A Portland (insert Seattle) Dreamtrip

I’m only 4 months late on this blog.

Back in February we took an 8 day trip to Portland/Seattle. The Dreamtrip we took to Portland with our travel company was 4 days and we spent an additional 4 days in Seattle.


We got into the Portland airport late at night, grabbed Thai food, and crashed at the cheapest airport hotel we could find.

The next morning we drove about 4 hours up to Seattle (the drive really does remind you of Twilight) where we’d stay for 2 days. The cool part about this trip was that my brothers best friend from middle school, lives in Seattle with his wife and two cute babies so we had a place to stay, locals to show us around, and instant, quality company.


Being able to be in Seattle and hang out with my brother, mom, my husband, and Jeff and his family was truly amazing. It’s really interesting to see someone you’ve known since the 7th grade married with two babies. (P.S. this was my brothers and my first ever vacation with my mom).


  1. Ivar’s Seafood Restaurant

We stopped by this place to grab food. I’ve always known walk up seafood places to be greasy and upset my stomach so at first I didn’t get anything, until I tasted someone’s clam chowder and completely changed my mind. I was wrong about this place.


2. Pikes Place Market

This is on every single Pinterest blog for what to do in Seattle for a reason. Between the brick road, beautiful array of colored veggies and fruits, old fashioned whiskey bar, multiple coffee shops, smell of fresh bread in the streets, watching cheeses be made, handmade goods, photography, etc. this place is visually stimulating and I don’t really see how a person couldn’t like this place.


3. The Views

I don’t remember how we got to this particular place. We just roamed down to the water and found a boardwalk to walk on. These views man. The piercing blue water. The sailboats. People fishing off of the boardwalk even though it’s freezing. Seeing a bald eagle out of an older gentleman’s telescope. The mountains behind the water. It’s a sight to see.


On our way back to Portland for the start of our Dreamtrip, we wanted to hit a few other stops.

1. Astoria Oregon

The drive from Seattle to Astoria is about 3 hours and 15 mins. Astoria is a small port city where the Goonies was filmed. Beautiful little town. We stopped to get lunch at this restaurant called Bridgewater Bistro. What a view. This was a place that I’m glad we stopped at, but after lunch we were ready to move along.


2. Cannon Beach 

From Astoria to Cannon Beach was about 45 mins. Once we got there, we parked the car, walked down, and stared at the huge rocks that stand smack dab in the middle of the water. It really does feel like something from the Pirates of the Caribbean. Again, Cannon Beach is a must see but after about 20 minutes we were ready to move on. I personally wouldn’t make this a day trip. For us it was more of a drive by stop.


We arrived in Portland in the afternoon. At check in (Hotel Modera) the woman behind the desk handed us 3 gift cards worth $60 each for the French restaurant downstairs (which was phenomenal). Our travel company throws in different perks on every Dreamtrip and you never know what you’re going to get so it’s like opening up a Christmas present.


We had a few hours to kill before the Welcome reception so we sat outside in the courtyard and drank wine next to the fire pit. Moments like these can wind up being precious memories in the future. This one was because Derek, myself, and my brother sat there and talked a lot about the business that Derek and I were launching two weeks after we got home from this trip.


On every Dreamtrip you go on, no matter where it is in the world, there is a host on that trip and a Welcome Reception on the first night so that everyone can meet each other. When we walked into the room there was food and local wines and beers spread out for us. On this trip there were 50+ people. Getting to know different people and where they’re from and why is a really fun part for us. One couple had a 4 week old baby and had been on 20+ Dreamtrips. Some people were from different parts of Asia. It’s a solid experience. If you don’t really like people, you’d probably dislike going on a Dreamtrip lol.

  1. Voodoo Donuts 

When I read Pinterest blogs prior to going, this was a name that popped up a lot. I’m not a donut or a sugar person, but here is what I do know. On any given day, there will be a 45 minute wait to get a donut. There is a line wrapped around outside, and people will wait 45 minutes in the rain to get their hands on this donut. Our host knew this because he’s a local so he had the donuts delivered to us instead. I cannot tell you how adamant the people from Asia were about getting pictures of these donuts lol.


2. Creo Chocolate

At first when our host told us we were going to go get a tour of a chocolate factory we were like, “coooool”. But what the hell right? Turns out it was really impressive. Holy cow what a niche business to go into and what a craft skill to develop. One of the cool things was that these people pour their hearts into this business and into the farmers they do business with in (I believe Ecuador). We bought two bars of chocolate at the end. One was a mint chocolate and the other was a sea salt chocolate. If you like chocolate ^^


3. Lunch at Ruth’s Chris Steakhouse

When we got to Ruth’s we were guided up to one of the banquet rooms where everything was set up for us. We just plopped our butts on a seat and talked to whoever sat at that table. Again, we appreciate these kinds of experiences. One gentleman was born and raised in NY. Learned a bunch about him. Another couple was from Seattle and the husband worked for Microsoft way back in the day and told us some cool stories. Our host sat at our table so we asked him a bunch of questions about his experiences and different trips he’s taken. It was a lunch to remember.


4. The Waterfalls at the Colombia River Gorge 

What a beautiful drive up to this place! Once we got there it was just one waterfall after another. Note to self: Wear a jacket that’s actually waterproof, not water “resistant”. From what we were told it’s better to visit these waterfalls in the summer. There are trails that will allow you to go towards the tops of the waterfalls to get different views. The trails at the time we were there were closed down due to snow. (Yet another excuse to buy a Drone).


5. Farmer’s Market at Portland State University

We went to some museum and then our group heard there was a Farmers Market a few blocks down so we ditched the museum to go there. From my perspective living in Jacksonville FL, this Farmers Market was LEGIT. The money I would spend if we had one like that here.


The picture below is 50% of the total group of Dreamtrippers. This was our group for the day.


6. Watching a riot 

If you’d like to experience watching a riot take place in person vs. watching it on TV, go to Portland. We were having breakfast when the riot started and after we were done we walked outside and watched it progress for over an hour. It was highly entertaining.


7. Wineries

On one of the days we drove to Willamette Valley wine country and went to Willamette Valley Vineyards. We got a tour of the whole place also while we drank wine. We obviously ordered a cheese board. Derek and I love winery days. We’d go back to this place hands down if we ever visited again.


Our Dreamtrip experience in Portland was yet again another successful trip taken. Between the hosts, the people, the experiences and activities, the special care from the staff at the hotel, and the stress of having to figure everything out for ourselves completely taken off of our hands, our travel company delivered big time. The total price for 3 people for this Dreamtrip to Portland cost us $750. (That does NOT include any money spent in Seattle, airplane tickets, or extra food).

However, even though the Dreamtrip was awesome, we personally did not like Portland Oregon as a city. To us it was super dirty and gloomy (and that’s coming from someone who has lived in New York). Homeless people are EVERYWHERE, on every single corner, outside of every single business. Tents are visible from every street. The amount of people who asked us for money was astounding. The people are very Liberal. We are not. Riots are the norm. The dynamics were like nothing I have seen. I wouldn’t personally go back to Portland, but I would absolutely go back to Seattle. I don’t say this to scare anyone away from going. I just can’t write this blog and not add in that section of my perspective, and in this case I am speaking for myself, Derek, Justin, and my mom.

1daymainwalking3253956375_72f5845e6c_zHomelessness in Portland

Originally we were going to spend our last two days in Portland, but we were pretty over it. We called up our friend in Seattle and asked him if they’d be open to company for 2 more days. They said yes so we drove a second time back up to Seattle, and then drove back down to Portland two days later to catch our plane home.


  • The entire trip for 8 days and 7 nights for 3 people totaled 2000.00. That included airfare, car rental, gas, all of our food, Dreamtrip package, beer and wine, and hotel parking. (Keep in mind when we travel we go pretty hard on quality food and drinks and if our trip is over 3 days, we always rent a car).
  • If we were to go out this way again from Florida we’d do it one of two ways: 1. Visit Cali and Seattle in one trip 2. Visit Seattle and then head up to Vancouver BC.

Traveling brings new perspective to life. We learn what we do and don’t like, we develop patterns of things we like to do on each and every trip, on this trip we experienced new dynamics within our family, and we gather new data that will help us on our next adventure. Each trip is different. That’s probably why we continue to prioritize traveling. We’re always learning. We crave it.



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