Healdsburg is one of the most-requested wedding destinations in California. Couples come for the combination of vineyard scenery, walkable downtown hotels, and world-class food. Below is our shortlist of the venues we shuttle to most often, along with the logistics that drive shuttle planning.
Montage Healdsburg sits on a 258-acre hilltop above the Russian River Valley. The switchback drive requires smaller executive shuttles rather than 56-passenger highway buses, and most parties stage guests at downtown hotels and run multiple shuttle waves up the hill.
The Madrona is a restored Victorian estate on West Dry Creek Road. The narrow historic driveway favors 14–27 passenger Sprinters and executive shuttles. Expect two to three guest waves plus a late-night safety shuttle.
Chalk Hill Estate covers 1,300 acres in the Chalk Hill AVA, with separate ceremony, cocktail, and reception sites. Most Chalk Hill weddings combine guest shuttles from downtown Healdsburg with on-site point-to-point movement between sites.
Trentadue Winery and Soda Rock in Alexander Valley both accommodate full-size 40 and 56 passenger coaches. These are good options if you want to clear a guest wave in one or two trips.
Whichever venue you choose, plan a late-night safety shuttle. The single-best decision a wedding planner can make in Sonoma County is to give every guest a ride home.