Another #jasongetsaroundwithjackie European adventure is taking flight! From Portland to New York to Lisbon to Prague, with more of Europe to come.

This afternoon, Jackie and I are heading over to New York for a couple of long days before we depart on another adventure together in Europe. We’re both super excited about making this trip that I had planted the seed for way back on January 9th when I bought two tickets from New York to Lisbon, Portugal in Europe. It’s now grown to include a few days in Lisbon, attending a wedding in Prague, exploring other villages in Czechia, and if all goes well, some time in Ireland or Greece before we head back to Portland. We’ve left the end of the trip open to allow us some flexibility, but things are beginning to fall into place as the trip unfolds.

There’s a lot to consider when traveling during this time outside of just booking flights and hotels. COVID is still very real and though we’re both fully vaccinated, we are still being cautious and following local guidelines around COVID as we all have learned that vaccinations aren’t always enough.

I will continue to update this post as the days go on over the trip, so please bookmark this page and stay tuned!

Planned Itinerary

• 9/17
  • 5:30-6:30pm: PDX-SEA (Portland to Seattle)
  • 9:30pm-5:30am: SEA-JFK (Seattle to New York)
• 9/18
  • 2pm: Arrive Holiday Inn Express Manhattan Times Square South
• 9/19
  • 2pm: Depart Holiday Inn Express Manhattan Times Square South
  • 9-11pm: SAS Lounge
  • 11pm-11:20am: EWR-LIS (New Jersey to Lisbon)
• 9/20-23
  • Heritage Avenida Liberdade Hotel
• 9/23
  • 2:20pm-6:35pm: LIS-PRG (Lisbon to Prague)
• 9/25
  • Jackie’s cousin’s wedding!
• 9/28-30
  • Extended time in Prague
• 9/30-10/3
  • Budapest, Hungary
• 10/3-8
  • Ireland

Booking Details

This trip has been slowly becoming a real trip over the last few months and I wanted to break down how it all came together.

The Seed (Saving $3,000 Per Ticket)

Way back in early January, just after arriving in Sayulita, I don’t recall how I heard about the ticket, but I read somewhere that I could score some TAP Portugal business class seats from New York to Lisbon for 35k Avianca LifeMiles. I had a bunch of American Express Membership Reward points that I transferred over to LifeMiles after confirming the flights and required miles.

I’m glad I booked these when I did at 35k miles because these same tickets with cash are over $3,000!

With one flight from New York to Lisbon set, the next thing to do was get us from Portland to New York which required some creative bookings.

Getting To New York (Saving $850 Per Ticket)

Finding our way to New York was the next thing to do! Earlier this year I had just earned 100k jetBlue miles from the jetBlue Business Card and I found some transcontinental flights from Seattle to New York for 47k miles a ticket in jetBlue Mint business class! I was looking at these flights a few weeks back and they were charging close to 100k each or as of today, $848 a ticket! Not as great as the $3,000 savings, but 1.8cpp isn’t too bad for jetBlue!

Since I wanted to try out the jetBlue Mint product and it wasn’t available from Portland, we had to go from Seattle. Also, flying from San Francisco or Los Angeles was over the number of miles I had with jetBlue.

To get to Seattle and to begin our journey, we’re taking an Alaska flight later today on the afternoon of the 17th. I was just going to book economy, but since we’re doing the rest in business class to get to Lisbon, I decided we should start out our journey in the upper class. There was a promotion in the last few months that landed us two first-class seats for our 1-hr flight to Seattle for $65 each. Now those tickets are about $260 per person! I used dollars instead of points because I had a bunch of Alaska bucks in my Alaska wallet from canceled flights in 2020.

A Few Nights in Lisbon Luxury

A few months back I received an email from TravelZoo and saw there was a promotion for some fancy place in Lisbon, the Heritage Avenida Liberdade. Normally this place would run 187€ ($220) a night, but TravelZoo had the place for $109 a night! Since we still hadn’t booked a place to stay, I grabbed a few nights at the property and we’re excited about our stay!

Elegant quarters in a vintage-chic, 18th-century property with a gym & a bar, plus free breakfast.

Google Maps

TravelZoo promotion

• Buffet breakfast served in the lounge or continental breakfast served in the room (until 12 p.m.)
• One welcome glass of Moscatel wine per person
• Free entry to 20 Lisbon museums (list available at the hotel reception)
• VAT (value­added tax) is included in the price, though a city tax of €2 per person, per night (approx. $2.50) is not included and will be paid on site.

Not too shabby!

Getting To Prague (Saving $375)

We wanted to get to Prague after leaving Lisbon direct, and the only airline offering this was TAP Portugal which happened to be the airline we’re taking to get to Lisbon from New York. I tried to book a couple of award tickets using Avianca LifeMiles like I booked New York to Lisbon, but their system was having issues. I couldn’t even find award availability through TAP themselves, so I used the Chase Ultimate Rewards travel portal to book two economy plus tickets from Lisbon to Prague for 29,851 points saving us $375. I gained a bunch of Ultimate Rewards points this year through a number of different cards (75k from Ink Cash, 100k from Sapphire Preferred) so was an easy redemption. One cool benefit to booking this way is that I earn miles from TAP for the flight!

Prague City Leaf ApartHotel ($0 Saved)

For staying in Prague, I wanted to use my Chase Ultimate Reward points, but the place we narrowed down to, City Leaf, was not available, so we booked it through Expedia for cash. We planned to be in Prague for five nights, and booked the place for $386. The look of the place was great and the location was even better!

City Leaf, however, ended up not being a big letdown. First off, I had to go to a completely different spot about a ten minute walk away to get the keys for the place. Then we got into what looked like an office building that was closed down as it was very dark inside. Our room was on the 3rd floor and since we had a few bags each, we used the lift which barely seemed to function, in fact, it got stuck a few times going up and down. The room itself was boring, lifeless, and poorly laid out. It was very disappointing and we were both put into a mood as it was not what we expected at all, and thought we had to spend our five nights in one of the most beautiful cities, in this letdown of a place. If we were just going to be here a night or two we would have been okay, but five nights was not going to fly.

I messaged the hotel a couple of times through Expedia with no reply and it wasn’t until I reached out to Expedia Customer Service and had them contact the location we grabbed the key from that I got some help. Eventually after most of our morning and early afternoon of going back and forth, I was able to get them to give us a refund for the remainder of our stay and we rebooked into a new place, hoping for the best.

EMPIRENT Garden Suites (Saved $570)

The place that ended up being our saving grace for our time in Prague was the EMPIRENT Garden Suites!

More Details to Come

I have a lot more to share, but writing this takes some time, so be patient, and I’ll do my best to share it all!

Bookmark To Follow

There’s still so much more to add and more to come, so again, please bookmark this and come on back to view more content as the trip unfolds!

The Trip Unfolds (Updates)

9/17 4:45pm: We started our trip with a quick stop at the Alaska Lounge to have some wine for Jackie, a beer for me, and some snacks before our quick flight to Seattle.

6:30pm: Our flight was delayed, but since it was already planned to be short, it wasn’t a big deal. We both had a cozyv flight in first/business to Seattle.

7:30pm: Since we had Alaska going to Seattle and jetBlue going to New York, we had to get our bags from baggage claim and rechecked into jetBlue. Simple enough, though jetBlue was a good distance from where claim was.

9/17-18: Flying to New York on jetBlue Mint business class was a real treat. The sleeper seats were really cozy, had a great pillow, and comfy blanket that Jackie wanted to take home. The chairs even had a massage feature! The food was alright, though wasn’t as good as I would have figured. The flight was also pretty short, so having an overnight really made it a red-eye flight. It took a while to get our dinner, so I watched a movie which only left an hour and some to sleep. So, when we arrived into JFK at 5:30 local time, which meant a long while before a bed was available for more zzzzzs. We got our bags and ordered a $70 Uber to our hotel near Times Square. We arrived the Holiday Inn Express around 7am and left our bags as our room wouldn’t be ready until closer to 2pm. With plenty of time on our hands, we walked around Times Square before we grabbed some breakfast and decided to make our way to the north side of Central Park.

9/18: Central Park, Oktoberfest parade, checking into room, Irish bars and more.

9/19:

9/19 7:45pm: Booked our Uber to Newark airport for our journey to Lisbon!

9:52pm: We’re at the Lufthansa Lounge before our flight to Lisbon. Only basic food and snacks, with no alcohol at the lounge, but at least the place is comfortable enough to wait. Leaving here shortly to board!

10:30pm: We still haven’t boarded as our plane wasn’t here yet (here now) and there was some commotion near the gate because someone went through the door downstairs that said DO NOT ENTER. Police arrived and has put us on edge, so here’s hoping nothing occurred to delay our flight any longer.

11:20pm: Though late, we did finally bored and got situated in our snazzy business class seats, 3F and 3D. The seats were very similar to our jetBlue seats, though the jetBlue experience had a way better pillow, cozier seats, and even a massage feature. I will say, the food was much better than on jetBlue. I had the beef with risotto and Jackie had the mushroom raviolis. With jetBlue we had some sandwiches which neither of us were big fans of.

9/20 1am: I ended up watching a good, but sad movie called The Father staring Anthony Hopkins. Worth a watch, but shows what losing your memory is like for a father and a daughter trying to care for him. Right after, I rolled around trying to sleep before going to dreamland.

9/20 11:20am: We just landed in Lisbon. Before we landed we had an enjoyable Portuguese breakfast with bread, meats, and cheese. We both enjoyed it and an hour or so of relaxing before landing.

9/20:

9/21:

9/22:

9/23 12:30am: Just got back to our hotel after a wonderful day. We went on an 11am walking tour through the Alfama neighborhood and had a wonderful could of hours learning some history of the area. We then went on train to Sintra and explored Quinta da Regaleira, a 20th-century castle and gardens with underground passages. Definitely a must if you go to Sintra which is about 40 minutes from Lisbon. The day ended having dinner and drinks at Taqueria Patron in the Bairro Alto neighborhood. We met an Irish couple at dinner when the rain started pouring after not a drop the whole time we were here, we were not prepared. They were super great and we’re now planning to meet up with them in Dublin if Ireland is where we’re headed… which it sounds like it is! Tomorrow we leave to Prague in the early afternoon, which means we’re going to sleep in and rest up before the next leg of the trip!

1:30pm: We’re just about to depart from Lisbon to Prague. Currently enjoying some wine and snacks in the ANA Lounge we had entry to via the Priority Pass. Dropping off our checked bags and getting through security was simple enough and fairly quick. Getting the the airport was very smooth and inexpensive by booking our ride using Uber rather than taking a taxi. Right before we ordered or ride and right after checking out, we visited the nearby Fabrica da Nata shop for two more egg custard treats. We checked out of our hotel which included getting refunded for the museums we visited and then paying our taxes and the two beers we had on our bill. All of this after waking up, grabbing breakfast downstairs, and then packing for our departure. Lisbon was awesome and we will for sure be back as we barely scratched the surface of this beautiful city.

9/23-28: Prague!

9/28 1am: Wow, I haven’t updated in a long while! Just know that we’re alive and well enjoying our time in Prague with a couple more days to go before we depart on a train to Budapest, Hungary for a few nights before we begin our journey back west by flying to Dublin, Ireland for the rest of our time in Europe!

9/29: Prague

9/30: Today we left Prague to go visit the home of Pilsner, Pilsen! The birth of Pilsner is said to be October 5th, 1842 and all from this lovely city of brewers!

9/30 10:30am: We have just had a delicious breakfast with Jackie’s cousin, Blanka, and their handsome little boy, Tony, and now we’re in an Uber to the Prague train station to catch our train to Budapest, Hungary–my 39th country!

9/30-10/3: Budapest

10/3 12pm: We have just departed from Budapest to Dublin. We are flying on Finnair to Helsinki before our connecting flight to Dublin. I chose this set of flights because it was about the same number of miles to fly in business as it would have been in economy and flights got us into Dublin earlier than a bunch of others. Also, I’ve never flown Finnair and never landed in Finland before, so why not! Our morning was early to get everything together, but it all went well, even the taxi booked using the app Bolt. At the airport went through security, and then we had access to the MasterCard lounge (which I didn’t even know existed) due to my World Elite cards while we waited for our flight. Bonus!

10/4 3pm: We just left Kilkenny Castle and the lovely town surrounding it. The castle is from the early 12th century and is very well kept. The castle grounds are open to walk around and entry inside is currently free, though you still have to get online and register for tickets. The self-guided tour took about 30 minutes. Since we also are planning to get to Blarney Castle near Cork to kiss the Blarney Stone before last entry at 4:30, we didn’t have a lot of time to explore the grounds of the castle and the town other than the gardens and the bathrooms nearby. Jackie started off driving towards Cork through some very narrow sketchy roads before we made it to M8 freeway heading to Blarney Castle another hour and fifteen minutes away!

10/4-6: Cork and Dingle

10/6 6pm: Not long ago Jackie and I left the Cliffs of Moher, a place that I visited last time I was in Ireland, but couldn’t see more than 10 feet in front of me. This time, however, the weather worked out in our favor and we got some great views of the cliffs and the surrounding area. I was so happy to have had such a better experience than the last time! Jackie really enjoyed it as well and we were both just thankful the rain wasn’t continuing to fall. It was overcast, but that didn’t take away from the beauty of these cliffs! If you’ve never heard of these cliffs, that’s pretty common, but you probably have seen it in scenes from The Princess Bride and Harry Potter. Definitely worth a visit! Now we’re in our way up north along the Wild Atlantic Way to Galway where we will be staying for our last two nights here in Ireland and this adventure in Europe. I’m sad it’s coming to an end, but we have had one hell of an amazing adventure!

10/7: Galway

10/8 10:45am: Jackie’s currently driving us to Dublin Airport from Galway. We’re an hour in and still have an hour or so to go. We have our flight at 1pm, which means we need to check our bags well before noon. We still have to return our rental car and get through whatever line is at the check-in counter before then, so here’s hoping that all goes smoothly! It’s the end of our three weeks in Europe and as it comes to a close we are taking some time self-reflect on the many excellent and trying memories we’ve shared. We’re both looking forward to getting back to Portland to see our cats and eventually our friends and family after we get some recovery time in from all the traveling. Coming up next is an 8 hour flight, a 4 hour layover, then our final 4.5 hour flight into PDX landing around 10:30/11pm tonight.

12:45pm: We made our flight! We almost weren’t able to check our bags, but the lady called and they approved our checked bags! I was pretty surprised as we still had 10 minutes before 12pm, but checking bags closed at 11:45, not 12! We’re so thankful to have had a kind agent to get us through! We rushed all the way through the security area, and then to another security area just for those going to the USA. One of the agents at the second security asked “why are you rushing when the plane wasn’t even boarding yet?” We responded saying “that’s what we were told to do!” We made it with plenty of time to just sit on our plane as we catched our breath. The flight has plenty of open seats, so our flight attendant moved us forward to some seats that had much more room and here we are now, just about to take off on the next ten to fifteen minutes.

10/8 10pm: We made it back to Portland! If was a really long day of traveling to get home, but it all went without too much of a hitch. Only real downside was 5 hours waiting at the O’Hare Chicago airport, but otherwise the return home was just fine. Much needed sleep coming soon!

10/10 10:10am: Getting adjusted to a normal sleep pattern is slowly coming back together. Yesterday, I went to a wedding at noon for a few hours, then came home and slept for a few, then went out to a party at a friend’s place. Guess I do this to myself! Haha, but I love it! In the next weeks, I’ll be going through 3,600+ photos to find my favorites and taking some time to write some posts of the adventure. I’ll also update this more with more details of the trip unfolding!

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