A lovely local spot for an easy hike through nature trails.
A stunning preserve showcasing California's giant redwood trees. You can find both flat paths for casual strolls or steep hikes for a challenge.
Fun family friendly museum with Snoopy & Peanuts exhibits in creator Charles Schulz's hometown of Santa Rosa.
Open-air wildlife safari tours among giraffes, rhinos, and more; reservations required
Historic winery with a variety of wine styles and a laid back ambience. Also pays Olivia's bills. Appointments recommended.
If you're craving a glass of bubbly, J Vineyards is conveniently located just next door to Rodney Strong Vineyards. Appointments recommended.
Iconic and scenic spot for old vine zinfandels and more. Appointments recommended.
Beautiful new winery known for food and wine pairings. Appointments recommended.
Beloved brewery (king of the IPA), with relaxed outdoor seating and bar bites. Good option for large groups. Also pays Matts bills.
The new brewery site in Windsor, famous for its Pliny beers. Good for groups and a casual bite to eat.
Casual late night billiards bar within walking distance to the Hampton Inn & suites
Stellar upscale southern comfort food. Walking distance from the Hampton Inn.
Hands down, the best pizza in town! Gets busy on the weekends so you might want to call ahead.
Upscale dining focusing on locally sourced ingredients.
If you're craving a great margarita or some nachos.
New Zealand style bakery with sweet and savory pies, sandwiches, pastries and other treats. Within walking distance from the Hampton Inn.
Excellent homestyle Italian food with a great wine list.
Trendy fine dining, with a rooftop cocktail bar overlooking the Healdsburg plaza.
Quaint town square with restaurants and shops. Hosts farmers markets on both Thursday evenings and Sunday mornings and live music from local artists on Thursday evenings.
Healdsburg town square with lots of options for shopping, dining, and wine tastings. Also happens to be where Matt proposed to Olivia!
Open-air district of tasting rooms, breweries, eateries, arcades and shops—great for groups to wander and snack.
For a fun day trip, take a drive out to the coast to visit Bodega Bay and Point Reyes. Dramatic coastline views, walking trails, and tons of fresh seafood. Think chowder, Dungeness crab (in season), oysters, and fish-and-chips, as well as a few artisan creameries. Make sure to pack layers - the Sonoma coast can get very breezy!