Seattle & the Magical San Juan Islands

The trip begins in Seattle, so book your round-trip flights to/from SEA airport. Grab a cab or an Uber and have them whisk you to our boutique hotel - Palihotel - located directly across the street from downtown Seattle’s famed Pike Place Market and the Elliott Bay Waterfront. We'll convene as a group in the evening for drinks and dinner, and a brief orientation about the trip.

Depending on when you arrive, there's so much to see and do in this dynamic city. (You may want to consider arriving a day early). Stroll and shop in Pike Place Market; walk along the waterfront; pop into the aquarium; visit the iconic Space Needle; take yourself to lunch in the International District. We highly recommend the Chihuly Garden and Glass if you've not been before.

After our dinner together, rest up at the hotel. Tomorrow, we leave for wine tasting and waterfalls!

After breakfast, we'll head north towards the San Juan Islands.

Our first stop is the drama and rush of Snoqualmie Falls where we'll have time to snap some photos and enjoy a gentle nature walk. 

Next up, we’re off to the vinos! Woodinville is famous for wine tasting. We'll sip and tip at William Grassie Wine Estates, a winery specializing in Bordeaux-style blends, with lunch afterwards at the Estate. 

After lunch, we’ll hit one more winery. Fortified and feeling fine, we're back in our private van and heading north. Look out the window as we cut through the Skagit Valley, home to some of the most fertile farming land in the region and a host of quaint small towns.

La Conner is an artistic hamlet set right on the water. We'll walk along the canal and explore this peaceful town. You’re sure to find something whimsical at its many boutiques and art galleries. 

We'll check into La Conner Channel Lodge and enjoy a bit of downtime. Later, we will come together for dinner as a group at Nell Thorn Waterfront Bistro, a restaurant right on the waterfront.

Enjoy breakfast at the hotel. 

Hop in the van with our guides and get ready to be impressed. Its name may be “Deception,” but there is nothing disappointing about this pass. Stop and take in the dramatic vistas at Deception Pass. Admire the sweeping views of the Salish Sea and the surrounding islands from the 180-foot bridge spanning the pass. This is an ideal place for a selfie and a few more pics for your camera roll.

Have lunch with our group picnic style before getting ready to spot some of Washington’s most famous residents. Take part in an exploratory water adventure around some of the most wildlife-rich waters in the nation. Our boat departs at 1PM. 

Possible sightings include Humpback whales, Minke whales, Grey whales, multiple species of porpoises and seals, sea lions, over 200 different species of birds, and of course, two different species of orca's whales. No two tours are the same in this dynamic environment, but every day is special in the Salish Sea. Our whale watching excursion lasts between 3 - 4 hours. 

After an afternoon on the water, we’ll stop at Mt. Erie on our way home for the evening to take in the stunning views across the islands. 

Dinner is on your own tonight. La Conner offers many nice bars and restaurants. Take your pick or stay in for room service at the hotel.

Wake up in La Conner and enjoy breakfast at the hotel. 

It’s time to get on the ferry and discover Orcas Island. The ride from Anacortes to the islands is absolutely part of your adventure. Sit on the top deck and take in the water views. Keep an eye out for water animals and seabirds. Soon, we will arrive at our base for the next few days. 

Named not for the local favorite marine mammal, but after a viceroy of Spain who sponsored a Spanish exploration of the Pacific Northwest during the late 1700s, this island is rich in history and natural beauty. 

Arrive at the port on Orcas Island and then journey across the island to Girl Meets Dirt, an island-maker of delicious jams, wines, and other goodies. 

Then we’ll check into our accommodations for the next couple of nights in the quiet town of Eastsound. We will enjoy lunch at a local restaurant together as a group. 

Check into the hotel and enjoy some downtime. Eastsound bursts with boutiques, bars, bakeries, bookshops, and parks perfect for pausing and savoring an ice cream. 

In the afternoon, we’ll visit Moran State Park and Mt. Constitution (don’t worry, we are not climbing Mt. Constitution. We arrive at the lookout by van). 

Lace up your sneakers for a gentle nature stroll experience at Cascade Lake and the forested trails surrounding it before driving to the top of Mt. Constitution to take in the best views of the San Juan Islands.

Tonight, we will tuck into a delicious dinner together at Hogstone. We'll stay at The Outlook Inn on Orcas Island.

Enjoy breakfast at Brown Bear Baking in Eastsound, run by pastry Chef Lee Horswill and his partner, Bread Baker David Ellertsen.

This morning let’s stroll in Obstruction Pass State Park. This gentle trail will take you to secluded beaches and pretty lookouts that will prompt the “Wows!” and have you reaching for your camera to capture the moment. (Note: You do not need to be a hiker to walk this trail. It is accessible for most skill levels and is less than 2 miles.)

Then, head to Buck Bay Shellfish Farm for lunch (seafood-free options available) and take the opportunity to learn a bit more about Washington’s shellfish farming community. Western Washington is a watery paradise and seafood is a big part of the culture.

Then, we are off to visit Orcas Island Artworks and admire some of the fine art and crafts produced by the multitude of creatives who call Orcas home. It’s easy to see why such a dramatic landscape would inspire works of art. 

Enjoy some downtime in Eastsound. Nap. Browse the many shops in town. Have a cocktail and enjoy the views from this beautiful hotel. 

Let’s gather this evening for a group dinner together at elegant Matia. 

Have breakfast at Island Skillet in Eastsound. 

Enjoy a last look around town and then pack up and get ready to check out of the hotel. 

Alas, it is time to catch the ferry back to Seattle and depart from Orcas. Enjoy lunch as a group at Orcas Hotel Café as we wait for our ship to arrive and take us back to the mainland. 

We will take the ferry east and drink in late summer views over the water as we cruise toward the Emerald City. 

Check into our downtown Seattle hotel and take a moment to rest before we head out to dinner together. 

Meet the group this evening for a farewell dinner in Seattle. Raise a glass to a wonderful trip in a truly beautiful place.  

Enjoy breakfast onsite at the hotel. 

Most of the group will fly out today. If you choose to stay in Seattle a few more nights, you can add additional hotel room dates to your reservation and see more of Washington. 

If you have a late-afternoon flight, then stow your luggage at the hotel and then venture out to see more of Seattle on your own. Shop the many boutiques near our hotel, browse titles in Elliott Bay Book Company, or take the water taxi over to Alki Beach. 

Make your way to the Seattle International Airport by taxi or train (the hotel will arrange a taxi to the airport for you).