A Carry-On Only Packing Guide to Portugal

October 19, 2016

7 Days in Europe in the early Fall, in just a carry-on bag. 

It's possible.

This week's post is sharing my personal packing guide from my 7-day trip to Portugal with my boyfriend in early October. It's season specific (Fall), but would definitely be applicable to similar climates and possibly even an early Spring timeframe as well. 



We flew in and out of Lisbon, Portugal spending two days in Lisbon and the remainder of the trip in Lagos, in the more southern Algarve area of Portugal.

Average temperatures ranged from 20 - 28oC during the day down to 9 - 14oC during the evening. Keep in mind, I'm Canadian, so 14oC is balmy!


Bags I Brought

Main Carry On Roller - TUMI International roller | Second Bag - North Face Backpack | Purse - Treesje Beige Crossbody Purse

I used our printable Carry On Only Packing list as a basis for packing (you can grab your copy here). We've gotten some push back from travellers before on our recommended bags for travel on the list saying that it's too many.

I wanted to address this directly -- it truly depends on WHO you are flying with, and to WHERE.

It's airline dependent. I flew with Air Canada Rouge (Air Canada's "leisure" brand), and I've travelled on Air Canada extensively internationally and domestically. They allow you to have a traditional carry-on roller (up to 20kg), plus an additional small bag (laptop, small backpack up to 20kg) plus a purse. I know that US airlines tend to be more strict, so typically when flying with those airlines I'll stuff my purse into my backpack. 

My Packing Strategy 

As some of you may have seen on an Instagram story I shared the week before the trip, I've always had a very clear packing plan.

  1. Agenda out my days on the trip, notating any weather, key plans and events (I do this in a spreadsheet, yes, I'm serious - I've used the same template for years. It's similar to the outfit planner in our free printable, but more extensive)
  2. Map out of my outfits for each day/night. I make sure to re-wear things at least twice, sometimes three times depending on the laundry situation at the destination.
  3. Notate any shoes, and accessories that I need to bring.
  4. Test each outfit. Adjust. Then test pack everything.
  5. Review what I've packed, weight the bag (and then inevitably take a few things out!)

7-Day Outfit Guide to Carry-On Fall Travel in Southern Europe 

Day 1 - Plane from Toronto to Lisbon (overnight)

An airplane outfit for a long flight, in particular an overnight one, must be comfortable. I love leggings for air travel. Our Minimalist legging is high-waisted but you can fold down the waist as well. 

Wearing: Encircled Minimalist Leggings in Black / Encircled Grey Nomadic V-Neck / Moto Jacket / Encircled Chrysalis Cardi in Charcoal / Stan Smith Sneakers.


Day 2 -  Day in Lisbon

On arriving at the airport post overnight flight, adjusting to the new climate is imperative. Lisbon was quite a bit warmer than Toronto. I folded up my leggings to a capri length, and packed the Moto Jacket away. We took a car into Lisbon to our Airbnb. 

Once we'd rested a bit at the Airbnb, I changed into a comfortable outfit to explore the city on foot. We stopped at the time-out market for a bite to eat. The weather was a bit hotter than expected that day but my outfit worked.

In the evening, we dined at a local favourite restaurant recommended by my boyfriend's colleague that was about a 10-minute walk from our Airbnb in Chiado. One of the things I loved most is how walkable Lisbon is.  

L: DAY Ripped Black Jeans (cuffed) / Marled Grey Tank Top / Stan Smith Sneaks / Cross-Body Bag
R: NIGHT Swap the top for a Dressier option (A flowy Blue top), the shoes for wedges, and the bag for a clutch.


Day 3 - Day trip to Sintra/Cascais + Lisbon

Our third day in Portugal consisted of a pre-planned day trip to the famous castle-laden area of Sintra, and stunning coastal area of Cascais. The tour was awesome -- by a funny, laid back local tour company called We Hate Tourism!

Sintra is at a higher attitude, so I knew to expect colder temps than Lisbon. As we were leaving Lisbon, it was clouding over and getting a little chilly. However, we'd also be spending a long day in a van. I wanted to have layers!


In the evening, we dined at a renowned seafood restaurant called Sea Me in the vibrant Barrio Alto area of Lisbon, and then visited Park Bar (it's literally a rooftop bar on top of a parking garage. So cool!). I also did a load of laundry so that I'd have my airplane clothes clean for the trip home, and enough socks and underwear for the trip.

T: DAY Striped T-Shirt Dress / Encircled Chrysalis Cardi in Charcoal (styled as the Cape, Scarf, and Wrap) / Straw Fedora / Cross-Body Bag / Stan Smith Sneakers B: NIGHT Black Shirt Dress / Moto Jacket / Clutch / Wedges / Necklace

Day 4 - Road trip to Lagos

Lagos is a resort town, just a 3-hour drive south from Lisbon. Imagine, instead of driving to a cottage- driving to the Ocean (amazing!). However, the drive is oh-so-boring. Comfort, again is key. I knew this road-trip called for our Dressy Sweatpants. Comfy without looking sloppy (I must mention in my experience Europeans don't wear sloppy sweats!)

At night, we took a taxi into Lagos to eat a local seafood restaurant called Restaurant Reis, dining outside in the cooler temps. The food in Portugal is AMAZING. I cannot say that enough. A local dish, called Cataplana was a favourite of mine!

L: DAY Encircled Dressy Sweatpants / Encircled Chrysalis Cardi in Charcoal (styled as the double-loop scarf) / Straw Fedora / Striped White Tee / Cross-Body Bag / Stan Smith Sneakers R: NIGHT Encircled Chrysalis Cardi in Charcoal styled as the Grecian Tunic / Moto Jacket / Wedges / Rose Gold Earrings / Clutch


Day 5 - Lagos

A day in Lagos is not complete without visiting some of the most visually stunning sights. Starting with Ponta da Piedade, a series of rock formations formed by the Ocean's power. To get to the bottom of Ponta da Piedade, you need to walk down about a hundred steps. Good walking shoes are key!

Next up, the gorgeous and secluded Praia do Camilo beach. It's 200-steps down to this gem. So, yes, lots of walking (thankful for this given how much food I consumed!). 

On the beach there was no where to change, so I snapped our Chrysalis Cardi into the Grecian tunic and changed underneath it. It was the perfect solution!

The day wrapped up with more exploring in and around the historic fort/walls of Lagos, idyllic narrow streets and lunch at a local place. My boyfriend particularly enjoyed when I accidentally took our navigation into the old town while driving. It was like the movie the Italian job. Honest. 

Dinner was at a casual Italian restaurant in Lagos, outside. It was a really cool night so I was thankful that I threw a light sweater in last minute. Key lesson: Layer, layer, layer. 

L: DAY White denim shorts / Encircled Chrysalis Cardi in Charcoal (styled as the cardi, and used as a changing tent / Straw Fedora / Blue Flowy Top / Cross-Body Bag / Stan Smith Sneakers (and flip flops packed with a bathing suit).

R: NIGHT Black Ripped Jeans / Encircled Nomadic V-Neck in Heather Grey / Lightweight Cream Sweater / Moto Jacket / Stan Smith Sneakers / Cross-body bag


Day 6 - Day trip to Sagres

While waiting at the Toronto airport for the security breach to be cleared, my boyfriend and I met a nice couple from San Diego en route to honeymoon in Portgual. They tipped us off about Sagres. A small, laid back surf and sea town on the most south-western tip of Portugal.


A short 35 minute drive from Lagos, we spent the day exploring the scenic Cabo Sao Vicente lighthouse perched high above the Atlantic ocean. A lunch at a marina seafood restaurant complete with Oysters (literally fresh from the ocean, opened at our table), and grilled Dourada. 

In the late afternoon, we returned to our resort in Lagos, and took a taxi into the edge of Lagos to a truly local establishment for our last indulgence in Portuguese cuisine. Ate more Cataplana! 

L: DAY Striped T-Shirt Dress / Encircled Chrysalis Cardi in Charcoal (styled as the scarf) / Straw Fedora / Cross-Body Bag / Stan Smith Sneakers (and flip flops packed with a bathing suit). R: NIGHT Black Shirt Dress / Fancy Necklace / Moto Jacket / Clutch / Wedges


Day 7 - Road trip to Lisbon Airport. Plane to Toronto.

Our flight was out of Lisbon, so we got up super early and drove back from Lagos. One lesson learned is that Portugal likes to sleep in. There were no food establishments open prior to 8am. Big time regret: The gas station 'croissant' we shared for breakfast.

I repeated my outfit (clean of course) from traveling to Portugal for the trip home. It was perfect. A good thing to get over when traveling light is wearing the same thing twice. Trust me, no one cares. Especially if you're traveling around to multiple places. A 'quick' 8 hour flight home, and multiple episodes of the Real Housewives of Melbourne, and we were back on Canadian soil.

DAY + NIGHT: Encircled Minimalist Leggings in Black / Encircled Grey Nomadic V-Neck / Moto Jacket / Encircled Chrysalis Cardi in Charcoal / Stan Smith Sneakers


Beauty + Personal Care Care Products I packed

I was able to fit all of my personal care items into the 1L clear TSA-approved bag (my dear boyfriend on the other hand, had his 150ml gel confiscated at security!). 

Remember to keep gels/liquids under 100mls. 

I brought mostly mini sized stuff. Miniature toothpaste, moisturizer, face oil, eye cream, lip balm, mascara, face powder, bb cream, concealer, perfume, deodorant, conditioner (I left out shampoo - most hotel shampoos are ok for me). Hair spray. Natural bar soap, cut in half. One eye shadow. Tweezers. Mini Nail clippers. Mini scissors. Band-aids. Typical travel meds. 

The only semi-regular size product was my Neutrogena sunscreen (which is relatively flat, and under 100mls).

Curling Iron / Hair Brush (skip bringing a blow dryer, most hotels, airbnbs etc have them)

I don't wear a lot of makeup to begin with but my biggest concern was the 1L limit (as is for most women). The key is to source out and save amazing minis. Sephora is a good source, as is your local drug store. 


What I'm most glad I packed

My leather moto jacket, Chrysalis Cardi, Lightweight Sweater and comfy shoes

The evenings really cooled off in both Lisbon and Lagos, having options for layers, and an easy dress up/dress down neutral jacket (like a moto jacket) is perfect. The Cardi as a scarf and cardi/wrap were a lifesaver on my day tour to Sintra, where it's often a few degrees cooler during the day/evening. 

Comfy shoes - a must. Walking the slippery cobblestone streets is even difficult in flats. I saw a few people tip right over. Good thing that comfort + style are not mutually exclusive. So many great travel shoes that look and feel good.


What I wished I packed

A mini spray perfume- I brought a rollerball version but it didn't come out very well of the bottle. I love a nice spritz of light perfume before a night out!  


    What I wish I didn't pack

    Workout clothes- I brought yoga crops, and a workout top. Never used them. We walked so much that a workout felt unnecessary. Plus, I made the decision on the trip to truly be present and enjoy every minute (versus sweating away in the gym!). I did however wear my workout bra a few times in the hotel room. I find it a more comfortable alternative to a traditional bra, so I'd keep that next time.

    The clutch- it was beautiful but if I had a purse that detached it's strap in a neutral colour that would've been perfect. My Rebecca Minkoff MAC bag would do the trick but it's light blue. Something in beige, black or grey would've worked just as well. At any rate, the clutch is flat and takes up almost no space.

    I think I did pretty well with the packing light on this trip. There are only a few things that I felt like I didn't wear as much. And, if I had more access to laundry later in the trip, I would've been able to reduce that even more.

    I had such an amazing time traveling in Portugal, and am happy to share my packing tips with you in this short guide. 

    If you liked this post, share it with other wanderlusters who'd love to travel lighter.

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    1 Carry On, 1 Week In Portugal. Find out How  @encircled_ #carryononly #traveltips #travellight

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    With gratitude,


    Founder + CEO, Encircled

    Love travel? Join our League of Travelistas -- a community for women who love to travel. Click her to request access to our private facebook group.

    All photos are copyright Encircled. You may use these with permissions but may not alter the photos. Please link back to our websites. TIA!

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