Award Trip Breakdown: What To Do in Seattle for a Long Weekend

In the first installment of this two part series, I posted about how we were visiting a friend of ours who moved out to Seattle for only $11.20. While the purpose of this trip was to see our friend, we also wanted to explore Seattle as neither my wife nor I had ever been. I thought I would present what we did in a timeline of sorts which really shows how much you can do in a long weekend if you need to minimize vacation time (I only took Friday off from work) while maximizing sightseeing time.

Great view of Mount Rainier from Observation Deck of the Space Needle

Great view of Mount Rainier from Observation Deck of the Space Needle


4:00 pm EST- Left work in NYC and took LIRR/Airtrain to head to JFK Terminal 4 for flight.

~6:40 pm EST – Departed JFK on-way to Seattle. Watched several episodes of Sports Jeopardy and realized I’m better than 70% or so of the contestants I saw.

10:20 pm PST (1:20 am EST) – Landed in Seattle and after taxing to gate, taking train to central terminal and waiting, we grabbed a taxi to Hilton Seattle.

~10:45 pm PST (~1:45 am EST) – Arrive at Hilton Seattle, checkin and being too tried for a drink, head straight to bed. Lame, I know.


9:00 am PST – After eating breakfast in the executive lounge at the Hilton, our friend Eileen picks us up for an hour drive to Wallace Falls State Park for a 5.5 mile hike.

Great views on our hike

Great views on our hike

2:00 pm PST – After the hike, get back to Seattle and enjoy lunch by Alki Beach. We were absolutely blessed with sunny, 70-80 degrees weather our whole weekend. I hear this is rare for May. 

5:00 pm PST – Head to a bar near Safeco field to watch my NY Rangers lost game 7 to Tampa Bay. I did get a free drink – it didn’t make me feel any better.

8:00 pm PST – Grab tickets off a scalper for the Mariners-Indians game for cheap as the game is already in the 3rd inning. Sneak down to the 100 field level seats. Apparently it was “90s Firework” night after the game so of course we stuck around to watch fireworks and listen to Nirvana. #SmellsLikeTeenSpirit



10:00 am PST – Skip breakfast at the Hilton and head to the new Starbucks Roastery & Tasting Room. What a beautiful space – includes displays with how Starbucks roasts coffee with some impressive looking machines. Also part Starbucks store with several unique food and drink offerings only at this location. Highly recommend a coffee or espresso flight if you are into coffee.

12:00 pm PST – After walking through downtown for a while,  we picked up our rental car from Hertz for the day (grand total of $1.75 in fees since I used Hertz points) and drive 30 minutes to visit Boeing for the Factory Tour.

1:00 pm PST – Boeing Factory Tour. If you are an #AVGeek, this is a must do when in Seattle. In the world’s largest building by volume (the tour guide stated you could fit Disneyland in the building AND still have 12 acres leftover), we were able to see 747s, 777s and 787 Dreamliners in various stages of production. Really informative and fun.


Snagged a picture of the Dreamlifter

Snagged a picture of the Dreamlifter

4:00 pm PST – Get back into Seattle, drop off rental car, quick refresh at the hotel and head to the Space Needle. Protip – Buy your tickets in advance as it is a timed entry so you don’t waste too much time in line. Had a great view of the city and Mount Rainier as mentioned earlier. Didn’t spend a time of here but on a nice day, I think the views are worth it.

Touristy Photo at the Space Needle

Touristy Photo at the Space Needle – No I don’t know those other people who crashed our photo

6:00 pm PST – Eileen picks us up and we head out to Golden Gardens Park. Grab a nice spot on the beach and enjoy the sunset with some cold beers. Great vibe at the park – worth a stop by if you are near Ballard though parking can be a pain.

8:00 pm PST – Head back to Eileen’s house in Queen Anne and BBQ for dinner & drinks with friends.


8:00 am PST – Up early and head out to the Starbucks Roastery again as I wanted to try some of their different coffee drinks I couldn’t have elsewhere. If you order a coffee flight, you will learn a lot about the different coffee from your barista.

9:00 am PST – Head off to Pike Place Market to see the infamous “flying fish” along with everything else for sale. Maybe its me but I wasn’t impressed on the whole. Felt like a lot of touristy junk for sale mixed with fish and other food for sale. Saw the original Starbucks which actually isn’t the original Starbucks (the very original Starbucks was several blocks away and moved to that location). No desire to come back and see this – sorry Pike Place fans.

Obligatory Pike Place Sign Photo

Obligatory Pike Place Sign Photo

11:00 am PST – On a recommendation, we check out the Chihuly Garden & Glass Exhibit. Featuring the glass work of the renowned Dale Chihuly, this was one of the most stunning exhibits I’ve ever seen. I kept asking myself how the heck did we blow glass into that!?! We spent an hour here and left very impressed.

Yes, that's all glass.

Yes, that’s all glass.

2:00 pm PST – Took an Uber to CentruyLink Field to catch the Sounders vs. Red Bulls soccer match. Walked around the stadium pre-match and it was a great atmosphere. It was my first MLS game but I was hooked! Sounders fans are loud and kept it going the whole match. A great time even for my wife who never watched any soccer match before this.


4:00 pm PST – We did a mini bar crawl on the way back to the hotel to celebrate the Sounders victory. We checked out the Triangle Pub (yes, it’s really in the shape of a triangle) and some German Biergarten as we slowly made our way back to our hotel. We figured the best way to get through our red-eye flight home was to not remember it 😛

7:30 pm PST – Finally stumble back to the hotel where we pick up our luggage we stored there for the day. Requested an Uber and was off to Sea-Tac for the flight home.

8:45 pm PST – Had some crappy dinner in the dinner. In the Delta S gates, there is nothing to eat. All awful choices with some meager food-court and a gross restaurant. Please eat before you get here, you’ll thank me later.

~9:50 pm PST – Depart Sea-Tac for the short 4.5 hour red-eye home to JFK.


5:45 am EST – Land at JFK, quick Uber home so I can shower & change and then off to work. Successful long weekend in Seattle complete!

Who says you can’t fit a lot in a long weekend? I felt we did a wide range of activities and hit the big attractions in Seattle. This was a perfect long weekend for us and we’ll be doing this type of trip soon in Chicago next month.


2 thoughts on “Award Trip Breakdown: What To Do in Seattle for a Long Weekend

  1. I’m from the Seattle area and headed back later this summer for a wedding. You definitely got perfect weather! My boyfriend (who’s never been to Seattle) and I plan to go to a Mariner’s game, the Starbucks Roastery, which I’ve heard awesome things about and do a hike with friends as well! Won’t be able to make it to a Sounders game but we’ve been hitting up some NYCFC/Red Bulls games in NY and I’m enjoying them even as a non-sports fan! Thanks for the write up.


  2. Nice! I like posts like this as it breaks the monotony of all the posts about Deals and Credit Cards. I’ll be heading to SEA in a couple months. Thanks for all the ideas!


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