By Wendi Gordon
Recently my husband and I took our first trip to Portland, OR. We chose Portland after hearing about how much fun the city is and all it had to offer. Two additional couples decided to join us, and as luck would have it, the Points Mom herself, was on our trip! It was like having our own personal “activities director” and we were able to get the most out of the city as possible.
We stayed at the Nines Hotel (Starwood) in the downtown area. Although, the hotel had mixed reviews on Trip Advisor, we found it to be lovely with good service. Unfortunately, we did have a problem with our room upon checking in, but it was rectified quickly and effectively. We even received additional Starwood points for our inconvenience. If you happen to stay here, make sure you go up to the top of the hotel for a drink or dinner at Departure Restaurant. There are great views of the city!
We hiked at Multnommah Falls, a beautiful hiking area approximately 30 minutes outside of the city. The water falls were gorgeous as was the scenery. We did a 6 mile hike, but you can easily shorten that depending on your ability and time constraints. The parking lot and the hike get crowded quickly, so get there early. We were there by 9:30AM, which worked.
In addition to hiking, we spent an afternoon on a bike tour visiting breweries and sampling numerous varieties of beer. We also spent an afternoon at the Rose Garden and Japanese Garden. There is no charge for the Rose Garden and an entrance fee of $10 for the Japanese Garden. Personally, I found the Japanese Garden to be somewhat boring and much preferred the roses!
A must visit is Voodoo Doughnut. We arrived there at 6am to be the first on line and moments later a line formed behind us. Although it is open 24/7, long lines are inevitable due to its popularity. 
Doughnut choices were extensive and they were amazing! Powell’s Books is also a fun place to visit. It is a huge three story book store with an enormous selection of books that spans an entire city block.
Finally, in the city, food trucks are very popular. On our first day, we visited the trucks for lunch. Everything from the tacos to the pulled pork was fresh and flavorful. The food in general in Portland is great and unique. Our favorite restaurant was Andina. Also, don’t leave the city without visiting Salt & Straw for some very unusual ice cream. I really enjoyed the apple and blue cheese ice cream.
After three busy fun-filled days in the city, we traveled to the The Allison Inn & Spa in the Willamette Wine Valley. The hotel was beautiful, surrounded by lush greenery and vineyards. The rooms were modern and spacious.
On our first day there, we hired a tour guide to take us to the wineries. The hotel booked the tour for us and it was one of our favorite days. Portland is known for its Pinot Noir and we indulged in many samples throughout the day. Tip…pace yourselves, it’s a lot of wine!
Our last day, I spent an afternoon at the Allison spa getting a massage while my husband played golf at a nearby course. It was a relaxing and perfect way to end our trip.