people on a beach with umbrellas

To get away from the winter chill this year, we took the opportunity to visit friends we had made on Necker Island.  We paid for the trip with points and miles, but the destination was chosen first.

See: Westin Grand Cayman Seven Mile Beach Resort Review.

2019 Cornwall, UK (destination: hike South West Coast Path)

a green hills with a cliff and a body of water

This trip was partly inspired by our trip to Dorset the year before.  During the previous trip we saw firsthand how awesome the British coastline was.  On this trip we found a service that moved our bags from one inn to another as we hiked the South West Coast Path around the tip of Cornwall (starting from just east of St. Ives, we hiked around the tip, and ended at Penzance).

In this silly video I show off the hike:

2019 Hawaii (deal: Delta lie-flat awards + Marriott certificate)

a view of a valley with trees and mountains
View of Na Pali coast viewed from Koke State Park

Delta had just added nonstop service between Detroit and Honolulu and then blogs (like Frequent Miler, of course!) reported that first class awards were (at the time) wide-open  and bookable for only 37,500 miles one-way with Virgin Atlantic miles.  I booked it and encouraged friends to do the same (they did).

I also had a Marriott 7 night stay certificate that I wanted to use before it expired.  As you’ll see from my review, this was perfect for a group trip: Koloa Landing Resort at Poipu (Kauai, Hawaii).

2019 Grand Cayman (deal: IHG free night certificates)

a pool and beach with buildings and trees

Even though we had been to Grand Cayman in the beginning of the year, we decided to return because we had three uncapped IHG free night certificates that were about to expire and I believed that the Kimpton Seafire resort would be our best use of those certificates.  The resort was fantastic.

See: Kimpton Seafire Grand Cayman. Bottom Line Review.

2020 Colombia (destination)

a man and woman standing on a ledge with a lake in the background
Lake Guatavita

This year, my mom and I decided we should take a trip together.  We knew we wanted to go someplace warm, but otherwise we were unconstrained.  I had heard great things about Colombia and neither of us had been before, so we chose to go there.  We originally planned to visit two cities, but with only 5 days we ultimately decided to stay in Bogotá.  We had a great time.

See: The Artisan D.C. Hotel Bogotá, Autograph Collection (Marriott). Bottom line review.

2020 California Carmel Valley & Big Sur (destination)

McWay Falls on a beach
Pfeiffer Big Sur State Park

My wife and I were supposed to go to Singapore for her work, but that trip was scuttled due to COVID-19.  Since we had time blocked off, we decided to take a domestic vacation.  Since we love the California coast, especially around Big Sur, we decided to return to that area.  It was only after picking the general area that I found two great Hyatt resorts in the area: Carmel Valley Ranch and Ventana Big Sur


What’s your approach? Deal or Destination?

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Destination, deal and also season driven. It was important to catch moments like Japan during cherry blossoms, Montreal in fall or in some cases shoulder seasons to avoid the crowd etc.

I’ve never taken a trip purely based on a great deal though. I usually come up with 4-5 trips I’d like to take and then wait for the right deal to come along or the right awards availability to open up. I imagine becoming more destination driven with time as I cross things off my list.


A combination for me also. Our best “deal” was participation in an anniversary promo with Small Luxury Hotels 15(?) years ago. We agreed to pay $20.05/nt for whatever deal SLH randomly assigned us. We “won” the Galapagos Islands, leaving in about 6 weeks! That was a trip of a lifetime we otherwise probably would have never booked.


By volume, we are deal-driven. Using the SWA CP, we often take weekend trips to anywhere SWA flies. We’ve done dozens of these trips over the years, almost all on points.

Most of the international trips are destination-driven. There are exceptions like $300 flights to Spain and Etihad apartments from Sweden.

If an amazing deal pops up, we’ll try to go for it. But many of those deals require flexibility on travel dates so we often don’t get to partake.


I’ve described myself as an “opportunistic” traveler.

I just like traveling period, so when I was in my 20s I would just go wherever there were good deals because I wanted to go everywhere at some point anyway.

I guess now that I’m in my late 30’s and have been to over 100 countries, it’s become somewhat more “destination-driven”, but it’s still in the middle. I’ve got time to take 2 weeks off in September? Let’s check to see which of the places I wanna go that’ll be nice at that time has the cheapest flight prices. Gonna be in Florida for a week for work? Let’s see if I can get from there to anywhere in the Caribbean that I haven’t been yet for the weekend before/after. My parents want me to join them for a week vacation in Iceland? Sure, but let’s see if I can tack on a few days in Greenland or the Faroe Islands since it’ll never be more convenient for me to get there.


Actually I am just about to embark on a European castle road trip (european reader here). Booked the first night at an European castle for 15k Marriott points and then somehow built itinerary around that. I love destinations too – I am trying to hit every country but over my entire lifetime. Calculated I need about 3 new countries every year and somehow always managed to factor that in my plans. The reason Gwinganna I like going to places which are undiscovered… were it not fit my goal I wouldn’t have had a blast in Lichtenstein or Azerbaijan.


Autocorrect fail: not Gwinganna but being and for my goal


It was amazing. If you go next year I’d recommend to go during their national day when the king opens the castle to the public. Also great in autumn to see the foliage. It’s a great place for wine as well and overall very quaint. We stayed at the Relais and Chateaux property – quite expensive but doable since we were splitting costs. It has some of the best pool and spa facilities around and amazing views! Best omelette too!


Which hotels did you use in Japan? I don’t remember you saying.


I do not think Greg ever mentioned it. He mentioned he does not like to review hotels in general. Bottom line review is the way for Greg to put out more hotel reviews.
Personally, I would like to know more about the trips. Like any tips in the visiting cities, funny story, or Nick’s favorite-Greg’s confession. It may be a good addition to the future FM on the air. Talk about some past trips since no new trip is happening.


Thank you!!!


I was waiting for the punchline… did you find that you had greater enjoyment where you were spurred by the deal, or where you decided first and then looked for deals? Or neither?

Larry K

What a great topic and article. While I’ve had the issue in the back of my mind I’ve never really thought about it explicitly in these terms and now I think I am going to give it some hard thought. I’ve done both and my seat of the pants thought is that the destination driven trips were mostly better. But not universally so.


I think the steps for me go:

  1. Create a mental list of all the places I want to visit, time of year, and length of trip
  2. Wait for an airfare deal or decent airline redemption that matches a place for the list
  3. Book trip 🙂

Loved this post! Your blog has always stood out and you have definitely done the best job of keeping things relevant during this time when most of us are grounded. Maybe because you and Nick just generally seem like nice, down-to-Earth guys, but I genuinely look forward to visiting your site first thing each morning.


And I forgot to add, our own travel is definitely a combination of both. We went to Iceland on a whim several years ago when Wow Airlines launched service for $99 and had the best time. And we visited Dubai last year because of the amazing value we were able to get in hotels with points. But several other trips (Africa, Galapagos) were destination driven and expensive, but using points for airfare really helped offset the costs of the cash portions (safari lodge, Galapagos cruise). By the way, we went on an Alaskan cruise and totally agree with you – we aren’t cruise people. But, before the cruise we drove from Anchorage to Denali for a few days and LOVED that part! We have a trip to Antarctica planned for December, which is now very much looking in doubt . . .


It is a combination for me. Initially, I would have said I lean more towards a destination focus, because I rarely choose to go somewhere just for a deal, but in many cases, the availability of a deal is the deciding factor for choosing between destinations and/or for taking trips that are not “bucket list” destinations. Also, learning about deals made me aware of several destinations that became places I really wanted to visit.

One kind of surprising realization when considering my travel since I got fully engaged in points and miles about 10 years ago is how large an influence hotel “deals” (like free night certificates, great redemption value properties) have had on my travel plans. This is especially true for many shorter US/Canada trips that basically were “extra” trips enabled by free nights. Back in the day, the Radisson BOGO award nights factored into my decisions about many trips, both domestic and international.

Also, great (now dead) airline redemption values such as the USAirways routing and stopover rules that enabled flying RTW in business class for the price of a European round trip and British Airways 4500 mile short haul redemptions influenced many of my previous travel decisions.


I did Deal trips back when IHG Point Beaks nights were only 5K points. Now it’s mostly Destination trips.


Probably about 50/50. We have certain events around the world that we want to attend that are destination driven but we have the work flexibility that if a deal comes up, we’re on it. Last year, we had trip to Belgium in April and a trip to Sweden in end of May that were event driven destinations. $375 flights to Croatia from our regional airport came up so we squeezed in a week in Croatia between the two planned trips. Three times to Europe in six weeks was a bit overboard. 🙂


I’m lucky that I get to travel multiple times a year. I make sure that one of those trips is always destination-focused…somewhere that’s been on my wishlist that I usually book far in advance and enjoy the research/anticipation for months leading up to it. The other trips are often “opportunity” focused, which might mean a good deal but could just as easily be spurred on by weddings/events or work trips that get extended.

FWIW, I do tend to enjoy my destination trips a little more. I guess I’m good at guessing where I want to go!


I’m more destination. I just choose to go with my interests but still try to get the best deal.