Portland Itinerary A Perfect Weekend in Portland, Oregon by JetSettingFools.com

Portland Itinerary: A Perfect Weekend in Portland, Oregon

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Hip, funky and fun, Portland, Oregon is a perfect weekend destination! Boasting abundant green space, cool urban districts and a fabulous foodie scene, travelers visiting Portland in a weekend can experience the best of the city. Our Portland Itinerary features the city highlights – and visitors can use our outline to create their Best Weekend in Portland trip plan.


Portland in a Weekend

Spending a weekend in Portland is an excellent way to get acquainted with the city that so proudly proclaims to be weird. With an easy-going atmosphere and culture, visitors will find there is plenty to do on a weekend trip to Portland.

On my first weekend trip to Oregon, I traveled to Portland to visit a friend. Being in the company of a local, I wasn’t tasked with creating a Portland, Oregon itinerary; she knew all the best places to go and had insider secrets. On that trip, I spent two days in Portland – and absolutely fell for the city.

On a subsequent visit – when my friend no longer resided in Oregon – I took on the responsibility to plan a trip to Portland, Oregon that included the city’s top sights, beautiful nature and the best food.

Based on diligent research and the best experiences from many visits, we have created a 3-Day Itinerary Portland that is perfect for weekend trips.


3 Days in Portland

In our weekend trip planner for Portland, we outline a day-by-day plan for visiting Portland in 3 days. It is assumed that you will arrive mid-afternoon on Friday (or Saturday) and stay until the evening on Sunday (or Monday). Although our Portland weekend itinerary does include a few ‘weekend only’ events, those activities can easily be substituted for other fun city adventures. Therefore, this itinerary for Portland, Oregon can really be used for a trip over any days of the week!

Furthermore, we understand that not all travelers are planning a Portland, Oregon 3-Day Itinerary. Some visitors are limited to just one day in Portland, while others are creating a 5-Day Portland Itinerary. To best help fellow travelers, we offer suggestions for alternate Portland trip itineraries at the end of the post. Whether you are planning to see Portland in a day or are devising a longer Portland trip itinerary, you can use our tips to plan an ideal vacation.



In our trip plan, we have outlined how to spend 3 perfect days in Portland. In addition to our day-by-day plan for a weekend trip to Portland, Oregon, we also include a useful map of attractions and essential tips – like how to get there, where to stay and what you will need to pack.

This Portland blog post contains everything you need to plan your trip! Save, Bookmark or Pin this Portland, Oregon travel itinerary so that you can easily access it while planning (and during!) your trip!


Day 1 of Your Portland Weekend Trip

On Day 1 of your Portland 3-Day Itinerary, get settled into your accommodations (suggestions below!), then set out to discover one of the cities most vibrant districts, Pearl.

How To Plan a Weekend in Portland Oregon by JetSettingFools.com


Pearl District

The Pearl District is an absolute must in every Portland, Oregon vacation itinerary! Once the warehouse district in the city, the Pearl has evolved into a stylish enclave of residences, art galleries, green parks and fabulous restaurants.

Start your exploration of the district at the landmark Powell’s City of Books, which claims to be the largest independent bookstore (for new and used books) in the world. The massive bookshop covers an entire city block and ranks on many lists as one of the Top 10 Bookstores in America. After perusing the selection of books (and perhaps making a purchase), take a walk through the North Park Blocks, a green city oasis since 1869.


Detour into Old Town Chinatown

Detour from Pearl District into the Old Town Chinatown District. Although not as impressive as other American Chinatown districts – like the one in San Francisco – there is an ornamental gate (at NW 4th Ave and W Burnside St), but the highlight of Chinatown is the lush Lan Su Chinese Garden.

Other attractions in the district include the Steel Bridge (a double-decker bridge built in 1912) and Union Station (the city’s main transportation hub, which was built in the late 1800s and is listed on the National Register of Historic Places).

Make your way back into Pearl District and walk through Jamison Square, which features fountains where you can cool your feet in the summertime.


Dinner, Drinks and Live Music

Nicknamed ‘Beervana,’ Portland has more breweries than any other city in the world – so getting a taste of locally produced craft beer is essential!

Pearl District is home to a range of restaurants and some of the best breweries in Portland. Among the many, our favored spot is Deschutes Brewery and Public House – for both food and craft beer. The menu is upscale pub grub and the fresh brewed beer – of which there are 18 brews on tap – is exceptional.

From Deschutes, visitors can create their own brewery tour in the district, making stops at 10 Barrel Brewing, Rogue Pearl Public House, Back Pedal Brewing and Von Ebert Brewing. For handcrafted cocktails, try Teardrop Lounge and Vault Cocktail Lounge.

If live music is your scene, check out who is playing at the historic McMenamins Crystal Ballroom, which has seen a slew of acts grace its stage since the early 1900s. They even have an in-house brewery!


Day 2 of Your Weekend in Portland

On the second day of your Three Days in Portland, start with some classic Portland food experiences, then see Downtown Portland sights, and end the day across the Willamette River in the Buckman District.

How To Spend 3 Days in Portland Oregon by JetSettingFools.com


Voodoo Doughnut Old Town

In 2000, Voodoo Doughnut opened in Portland…and so the doughnut craze began. With a line of creative flavors – like Bacon Maple Ale – the shop quickly made headlines and their Portland Cream Doughnut has been proclaimed the city’s official doughnut. Who ever knew there was such a thing?! Patrons line up out the door and down the block everyday for the sugary breakfast treats.

Visitors who don’t want to stand in line, but still want a darn good doughnut, might want to check out Blue Star Donuts instead. Their gourmet donuts include flavors like Blueberry Basil Cake and Mexican Hot Chocolate.

Pro Tip: If you really want to go crazy, try donuts from both spots! Or, better yet, join a guided Donut Tour


Portland Saturday Market

Recognized as the longest running outdoor arts-and-crafts market, the Portland Saturday Market is a must-see on your weekend getaway to Portland, Oregon. Opened in 1974, the market features more than 350 local vendors – plus there is always live music and heaps of international food truck options, and it’s open Sunday as well!


Downtown Portland Bike Tour

In the afternoon, hop on a bicycle for a guided tour of Portland downtown attractions and districts. Biking is one of the best ways to get around the city – and on the tour, you can learn more about the city as you pedal through the city streets. Sights on the route include Pioneer Courthouse Square, Tom McCall Waterfront Park and Fifth Avenue Food Cart Pod. Find out more!

Another Popular Portland Tour

Alternatively, visitors more interested in learning about the food culture in the city can join a popular Portland Food Tour. The small-group walking tour includes 5 food stops at some of the best restaurants and food carts in the city – and the guide shares the city history throughout the tour. This tour is limited to just 12 people, so reserve your spot in advance!


Buckman District

In the evening, delve into the Buckman Neighborhood, a foodie haven and craft beer paradise. If you need a late afternoon pick-me-up, stop at Rimsky’s – an eclectic (and some say haunted) coffeeshop located in an old Victorian style house. Next, if you want to stay on theme, take a walk through nearby Lone Fir Cemetery, an enchanting final resting place for many of Portland’s most prominent citizens.

For dinner, head to Hawthorne Street – which is filled with character and lined with vintage stores. The district hosts numerous restaurants – from fine dining to farm fresh to funky fare. Our favored spot for a meal is the Cartopia food cart pod, located on the northwest corner of the Ladd’s Addition neighborhood (one of the oldest planned neighborhoods in the city). After dinner, sample more Portland craft beer as you bar hop from brewery to tap room in Buckman. Use this link to Google Maps for the locations of 6 Buckman brewery tap rooms.

On the other hand, you could leave Buckman and go a bit further south to Division, where you can feast on famous Ikes Fish Sauce Wings at Pok Pok – and then attend the Saturday midnight showing of The Rocky Horror Picture Show at Clinton Street Theater.


Day 3 of Your Portland Weekend Itinerary

On Day 3 of your weekend in Portland, Oregon spend time in the beautiful outdoors – or, in the event of foul weather, check out some of the museums in Portland. Then again, if you want to see more of the region, embark on one of the day trips around Portland, Oregon.

3-Day Portland Itinerary by JetSettingFools.com


Washington Park and the Portland Japanese Garden

A city park since the 1870s, Washington Park is a 410-acre park featuring several city attractions – and visiting is a must on your Portland, Oregon itinerary!

In addition to the 15 miles of hillside, forested trails, the top park attractions include the Oregon Zoo, Hoyt Arboretum, the International Rose Test Garden and Amphitheater and the exceptional Portland Japanese Garden. Memorials, statues, museums and playgrounds are more park highlights.

In the afternoon, wander through the quaint Northwest District and eat lunch at a hip local restaurant – or dine at the charming Nob Hill Food Carts. Afterwards, cool down with some ice cream from Salt and Straw, an artisan Portland-based ice creamery featuring unique flavor combinations.

Alternatively, hop on a Willamette Jet Boat or Lunch Sightseeing Cruise.

Pro Tip: If you are hanging out on the east side of Portland, there are two excellent neighborhood parks: Mount Tabor – and extinct volcano – and Rocky Butte Natural Area – a gorgeous lookout point. Numerous paths weave through forests, around reservoirs and up Mt Tabor and the elevated Rocky Butte Park offering stellar views of Mount Hood. 


Indoor Activities: Portland Museums

If foul weather keeps you from being outdoors, then consider visiting one of the many fascinating Portland museums. Top city museums include OMSI (Oregon Museum of Science and Industry), Pittock Mansion (which is located just north of Washington Park and has a phenomenal viewpoint!), Oregon Historical Museum, Portland Art Museum and the bizarre The Freakybutture Peculiarium and Museum.


Portland Day Trip Option

Taking a day trip from Portland is a perfect way to see more of the stunning surrounding region. Top trips are to waterfalls, wineries, the river gorge and the coast. We are featuring a few of the most highly-touted Portland tours. 


Morning Multnomah Falls and Columbia River Gorge Waterfall Tour

This extremely popular and highly rated tour features the area’s beautiful waterfalls along the scenic byway. A guide offers interesting information about Oregon, while participants get to take in the breathtaking vistas. Book your spot!


Willamette Valley Wine Tasting Tour

Spend the afternoon visiting 3 incredible wineries in the picturesque Willamette Valley. The small-group tour features travel by minivan (and pick up/drop off at downtown hotels) and wine tastings at the 3 stops. Get more details!


Columbia River Gorge Adventure

Discover the outstanding beauty of the Columbia River Gorge on bicycle. The tour guide leads participants on an easy bike ride, making stops along the way to hike to nearby waterfalls. Guests can choose from morning or afternoon day trips from Portland. Find out more!


Oregon Coast Tour from Portland

The coastline in northern Oregon is a magnificent sight! We actually recommend taking a few days to complete a coastal drive – which you can read about in our blog post: Oregon Coastal Drive! However, visitors short on time can still get a glimpse of the coast on a full-day tour. Learn more here!


More Portland Itineraries

Many people planning a trip to Portland wonder, “How many days in Portland, Oregon is enough?” While we think three days in Portland, Oregon is an ideal amount of time to see the city sights, we could easily spend weeks exploring the city and region. However, what ultimately determines how long to plan a Portland vacation itinerary is interests, money and overall allotted time-frame.

Perhaps your time is limited to just a 2-Day Itinerary for Portland – or maybe you are planning a week-long Oregon vacation itinerary. To help in the planning process, we are sharing our top suggestions for alternative itineraries.


Portland Itinerary 1 Day

Whether you are taking a day trip to Portland or are planning to see Portland in one day as part of a larger regional itinerary, there are numerous ways to spend your time in the city. For us, a perfect Portland 1-Day Itinerary would include top sights, the best districts and iconic food.

To make the absolute most of your day, we recommend starting with a half-day tour by vehicle  that takes in the top city sights. Then, in the afternoon, pick one district (or park!) that is most appealing to you – and go discover it on foot! Depending on which neighborhood you choose, you could stop for a Voodoo Doughnut or Salt and Straw ice cream, then pop into a few craft breweries to get a good taste of what the city has on offer!


2-Day Portland Itinerary

With 2 days in Portland there is just enough time to see the city highlights. In order to create the best Portland 2-Day Itinerary, we recommend using parts of our above outlined 3 Day Portland Itinerary. However, for the best flowing Portland Itinerary 2 Days, on your first day, we recommend following our tips for Day 2. Then, on the second day, spend the morning at a park or on the Multnomah Falls tour; spend the afternoon in the Pearl District exploring the sights on foot.


Alternate Portland Itinerary 3 Days

While we think our outline for a 3-Day Itinerary in Portland, Oregon is the best way to see the city, it is certainly not the only way! Visitors who want to spend more time in nature can easily cut out some of the city sightseeing in favor of urban parks and the waterfalls tour.

And, vice versa, travelers most interested in city attractions can eliminate some of the outdoor adventures and spend more time in city districts – like the Alberta Arts District or Mississippi/Williams.


4-Day Portland Itinerary

With 4 days in Portland, visitors have enough time to see the top city attractions and go on a day trip from Portland. To create the best Portland Itinerary 4 Days, we recommend following our outlined plan for 3 days in Portland, then, on the last day, go on a full day tour from the city.


Portland 5-Day Itinerary

Creating a 5 days itinerary in Portland, Oregon allows ample time for sightseeing, active adventures and a day trip. With 5 days in Portland, we recommend following the 4-Day Itinerary for Portland, Oregon (directly above), then spend the last day exploring another neighborhood – like Mississippi, going to Forest Park or hop on the other side of the Columbia river and visit Vancouver, WA!


Oregon Itinerary One Week

As we already mentioned, we would have no problem planning a Portland travel itinerary for several weeks. That said, we think the best way to plan a Portland 7-Day Itinerary is to spend time in the city and time on the coast. In fact, to create the best Portland and Oregon Coast Itinerary, you can simply use our day-by-day 3-Day Portland Itinerary – and then use our Oregon Coastal Drive Itinerary – that spends four days driving down the coast, hiking some amazing Oregon trails and then looping back up to end in Portland.

Pro Tip: Visitors who have already been to the coast could instead create a similar Portland to Crater Lake Itinerary. Spend 3 days in Portland (as outlined) then take a 4-day round-trip adventure to Crater Lake.


Visit Portland or Seattle?

Many people debate whether to visit Seattle or Portland – and, we admit, it’s a tough call! We think both cities are fabulous! Because of their proximity and ease of getting between the two cities, instead of picking one over the other, we suggest visiting both by creating a Seattle and Portland Itinerary. To make the most of a Seattle-Portland Itinerary, we think you should plan at least five days to see the two cities (but a week would be better!).

To plan a Seattle and Portland vacation, you can use the tips from our Seattle Itinerary!


Portland Map


More Tips for Your Portland Itinerary

Now that you know what to do in Portland in a weekend, we have a few more tips for your trip!


What is the Best Time to Visit Portland?

We think the best time to visit Portland, Oregon is in the summertime; specifically, from June until early October. Summers in Portland tend to be dry and sunny – which is perfect for outdoor activities (and the rose gardens!). However, while the temperatures are usually mild, humidity can be high.

Late autumn through spring can be rainy, which could seriously put a damper on hikes and even neighborhood exploration. That said, winters tend to be mild – and with an umbrella and raincoat, it can be a great time of year to visit the city.


How To Get To Portland

Portland can be reached by plane, train, bus or car. We prefer flying – we are JetSetting Fools, after all! When we need to buy plane tickets, we start our search for the best airfare on SkyScanner.

The Portland International Airport – PDX – is the main city airport. The airport is well-connected to the city via public transport, but private ground transportation from the airport is also available and can be booked online


Do You Need a Car in Portland, Oregon?

For our Weekend in Portland Itinerary, it is not necessary to rent a car. The city has an exceptional network of public transportation and Uber is also available. It is easy to get around the city on foot and by bicycle, too.


Where to Stay in Portland, Oregon

We think the best place to stay in Portland is in the heart of the city. We have stayed in various hotels on our trips to Portland – and can personally recommend staying at The Paramount Hotel. Located right in the heart of downtown, The Paramount Hotel offers clean rooms, comfy beds, an on-site restaurant, and sincere staff – all at an affordable price! Check rates and availability!

Pro Tip: We have yet to stay at the historic Benson Hotel, but it is an iconic, luxury hotel in the city center! 


What To Pack for Your Portland Trip

We have just a few final tips for your Portland vacation! Go to our Packing List page for more packing tips!

Walking Shoes

We cover a lot of ground in our Portland 3-Day Itinerary! We recommend wearing a pair of comfortable city walking shoes during your neighborhood exploration. I like to wear these Columbia shoes for women and Kris likes Merrell trail shoes. Both of these shoes are good for most of the nearby hikes, too!


Weather Appropriate Clothing

While summer days can be hot, nights can be cool. We recommend packing clothing for your trip that can be layered – and even in the summertime, you will likely want at least a lightweight jacket. Extra layers are also essential if going on a jetboat tour or into the mountains. Remember to bring a wide brimmed hat, good sunscreen and insect repellent, too.

In the non-summer months, it is ideal to have a packable raincoat and a travel umbrella, too!


Portland, Oregon Travel Guide

In our Portland weekend trip itinerary, we have outlined the best things to do in Portland, Oregon. However, it is always a good idea to have a travel guidebook – like this one! – for more information.



Portland is an incredibly photogenic city! Rather than capturing the sights with your phone, we recommend upgrading to an actual camera. We use a Canon Rebel with an everyday 18-135mm lens. The camera comes bundled with all kinds of fun accessories, making it perfect for a budding photographer.



Not necessary in the city, but if you do plan on taking day trips into the nearby nature, we highly recommend bringing binoculars with you!


Start planning your trip to Portland, Oregon! Search for the lowest airfares, the best accommodations and fun things to do…then start packing!  Want more travel planning tips? Head over to our Travel Planning page for more information and tips on traveling – and for country-specific information, take a look at our Travel Guides page!


We Want To Know: Is there anything you would add to our Portland Itinerary? What is your favorite way to spend a Weekend in Portland? Give us your best tips and advice in the comments below!


Visiting Other Top Destinations In The USA? Have a peek at our detailed guides for Denver, Chicago, Boston, NYC, Austin, San Diego and many more at our Travel Guides USA Page!


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Portland Itinerary A Weekend in Portland, Oregon by JetSettingFools.com

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