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Weekend Guide: The Ultimate Itinerary to Portland, Oregon

Weekend Guide: The Ultimate Itinerary to Portland, Oregon


Have you ever wanted to travel to Portland? Here’s an Ultimate Itinerary for you to use to plan your trip today! We lay out a detailed schedule and tips for visiting each location.

Portland, Oregon is a city that is known for its eccentric and laid-back culture. It is best known as the city of Roses. We loved visiting the area because it is very eco-conscious. It is one of the greenest cities in the United States. A lot of people cycle, walk and go on hikes. As you can imagine, the vegan scene here is on the rise. In addition to all of this, the city is budget-friendly destination!!

Disclaimer: This post, Weekend Guide: The Ultimate Itinerary to Portland, Oregon is sponsored. As always, all opinions are my own.

American Airlines flight to Protland Oregon Weekend Guide: The Ultimate Itinerary to Portland

If you are a first-timer in Portland, or a local, this is the perfect guide for you. There are so many things to see and do. If you find yourself in Portland, use our Ultimate Itinerary to guide!! It will blow your mind.

Some of the activities listed in this itinerary included:

  • Willamette Valley Wine Tour

  • Powell's Books

  • International Test Rose Garden

  • Pittock Mansion

This guide is jam-packed with amazing experiences. We included restaurants (vegan-friendly), entertainment, outdoor adventures, and more to help you get the most out of your vacation! For more Portland fun read our top picks for the best Instagrammable spots and the best restaurants for vegan food and drink.

We are working to get the vlog up ASAP. Until the video is up, you can watch a video recap of the trip on our Instagram page.

Day 1 – Donuts, Landmarks and More!

• 8:00 am – Breakfast: Head over to Blue Star Donuts for a delicious breakfast. Blue Star Donuts is not your basic donut shop! Each donut is made with fresh fruit, herbs and spices. We got the chance to taste all 6 of their vegan donuts: Passion Fruit Cake, Mexican Hot Chocolate, Orange Olive Oil, Blueberry Basil Cake, Sugar and Spice, and Strawberry (special). The Passion Fruit Donut was our top pick. ($3-4 per donut)

9:30 am – Coffee break: If you need a shot of expresso after the donuts, grab one at Presso Coffee. It is the cutest place. There is a pink wall on the exterior for you to use as a backdrop to your photo. ($5)

10:00 am - Check in: For our trip, we stayed at the Kimpton Hotel Monaco. We listed them in this blog post because of their eclectic, chic design. The decor is top notch! In addition to the decor, we loved staying here because of their amenities. They have loaner bikes for you to use, complimentary happy hour and live music, and in-room yoga mats. Their staff is so friendly and helpful. Highly reccomend staying here!

• 10:30 am – Activity 1: Lan Su Chinese Garden is one of Portland's greatest treasures. Built by Chinese artisans from our sister city Suzhou (home of China's famous ancient gardens), it's among the most authentic Chinese gardens outside of China. The garden itself is modeled after Ming Dynasty. We published a picture to Instagram and several people thought I was in China! ($12.95 general admission or $9.95 for students)

12:00 pm – Activity 2: Pittock Mansion is a historic house museum nestled in a wooded area in Portland. You can opt to do the self-guided tour or a guided one. Guided tours are subject to volunteer availability. For example, when we arrived there wasn’t a guide on duty. The museum has maps and interpretive panels to lead you through the mansion. Plan on spending 1-2 hours here. ($12)

3:00 pm – Light Lunch: ¿Por Qué No? Taqueria is a small Mexican restaurant with two locations in Portland. If you want a drink and snack, head to the location off Mississippi Ave. The restaurant is so colorful and cute! There’s both vegan and non-vegan options here. We ordered the guacamole, salsa, chips and verduras tacos without cheese (aka veggie tacos) and mezcal margarita. ($20)

5:00 pm – Happy Hour: Tope is a rooftop restaurant located in The Hoxton Hotel. It is a taqueria inspired by the street food of Mexico City. We loved this place because of the views. Whether you sit inside or outside, you can see stunning views of the city. We ordered the potato taquitos without the cheese/aioli sauce to make it vegan. To drink, we tried the spicy margarita, sex on the beach, fist bump and mr.manager. The fist bump and spicy margarita was our favorite!


8:00 pm – Dinner: Sudra is an Indian inspired restaurant and bar that hosts a completely vegan menu. This place is THE BOMB. Highly recommend ordering the chicken-less tikka masala bowl. It is the best vegan Indian we ever ate in life. You will not be disappointed. ($15)

Total Per Person: $88.95 plus tax and tip

Top 10 Vegan-Friendly Bar and Restaurants in Portland

Day 2 – Willamette Valley Wine Tour

8:00 am – Breakfast: Nectar Café is a vegan spot with fresh juice bar & house roasters coffee with local art. We ordered the vegan sausage waffle sandwich and the Portland scramble. The Portland scramble was our favorite dish. It had scrambled tofu, sausage, zucchini, red onion, red potato and vegan cheese. We were also able to try some of their homemade desserts too. We recommend trying the blueberry pie if they have it available. ($12)

• 10:30 am – Wine Tour: Sea to Summit is a tour and adventure company providing fun and informative experiences. They specialize in Oregon Wine Tours & Portland Brewery Tours during all seasons of the year. You can join public tours headed out from downtown Portland or you can customize a tour.

We went on the Willamette Valley Wine Tour and visited three wineries: Rex Hill, Erath, and Stoller Estates. All wineries are breath-taking. However, Stoller Estates has the best tasting room. It won the USA Today’s “Best Tasting Room” award in 2018. ($139)

5:00 pm – Break:

7:30 pm – Dinner: Housed in the same building as Vtopia, Ichiza Kitchen is an Asian spot offering vegan noodle dishes & small plates, plus sake and teas. Try the ba wan buns, mapo tofu and pompano ramen. ($10-30)

9:30 pm – Nightcap: If you had to pick one bar to visit in Portland, it should be Multnomah Whiskey Library. It is a cozy upstairs lounge with brick walls & a vintage feel features, 1,500+ spirits & small plates. The décor is unreal. It reminds me of the library of an old liberal arts or ivy league school in the best way! The tables have those vintage desk lamps with the green shades on them. Pro tip: They do not accept reservations. Head in before dinner and put your name on the list. While you wait, grab a bite to eat. They will call you when a table opens up. ($12-30)

Total Per Person: $173-211 plus tax and tip

10 Most Instagrammable Spots in Portland

Day 3 – Walking Tour, Brunch and Museums

8:00 am – Quick Breakfast: There are tons of coffee shops in Portland. Head to the closest one near you for a quick snack and coffee ($10)

9:00 am – Activity 1: Head to Powell’s Books! It is the largest Independent Bookstore in the world. Powell's Books is located in the Pearl District on the edge of downtown and occupies a full city block between NW 10th and 11th Avenues. (FREE)

11:00 am – Activity 2: Take a free walking tour of Portland. This is the daily free tour that you’ve been looking for! Seven years and 500 5-star TripAdvisor reviews later, this tour has become a legend. There is no reservation necessary foe the tour. You can just show up! Your guide will be there wearing a neon shirt at the meeting point. (FREE)

1:00 pm – Brunch: No Bones Beach Club is vegan restaurant with an eclectic menu full of fantastic food and cocktails. We ordered the brunchos, cauliflower wings, huevos, Benedict and mimosas. Our favorite was the brunchos. These bunchos (aka nachos) are made out of housemade tortilla chips that were smothered in poblano cashew queso, refried white beans, crumbled tempeh bacon, scrambled tofu, and smoked pepper aioli topped with fresh tomatoes and scallions. ($18)

3:00 pm – Activity 3: The Oregon Historical Society is dedicated to making Oregon’s long, rich history visible and accessible to all. We highly recommend that you visit the Museum. They do a great job at navigating the state’s history with race. ($10)

5:00 pm – Break

7:00 pm – Dinner: Vtopia is an all vegan restaurant & cheese shop. One of the best meals we had was at Vtopia! The shop is small but the menu packs a punch. We order the Caprese and SBLAT (shittake bacon, lettuce, avocado and tomato) sandwich. The SBLAT was the greatest sandwich we ever had. It came with organic shiitake bacon, mayo, garlic dill aioli, avocado, lettuce, and tomato. We also got their Mac & cheese, which was also delicious. ($15)

Total Per Person: $53 plus tax and tip

Day 4 – Gardens

• 10:00 am – Brunch: Modern Times: Belmont Fermentorium is a hip craft brewery with a large tasting room with 32 beers on tap. In addition to drinks, they have a full vegan menu. We recommend getting the asada burrito to eat and OG edition flight to drink. Our favorite beer was Fortunate Islands. Get a glass of this beer if you don’t want a flight ($20)

• 12:00 pm – Activity 1: Portland Japanese Garden is the one out of three gardens we visited on our trip. In addition to the garden, the space has a cultural village where visitors can immerse themselves in traditional Japanese arts. Pro Tip: The garden is located right across from the International Rose Test Garden. Parking is challenging if you drive. You will either have to pay to park ($1-2) or find street parking. ($18.95)

• 2:00 pm – Activity 2: International Test Rose Garden is a rose garden in Washington Park. There are over 10,000 rose bushes of approximately 650 varieties. The roses bloom from April through October with the peak coming in June, depending on the weather. Feel free to pack a light picnic and eat in the garden! When you walk in turn to your left and walk down the path until you meet a big, grassy knoll. We saw several people laying out and snacking. (FREE)

•4:00 pm – Head home

Total Per Person: $38.95 plus tax and tip

Thanks for reading this Weekend Guide to Portland, Oregon! Let us know what you think of this guide in the comments below.


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Until Next Time, 


“Your life is happening now. Make it amazing!”


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I would love to visit Ita!y.


I live in Newberry,SC, which is a small town on the east coast. I have lived here all of my 54 years and have vacationed at many of the beaches on the east coast over the years. My husband and I have some favorite beach spots such as Myrtle Beach,SC, Folly Beach,SC, Jekyll Island,GA and Hilton Head,SC. These are some wonderful places to visit whether you are after relaxation, good restaurants or some fun family time. All of the locations are within six hours of our home so we take road trips which we thoroughly enjoy! My husband was diagnosed with cancer two years ago so we have been putting our trips on hold. I had no idea how mu…


I have never been to the east coast but I am dying to! I've lived on the west coast all 42 years of my life and I have seen a few states but never the east coast.

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