Ahhh, Portugal again so soon? Damn, so lucky.
This go around, we get to work in wine country? Cherry on top.
Throw in the insane underwater beauty of the Azores islands, and wala! A trip is born.
This trip, we headed north upon arrival at LIS, and before we knew it, we were sipping fine Portuguese vino & port in a stunning setting. On a boat.
Life. is. good.




How to get there.




Oh yea, you know our Chase Reserve Ultimate Rewards points were involved. Looks like we had racked up a cool 100k points since the last point spend, and this got us a full RT ticket to LIS + a portion of our second ticket. The points + ~$900, and we were on our way.
With the tickets at about $1200 once you add in those lovely TAP Airline baggage fees, flying just isn’t cheap these days. And yet, each escape is ever more priceless.
We then easily grabbed internal flights within Portugal using – you know it – Skyscanner! It felt surprisingly easy to find flights through the only two airlines that operate to get you to & from the Azores: Ryan Air & SATA, I think because trying to get us to Green Island, Taiwan [Google Maps] later this year is not proving nearly as simple for this girl. I smell a new language being added to the list of hopeful life skills, friends (Mandarin, people).
We booked Ryan Air given a pref for early AM flights. Approx $140/pp on the way over, from Porto, and $200/pp back to LIS. While simple to book, there isn’t much shopping around for these bad boys. For what we anticipated would be the underwater adventure of a lifetime, small price to pay.
We also loved the flexibility of flying to the Azores from Porto, yet back into Lisbon for our final wknd of Portuguese debauchery, with both flights hovering at ~2 hours a piece. Highly recommend to save time and maximize exploration.
Runabout tips:
- Multi-city flights searches are totally worth it! While R/T flights tend to be cost-friendliest, getting back home without a connection after a voyage abroad is clutch. Cannot beat that time and energy save, and you may get just as lucky on price like we did here, i.e. it was not significantly cheaper to fly to the Azores to and from the same city.
- Baggage? Pay that extra Ryan Air fee for a large cabin bag (up to 10kg, altho no scales in sight – lucky ducks), which comes with priority boarding, i.e. no one is scouring your luggage. At ~26 euros for each of us, made for flawless travel. On Ryan Air at that. Honestly, zero complaints with this budget airline. We were on time and cozy in our chosen aisle seats throughout each of the two Azores flights.
- We’ve said it before and will say it again. Friday night flights out of O’hare are the shizzzz. We left at 6pm Chi time and easily slept through the flight & shifted time zones to fully enjoy a day of boating and wine tasting on arrival. Huzzah!
- Getting 6 hours on the way back is ridic amazing. We left Lisbon at 1pm on Sunday & were back by 4pm. This too, with ample talk of the ground workers’ strike at LIS. We felt oh so lucky to be totally unaffected (major props to Wally for keeping up with this one!).



How to get around.




Given that we wanted to hit the vineyards on arrival that fine Saturday AM, a rental was the natural choice. Add in our early Tues AM flight to the Azores out of OPO in Porto, and this was a no brainer.
We suspected any rental would carry a one-way fee, and that it did. We searched our usual Skyscanner for a reasonable rental, found that Carla is is all the rage for Portugal rentals, and spotted the 101 euro one-way fee. With the 4-day rental stint running less than 100 euros, we found that this option suited us best even with the added fee.
Upon arrival at Sâo Miguel, we scooped up our second rental of the trip. I had read that getting a small car is clutch to account for narrow roads and tiny parking spots. We turned back to handy Skyscanner to search for rentals at PDL, we scooped up an economy, automatic car for $260 through Discover Cars for the 3 night/4 day stint.
I didn’t mess around with “meet & greet” options or even shuttle buses to rental car lots and instead opted for all in-terminal rentals. Highly recommend following that lead to save tons of time & energy, particularly after jumping off a flight. While more $, very well worth it.
We looked forward to our final wknd stint in Lisbon sans vehicle. No need for a car in that Bolt & Uber super friendly city, particularly among the awesome hustle & bustle that Lisboa has to offer.
Runabout tips:
- Download the rideshare app Bolt! It’s super prevalent in the EU, and very easy to use. That said, Uber has a large presence as well. Prices are comparable, depending on where you’re at. We used only Bolt in Lisbon because the prices were on point.
- We def had issues with Carla, seemingly the most-prevalent third-party for booking Portugal rentals through Skyscanner. To avoid the company your car is through raising eyebrows, see if you can get on the phone (or better, email) with them prior to arrival to confirm the reso & price. Goldcar stated that our reso was for a phantom car, so we quickly grabbed the automatic they had this busy wknd and paid ~50 euros/day additional.
- Upon arrival on the island, Discover Cars straight up cancelled our reso without any heads up. Nice. I was thrilled to simply jump on Skyscanner and book a new reso… again through Discover and this time with local car company Way2Azores. Go Skyscanner! We actually saved a pretty penny even with the last min booking and ended up loving Way2Azores. Great service, car, and restaurant recs, huzzah!
- Parking on the island. Just be sure you have coins/change, and you’ll be good to go. We did not and suffered yet another ticket. At only 6 euros, the suffering was minimal. Park at your hotel where the option exists. At 9 euros/24 hours, our garage was perfect. If you’re able to deposit a balance into iParque Driver, awesome and you can ditch those coins.
Where to stay.




One of my fave parts of booking a trip is perusing hotels. Altho don’t be fooled. Nothing I do is done leisurely, with the search for our lil love nests included.
Every destination on this adventure offered a large variety of options. So, our tried & true process to the rescue! With a quickness, we had our home base for each leg of this awesome journey.
Douro Valley
I knew nothing about where to stay in the wine haven that is the Douro Valley, other than that a friend had raved about the Six Senses. Of course she did. We are lucky enough to know from experience that these properties are beyond stunning. However, for a duo that capitalizes on exploring every destination to the fullest, which often means we are not spending a ton of time in our Airbnb or hotel, $1700/night for our single night here was simply not going to happen.
I did a lil blog research and came across Lamego [Google Maps] as a solid home base for Douro Valley wine hopping. Lamego Hotel & Life was then an easy find, and damn it looked gorgeous. Gym? Check. Sauna? Check! Renowned spa? Wowwowwow.
How this was priced at $194/night is beyond me. Oh, did I mention a stellar breakfast was included?
With massages running only 45 euros for 30 minutes at the hotel’s Le O’ccitane spa, we indulged before the next adventure. Lil slice of heaven in Portuguese wine country. You heard that right. Pinch me.
Braga
Braga had tons of options. After prioritizing our love for a gym and sauna, those dwindled, and the Innside by Melia, Braga Centro hotel quickly emerged.
At $304 total/ 2 nights, with breakfast to boot, another awesome steal for this super modern property that boasted that lovely new smell vibe.
Gym and sauna rocked, and breakfast was good, just a bit bustling with people and noise after experiencing the serenity of our beloved Lamego home.
Sâo Miguel, the Azores
I had wondered whether the options in the Azores would be limited. Much like many other surprises these gorgeous islands had in store, that was not the case. We knew a sauna would be clutch for post-dive chills, and the Azoris Royal Garden delivered.
At $590 total/3 nights, with breakfast and a gym to boot, we were very happy with our island home away from home.
With live music in the lovely garden setting each evening and awesome amenities – indoor & outdoor pools, and tennis courts to boot – while the rooms did not scream luxury, the rest of the hotel more than made up for it.
Our beloved Lisboa
I struggled a bit with Lisbon because of: 1. The number of options, and 2. Our strong love for the Heritage Avenida Liberdade Boutique Hotel, where we stayed on our first visit to Portugal. Alas, we opted to branch out… to a spot directly across the Avenida Liberdade, goodness.
The Bessa Hotel Liberdade boasted a similarly awesome location and yet, added on a stellar gym + sauna. Oh yea, an amazing breakfast (complete with bubbles!) was included too. We don’t snooze on that option, pun intended.
At $489 total/2 nights, this also was a decent amount less $ than our cherished Heritage collection hotel. The sauna tipped the scales, shocker. Cannot say enough good things about the bar and restaurant staff. They were friendly, courteous, and genuinely seemed happy to be there. Working. Wowza. In direct contrast, the reception staff was not quite so warm or accommodating.
Runabout tips:
- We do tend to ask about the avail. and cost for parking on-site when we have a rental in-tow. The info. is useful, but more so, we get a great sense of the customer service, particularly when asking for early check-in if we arrive in the AM. Simply google the hotel’s email address to reach out.
- Speaking of check-in, this was a rare trip where two of our hotels did not have rooms ready for a solid few hours after we arrived. Clutch to have those amenities (here we go again…). We made full use of the gym, sauna, and pool at those spots to quickly pass the time & then jet on adventures in paradise.
- You may be asked to pay a city tax, so it’s a good idea to actually check out v. in the States, where we simply bounce and share the room keys with reception.
How far does your mula go?
We didn’t have any euros in tow from prior trips and did need a single euro save for the single (insanely delicious) restaurant with its wifi down.
Not the first time, but it continues to astound me that we are such a cashless society. It would have been nice to have change for parking, so def recommend carrying at least 100 euros or so as back up, and for lil markets and pop-ups.
The prices? Almost everything felt very inexpensive, altho depending on the caliber & ambiance of the spot, def varied. On average, we prob ate & drank for about 60% of what we pay here in Chi/the US. Yes, please.
What to do.
Douro Valley!
We easily could have spent two nights here and would recommend that to fully enjoy the area and that Lamego gorgeous hotel.
Our afternoon & evening consisted of a lovely private car traipsing us around to:
- Cantina de Ventozelo for our first sips & bites. Stunning setting. Musts: fresh tomato starter, tiny boar’s meat pies, and the meat and cheese. So, you can’t go wrong, and the bubbles and red to wash it all down were a perfect compliment. Add in stellar, friendly service, and we couldn’t have been happier. Bertha the bee was even friendly, go figure.
- A serene boat cruise beginning in Pinhao [Google Maps], with Daurum solar boats. The hour-long length was perfect for us, and I liked the environment-friendly nature of this company. Enjoy sips & small snacks to accompany the pretty ride.
- A pit stop at Doc, an acclaimed grub spot in the Valley. Jon & I would’ve loved to try a few seafood dishes and will return! Service was over the top, and the setting was surreal. Perhaps otherwise a bit too fancy for this group, but would def recommend a stop here to take in the views while enjoying a Douro red.
- Final debauchery at our lil Lamego & Life haven. Because life never quite hands you too much tequila. Yowza.
Along with staying for a longer stint, we might give the Douro Valley train a go. It sounds like the trains are BYO food & drink, so you can have yourself a merry time sipping the region’s famous port wine along the journey. To be honest tho, seeing the train by way of boat was a fun surprise.
Runabout tips:
- We don’t think you can go wrong in Douro in terms of where you grab vinho & bites. I simply (and quickly) visited a blog for the 2 spots we grubbed at. For the boat, I found that Daurum had great reviews, an easy to navigate website, and at ~$20/pp, a solid price.
- Not sure you need a private boat for the cruise. None were avail. when I booked, so we ended up with 3 other folks that were nice and friendly, obv at a lower price point.
- I originally booked a private tour with a company that would provide transport, choose the places we visited, and book the boat for us, simply to give Jon driving reprieve on the transport front. They ended up communicating poorly, so we pivoted from that 160 euro/pp tour to booking our own. The hotel booked us a private car at $430 total/4 of us (inclusive of tip & our driver rocked). A pretty penny, but worth choosing our own spots, esp for that Ventozelo visit.






The North.
We did Braga over Porto or more time in wine country primarily because one of our trip companions is from there. Very cool opp to do witness a European soccer game in the flesh and take in a slower pace than bustling Lisbon.
What to do.
- Gooooooooooooooal! Yea, you’ve heard it. It was awesome to see the S.C. Braga play Morirense, and even cooler that R’s family are giant fans that frequent the stadium. We purchased our red & white superfan gear and enjoyed the live action. Sneaking down to the lower level was a lil thrill, and we absolutely loved being able to walk to & from the stadium back to the happening area.
Where to eat & drink!
The traditional cake and bubbles to kick off the Braga visit at the GP’s did not disappoint. It was cool to see how much much Braga’s finest pride themselves in their city and its history (other than the roads that once led to Rome, obv). Given the late finish on the game and start of the work week, we didn’t have much time to explore Braga, but did have a few faves!
- Antú – Super cool spot, from its outdoor space to various levels, each with a kitschy ambiance. I unbeknowingly ordered (& devoured) the famous Francesinha! Yum. Jon enjoyed the octopus as well, but we had insanely good seafood coming our way next on the island.
- Alma – Hugely focused on presentation, this sushi spot pulls out all of the stops. The sushi itself was just okay, but we enjoyed the experience nonetheless. Not too expensive for what you get, either.
- (mostly drinks) @ 43SaoMarcosStreet & Cafe-Concerto RUM because it was late post-game, and all other joints were closed. Loved the QT before we all went on separate adventures.
Runabout tips:
- OPO, Porto’s international airport, is a mere 30 min drive from Braga. Easy peazy for our early AM flight to the islands. You might do a night in Porto to explore & make that journey even easier. We def would have but for not knowing what this leg of the trip held in store.
- Try Omakase for dinner.
- Don’t snooze on Taberna Don Rodrigo [Google Maps] in Amarante, a town leading to Braga. One of my fave meals of the trip.













São Miguel, the Azores
Holy smokes. Breathtaking beauty everywhere we turned. Couple that with stellar diving, delectable eats, and quaint oceanside towns. Did Javanti dream this up?
What to do!
- Dive! We went with Best Spot Azores given the clever name, strong reviews, and 5 min drive from our hotel. After navigating interesting miscommunication regarding our dive date (seemingly imp detail), it was smooth sailing from there. The crew was super professional, helpful, and knowledgable, and the equipment stellar.
- Best creatures we saw: giant octopus, schools of barracuda, frog fish, lionfish, sting rays, sand rays, and more. The wrecks weren’t too shabby, either.
- Hike! Our fave was Salto de Prego given the exploration of the far east side of the island, varied terrain, and pretty waterfall at the end. Fairly uphill but def not a super long hike, so very doable.
- Visit the many, many miradouros. In order of faves:
- Grota do Inferno – Don’t go when it’s about to turn pitch black like we did. Altho, what an adventure in paradise, Javanti style.
- Just below the stunning site above, Lagao do Canario
- Pico da Barrosa
- Vista do Rei – You might – at your own risk – check out the abandoned hotel very near for a unique view of Sete Cidades.
- Lagao do Fogo
- We simply stopped at the ample gorgeous pop offs at our whim. Breathtaking.
- Bike around! Ponte Delgado was a perfect place to cruise around for a bit of driving and parking reprieve, with its tiny streets and fast driving population. Our hotel rented these for a mere few euros, and the rental car company offered bikes as well. Just keep a mindful eye on those turns, as cars fly out of nowhere.
- Play tennis! Another perk of the Azoris Royal Garden. Amenities for days.
- Visit the hot springs. Alright, so we did Parque Terra Nostra on a rec. This is a giant thermal pool set in a large garden, almost amusement park like setting. Does not scream Javanti. However, enter a beloved cheese shop & cafe in Furnas [Google Maps] thanks to this visit: Queijaria Furnense. Do yourself a favor and pay these guys a visit. Delish.
- If you visit Terra Nostra, don’t snooze on the acres of trails and foliage! Almost better than the main attraction.
- For a more natural experience, you might try Caldeira Velha [Google Maps] or Ponte da Ferraria [Google Maps]. There are a few natural pools on the island that are not heated as well.
Where to eat & drink!
- Jardim Antonio Borges – What a treat for our first meal on the island. Set inside a public botanical garden, the lil restaurant is the perfect setting for a post-garden stroll vinho ou cerveja & scrumptious grub. Highly recommend the full experience.
- Bar Caloura – Just wow. Jon took our rental company’s rec on this one, and boy are we happy to have enjoyed this spot. Some of the best fresh seafood we’ve had. The setting is relaxed and island perfect, particularly after a hike or traipsing around the miradouros. The folks working here are friendly and proud of their catch. Absolute gem, and what a steal. Mmm, that tuna.
- Equina Steakhouse – Chicagoans hitting a steakhouse on a Portuguese island? Come on. Hell yes, people. Speaking of pride, the restaurant cooked for us just after the kitchen had closed, at their insistence. Clearly a local favorite, quality is king, and I dare say we were lucky to try a meat that few people in the world have. Wash that down with a smooth Azorean red, and this duo left with happy bellies.
- Focaccia – Wildly delicious Italian on the island. Musts: garlic bread (read, with a mound of scrumptious burrata in the middle), any pizza. Super cute ambiance, which is what drew us in.
- Otaka – For Japanese bliss.
- Xitaka – Amazing shrimp curry with Indian flavors, steak was on point, and the pineapple dessert took the cake. Not the coziest, but seemingly a local favorite. And for good reason.
- Faria [Google Maps] – Another Jon find! Super laid back, home-feeling ambiance. No frills, delish bacalhau and beef dishes that we ordered on our server’s strong recs. Giant beers were a fun way to wash it all down.
- A Merenda – Just a few blocks from Faria, do yourself a favor and do a post-lunch red with a delectable dessert (there are tons) to round out a perfect meal. Someone planned a lunch date made in heaven for this girl.
- Luvre Michaelense [Google Maps] – Super cute cocktail bar that was not serving food during the siesta hours we tried to go. A girl’s gotta have her bites.
- Countless other restaurants all over the island.
Runabout tips:
- If you can brave the driving, having a car is clutch, no pun intended. The roads were generally smooth; however, the streets in each town are tiny, and people fly by. This girl def left the maneuvering to Jeff Gordon.
- We opted to make central Ponta Delgado, where PDL airport is located, our home base and would recommend this. The farthest we drove, to the far eastern side of the island (Nordeste [Google Maps]) was ~an hour. Ponte Delgado appears to be the largest and most bustling of the towns, and is centrally located on the island. The 6 min drive from airport to hotel was not too shabby, either.
- You will def see that people stay in Furnas, Coloura, and elsewhere. You can find charm, gorgeous look outs, and hiking in any of these hoods and just may find yourself driving a good distance to get to other spots. That said, this is not a giant island by any means, and if you prefer to stay in nature or at least far from (small) city bustle, have at it.
- Siesta hours are real, with many places closing at 3pm, until 6 or 7. For us on the fly folks, we had to pay a bit of attention, esp for the off the beaten path grub spots.
- Try not to get too stuck on an itinerary to instead take it all – whatever crosses your gorgeous path – in. There’s tons to do, and you won’t get to it all. The solace? Everything about the island is beautiful, and it lacks a commercial feel in the best way.



















Lisboa, round trés!
No better way to round out our Portuguese journey than a weekend in the City of Light (fun fact – Lisbon is known as one of the top sunniest European cities). More fun – Valetta, Malta is #1 and was our adventure of choice a mere few months back. There’s a theme here.
What to do!
- Parque crawl! We love parks, strolling… exercise. Wait a min. Jon planned a perfect few mile excursion traipsing around various parks and gardens around the city. The best part? We were able to explore a few hoods we had not otherwise traversed.
- We tend to save bicycle fun for island life, but would be a fun way to see the city as well, or by tuk tuk. You know we recommend just jumping in one and enjoying the city, but you can def do organized tours as well.
- This time, we hit up a farmer’s market for fresh veggies and handcrafted items, in the Jardim do Principe Real [Google Maps].
- Pop ups. We’ve been lucky enough to visit on weekends each time we’ve hit Lisbon, and running into a pop market with tons of unique goods never fails. Love these.
- Check out the Amazing Store.
- What’s left but to soak up that seafood & tinto?!
Where to eat & drink!
Our faves!
- Let’s Pastrami – Chicago meets Portugal at this warm, quaint sandwich shop boasting loads of meat (& fish/veggie options). With giardiniera to boot? Damnnnn.
- Taberna da Rua das Flores – Wowowow. Charlotte, how were those scallops? Run over here, visit off-hours to actually get in, and enjoy. Best meal of the trip.
- Landeau – We visited thanks to our new Maine friends. Delish choc cake, perfectly complemented by several glasses of vinho da Madeira. This spot is across the street from By the Wine, another fave from our last stint.
- Maria Catita – Awesome shrimp dishes, awesome service, and stellar vinho tinto.
- Obacalhoeiro – Our friendly server at Catita walked us right over to this glorious haven of wine and all things cheese and meat. This will be a staple to kick off every. future. visit. Super cute date spot <3.
- A Cevicheria – Elevated cuisine, with prices to match. Loved every min of our visit and also not dying to return. Famous for its pisco sours, altho this girl indulged in vinho for days.
- Las Dos Manos – Recommended by our server and part of the same group as Cevicheria. Similarly strives for food as art, and taste is none the compromised. The margs were bomb.
- Instant Crunch – Do not sleep on the zucchini waffle! One of our best bites. Our server was passionate about wine, and the patio is super cute. All around lovely.
- Zapata for god’s sake – Another miss this go around, with the spot closed for renovations (I think) for a few weeks. Next time!
- Com Certeza! – Do yourself a favor and book a reso for this dimly lit, fairly small cozy spot with stellar reviews.
- Seventh Brunch – Super well rated and looks cute for… you guessed it, brunch.
- Any sister restaurant to Taberna da Rua Las Flores.
- It’ll be some time before we head back to Portugal, but next time will likely hold a trip to the Algarve south of Lisbon, voyage to Pico in the Azores, and back to Lisboa for a final wknd to round out the adventure.
Runabout tips:
- No need for a car in this very walkable, Bolt & Uber friendly city. Don’t plan too much, putz around, and enjoy!










Just wow on those Azores islands. Flying to the middle of the ocean pays off, my friends.
Next up? Taiwan!








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