We’re headed to Portugal for 18 days at the end of May 2025, and this is our plan.
We’re headed to Portugal this Spring and I cannot wait. We’ve been saving up our Chase Reserve Credit Card points for this trip, and the timing couldn’t be better. We booked our flights, most of our hotels, and a couple of activities already in Portugal with our Chase Points. It is making the budget look very solid for this trip. This article is not an ad and in no way is Chase sponsoring me or this article, I’m just a fan. I was shocked at how many hotels and activities were available on Chase Travel!
For Portugal I am trying out a couple of travel planning apps to help me build our itinerary and keep track of our reservations. Our friends are using Tripit, but I am enjoying the social-import feature of Nowy. While building my itinerary and booking hotels I kept referring to my free trial of TripsyPro. The UX/UI are great and it keeps my daily itinerary really easy to scroll and reference while making daily plans and reservations. I’ve decided to keep the paid version of the app and after our trip, I’ll share a link to my itinerary here.
What about you? What travel apps are you using to track and build your travel plans?
Portugal: Where to Start
So for Portugal, the fun part about this trip is that we are going for a family wedding in Cascais, a beautiful beach town about 30-minutes outside of Lisbon.
This helped me to determine that we’d at least fly into Lisbon; after watching flight prices for several months, looking at options in and out of Porto, Madeira, and Lisbon, we finally decided to buy on Dec 31, 2024 for roundtrip DFW <> Lisbon via Heathrow. So far I haven’t seen the flights dip any lower, because I’m a nerd and keep watching them with Google Flight Alerts.
Once our departure/return dates were set I started researching all the different options of what we could squeeze into 10 days after the wedding. My husband enjoys driving and relaxing, while I prefer seeing all the sites, hiking, and eating all of the baked goods. I knew I wanted to visit either Madeira or 1-2 of the Azores Islands, but ultimately, selected Madeira because of the amazing hikes and the flight options out of Lisbon.
Portugal: Transportation
So while Portugal is a very public transit-friendly place, and even though photos from one of my favorite photographers of all time is one of the first things I ever saved on Instagram is of the most beautiful train station in Porto (see below, and do follow Jess!), my husband does love to drive.
So after booking flights to and from Lisbon, then deciding that Madeira would be the one island trip we’d take in our remaining 10-days, we booked rental cars. We looked at both Ryan Air and TAP Air to fly to/from Madeira, and decided to pay a little more for TAP since we’d be using our larger Away carry on bags (and apparently they fly OK as carry ons on TAP Air!) and… Madeira’s airport is a bit of a scary place to land.
Portugal: 10-Day Itinerary
Days 1-3: Madeira
So after the wedding concludes in Cascais on Sunday night, we’ll get up early and fly over to Madeira where we have booked an AirBnB for three nights in Funchal. Since we’ll have a rental car and we can only do 3 nights on Madeira, we’ll try and maximize our time on the island by staying centrally.
My big wish list items while in Madeira are:
- Hiking the Pico de Areeiro to Pico Ruivo (hopefully it fully reopens)
- Riding at least one cable car (apparently there are 7!)
- Seeing the adorable houses in Santana
- Relaxing in some sunshine
Day 4: Madeira -> Lisbon -> Costa Nova
It may be ambitious, but we’ll wake up in Madeira and take the slightly less than 2-hour flight back to Lisbon, pick up our rental car at 4:30 in the afternoon at LIS, and drive north to Aveiro/Costa Nova, which should take us about 2.5 hours. Since the sunset in May in Portugal isn’t until close to 9 PM, we’ll hopefully get to see a bit of the countryside while we drive and make any stops along the way to eat or enjoy the views.
We wanted to head up north to get over to Porto and out to the Douro Valley for a few days since we both enjoy wine tasting, but the striped homes in Costa Nova just look too cute not to stop and see on our way there.
Day 5: Aveiro -> Porto
We’ll wake up in Costa Nova (in a hotel we booked on Chase points!), get in a stroll around the town, hopefully grab some pastries and coffee, then drive into Aveiro to explore along the Ria de Aveiro canals, and see more beautiful tile work.
Once we’ve had our fill, we’ll head up north to Porto, which should be just about a 1-hour drive, and get us there in time to check into our hotel for the next 2 nights. And yes, we booked this one with Chase points, too! The plan will be to grab dinner to go so we can get to a hill and experience sunset in Porto. I’ve read that the Jardim Do Morro is an excellent option at the top of a cablecar station.
Day 6: Porto Mountains 4×4 Adventure & Porto
So where my perfect day would be to leisurely walk through Porto on my own little food/walking tour, my husband likes adventure and off-roading, so here’s another day where we split the day.
Our morning will start with a 3-hour 4×4 tour of the Porto Mountains (which I’m not going to lie, sounds extremely fun, and we booked it with Chase travel points, so it is basically “free”) and then we’ll spend the afternoon wandering and eating along the streets of Porto.
While in Porto, my top hit list of places to see and food to eat include:
- The Porto São Bento train station (as mentioned above, gorgeous tiles) and eat at the new Tapabento there
- Drink coffee at Combi Coffee
- Walk across the Dom Luis Bridge
- Stroll the Crystal Palace Gardens
- Find and appreciate more tile shots like on the Igreja do Carmo Church
- Walk along the Ribeira
We’ll see how much we get to on our two afternoons and final morning in Porto!
Day 7: Porto morning and Octant evening
We’ll see when we get up and leave our cute Porto hotel to head out to our first stop in the Douro Valley. Our hotel for the first night is the Octant Douro (booked with Chase travel points) and it sits about 45-minutes southeast of Porto. I am seriously so excited to stay at this hotel and enjoy the beautiful vistas from our balcony and the A Terra Bar, and appreciate some of the Douro’s finest wines from their “most comprehensive curated Douro wine lists in all of Portugal.” Not to mention, we’ll take a walk down the Unesco World Heritage wooden Paiva Walkways.
Day 8: Douro Valley
From Octant our day is open for exploration as long as we end our day at our next hotel for 2 nights further east in the Douro, about a 1.5 hour drive, Quinta do Vallado.
I love how so many of the wineries, or “Quintas” in the Douro have attached wine hotels, and Quinta do Vallado is just such a place that we’re as excited to enjoy the stay as we are to taste and experience their wine and their Turkish bath and sauna. I know we’ll find lots along the way to stop, see, and explore, but just spending time at Quinta do Vallado is going to be wonderful, so hopefully we make it in time for a 2:30 or 4:30 pm winery tour before finding dinner for the night at the hotel or nearby.
Honestly, there are so many gorgeous such hotel and wineries that it was nearly impossible to pick just two for this trip!
Day 9: Douro Valley
We’ll enjoy the Quinta for the morning and then head out another 45-minutes east to do a half-day winery tour, and lunch pairing tasting at Quinta do Crasto, recently recognized as a top winery in the world!
Then the one big meal we have booked for the trip–at a recommendation from our most well-traveled friends, we’ll have dinner at the Six Senses, Douro at the Vale de Abraao restaurant. Should be a splurge and well worth it–plus it is only 10-minutes from our hotel!
Day 10: Douro -> Obidos
This will be our day with the longest drive planned. We need to head back toward Lisbon and while there are many places to see along the way, we’re going to make the approximately 3-hour trek from the Douro Valley down to the near-coastal town of Obidos without any set/planned stops… at least as of now.
We’re looking forward to exploring the coast, we’re staying at the Royal Obidos Spa & Golf Resort (booked with Chase points), and the walled village. Depending upon when we get into town we’ll either explore Obidos this evening, or in the morning before heading back to Lisbon for our last two nights.
Day 11: Obidos -> Lisbon
We’ll see how much we like Obidos and if we need more time there or along the way back to Lisbon, but at some point on day 11 we’ll check into our our last hotel of the trip in the Sao Mamede district of Lisbon. Like many of our other hotels, we’re using our Chase points to cover the stay, so we’ll see how it pans out. There were far more options that I expected on Chase Travel Rewards for hotels all around Portugal!
This afternoon/evening will be an opportunity to check of any remaining places we’d like to eat/see in Lisbon. Thanks to Somebody Feed Phil and a ton of IG stories, the Lisbon list is long! Here are some of our top places we hope to experience while in Lisbon:
- Eat:
- Dear Breakfast
- Ponto Final
- Jesus e Goes
- A Cevicheria
- Nannarella
- Prado
- Restaurante Adega de Belem
- Pasteis de Belem
- Belcanto
- Icon Bar and Rooftop (I’m a sucker for rooftops)
- See:
- Estufa Fria
- The National Tile Museum
- Jeronimos Monastery
- Shop:
- Mercado de Santa Clara (only on Tuesdays and Saturdays for local handmade goods)
- Store the Spot Market
We’ll see how much we can pack in during the first few days of our trip and the family and wedding activities, because I still have one last day trip I’d really like to cram into our final day of the trip, to Comporta!
Day 12: Comporta & Lisbon
We decided we’d skip the southern beach region of Algarve, Portugal on this trip since my red-head husband doesn’t love the sun, and we’ll get a lot of pool time in between our various hotels and the couple of days in Madeira. But, south of Lisbon about an hour and a half by car, is the adorable, chic, and shopping-friendly beach town of Comporta.
The list is long for things I’d like to see and eat here, but I’m really excited to do some shopping since this town is known for their textiles and hand-made goods. Shops on my list (largely influenced by this post) include:
- CoteSud Qintado Lago
- Vida Dura
- Lavanda Comporta
- Noemina
- Kakos
- Briffa Comporta
- Lavanda Comporta
- Spot Market
- The Life Juice Comporta
- Caju
- Fashion Clinic
- Loja de Ca
- Stork Club
There are a bunch of great restaurants here as well, so we’ll see how long of a day and how much shopping we can get in on our last day of the trip!
Day 13: Technically day 19: Fly Home
We’ll get up early and return our rental car and head to the Lisbon airport for a long trek home back to DFW.
Closing Thoughts
We cannot wait to take this trip and are so ecstatic about seeing Portugal for the first time. What else should we not miss on our travels around Portugal? If you have recommendations for Lisbon, Cascais/Sintra, Madeira, Porto, Obidos, or the Douro Valley, I’d love to hear them!
If you haven’t already found yourself a travel credit card, I am going to refer you to Chase. We love our Chase Sapphire Reserve Credit Card and cannot recommend it highly enough–from the travel concierge services to the lost baggage coverage to the free lounge access. Having this card has already saved us thousands. We never pay for food or drinks at the airport any longer. We love lounge life. Hope to see you there!
Follow me on Instagram for more travel plans in Portugal, DFW and abroad @localgirltravels
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