top of page




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... 


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 Maison (wine only) or Lo & Behold (fab cocktails)

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 BrennerErickson

Great shops: Tamarind​, Rête, Outlander, ereloom, Bon Ton StudioAnthem, Forager, Gathered, Plaza Gourmet, Mr. Moons


bottom of page