After staying put in Toronto for a few months following two whirlwind Mini-RTWs to kick off the year, I’ll be embarking on my next big trip very soon. This one brings me to a hugely significant part of the world that I’ve never set foot in before: the Middle East. 

We’ll be spending time in Turkey and Greece to kick off the trip, before heading down to Egypt, Jordan, Oman, and the United Arab Emirates throughout the rest of May. As always, allow me tell you all about the trip and walk you through the rather involved booking process for this one.

The Trip

The planning for this trip was motivated by three primary factors:

• Both Turkey and the Middle East were parts of the world that I’ve been longing to explore, and my short day-trip through Istanbul earlier this year, courtesy of Turkish Airlines, only left me craving more 

• Prior to March 5 of this year, there was the incredible sweet spot of booking top-tier Marriott luxury hotels for the Category 7 pricing of 60,000 points per night

• I really, really wanted to fly Emirates First Class

Since Jessica and I had an open travel schedule in May, it seemed like the perfect opportunity to fulfill all of those objectives, exploring a completed uncharted part of the world for both of us, and experiencing a fair bit of luxury in doing so as well. 

And so the planning began from there. We knew we wanted to immerse ourselves in Turkey for a bit longer, so we planned to stay one week in Istanbul with a side-trip to the Cappadocia region in between, whose picturesque hot air balloon scene was simply not to be missed.

After Turkey, it’s a short hop over to Santorini, Greece, where I’ll be celebrating my 25th birthday with three nights at Mystique, a €700/night luxury resort which I had booked prior to March 5 for only 60,000 Bonvoy points per night. As clichéd as it may be among travellers, I can think of no better way to celebrate a milestone birthday and looking ahead at the year to come than watching the sun rise over the spectacular Santorini caldera.

From Santorini, we’ll head to Jordan, although not before stopping in Cairo for a long layover and a half-day trip to see the Great Pyramids of Giza.

In Jordan, we’ll spend two days exploring the city of Amman, before making our way down to the ancient ruins of Petra and the surreal desert landscapes of Wadi Rum for a day each. Both of those experiences have been recommended to me as extraordinary experiences by several travellers I know, so it goes without saying that I’m feeling giddy with excitement. 

Across the Arabian Peninsula, Oman is another place that I’ve heard makes for an awesome country to visit, even though it’s not necessarily on many travellers’ radars. We’ll be there for four days, primarily based out of the capital, Muscat, but we’ll definitely be taking day-trips to many of the country’s historic forts and natural scenery. 

After that, the trip concludes with a week-long stay in the United Arab Emirates – four days in the city of Dubai and three days at – you know it – the $1,000+/night Al Maha Desert Resort, which I again booked for 60,000 Bonvoy points per night thanks to the pre-March 5 sweet spot.

I’m excited to experience all the over-extravagant things associated with Dubai, like indoor skiing and a high tea sitting in Burj Khalifa, the world’s tallest skyscraper, before retreating to Al Maha to round off the trip in a vast desert oasis.

As a first-time visitor to the Middle East, I expect to encounter all sorts of novel sights and sounds as I interact with cultures and ways of life to which I’ve had little exposure thus far. In particular, what fascinates me the most is that I’ll be in the region during the month of Ramadan, which is from May 5 to June 4 of this year, and I’ll be privileged to get a glimpse into how the people observe their faith in the countries I’m visiting during their month of holy celebration.

Many of you have already sent me your tips and recommendations for the places I’m visiting, which I’m hugely grateful for, so please do keep them coming. And if anyone’s been to the Middle East during Ramadan and has any special advice to dispense, I’d love to hear from you!

The Outbound

Let’s delve into the trip planning process in more detail. For the outbound, I needed to get from Toronto to Istanbul, and there was no better candidate for this long-haul journey than Turkish Airlines business class.

I flew Turkish for the very first time earlier this year on their Airbus A330, and then flew with them again shortly afterwards on the Boeing 777. While the forward-facing business class seats are a little past their prime, they’re perfectly well-suited to couples travelling together, so I don’t mind them all too much.

Of course, the DO&CO-catered onboard dining is what sets Turkish Airlines apart from the rest, and Jessica and I are both looking forward to consuming many more portions of their incredible pistachio ice cream. 

Unfortunately, there was no availability on the direct flight out of Toronto, so I booked the flight out of Montreal instead, with a connection from Toronto in Air Canada premium economy class. I’ve already reviewed the Turkish A330 business class, so I likely won’t be reviewing it again, although the four-hour connection in Montreal will definitely allow me to review the Air Canada international Maple Leaf Lounge there, widely considered to be one of the best locations in the Maple Leaf Lounge network.

I booked this flight using Aeroplan miles and paid minimal taxes and fees, since Aeroplan doesn’t levy fuel surcharges on Turkish Airlines. And if you attended PointsU Toronto last year, you’ll know which useful Aeroplan trick I used to score some significant savings here 😉

The “In-Between” Flights

I’m hopping between a whole bunch of places with this trip, so I needed to book several flights to get myself from place to place. For these short-haul flights, I’m totally fine with flying in economy class rather than splurging for business, although even in economy class, the cash prices of $100–200 per segment can start to add up very quickly. 

The added challenge with booking these types of flights is that there’s so many different possible permutations of redeeming miles through so many different airline programs (in addition to the possibility of simply paying cash), and you need to try to find the most cost-effective way to stitch the entire trip together. 

First off, I needed to book a side-trip from Istanbul to Cappadocia. Luckily, the cash fares on Turkish Airlines’s domestic flights are extremely reasonable, with the round-trip flight costing me only $73 per person.

Then I had to figure out a way to get to Santorini. Back in the day, I used to chase Star Alliance Gold status with Aegean Airlines every year, and in doing so I had racked up a healthy balance of about 50,000 miles within the Greek airline’s Miles+Bonus program. One of the sweet spots within this program is to redeem miles for travel on Aegean-operated flights, since you can often redeem intra-Europe journeys on Aegean Airlines for 10,000–12,000 miles apiece. 

The cash flights from Istanbul to Santorini were going for about $150, so while it wasn’t the best redemption in terms of value on paper, I really didn’t have much use for these Aegean miles anyway, so I went ahead and booked one-way tickets from Istanbul to Santorini via Athens for 11,000 miles per person. 

Regrettably, while I will be flying through the new Istanbul airport, I won’t be getting to visit the new Turkish Airlines lounges there, since I’m departing in economy class rather than business class. You can’t win them all, so that one will have to wait until next time, and a friend who’s visited the lounge has told me that it’s not quite worth jumping through hoops to change my ticket anyway.

When I was searching for ways to get myself from Santorini to Amman, a cursory look on the Aeroplan search engine revealed a routing via Athens and Cairo that would also allow me to spend 16 hours overnight in Cairo.

That would be enough time to check off a major bucket list item by taking a half-day trip to the Pyramids, so I jumped on that opportunity, redeeming 20,000 Aeroplan miles per person for the entire one-way journey (Europe 2 to Middle East & North Africa). 

Considering the vast size of Aeroplan’s Middle East & North Africa region, and how expensive it can be to travel to those countries from Europe, I’d consider it the price point of 20,000 miles one-way in economy class to be a very good deal, especially once you throw in the ability to book long layovers like I’m doing.

After Amman, I then needed a way to get to Dubai and Muscat, although I was flexible in terms of the order in which I visited these two cities. Nevertheless, this part of the booking process left me a little frustrated.

You would think that redeeming British Airways Avios for travel on Royal Jordanian would be a natural sweet spot, and in terms of the mileage requirements, it certainly was – getting from Amman to Dubai would a reasonable 10,000 Avios in economy class or 20,000 miles in business class. 

However, the fact that British Airways Avios passes on fuel surcharges on Royal Jordanian somewhat kills the value of redeeming Avios here, because I’d end up paying an additional $220 per person in surcharges, and at that point I’d be much better off simply paying cash.

In the end, I decided not to play stupid games with Avios; instead, I discovered that Oman Air allows you to add a complimentary stopover in Muscat on your way from Amman to Dubai as part of their regular cash fares, so I went ahead and booked an Amman–Muscat–Dubai ticket for $323 per person in economy class.

Since the Oman Air fare allows a stopover, I’m therefore able to fly from Amman to Muscat, stop there for four days and five nights, and then continue to Dubai all as part of the same ticket. 

Even better, I was able to use the 105,000 HSBC Rewards points and $100 Travel Enhancement Credit I had earned from last year’s incredible HSBC World Elite MasterCard promotion to offset the cost of this ticket entirely. This is an illustration of where fixed-value points come in super handy: when the nuances of flexible rewards like Aeroplan or Avios simply don’t make sense for your travel plans, you can go ahead and buy cash fares and use your fixed-value points to wipe the charges off your statement.

The Return

For the return journey, I had set my sights on Emirates First Class from the very start. And having earned a boatload of Alaska miles from last year’s Marriott Travel Packages bonanza, I wasn’t hesitating to drop 150,000 Alaska miles per person on a truly world-class luxury flight whose memory would last me a lifetime.

However, I actually haven’t completely finalized this portion of the journey yet, so I’m going to leave the detailed explanation of the booking process for a future blog post.

That’s because while I definitely will be flying Emirates First Class on the Airbus A380 from Dubai to Toronto and getting to experience the famous onboard bar and shower, I might also get the chance to fly Emirates New First Class on the Boeing 777 as well, where I’d be treated to a Mercedes-Benz-inspired fully enclosed First Class suite.

Suffice to say, I will truly be outdoing myself once again if I do pull this off, so let’s cross our fingers and see how things play out. Stay tuned!

So, here’s the plan for the next month or so:

• Toronto to Montreal on Air Canada, departing 6pm and arriving 7:15pm, premium economy

• Montreal to Istanbul on Turkish Airlines, departing 11:05pm and arriving 3:35pm the next day, business class

• Istanbul Sabiha Gökcęn to Nevşehir on Turkish Airlines, departing 9:35am and arriving 10:45am, economy class

• Nevşehir to Istanbul Sabiha Gökcęn on Turkish Airlines, departing 11:15am and arriving 12:30pm, economy class

• Istanbul to Athens on Aegean Airlines, departing 4pm and arriving 5:25pm, economy class

• Athens to Santorini on Aegean Airlines, departing 7:45pm and arriving 8:30pm, economy class

• Santorini to Athens on Aegean Airlines, departing 9:10pm and arriving 9:55pm, economy class

• Athens to Cairo on Aegean Airlines, departing 11:55pm and arriving 12:50am the next day, economy class

• Cairo to Amman on EgyptAir, departing 4:55pm and arriving 7:10pm, economy class

• Amman to Muscat on Oman Air, departing 7:10pm and arriving 11:40pm, economy class

• Muscat to Dubai on Oman Air, departing 8:40am and arriving 9:50am, economy class

• Dubai to Toronto on Emirates, departing 3:30am and arriving 9:30am, First Class (for now…)

The Hotels

As most of you know, I’m generally loyal to the Marriott hotel chain, since my elite status with Marriott Bonvoy allows me to get so much more value out of my stays compared to other brands.

With so many hotel nights to cover on this trip, I needed to put a lot of thought into how I booked my hotel stays. I was looking to employ a combination of legacy seven-night hotel certificates from the Marriott Travel Packages, redeeming points when the value was there, and straight-up paying the cash rate when it was not.

A few weeks ago, I wrote about how I found myself paying cash for hotels a lot more nowadays, and this trip demonstrates those principles in action. With the value slipping away from Marriott Bonvoy compared to before, there were many more occasions when I found it to be a better deal to book the cash rate directly and save my points for future hotel stays where I could get greater value. Furthermore, the recent eBates 10% cash back events on Marriott hotels would allow me to earn back a nice chunk of those cash outlays.

In Istanbul, I redeemed a Category 5 seven-night certificate at the St. Regis Istanbul, allowing me to kick off the trip and adjust to the timezone in luxurious surroundings. Most St. Regises around the world are categorized much higher, so I thought it was an excellent deal to burn a certificate here. (Note that the St. Regis Istanbul had actually risen to Category 6 as part of the recent category changes in March, but I was able to get my booking locked-in before then.)

While I could’ve redeemed a Category 4 certificate at the W Istanbul as well, but a friend who had recently patronized both properties had informed me that the St. Regis was much better and well worth the higher category. 

In Cappadocia, the general advice I’ve received was to skip the chain hotels and stay in one of the distinctive cave houses in Göreme instead. Jessica found us an awesome-looking property called the Sultan Cave Suites, with incredible views of the fairy chimneys and hot air balloons, which I was able to book via Expedia for the affordable rate of $110 per night for two nights.

Santorini would be the site of a three-night stay at the gorgeous Mystique, as I had outlined above, for 180,000 Marriott Bonvoy points in total. Every suite at this award-winning resort is carved into the rockside, featuring a private balcony with views of the caldera and – get this – complimentary room-service all-you-can-eat à la carte breakfast for Platinum Elites and above. 

While the resort doesn’t allow cash upgrades to higher-tier suites on points stays, I’ve sent a note to the resort expressing my hope for an upgrade to one of their suites with a private whirlpool on the deck. Could a birthday boy ask for any more?

In Cairo, since we’d merely be having an overnight layover, I booked one night at the Le Méridien Cairo Airport so that we can quickly get some rest after our 12:50am arrival and head out early to the Pyramids the next day. This property is only a Category 2, so I gladly paid 12,500 Bonvoy points for the overnight stay.

Then it’s off to Amman, where the W Amman caught my eye as a newly-opened W that was getting excellent reviews. I couldn’t quite justify paying 35,000 Bonvoy points per night for this Category 5 hotel when the cheapest cash rate was only $195, so I went ahead and paid cash for one night and redeemed my annual Category 5 free-night certificate from the Amex Bonvoy Card for the other. 

The good thing about travelling to the Middle East in the summertime is that occupancy tends to be quite low, and so hotels often have Summer Sale rates that are 25% off the usual member rate, which further justifies the cash expenditure instead of redeeming points. 

In Petra, the Marriott Petra Hotel is a Category 4, so I thought the points rate of 25,000 Bonvoy points was a reasonable value compared to the cash price of $250. Meanwhile, further south in the valley of Wadi Rum, I could look no further than the Wadi Rum Bedouin Camp, which allows you to stay overnight in the surreal red-rock landscape. The price for a half-day jeep tour with an overnight stay is 60 JOD ($114) per person, which I thought was very reasonable as well.

Next up, having racked up a fair bit of out-of-pocket expenses by now, I opted to redeem one of my Category 4 seven-night certificates at the Sheraton Oman Hotel in Muscat, even though I’d only be staying for five nights (hello, two extra elite qualifying nights!) 

Lastly, Dubai was another one of those cities where paying cash for hotels made a lot more sense than redeeming points, especially with the Summer Sale 25%-off rates suppressing the cash prices even further. For example, I was able to book three nights at the JW Marriott Marquis Dubai – which holds a claim to being the tallest hotel in the world – for only $150 per night, all-in, which I thought was an incredible deal, particularly once you factor in the daily meal presentations in the hotel’s massive Executive Lounge.

I also decided to splurge for a night at the W Dubai The Palm, another newly-opened W hotel that looks to have the correct amount of over-the-top extravaganza for a city of Dubai’s lavish reputation. That came out to $250 all-in – a little more than what I’d normally be willing to pay, but just about the maximum that I’d spend for a night on the famous Palm Jumeirah. 

Whew! It’s certainly going to be a lot of time spent on the road between all these places, so I’m thankful that I’ll finally be able to unwind at the Al Maha Desert Resort for three nights for 180,000 Bonvoy points in total. 

The best part of redeeming points at Al Maha is that it comes with three meals and two desert activities per day included in the price. It’s worth noting that the resort tried to backtrack on providing these offerings on points stays late last year, but they quickly reneged on this action once they were (rightfully) bombarded with one-star reviews on TripAdvisor. 

Besides eating, drinking, and participating in exciting desert activities like camel rides and falconry, there’s really not much to do at the resort itself. I therefore expect the sweeping desert landscapes to be ideal for a few days of quiet contemplation… as well as for preparing my appetite and energy for a spectacular trip home in Emirates First Class!

Adding it all up, my total out-of-pocket costs for this trip came to the below, per person:

• Aeroplan taxes and fees, YYZ–YUL–IST: $70

• Turkish Airlines, SAW–NAV: $73

• Two nights at Sultan Cave Suites, Cappadocia: $113

• Aegean taxes and fees, IST–ATH–JTR: $71

• Aeroplan taxes and fees, JTR–ATH–CAI–AMM: $57

• Two nights at W Amman: $195

• One night at Wadi Rum Bedouin Camp: $114

• Three nights at JW Marriott Marquis Dubai: $225

• One night at W Dubai The Palm: $125

• Alaska taxes and fees, DXB–YYZ: $109 (for now)

• Turkey e-Visa (for Jessica only): $80

• Egypt e-Visa: $34

• Jordan Pass (covers Petra & Wadi Rum entrance fees and Jordan visa fee): $142

• Oman e-Visa: $17

• Total: $1,385

Conclusion

I can’t remember the last time I felt this excited about an upcoming trip. Every time I’m reminded of one awesome travel experience that I’ve got planned (like waking up to the caldera views in Santorini or visiting the ruins of Petra), it always takes me a while to remember the so many more exciting things on other parts of the trip (like the hot air balloon ride over Cappadocia or the sheer unbridled joy of taking a five-minute shower at 37,000 feet in the air). 

One thing’s for sure: the reviews and new blog content from this trip are going to so much fun to write. Like I said, I genuinely feel as though I’m outdoing all my past trips with this one – but hey, that’s why we do what we do, isn’t it?