2019 was a big year of travel in our family. We did the most travel we’ve ever done and went to some amazing places and created lasting memories.

New Years’ Eve 2018 was spent in a hotel 5 miles from our house to get one last qualifying night for that year. That night put my wife over the top to re-qualify for titanium status which we put to good use over the course of 2019.

Dubai

In February we spend 10 nights in Dubai. We were a bit apprehensive about going there as it was way outside our comfort zone. We weren’t sure how we were going to like it though we were optimistic there would be tons for us to do while there.

The flight was long but not nearly as tedious as we expected with our flight on Emirates being better than we could have hoped for 11 hours in economy. Our first hotel “room” in Dubai was fantastic with our upgrade to a 2 bedroom apartment overlooking the palm islands from a nice high floor (with a balcony!). The apartment was enormous and had 4 (!!!!!) bathrooms, a full kitchen, dining area for 10 and gobs of space everywhere all in the fantastic marina district. There was never a dull moment during the trip with dune bashing, the Burj Kalifa, a tour of the old town, and the kid’s favorite, the Global Village all on the agenda.

The second half of our stay was outside Dubai at a desert resort at the Ritz Carlton Ras Al Khaimah Al Wadi Desert Resort. Due to my wife’s titanium status, we got free breakfast which helped ease the cost when we opted for the full board plan (which we didn’t regret for a second). Our villa had its own pool (!!!) and the full board plan we had also allowed us to choose one experience per day. This allowed us to do night archery, camel riding, and a dune buggy together and the boys to try their hand at fishing while we did a spa session. I’m not sure we’ve felt as relaxed as during that trip and we did things we’d likely never have done anywhere else. We’ll definitely be back.

Los Cabos, Mexico

In April we had the opportunity to make a quick 4 day trip to Mexico. As it turned out we were able to coordinate with some old friends from college and turn it into our first multi-family trip. Despite everyone (except me) in the family speaking Spanish, we haven’t spent much time in Spanish speaking countries so this was a treat for the boys to practice their Spanish.

The destination was awesome for the type of trip and the resort we stayed at fit the bill perfectly. It didn’t hurt that my wife’s status got us upgraded to one of the best rooms on the property with amazing views of the beach and ocean, all for a surprisingly cheap price due to an AAA discount. We had a blast catching up with friends and experience new places.

Hawaii

We had gone to Maui two years prior and had the most fantastic time. We knew we wanted to return and when we found award availability for flights which included a stopover on the Big Island we decided to jump at the chance and go again. It did not disappoint as we had some fantastic experiences this time as well. The Big Island was interesting, but Maui is still first in our hearts and the 10 days we spent there flew by. We got to do some things we didn’t have a chance to do before such as a sunset sailboat cruise, pineapple tour, and surf lessons among many other things. The days were fantastic and went by too quickly. We truly enjoyed our last 5 days at the Wailea Beach Marriott which is probably our favorite hotel we’ve visited. It’s hard to beat the Ritz Carlton from our Dubai trip but I think Wailea wins by a nose (or maybe by a waterslide).

Despite having to work most of the trip, my wife still got to enjoy her time there. She got to work with a much nicer backdrop than usual and when she was done work… she was in Hawaii!

Disney World

My youngest and I went on a solo trip to Disney World this summer as well. When Tomatico turned 8 I took him and promised his brother I’d take him when he turned 8, which was this year. I was able to leverage a lot of the planning and things I had learned from the trip with Tomatico to make this trip just as good. I’ve got a series of posts on this trip in the works so keep a lookout!

Toronto

We made a quick trip over Labor Day to visit family in Toronto. We got to stay right downtown and had a fantastic view of the CN Tower from our suite which was an upgrade due to my wife’s status. There’s another series of posts in the works for this trip as well.

Christmas Trip

For Christmas, we ended up doing a modified California Road trip including San Francisco, San Diego, Palm Springs, and the LA area. With the kid’s school schedule allowing a full 2 weeks off we decided to take advantage. There’s a series of posts I’m working through so that will be up in the coming weeks as well.

What Went Right and Wrong?

We had a lot go right this year with very few misses on hotels, flights, or destinations. We were very lucky, but we worked hard in our planning to make sure we made good decisions. We didn’t have any major delays or routing issues. There were almost all positives this year.

Best Upgrade

The Marriott in Dubai where we got upgraded to what was essentially an apartment overlooking the Palm Islands was easily the best upgrade we got all year. When you could seriously think about living in your hotel room because there’s so much space, that’s a good day.

Best Experience

We had so many great experiences it’s hard to narrow down. The boys would probably say the dune buggy ride in Dubai or the pineapple tour in Maui. I’d probably say the camel ride in Dubai. Can they all be the best?

Best Hotel

The best hotel we stayed at was the Wailea Beach Marriott. Despite our frustrations with the pathetic free elite breakfast, the hotel had the right mix of relaxation and activities. The boys felt safe enough to do a little exploring on their own and really enjoyed the amenities. It was so close to town anal the thinks we enjoy most about Maui that our time there flew by in an instant.

A very close second was the Ritz Carlton Ras Al Khaimah Al Wadi Desert Resort outside of Dubai. It offered such unique experiences and landscapes to go along with the amazing room (with our own pool!!) that it’s hard not to put it first, but Maui has the ocean so it gets the slight edge. We wouldn’t hesitate to recommend or go back to either one, though!

Biggest Surprise

The Sheraton Grand Los Cabos Hacienda del Mar in Mexico was definitely the biggest surprise. Given the low AAA cash room rate of around $160/night, we didn’t expect much. The pictures looked nice and the reviews were great, we just didn’t expect to be blown away by the view and the room, not to mention the service and food. There was so much to do and the staff was extremely helpful. It didn’t hurt that we had a fantastic time with our friends that we met there.

Biggest Disappointment

The biggest disappointment was the JW Marriot Desert Spring Resort near Palm Springs. We booked a suite because there were 5 of us staying in the room for the 2 nights we were there. The suite was one of the worst constructed rooms I’ve ever stayed in at any level of hotel. With paint on the doorknobs, wallpaper bubbling off the wall, water stains on the baseboard it seemed like it was rushed to be put into the room inventory for the holiday season by third rate contractors. The worst offense was the utter lack of customer focus by the property. The longer we stayed there the more we wanted to leave so we were thankful we were only there two nights. We won’t be back.

Worst Reservation

We had mostly good luck with our reservations. There are some things I could have done slightly different here and there, but nothing major. The one thing that sticks out is the rental car I got in Los Cabos. It was a piece of crap and likely not all that safe. I regret getting it and won’t be renting from that company again. Despite having Platinum status with the company (Sixt) I still got a horrible car that wasn’t even all that cheap. I didn’t get any upgrade that was supposed to be guaranteed for having status and the car felt unsafe (wheels would lock up easily if you hit the brakes even reasonably hard, putting you into a skid). The only good part about the reservation is that we got a fantastic restaurant recommendation 🙂

Next up – Looking forward to the new year!