Our ‘Free Willie’ Moment: San Juan Island, the Easiest Place on Earth to Spot an Orca

Orcas near San Juan Island

The San Juan Islands are well worth the detour if you’re visiting Seattle for a few days. Most people I talked to in LA have never heard of them. But if you’ve seen any of the “Free Willie” movies (admit it, you have!), the films were shot in and around Friday Harbor (the main tourist hub out of the 172 islands). The San Juan Islands are one of the easiest (and prettiest) places to spot Killer Whales, aka orcas. So I knew we had to make the journey.

Friday Harbor on San Juan Island

You can access the islands via ferry (North of Seattle) or take my preferred mode of transportation — an easy 45-minute pontoon airplane direct from Seattle’s Lake Union on Kenmore Air. Roundtrip flights from Seattle aren’t cheap ($325 per person), but it’s an experience in itself.

Arriving in Friday Harbor on Kenmore Air, where your pilot is also the luggage handler, check-in agent and flight attendant!

After spending a relaxing night at the Island Inn (located in the heart of downtown Friday Harbor), Kevin and I were ready to head out and see some whales. I did a ton of research and decided to go with San Juan Island Whale & Wildlife Tours. There are several operators to choose from. In fact, it was a little overwhelming! But what makes this tour so different is their approach — with an emphasis on not only educating their guests, but serving as an example for other operators to respect these massive animals.

The operator believes in keeping the group small as we join the well-equipped Natsilane boat

We met up with Captain Hobbes, who runs the operation, at 11:30 AM for a quick safety check and overview on what to expect on the 3-hour tour (which immediately prompted Kevin to sing the theme to Gilligan’s Island for the rest of the trip!).

Captain Hobbes, who is truly passionate about orcas and their habitat, gives the group an overview on what to expect.

Our fellow passengers were fantastic – a family from Seattle and a French woman. As the boat headed out into the open sea, we passed several boats packed to the brim with people. I was really happy that I went with Captain Hobbes, who knew so much about the area since he’s lived on San Juan Island since 2001.

The Seattle Clipper, one of the massive boats we saw looking for orcas.

Kevin has a great time asking many questions to our fellow passengers for the next 3 hours!

Depending on the time of year, spotting an orca can be difficult. The best time to go is between May and October when the salmon runs are strongest. Although, there is no set rules on this. Orcas can be seen year round, and even not always guaranteed in the peak season. Luckily we had no issues there!

Spotting my first orca – and thinking, just don’t drop your iPhone!

Keeping our distance – allowing the whale plenty of space to pop up

While we were out on the water, there were about 9 other boats. Captain Hobbes told us about his efforts to keep the others in check as some boats simply just get too close or break the rules altogether. Just the day before, a private boat headed out to the whales and its passengers jumped in with the whales.  A definite “no no” and they were caught and fined $10,000!  Now that’s an expensive swim.

A little chilly, but very calm seas

We saw about 15 whales and the captain explained their migration patterns and the origins of “Killer Whale” (as they can feed on sea birds, squid, octopuses, sea turtles, sharks, rays and fish). Though, they’ve never fed on any humans in these waters (even the ones who illegally jumped in the water with them).

Looking out across the bay – snowcapped mountains!

It was sadly time to turn back, but got to check out seals lounging along the coast and hear about some of the islands owned by some pretty wealthy people (like the guy who created Oakley sunglasses).

Kevin sports his new sunglasses he bought from the shop in the harbor (and definitely not Oakleys!)

We got back in town just in time for a little shopping and lounging at a coffee shop before our flight back to Seattle. It’s a trip that we’ll long remember!

One of the art shops in town, selling native artwork

Our flight back to Seattle – passing by the landmark space needle


  • Whale Watching Tour: San Juan Island Whale & Wildlife Tours
    • Year-round tours leave daily at noon (giving you time to sleep in!)
    • Cost: $99 per person
    • Operator believes in conservation and little environmental impact (i.e. small groups). Highly recommended.
  • Hotel: Island Inn at 123 West
    • Cost: rates start at $200 a night
    • Perks: central location, free fruit and granola in room, and high-end bath products
  • Where to eat: Backdoor Kitchen
    • Cost: entrees run in the $20-$35 range
    • Gorgeous outdoor patio, cozy interior and great service
  • Transport: Kenmore Air
    • Cost: $325 per person
    • Perks: 45-minute flight from downtown Seattle, and seeing the city and islands from a birds-eye view
Our 'Free Willie' Moment: San Juan Island, the Easiest Place on Earth to Spot an Orca
Article Name
Our 'Free Willie' Moment: San Juan Island, the Easiest Place on Earth to Spot an Orca
The San Juan Islands are well worth the detour from Seattle. A quick 45 minute pontoon plane ride from Seattle will get you into Friday Harbor. Here you'll experience relaxation and a chance to see orcas, aka killer whales, in the wild. This is one of the few places in the world to do this.

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