What to Pack for Lisbon and Sintra: Everything I Wore and What I Recommend Now

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Cloaked in an air of timeless enchantment, Lisbon and Sintra were the two locations I was most excited to visit in Portugal. Strolling through cobblestone streets, savoring pastéis de nata, and gazing at whimsical castles sounded like an utter fairytale. And while packing, my wardrobe quickly became the canvas for embracing the romantic charm and vibrant energy that I was seeking in these places. From exploring the colorful alleys of Lisbon to wandering the magical palaces of Sintra, allow me unveil my sartorial choices and what I recommend now:

Everything I Wore

Travel Blogger Jordan Gassner walking through a misty archway while wearing a cream faux leather jacket and a MinkPink Dress at Pena Palace in Sintra, Portugal
Travel Blogger Jordan Gassner holding a pair of white retro sunglasses at Pena Palace in Sintra, Portugal
A Low angle photo of Travel Blogger Jordan Gassner standing on a staircase wearing a MinkPink Dress at Pena Palace in Sintra, Portugal

Pictured: MinkPink Cora Midi Dress, Top Shop Faux Leather Jacket (Similar), Sam Edelman Ethyl Low Top Sneakers, Retro Cat Eye Sunglasses

A high angle photo of Travel Blogger Jordan Gassner leaning against a stair railing in a Faithfull the Brand dress in Lisbon, Portugal
A high angle photo of Travel Blogger Jordan Gassner sitting on a green public bench in a Faithfull the Brand dress in Lisbon, Portugal
A high angle photo of Travel Blogger Jordan Gassner near a stair railing and smiling in the Alfama neighborhood of Lisbon

Pictured: Faithfull the Brand Tempio Midi Dress, Sam Edelman Deacon Sandal

Travel Blogger Jordan Gassner wearing a lilac anna nata dress while making a wish at a fountain inside Quinta Da Regaleira in Sintra, Portugal
Travel Blogger Jordan Gassner wearing a lilac anna nata dress while traversing the caves at Quinta Da Regaleira in Sintra, Portugal
Travel Blogger Jordan Gassner wearing a lilac anna nata dress while exploring the gardens at Quinta Da Regaleira in Sintra, Portugal

Pictured: anna nata Sienna Dress, Beige Sandals (Similar), Gold Drop Earrings (Similar)

Travel Blogger Jordan Gassner wearing Capulet, Nonchalant the Label and a gold bracelet in front of a Bougainvillea tree in Lisbon, Portugal
Travel Blogger Jordan Gassner leaning against a post in front of a Bougainvillea tree in Lisbon, Portugal
Travel Blogger Jordan Gassner wearing Capulet, Nonchalant the Label and vintage rings in front of a Bougainvillea tree in Lisbon, Portugal

Pictured: Capulet Gracia Smocked Crop Top, Nonchalant the Label Fabi Pants, Sam Edelman Deacon Sandal, Gold Bracelet (Similar), Assorted Vintage Rings (bought in Porto at Wild at Heart)

Travel Blogger Jordan Gassner walking through Monserrate Palace in Sintra Portugal while wearing a Reformation dress and holding an orange scarf
Travel Blogger Jordan Gassner smiling in front of Lisbon's Belem Tower while wearing a black Reformation Nikita dress and orange bandana
Travel Blogger Jordan Gassner admiring the architecture at Monserrate Palace in Sintra Portugal while wearing a black Reformation Nikita dress

Pictured: Reformation Nikita Dress (Similar), Orange Scarf (Similar), Sam Edelman Sandals*

**I packed my tried-and-true Sam Edelman Sandals for Portugal and, while I have been able to wear them on many past adventures, they actually broke on my first day exploring. See what alt recommendations I have for traveling Portugal in the Next Section!

What I Recommend Now

Summer-y Day Dress

Pack 2-3 dresses to help you stay cool and look cool while conquering Lisbon and Sintra’s many stairs

Lightweight Blouse

Bring 2-3 options to mix-and-match with pants, a midi or a maxi skirt while exploring

Button-Up Shirt

To mix-and-match with pants, a midi or a maxi skirt while out sightseeing

Midi or Maxi Skirt

For days when it’s too windy to wear something short and you don’t want to wear pants, pack 1-2 options

Linen Pants

1-2 breezy pairs of pants to keep you cool while providing plenty of coverage for any religious sights

Summer-y Evening Dress

Pack 1-2 options for fancier tapas-style dinners and nights out in Lisbon

Lightweight Jacket

Perfect for layering on windy afternoons. I love jackets with patterns + color. Lisbon is the perfect place for it!

Sunglasses

Protect your eyes from the warm Southern European sun while out on your adventures

Costume Jewelry

Minimize the risk of loss, theft, or damage to valuable pieces by opting for inexpensive swaps

Flat, Sturdy Sandals

For daily adventures along cobblestone pathways and uneven ground

Sneakers

To keep your feet happy and clean while moving throughout Portugal’s walkable cities

Flat, Dressy Sandals

To pair with an evening look for fancier dinners and nights out in Lisbon

Sun Hat (alt option)

To protect your hair, scalp and face from the warm Portuguese sun

Lightweight Scarf

Handy for adding dimension to your outfit in photos and keeping you comfortable when it’s too warm for a jacket

Neutral Bag

Because of pickpocketing, I prefer neutral-color bags that don’t not call attention to themselves while in Europe

Swimsuit

An optional piece that is great for hotels and rooftops with pools or for side trips to the Algarve coast

Cover-Up

An optional piece that is great for hotels and rooftops with pools or for side trips to the Algarve coast

Warm Jacket

For unexpectedly misty mornings or evening dinners. An optional piece from late June to early September

These are the core wardrobe pieces I recommend based on my own travels to Lisbon and Sintra. This guide is simply meant to be a starting point to help you determine what to pack. Please remember that what’s best for you will ultimately depend on your travel style and trip duration.