MENU
LOVER'S WEEKEND
RECONNECT. UNWIND. EAT. DRINK. PLAY. RELAX. REPEAT.
If I were coming in from out of town and want to spend a long weekend with my special someone, here's what I would do...
Stay
​
The Madrona
This Victorian mansion on Westside Rd has been completely revamped and brought back to her glory--with an edgy twist.
Super romantic. A perfect escape. You'll hardly want to leave.
But you'll have to...Because there's so much you need to explore.
They have an incredible restaurant, beautiful bar, a wrap-around porch overlooking the valley and a pool for lounging.
Their thoughtfully unique approach to guest service will make your stay incredibly memorable. This place is an absolute MUST.
1001 Westside Rd, Healdsburg, CA
​
​
Montage Healdsburg
You want a next level scene?
Super high end service. People watching galore. A spa like no other in Nor Cal.
Think: Private decks with fireplaces overlooking the valley.
A lively bar with beautiful cocktails and nibbles. A pool scene. A fancy restaurant.
100 Montage Way., Healdsburg, CA
​
​
Hotel Healdsburg
This hotel helped put Healdsburg on the map 2 decades ago. It's right on the plaza in downtown Healdsburg.
You can't get any closer to the action.
Gorge living room bar. Great pool. Nice spa.
25 Matheson St., Healdsburg, CA
​
Harmon Guest House
Hotel Healdsburg's sister hotel and the newest hotel in downtown Healdsburg.
Awesome rooftop bar & lounge. Quaint pool.
227 Healdsburg Ave., Healdsburg, CA
​
​
Day 1 Agenda
​
Fly into Sonoma County Airport (STS)
[Fun Fact: Wine flies free on Alaska Air. 1 case/person]
Rent a car & head North to Healdsburg
Grab a drink & a nibble @ your hotel bar & settle in
Freshen up. It's time to go out.
Head into town. (The two hotels outside of town will drop you off.)
Gallery strolling + Quick wine-tasting before dinner @ The Harris Gallery
Dinner Reservation: Valette or Le Dîner
Night cap? Go to Burdock or Lo & Behold
​
​
Day 2 Agenda
​
Quick coffee & toast to-go @ Quail & Condor
Morning hike, either:
@ the Healdsburg Open Space by Montage or @ Foothill Regional Park (5 mi south in Windsor)
Grab a couple readymade sandwiches from Troubador downtown. (Or share one. They're huge.)
Wine Tasting Reservations @: (Pick 2, in advance...the day is long and you want to enjoy dinner)
Head back to your hotel and hang by the pool & relax...
Dinner Reservation: SingleThread. Too fancy? Your hotel restaurant then...
​
​
Day 3 Agenda
​
Quick coffee to go @ The Flying Goat or Little Saint (milk-alternatives only)
Morning hike wherever you didn't go yesterday:
@ the Healdsburg Open Space by Montage or @ Foothill Regional Park (5 mi south in Windsor)
Brunch @ The Madrona
Explore Downtown Healdsburg:
Gallery Strolling : The Harris Gallery Art & Wine (for fine art + premium wine-tasting),
Aerena, Bradford Brenner, Erickson
Great shops: Tamarind​, Rête, Outlander, ereloom, Bon Ton Studio, Anthem, Forager, Gathered, Plaza Gourmet, Mr. Moons
​
​
​
​
​
​
​
​
​
​