Please note that due to the elevated food and wine pairings experience on this itinerary, there is a slight price difference compared to our standard itinerary. If you would prefer an experience without elevated food and wine pairings, please see our San Juan Islands Weekend Cycling.

Our trip begins this morning on beautiful San Juan Island at the Friday Harbor ferry terminal. After brief introductions, a short transfer and bike fitting, we hop on our bikes for a ride to Cattle Point Lighthouse, which sits on the south end of the island. Along the way, our guides share the inspiration behind its name and insights into the contentious history of San Juan Island. After lunch we’re off on our ride to Lime Kiln State Park, considered by some to be one of the best shoreline viewpoints in the world to spot whales. At the end of the day we make camp at one of the island’s favorite resorts where we enjoy a delicious meal and get to know our fellow cyclists better. Lunch and dinner included.

Cycling: 35–38, Elevation gain/loss: 2,398'

After a hearty breakfast we break camp, pack up, and set out for a morning stroll through Friday Harbor. We then hop aboard a Washington State ferry for a quick sail to Lopez Island. An idyllic location for decompressing, Lopez also offers miles of quiet, scenic country roads—perfect for a day in the saddle. Our expert guide team has weaved together an exceptional cycling itinerary that takes us through farmland, forest and shoreline. At the end of the day we round out our sensory experience with an indulgent and well-deserved dinner and wine pairing in camp. All meals included.

Cycling: 32 miles, Elevation gain/loss: 1,680'

Our first four miles of the day take us from camp to the ferry terminal, where we hop aboard for a short jaunt to Orcas Island. After disembarking, we head straight from the ferry terminal to the historic village of Eastsound where we enjoy a guide-prepared lunch. We’re then back on our bikes for a six-mile ride to Cascade Lake, a perfect warmup for our push up Mt. Constitution, the highest point in the San Juan Islands. While our five mile ride up the peak is a challenge, the 360 degree views from the top make our hard worth work it. On a clear day, views extend to Mount Baker, the North Cascades, British Columbia’s Gulf Islands, and the rest of the San Juan Islands archipelago. Tonight we enjoy a final dinner and wine celebration at our cozy state park camp site. All meals included.

Cycling: 27 miles, Elevation gain/loss: 3,826'

After breaking camp and loading up our sag wagon, we’re off on a ride back to Eastsound. We take time to explore the quaint corners and charming stores in the village before riding to Deer Harbor Preserve for lunch at a pretty oceanside perch. Should time allow, we'll ride the last few miles back to the ferry terminal where we bid our new friends and the San Juan Islands a fond farewell. From here, each group member is on their own to decide whether they’ll return to Anacortes or explore more of the islands on their own. Breakfast and lunch included.

Cycling: 25 miles, Elevation gain/loss: 1,681'.