San Juan Islands and Seattle, Washington
We visited Washington State with my in-laws for our second multi-generational trip, and it was a huge hit. This itinerary reflects what we actually did—plus what we learned along the way. Use it as inspiration and adjust based on your group, pace, and interests.
📍 Jackson State Beach
Day 1: Seattle → Anacortes
Getting There: We flew into Seattle, rented a car, and drove about 90 minutes to Anacortes. The drive is straightforward on main highways, though traffic getting out of Seattle can slow things down depending on the time of day.
Stay: Majestic Inn & Spa — a charming hotel in downtown Anacortes with an awesome rooftop and incredible views
Evening: Early dinner at the hotel (surpringly good), followed by a casual stroll through town, popping into shops, and checking out the street art.
Day 2: Anacortes → San Juan Island
Breakfast: Calico Cupcoard Cafe & Bakery
Playground: John Stovik Playground & Splash Pad
Ferry: Boat ride to Friday Harbor
- Tip: Book ferry tickets in advance and read departure instructions carefully for a smooth experience.
🏨 Stay: Roche Harbor Resort
- Perfect for our group of six. We booked a 3-bedroom/2-bathroom unit within walking distance of the harbor and restaurants
Afternoon: Explored the harbor, stocked the kitchen, and played bocce ball on the property
Day 3: Bikes, Beaches, and Beer
Breakfast: Crows Nest at Earthbox
Bike Rental: Cycle San Juan
Ride: Pear Point Loop
- 6 miles with a small incline; we rented e-bikes and were glad we did
- Stopped at Jackson Beach Park—great for rock throwing, wading, and scenery
- Important note: there is no dedicated bike path—you’re riding on the road. It was fine in the end, but had I known this ahead of time, I may not have done it with kids. Fair warning.
📍 Jackson State Beach
Afternoon: Chill time at the resort
- Grandparents took the kids to the pool
- Parents snuck out for a beer at San Juan Island Brewing Company
Dinner: Madrona Bar & Grill
Evening: Bocce ball round 2
Day 4: Sculpture Park and Orca Watching (Sort of)
Breakfast: Lime Kiln Cafe Morning: San Juan Islands Sculpture Park
- Adults loved it, while the kids… not so much
- Total time: 30 minutes and one tantrum
Afternoon: Lime Kiln Point State Park
- No orca sightings, but stunning views, dolphins and seal sightings, and easy walking paths
📍 Lime Kiln Poinst State Park
Dinner: Home-cooked meal
Day 5: San Juan Island → Seattle (Fremont)
Ferry: 10:55AM ferry ride back to Anacortes Lunch: Gere-a-Deli Afternoon: More shopping in Anacortes Drive: Back to Seattle Stay: Airbnb in Fremont Evening: Neighborhood walk, grocery run, and takeout from a local burger joint
Day 6: Seattle City Day
Morning: Pike Place Market
- Browsed shops, grabbed food from various stalls, and people-watched
- Kids Break: Artists at Play Playground & International Fountain
- Bonus: Great view of the Space Needle on the walk back to the car. Overall, a low-stress, high-reward morning.
Afternoon:
- Paddle boat rentals on Green Lake
- Playground stop nearby for one last energy burn
Dinner: Tutta Bella (Wallingford)
Day 7: Travel home
What We Didn’t Get To (But Would Try Next Time)
As with most trips, we didn’t get to everything. These were on our list and still high-priority for a future visit. If you try any before we do, let me know!
Anacortes:
San Juan Island:
Between Anacortes and Seattle: Schuh Farms (strawberry picking)
Seattle:
Final Thoughts
This trip was a great reminder of why we love multi-generational travel. The mix of nature, walkable towns, and low-key city time made Washington an easy destination to tailor to different ages and energy levels. If you’re traveling with kids, grandparents, or both, this area gives you plenty of room to slow down, speed up, and adjust as needed—which is exactly what makes a trip feel successful.