Day One: Santa Rosa Base to Sebastopol Farms

Ride Creek Trail/Greenway ride to Sebastopol. Visit farms and orchards, van picnic en route. Lodging at Pearlessence Vineyard Inn for farm-to-table dinner

Kick off your luxe weekend with a gentle ebike spin from downtown Santa Rosa along the shaded Santa Rosa Creek Trail and Prince Memorial Greenway, transitioning seamlessly onto the flat Joe Rodota Trail toward Sebastopol’s vibrant farmlands. Our support van shadows the group, offering hydration stops amid apple orchards and glimpses of the Laguna de Santa Rosa wetlands, culminating in a gourmet picnic of local cheeses, seasonal salads, and artisan breads at a scenic farm overlook—echoing Cycle San Juan’s nature-immersed pacing.

Arrive refreshed at Pearlessence Vineyard Inn (4097 Hessel Rd), a serene 5-acre haven tucked among family vines and gardens with a private pond deck; unwind with inn-arranged farm-to-table dinner featuring estate produce, followed by fireside wine from the owners’ vintage in your heated-floor suite. This intimate B&B, praised for its peaceful seclusion and superb hospitality, sets the tone for boutique recovery after ~2-3 hours of moderate pedaling.

Day Two: Coastal Extension

Shuttle to Occidental (Inn at Occidental base); Harrison Grade climb to Bohemian Hwy vineyards, descend to coast. Cliffside picnic at Bodega Bay; evening wine tasting at inn. Ebike delivery included.n for farm-to-table dinner

After a hearty inn breakfast, shuttle comfortably to our Occidental base at Inn at Occidental, then conquer the iconic Harrison Grade—a steady 1.5-mile shaded climb along a bubbling creek through old apple country and Graton’s backroads—before cresting into Bohemian Highway’s rolling vineyards and redwood groves. The descent rewards with coastal panoramas, leading to a cliffside picnic at Bodega Bay’s dramatic bluffs with ocean breezes, fresh seafood, and Zinfandel pairings; van support ensures easy pacing for mixed abilities on this moderate 4-hour adventure.

Return to Inn at Occidental, a Sonoma wine country gem amid towering redwoods with ebike delivery perks (10% off rentals) and cyclist-friendly packages; savor an evening wine tasting on-site or nearby, relaxing in cozy rooms before a multi-course dinner highlighting hyper-local ingredients. This trail-adjacent boutique mirrors San Juan’s premium respites, complete with spa-like amenities for post-ride bliss.

Day Three: Dry Creek Valley Finale

Van to Dry Creek wineries (Zinfandel focus like Pedroncelli); rolling loops with tastings. Lunch picnic, depart Santa Rosa post-ride (or extend at Hotel La Rose).

Van transfer to Dry Creek Valley launches your rolling winery loops amid old-vine Zinfandel landscapes, hitting family gems like Pedroncelli (94-year legacy of approachable, estate-driven wines) and Dry Creek Vineyard for tastings paired with vineyard views and light climbs suitable for ebikes. The ~3-hour ride weaves quiet roads with sag wagon snacks, building to a farewell picnic lunch of charcuterie, olives, and valley-fresh fare overlooking historic sites— a nod to Cycle San Juan’s supported finales.

Depart post-ride from Santa Rosa (or extend at historic Hotel La Rose downtown, with its elegant rooms, Railroad Square walkability to trails, and cyclist conveniences like secure storage). Luggage handled throughout, this capstone ensures immersive nature, wine discovery, and zero logistical stress for groups of 4-8