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 (Opening April 2022)

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

the madronahotel.com

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

montagehotels.com/healdsburg

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

hotelhealdsburg.com

 

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

harmonguesthouse.com

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: Campo Fina 

Night cap? Go to Burdock

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)

Arista

MacRostie

Flowers

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

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),

Arena, Bradford Brenner, Stanford, Erickson

Great shops: Anthem, Forager, Gathered, Plaza Gourmet, Mr. Moons

Head home. Plan your return.