The Perfect Portugal Itinerary (Finally)

From cobbled streets lined with pastel-colored buildings to sun-kissed coastlines and mouthwatering cuisine, Portugal offers a vibrant blend of culture, adventure, and relaxation. Ready to discover the hidden gems of Europe’s best-kept secret?

Back in 2019, my early years working as a travel agent, I had constructed and pieced together, The Perfect Portugal Itinerary. Highlighting all the absolute “must see” and “must do” activities into the perfect 9-day getaway. As a travel agent I have the incredible resources and partnerships to essentially put together whatever itinerary I can dream of! For this particular trip I used Avanti Destinations, who is the absolute leader in the industry in terms of FIT (Flexible Independent Traveler) travel for Europe. Their itineraries offer maximum flexibility, multiple different aspects of travel (flights, hotels, tours, transfers, travel insurance) and quality properties in TONS of major European cities. They are my GO-TO for all customized European Travel between multiple destinations and for European Honeymoons!

Let’s dive into the itinerary (the perfect itinerary). Our tour starts in the one and only Algarve Region of Portugal.

Algarve: Portugal’s Sun Drenched Paradise

You almost hate to start here because the Algarve is so stunning and charming, you might never want to leave! With its golden beaches, picturesque coastal villages, and vibrant nightlife, this region is a must-visit for anyone looking for a little bit of everything. Trust me, stay at least 2-3 nights—you won’t regret it. With over 300 days of sunshine a year, the Algarve is a dream for beach lovers and outdoor adventurers. Plus, it boasts more than 200 kilometers of coastline, including the world-renowned Praia de Marinha, often hailed as one of Europe’s most beautiful beaches.

After a sun-soaked day on the beach, get ready to dive into the fun nightlife of Albufeira! This lively town is buzzing with great food, vibrant bars, and winding cobbled streets. Think Bourbon Street in New Orleans (but, you know, way cleaner… though I’ve never actually been to Bourbon Street, so someone please confirm in the comments if you’ve done both). Whether you’re gearing up for a wild night out or planning a bachelor/bachelorette party, Albufeira’s got you covered. But if the party scene isn’t your vibe, no worries—there are plenty of quieter villages and serene beaches in Algarve for a more laid-back experience.

And I have to mention Lagos and its stunning hidden caves! A highlight for us was a boat tour that let us cruise the dramatic coastline and peer into jaw-dropping sea caves. (I was tempted to try kayaking, but we went with the boat tour to keep things more accessible for our group). Seeing those towering cliffs from the water was absolutely breathtaking—definitely one for the memory books!

Lisbon: A City of Charm: Lisbon’s Must-See Wonders

Leaving the sun-soaked beaches behind, we hopped onto our coach bus (chartered just for our small group) and headed to Lisbon, the vibrant capital of Portugal. Traveling by coach was such a treat for us—we each had our own “row” of seats to spread out and get comfy. Some napped, others read, and I spent the ride listening to music and soaking in the beautiful scenery. For some reason, I’m always fascinated by those random gas stations and little towns along the highways—something about road trips just gives me that cozy, “homey” feeling.

We stayed in Lisbon for two nights, which felt like the perfect amount of time considering all the spots I wanted to see (despite my usual preference for smaller, quieter towns). Lisbon’s a major city, but it has its own charm—trust me, it’s cool.

Within Lisbon there is so much to do – like visiting the Belem Tower, Take a Tram Ride, catch views from the Castelo de Sao Jorge, walk along the Tagus river, and indulge in pasteis de nata (Portuguese custard tarts – SO GOOD).

During our stay, we took day trips to Sintra, Cascais, and Estoril, and let me tell you—Sintra is a MUST. This quaint town, nestled in the hills of the Serra de Sintra, was once a royal summer retreat and is now a UNESCO World Heritage site. It’s famous for its stunning palaces, villas, and historic sites, all set against lush forests and dramatic hills. It’s only a short drive from Lisbon, so if you’re in the city, it’s an easy day trip.

Sintra is massive, so do yourself a favor and go with a guided tour—seriously, tour guides are the best! Their love for their country is so contagious, and they make every stop more fun and interesting. And of course, you can’t visit Sintra without seeing the Pena Palace, with its iconic yellow exterior that makes it impossible to miss.

Cascais and Estoril also rank high on my list of day trips. Cascais has beautiful beaches, fabulous shops, and excellent restaurants, making it the perfect place to spend a day. Plus, the promenade from Cascais to Estoril, which runs along the coastline, is absolutely stunning. With cafes and beach bars lining the path, it’s the perfect spot for a leisurely stroll by the sea.

Obidos: A Fairtytale Town Filled with Medievel Charm

Back on the bus we headed towards Obidos stopping in both Fatima and Ourem before reaching our perfect little boutique hotel right outside the castle walls of Obidos. Fatima holds a very religious significance in Portugal and is a major Catholic pilgrimage site where millions of pilgrims visit each year. Whether or not you are there as a pilgrimage or an observer, the sights are truly beautiful and rich in history. After departing Fatima we arrived at a much anticipated hotel, The Literary Man. This boutique hotel is truly a hidden gem and book worm’s heaven! The interior of the walls and hallways are filled with books, as well as the rooms and common spaces. I truly – LOVED this hotel, not to mention their gin and tonic’s at the lobby bar were incredible. The village of Obidos is encircled by walls, making it truly look like something out of Game of Thrones. When walking through the cobblestone streets of Obidos be sure to grab a glass of Ginja! The Ginja is a very strong liqueur from sour cherries! Often times served in edible chocolate cups – it’s a iconic trademark of the town and should be on your list of things to do! The walls of Obidos allow you to walk around the perimeter – if you are scared of heights beware the high walls don’t have railings and can be a bit sketchy if you are not a fan of heights.

The next day, we set off on a day trip to Nazaré, a charming fishing village and legendary waves! Originally named after Nazareth, this spot is famous for its massive waves—and when I say big, I mean BIG! The beach was pretty much a no-go for swimming with those waves crashing, but we still found the perfect spot to relax, soak up the sun, and listen to the power of the ocean. We also got a chance to take in the jaw-dropping views of the coastline from above, and wow, the sights were unreal! Honestly, this part of the trip became a favorite for me and many others. If you’re curious, check out the Netflix documentary 100 Foot Wave—it’s all about the incredible big wave surfing that happens in Nazaré. Definitely a must-watch!

Porto: A City of Vibrant Culture, Port Wine, and Unforgettable Sights

Leaving our books behind in Obidos, we headed to Porto – en route to Porto we stopped in the city of Coimbra, home to the country’s oldest and most prestigious university. This gave me Harry Potter Vibes – we even saw students wearing full gowns on campus to complete the look! In Coimbra we also visited the Old Romanesque Cathedral of Coimbra, which was absolutely breathtaking! From there we kept on to Porto, the second largest city in Portugal situated on the Douro River. A trip to Porto would not be complete without experiencing the delicious port wine that comes from the area. A short ride deep within the Douro Valley we did a vineyard tour and boat cruise that included lunch, and some really amazing wines! The boat tour was beautiful as we cruised down the river and saw all the amazing wineries located in that region!

So there you have it – the PERFECT Portugal Itinerary (in my opinion- of course). Now onto some additional comments about this trip – feel free to stop reading if you only care about the itinerary.

The reason this article is titled The Perfect Portugal Itinerary (Finally) is because I first planned and booked this trip back in 2019—but we didn’t actually go until April 2023. In 2020, when the pandemic hit, it brought the tourism industry to a halt. Thinking back to March 2020, that’s when countries around the world started shutting down and implementing stay-at-home orders. Our trip was originally set for April 2020, but that was obviously never going to happen, so we postponed and rebooked for 2021, hoping things would be back to normal in a year (ha, hindsight!).

By the end of 2020, it was clear that 2021 wasn’t happening either, so we moved the trip to 2022. But 2022 was still uncertain, with some countries reopening but still enforcing restrictions. If you’re going to visit a bucket-list destination, you don’t want to deal with mask mandates or limited access to sights, so we decided to push the trip to April 2023.

Rebooking three times was incredibly time-consuming and honestly, a little disheartening. Some group members even considered asking for a refund back in 2020, but travel insurance didn’t cover the pandemic as a “covered reason” for a refund. That led to some tension, but I’m beyond grateful to everyone who stuck with me through the uncertainty. In the end, the trip was unforgettable, and looking back, I’m so thankful we didn’t get that refund. Had we, this trip might have stayed just another dream itinerary instead of becoming the reality it was. So, to everyone who stuck with me from 2019 to 2023—thank you! You made this trip so worth it.

Thinking of your next Portuguese adventure? Don’t wait – contact me today to help piece your adventure together and seize the day!  Follow me on Instagram: @ Highdeserthorizons