Vashon

Drive time: 2.5 hours
Ferry: 15 min

Calling this 37-square-mile island north of Tacoma “laid-back” is a little like calling the Autobahn “fast.” So few vehicles travel this sleepy island’s many country roads that they have time to grow moss. Seriously. But the lack of traffic makes Vashon’s bucolic blend of woods and sea a cyclist’s delight. Plus, a bike ensures you won’t miss all of the island’s peekaboo views. Start with a precisely poured latte from Burton Coffee Stand. Then wend your way along Quartermaster Harbor to Point Robinson Park. Culminate by landing at Vashon Village, a kind of four-block version of liberal-leaning Eugene with a fair-trade gift shop (Giraffe) and a beloved-by-locals vegan café (Pure). 

Anchor Point  Gardens paint the grounds of Artist’s Studio Loft with color that can be enjoyed from one of the four cottages or either Main House room. From $119 
nibbles  Restore your caloric deficit with a garlic chicken and parmesan lahvosh pizza from the Hardware Store Restaurant.
Dive In  Rent a ride from Vashon Island Bicycles ($20 for the day).  

Bainbridge

Drive time: 3 hours
Ferry: 35 min

The preponderance of Crocs at dockside sipping spot Pegasus Coffee House gives away Bainbridge’s flourishing gardening scene. At five miles wide the island lays claim to three impressive garden shops, nationally lauded garden designers like George Little and David Lewis, and the artful Bloedel Reserve, a historic 67-acre property turned gardener’s fantasy on the western side of the island. But in recent years, the island has homed in on another kind of horticulture, adding seven wineries since 2003. 

Anchor Point  The upscale Eagle Harbor Inn gives you easy access to Bainbridge’s tasting rooms. From $149
nibbles  The New Rose Café at Bainbridge Gardens doesn’t have quite the hype as Eagle Harbor’s Restaurant Marché, but it’s got a lot more eye candy. 
Dive In  Gazzam Lake Preserve is a less manicured—but equally beautiful—take on nature.    

Whidbey

Drive time: 3 hours
Ferry: 20 min

In a place as rich in natural beauty as Whidbey, even the baristas are wildlife experts. “The seagulls prefer clams to mussels,” says William Bell, owner of Local Grown, nodding to the pecking pack of birds outside his café on Coupeville’s historic wharf. Good thing, since the Seattle restaurants that covet the plump Penn Cove mussels don’t need any more competition. Humans can sample them at Prima Bistro in a Langley, a quaint gallery-rich hamlet. Of course, it’s easy to understand why artists have long been drawn here: Set on the shores of the Saratoga Passage, Langley’s perspective on Puget Sound and hulking, whitecapped Cascades is positively mesmerizing. Sit long enough at Ott & Murphy Winery’s tasting room, and nature might come to you: a pod of orcas regularly frequents the cobalt waters just beyond your picture window. 

Anchor Point  Put yourself on the water (but still mere blocks from the shops) at Langley’s Boatyard Inn. From $150 
nibbles  Former Four Seasons chef Matt Costello plates masterpieces like bacon fat roll, mustardo, and parsnip marshmallow from the local bounty at the Inn at Langley (but only once a night, so make a reservation). 
Dive In  Stay warm while whale-watching inside the 100-foot Mystic Sea’s heated cabin (from $49). If you don’t own sea legs, stick to Ebey’s Landing’s Bluff Trail, where the merger of sand and Sound paints an unparalleled watercolor in the memory. 

San Juan

Drive time: 4 hours
Ferry: 65 min

A gleaming Porsche SUV sandwiched between two mud-crusted work trucks on the hourlong ferry ride from Anacortes to Friday Harbor presents an apt depiction of this stoplight-free island’s cultural mix. Here, a vein of farms feeds a tradition of high-end culinary tourism best experienced at the Duck Soup Inn, the Market Chef, or one of the 82-acre Lakedale Resort’s instructive culinary weekends. Save time for a trip to Roche Harbor, where the former lime-mining company town turned lavish resort gives you an opportunity to wander the docks amid bobbing million-dollar yachts and daydreams about how the other half lives. 

Anchor Point  One block from the ferry’s dock, the Island Inn finished its conversion from condos to high-end hotel—think radiant-heating-floor bathrooms and softer-than-silk sheets—just last summer. 
nibbles  Besides entrées featuring freshly caught fish, two-year-old Cask and Schooner sets you up with live music and lively locals. 
Dive In  A drive along the West Side Road reveals San Juan’s stash of riches—both architectural (grand cliffside homes) and natural (Lime Kiln Point State Park, the country’s only dedicated whale-watching park).