Portland is a hipster’s paradise.

Vegan doughnuts, high-end coffee and craft beer make the city a trendy hangout for eccentrics.

But look past the man buns and plaid shirts and you will find a city rich with culture.

3 days is the perfect amount of time to see Portland, Oregon.

Explore the city, soak up the atmosphere and immerse yourself in nature.

This Portland itinerary will introduce you to the “City of Roses” and its many delights.

Plus, you’ll find out what is behind the slogan “Keep Portland weird”.

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3 perfect days in portland oregon usa

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When to visit Portland, Oregon

The best time to go to Portland depends on where your interests lie.

Unlike California, Oregon experiences cold and rainy weather in the winter. However, there are still lots of activities that work well during the colder months.

The Portland Winter Light Festival lights up the city in February and should not be missed if you’re in the area!

But, if you want to see the city’s roses in full bloom, plan your trip for summer.

Portland has the warmest weather between June and August, and can be a great addition to a US road trip.

Having a car means you can explore further afield, but isn’t totally necessary because Portland has an excellent public transport system.

Pacifica Tiny Home at Caravan Portland Oregon USA
Welcome to our (tiny!) crib!


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Where to stay in Portland

Portland has no shortage of cool and quirky accommodation, but I can’t recommend our hotel enough.

We stayed at Caravan – The Tiny House Hotel on Alberta Street. Located in the vibrant arts area, we could walk to most destinations.

Staying here was a truly unique experience because it was the first ever “tiny home” hotel in the world!

The six tiny houses range from 120-170 square feet and combine quirky design elements with space-saving functionality. Each house has a kitchen, heater, flushing toilets, shower, sitting area and a comfy bed.

Outdoors, guests are encouraged to socialise around the bonfire, which comes complete with a draw with all the ingredients to make (vegan) s’mores!

I found my Tiny House so comfy, I didn’t want to leave! Click here to read my full review of Caravan.

Luxury option: In downtown Portland the luxurious hotel The Duniway Portland, still maintains the city’s quirky feel. A minute’s walk from Portland’s best dining options, this stay would be perfect for couples exploring the city for the first time.

Budget stay: KEX Portland is a boutique hostel with a bar, designed in a European style. This would be a great option for solo travellers due to the communal vibe and proximity to local attractions.

Inside one of the tiny homes at the Tiny House Hotel in Portland Oregon USA
Inside, my tiny home was super cosy.

Portland itinerary for 3 days

This Portland itinerary is for travellers who have 3 days or a long weekend to spend in the City of Roses. However, it can easily be adapted if you only have a weekend. You’ll just have to be a little more organised and set on what you want to see!

I’ve also included some day trips for those who have longer to enjoy the city and surrounding areas.

Portland was one of my favourite stops on our United States road trip. After seeing the diverse options for things to do in Portland, I expect you too will be drawn in by its quirky charm.

How to spend 3 perfect days in Portland

Ready for a weekend to remember? Great – because Portland is full of unique things to do! Here’s how to make the most of your three days in Portland.

Day 1: Experience Portland’s best food and drink

One of my favourite things about travelling is trying new food and discovering local cafes and bars.

On your first day, I would spend some time exploring Portland’s many offerings, as well as enjoying the edgy vibe in one of Portland’s hippest neighbourhoods.

It is simply not possible to go hungry in Portland! There are so many options for foodies.

Whether you’re vegan, gluten-free or possess a serious sweet tooth, I’ve included some of my favourite spots. If you want to discover even more local favourites, join a food tour.

TRAVEL TIP: Travelling to Portland from outside the USA? Don’t forget your ESTA

Breakfast at Back to Eden Bakery

This vegan eatery is rooted in the community with a focus on locally sourced ingredients. The breakfast menu ranges from American classics like “biscuits and gravy” to healthy granola served with seasonal fruit.

Stop for a Blendily Glow Up Experience

Just a short walk down NE Alberta Street you will find Blendily skincare kitchen.

This organic skincare  brand’s products are made of ingredients mostly grown in the Pacific Northwest. The majority of Blendily’s skincare is suitable for vegans and you will not find any preservatives or additives!

The Blendily Store in Portland Oregon USA
Even if you don’t get the full “Glow Up” experience, the Blendily store is a must-visit for eco beauty lovers.

The focus is on a “seed to skin” approach which means you can witness everything being made by hand in-store.

You can book a “Glow Up Experience” if you want a truly relaxing treat. This involves a luxurious treatment mask, served with a botanical mocktail or herbal tea – the ultimate form of self-care!

Grab lunch at one of Portland’s legendary food carts

The city of Portland possesses over 600 “tiny kitchens”. For delicious street food of many different cuisines, head to one of the food cart pods around the city.

Unlike many other cities, Portland’s food carts stay together in areas called pods, which makes it easy to sample more than one at a time.

Tofu pad thai from a food truck pod in Portland Oregon USA
Tofu pad thai 5th Avenue Food Cart Pod

Some of the most popular pods include Fifth Avenue (Thai, Egyptian, Indian), Third Avenue (Vegan burgers, Mexican) and Portland Mercado (Latin American food).

Rose City Food Park is also worth a visit as it frequently hosts live music performances.

Don’t forget donuts!

If you’re a donut fan (who isn’t) – you will be spoiled for choice in Portland.

Head to Voodoo for iconic treats, Instagrammable colours and silly names.

Another delicious option is Blue Star Donuts, especially if you want to skip the lines (and get better, albeit less famous, donuts!).

With eight locations in Portland, you won’t have to travel far or disrupt your sightseeing to get your sugary fix.

Blue Star Donuts in Portland Oregon USA

Head to Ground Kontrol for some old school arcade fun

Let out your inner child with a visit to Portland’s largest arcade! Vintage video games, pinball machines, and – my favourite -the dance matt make this a place that can keep you occupied for hours!

Ground Kontrol was built to celebrate the “golden age” of video games. Open from noon until late and serving food and drink – this is a perfect way to while away a rainy afternoon or start your Saturday night.

Old arcade machines at Ground Kontrol arcade in Portland Oregon USA

End the day bar hopping on Alberta street

Stretching from Williams Ave to 33 Ave, The Alberta Arts District is one of the trendiest neighbourhoods in Portland. 

The area is full of independent galleries, restaurants and bars. You’ll also walls lined with colourful murals and street art.

It is the perfect place to experience Portland’s unique personality. Therefore,finish your evening with a bespoke cocktail, cold craft beer or an ethically sourced bar snack at one of these haunts.

Alberta Street Pub: At the end of the street, this high-end pub has great drinks, music and a gorgeous terrace for lazy summer afternoons that turn into evenings.

Radio Room: With two happy hours (afternoon and evening), seasonal cocktails and a menu chock full of vegan treats, this art deco designed bar should not be missed.

Bye and Bye: Southern-inspired vegan cuisine and an unparalleled craft beer list make this is a wonderful place to enjoy a relaxed drink with friends.

Alleyway Bar: Head to this grungy bar for a view into Portland’s nightlife scene. Expect live music of any genre and a cool crowd. The bar is also home to a pool table, karaoke nights and a photo booth. Check the schedule here.

Day 2: Get out and experience Portland’s diverse influences

Unlike San Francisco, Portland isn’t known for its Asian influences in food, culture and general city life. However, it could well give San Fran a run for its money.

Spend the day soaking in Japanese gardens, Chinese traditions and Taiwanese tea bars, sprinkled with some very American local favourites.

Get your caffeine fix at Tea bar

Before you begin your day of exploration, stop for a drink at Portland’s trendiest tea bar. The curated tea list includes fair trade, organic and dairy-free options. For fans of Taiwan-born bubble tea, there’s an extensive list of both hot and cold options.

Two glasses of bubble tea at Tea Bar in Portland Oregon USA
It’s always a good time for (bubble) tea!

Start the day in Lan Su Chinese garden

This beautiful garden was created as a collaboration between Portland and Suzhou – its sister city in China’s Jiangsu province.  Lan Su is an escape from the city and a window in Chinese culture.

Make sure you stop by the wishing tree and throw a coin onto its branches.

Wishing tree at Lan Su Chinese Garden in Portland Oregon USA
Make a wish!

Discover the city’s International Rose Test Garden

Visit the International Rose Test Garden and discover Portland’s love affair with this delicate flower.

The Portland Rose Society began back in 1889 when the wife of Oregonian publisher Henry Pittock invited her friends to view her rose garden.

The city soon became besotted with these beautiful flowers and rose gardens sprung up all over Portland.

By 1907, a festival celebrating roses was born and this is how Portland became known as the “City of Roses“.

Escape from the city at the Japanese Gardens

Portland’s traditional Japanese garden offers a tranquil escape from the busy city.

Complete with a tea house, waterfall and mountain view, it’s an authentic Japanese structure built to show the different types of garden.

Warning: this will probably make you want to travel to Japan!

A waterfall inside the Portland Japanese garden in Oregon USA

Visit Powell’s City of Books

I always find visiting bookshops to be a calming experience. Powell’s retains this ambience despite its size.

As the largest used and new book store in the world, it occupies an entire city block – I challenge you to leave empty-handed!

Enjoy unique ice cream flavours at Salt & Straw

At Salt & Straw, you will find handmade ice cream made from local ingredients in truly unique flavours.

They serve everything from the surprisingly nice pear and blue cheese to a traditional chocolate chip and mint!

The menu debuts new flavours every month and they have 4 locations all over Portland, so you definitely have an excuse to return.

Salt and Straw ice cream in Portland Oregon USA

Day 3: Experience Portland’s most unique attractions

Oregon Science and Technology Museum

There are lots of things to see at OMSI.  It has three auditoriums, a large-screen theatre and a planetarium, as well as temporary exhibitions.

When we were there, we stopped by the Exquisite Creatures exhibition and got lost in Christopher Marley’s quirky animal art.

Make sure to check out what exhibition is on during your visit.

RELATED READ : The Portland Light Festival – A Winter Extravaganza

Tour a real life submarine

Attached to the OMSI Museum is the UBS Blueback, a decommissioned US Navy submarine. One of my highlights of our weekend in Portland was a guided tour through this real-life submarine.

If you’ve never been inside a submarine before, it’s both a unique and educational thing to do in Portland. It is hard to believe people live in those conditions!

Inside a submarine at the OMSI Museum in Portland Oregon USA
Step inside a real submarine…

Hike to Witch’s Castle

Love nature? Portland is the perfect city for ecotourism in the USA.

You’ll love this short but quirky – this is Portland, after all! – hike.

Start at Portland Audubon Society’s Wildlife Care Center and walk to the beginning of the Wildwood trail.

You will walk through a forest and end up at a spooky abandoned building. These ruins are said to be haunted but are lots of fun to explore – if you dare!

Learn about Portland Pittock Mansion Museum

A visit to a new city would not be complete without learning a bit about Portland’s backstory.

Discover how Portland transformed from pioneer town to a modern city, through the eyes of the Pittock family, at this nonprofit museum.

Pittock Mansion’s viewpoint offers one of the best views in Portland. High in the West Hills, you will see Portland from 1000 feet up – plus stunning views of Mount Hood looming in the distance.

Oregon Public House non profit pub in Portland USA
Buy a drink and give back at Oregon Public House

Sip and support a charity at Oregon Public House

If you like your drinking completely guilt-free, then Oregon Public House can provide beer with a conscience. This family-friendly pub donates all profits to local charities!

Once you’ve made your purchase, customers can choose from a list of organisations to support.

With a warm and welcoming atmosphere and a delicious menu, Oregon Public House has a community feel to it. They also host meetings for non-profit organisations. I attended a NWGSD meeting while I was there.

TRAVEL TIP: You don’t want to travel the USA without travel insurance – here’s the one I recommend.

Enjoy live music at McMenamins Crystal Ballroom

At over a century old, this venue is as historic as it part of Portland’s thriving music scene.

Their slogan is “Where On Any Night, Anything Can Happen!”. Check their calendar to find out what is on during your trip.

Sauvie Island bridge with flowers blooming in summer

Adapting your Portland itinerary: 4 days or more

If you have time, there are plenty of exciting day trips out of Portland. Here are some of my favourites.

Sauvie Island

Sauvie Island is less than a 30-minute drive out of downtown Portland. The largest island along the Columbia River, it is famous for its farmland, wildlife refuge and pretty public beaches. Pack a picnic and camera to capture the vibrant flowers.

Multnomah Falls and Columbia River Gorge

Travel 35 minutes by car from Portland and you can find awe-inspiring waterfalls and an oasis of calm.

Oregon has more than 200 waterfalls throughout the state. Of those, Multnomah Falls is the most famous and tallest.

Go it alone and or join a guided tour where you will visit all the best spots and see breathtaking views of the Columbia River Gorge.

RELATED READ: Everything you need to know about hiking to Havasu Falls

Willamette Valley Wineries

55 mins away from Portland, the Willamette Valley wineries are one of the USA’s top producers of Pinot Noir. Wine lovers will delight at the many tasting rooms, while curious travellers can admire the picturesque landscapes.

This Willamette Valley tour takes you through the rolling hills of wine country and teaches you about the history of the area.

Cannon Beach and Haystack rock

Haystack Rock is one of the most famous attractions on Oregon’s coast and is only a 1 hour and 25 minute drive from Portland.

Rising 235 feet from the edge of the shoreline, this rock is home to tide pools, sea creatures and a wide variety of birds.

Puffins can be found from spring to mid-summer!

Mount Hood

A little over 2 hours from Portland is the magnificent Mount Hood.

Camping, hiking, fishing, skiing – Mount Hood is a haven for adventurers!

Oregon’s highest mountain can be seen from miles away and it maintains its snowy peak all year round.

This means it has the only year-round lift-served skiing in North America.

To see Mount Hood, you can join a tour like this one or drive.

If you choose to drive, make sure to take the Mount Hood Scenic Byway to get back to Portland. The views are breathtaking!

Mount Hood Oregon

Only have 2 days in Portland?

If you only have a weekend in Portland, you can’t possibly see everything. Choose one area based on your interests and explore!

Alternatively, take out one of the days on the above Portland itinerary.

The Japanese gardens, Pittock Mansion Museum and Witch’s Castle are all a little way out of the city centre, so you’ll save time by cutting any out.

I would recommend keeping the Japanese gardens on your itinerary for Portland no matter how long you have, though. They are simply breathtaking!

So… Why is Portland weird?

Anyone who discovers Portland will spot the “Keep Portland weird” slogan on bumper stickers, leaflets and posters throughout the city.

But what does it mean?

Originally meant to promote local businesses, Portlanders have embraced the slogan and attribute it to celebrating art and alternative life choices.

Portland locals are famous for their love of craft beer, coffee and trendy vegan eats. But they also have a reputation for advocating minority’s rights, freedom of expression and protecting the environment.

Black Lives Matter posters were seen around the city just as much as this slogan. So, if this is what makes Portland weird, then I’m definitely on board!

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Portland Oregon itinerary