‘Sleepless in Seattle’: An Itinerary for a Long Weekend in Seattle

Flying so close to the space needle I feel like I can touch it!

This year, I surprised Kevin for his birthday with a trip to Seattle (including the nearby San Juan Islands and Mt. Rainier). It was a big birthday year for him. You know, the kind of birthday where some people stop counting (or in LA, where we start subtracting!). To avoid the reality of getting older, we love celebrating our birthdays in style. Check out our itinerary below — perfect for any special occasion. It covers a lot (per usual!) but we guarantee you won’t get bored.

Who needs coffee? You probably will need a few cups on this packed itinerary! One of the great coffee shops you’ll find in the Ballard neighborhood of Seattle

Friday – Day 1:

  • Late afternoon – arrive in Seattle. Compared to LA, there is virtually no traffic so you’ll still have your night to see a lot of stuff
  • 5:30 PM check into your hotel for 1 night

Ballard Inn – located in the bank building. A European-style hotel where we stayed the first night and away from the main tourist hub

    • We stayed 1 night at the Ballard Inn – definitely not for everyone. It’s a tiny European style hotel with shared bathrooms.
    • It’s quite a deal though. Rates can drop as low as $100 a night (unless there is a big event, which then it doubles).
    • Ballard is a fantastic area, slightly removed from the tourist hub, but full of boutiques and restaurants. The hotel also includes a fancy 24-hour health club (Olympic Athletic Club) across the street.
  • 7:00-8:30 PM Bill Speidel’s Underground Tour. Tours run daily every hour. Cost $22 per adult.

Hitting the streets of Seattle on the underground tour. The group was BIG but it sure was a ton of fun

  • By far, this tour was our favorite activity of the entire long weekend. And that says a lot! The tour is led by a guide who will share hilarious stories about some pretty bad decisions made by Seattle’s early politicians and leaders (involving a lot of sewage jokes!). You start off on street level, before venturing below the sidewalks (once the actual ground level of the city). Seattle literally rebuilt on top of itself after the Great Fire of 1889.

Going in deep! Lots of steps on this tour and walking. But the stories helped distract.

At one point, they turned off the lights to show just how dark it is. It’s a little spooky!

The original foundation of buildings actually are a floor below Seattle that you see today. So trippy!

  • 9:00-10 PM,  After the tour, walk over to Pier 57 – home to a giant Ferris wheel, carnival games and other fun activities. We rode the “Wings Over Washington” ride. It’s impressive – like the “Soarin’ Over California” ride at Disneyland if you ever rode that (and one of my faves!). Cost: $17 for adults (with discounts for children and senior citizens)

Lots of activity on the pier – well worth a stop!

You won’t want to miss Wings Over Washington to get a sense of the beauty of the state.

  • 10:00 PM – midnight, it’s getting late (we know!). But we couldn’t pass up a chance to hit up a movie at Seattle AMC 10.

Dinner and a movie – a fun and late night!

  • The theater, a 15 minute ride from the pier, was part of the high-end Sundance Theater chain (recently bought out by AMC). But it still feels pretty similar, including a full menu of food and wine by the glass or bottle.
  • 1 AM – go to bed! Obviously this itinerary can easily be shifted earlier though.

Saturday – day 2:

  • 8 AM quick workout in. We’re crazy, but it was included with our night at the Ballard Inn.  And the gym was just too fancy to pass up.

Pump the iron Kevin! Quit smiling, you need to make it look painful!

  • 9:30 AM Grab some coffee, and head over to Kevin’s other favorite place of the weekend: Museum of Pop Culture (where we spent 3 hours!)

The very trippy exterior of Seattle’s Museum of Pop Culture

  • 10 am – 1 PM We could have easily spent more time here. There was so much that Kevin loves: science fiction, fantasy, Star Trek (where I nearly fell asleep. No offense to any Trekkies out there!).

Kevin is LOVING this

Look Star Trek – an especially large exhibit

The museum offers special rotating exhibits – and I loved the Jim Henson section (but first had to pull Kevin out of Star Trek land!)

  • 1 PM Hop on the futuristic monorail and ride it to downtown Seattle where you can walk to Pike Place Market for lunch.
    • Must-stop places at Pike Place include Beechers (for mac n’ cheese), Piroshky Pirosky (for heavy Russian meat pastries, especially the meat and cheese) and some fresh yogurt at Ellenos (my favorite was the marionberry but Kevin loved the yogurt and muesli)

The Seattle monorail – picks up right next to the Pop Culture Museum

It’s yogurt time! We ate 3 of these. But it’s healthy right?

  • 4:00 PM arrive at the Kenmore Air terminal along Lake Union to board a pontoon airplane (!) for the San Juan Islands
  • 4:30-5:00 PM Flight to San Juan Islands ($325 per person round trip)
    • Check into the Island Inn (located right in the middle of downtown Friday Harbor, rates start at $200 a night)
    • Grab dinner at the Backdoor Kitchen or craft beers at San Juan Brewery across the street (or both!)

Arriving in San Juan Islands

Friday Harbor on San Juan Island

Sunday – day 3:

  • 9 AM wake up, our first “sleep in day” if you want to call it that. And grabbed some coffee and shopped in downtown Friday Harbor
  • 11:30 AM – 3:00 PM, hop on a boat to see killer whales in action, one of the easiest places to spot orcas. Read about our full experience in our previous blog post here.

Orcas near San Juan Island

  • 5:30 PM, take the Kenmore Air flight back to Seattle, just 30 minutes away and the best views of the Space Needle

Flying so close to the space needle I feel like I can touch it!

  • Check into the Kimpton Monaco Hotel – 1 night (rates vary, but range from $200-$400 a night)
    • Since it was Kevin’s birthday, they even gave us free champagne and dessert at their bar!

Kevin is excited – and shows the free birthday dessert card in the room! Who says you’re too old for this?

  • 7:30 PM if you timed your trip to arrive on Sunday, you must visit the Pink Door Restaurant. They offer live trapeze performances every 45 minutes.  You can eat your pasta while performers swing overhead.  Let’s just hope they don’t drop anything! They also offer Tarot card readings if you arrival early. It’s such a lively place!

Inside the trapeze room at The Pink Door. Reservations in advance are a must

Monday – day 4:

  • 9:00 AM pick up the rental car at the airport and drive 2 hours south to Mt. Rainier National Park
  • 11:00 AM -12:30 PM, hike Grove of the Patriarchs
    • A very easy, and flat 1.5 mile hike.  It can get REALLY busy, but well worth it. The loop trail leads you through one of the country’s most outstanding examples of old-growth giants – Douglas fir and red cedar trees from thousands of years ago that reach a height of 200 feet!

  • After the hike, we planned to visit the Summit House Inn for lunch (where you can only arrive by a gondola!). But severe fires shut down the resort and we got diverted to nearby Enumclaw. It’s a cute town and had a surprising amount of good food options.  We ate at Kelly’s Mercantile, which hit the mark. Especially since it had mac n’ cheese (Kevin’s favorite!).

Guess who ordered what? Hint: mine doesn’t involve copious amounts of noodles and cheese!

  • 3 PM, drive 45 minutes north to Snoqualmie Falls, a spot you might have seen before if you’ve watched the TV show Twin Peaks. There are a variety of trails that go from 200 feet (basically walking from the parking lot) to very steep trails that lead to the base of the falls.  We hiked here for about an hour (and got super sweaty!).

Driving through the clouds of smoke from the nearby forest fire.

Snoqualmie Falls, a short 20 minute drive from downtown Seattle.

  • We’re sadly nearing the end of the long weekend.  Drive back to Seattle to do what Seattleites do naturally. Hang out with a cup of coffee. And where else to do it?  The massive Starbucks Reserve Roastery and Tasting Room, which is the first of its kind.  Inside you’ll find multiple stations offering various “experiences” (or translated, expensive coffee). Not sure I’d make this my regular coffee spot if I lived here, but was fun to visit as a tourist.

Inside the sprawling Starbucks Reserve in downtown Seattle.

Kevin gets a ton of questions answered – he’s so intrigued by Starbucks!

And with that, we grab our coffee and say good-bye Seattle!


'Sleepless in Seattle': An Itinerary for a Long Weekend in Seattle
Article Name
'Sleepless in Seattle': An Itinerary for a Long Weekend in Seattle
Looking for an itinerary for a special occasion or long weekend in Seattle? Check out our recommendations for a packed visit that includes museums, restaurants and killer whales

No Comments, Be The First!

Your email address will not be published.