Healdsburg Weekend Itinerary | Must-Visit Wineries and Restaurants

Healdsburg, CA Itinerary - Winery Options and Dinner

It’s nearly impossible to be disappointed when visiting Healdsburg, CA. Tucked more north in wine country, the landscape is picturesque, the crowds are less, the egos are removed, and the wines (dare I say it) are some of my favorites. The only thing that rivals the scenery and wines, might be the food.

There are two challenges when visiting Healdsburg: determining where to spend your time, and knowing you have to go home.

Over the years, Healdsburg has been one of my favorite weekend getaways. The ideal location is always to get as close to Healdsburg Square to maximize your time.¬†When Justin and I went just a few weeks ago, we stayed in the heart of Healdsburg Square — walking distance to tasting rooms, fine-dining, shops, art, and darling coffee shops. Even better, it had us in a prime location to drive to some of the top wineries in the area.

One of the most common questions I get living in the Bay Area, is where do you like to visit in wine country? Well, bookmark this page, friends. I hope to repeat this itinerary very soon, and whole-heartedly recommend every destination as a five-star experience. My only recommendation is to plan ahead as most of the wineries require a reservation (and all of them are worth it!).

Day 1:

Lunch at Oakville Grocery

MacRostie Winery

Gary Farrell Winery

Dinner at Valette

Day 2:

Brunch at JourneyMan Meat Co

Williams Selyem Winery

Accommodations: 235 Luxury Suites

Transportation: Pure Luxury Transportation

 

MacRostie Winery

Let me start by saying, this place deserves every award it has ever received, and it’s received quite a few. Sourcing grapes from prime locations to make their stunning wines, and having one of their vineyards on-site make for a truly captivating tasting.

My personal favorites from the tasting list were the Sangiacamo Vineyard Chardonnay and the Bien Nacido Pinot Noir.

The staff is just as lovely as their grounds, and they detail your tasting experience to make it truly unique. The views and sound of trickling water from their fountains really help you remove yourself from the everyday grind, and let you take in the beauty of Healdsburg.

Healdsburg, CA Itinerary - Winery, MacRostie

Healdsburg, CA Itinerary - Winery, MacRostie

Healdsburg, CA Itinerary - Winery, MacRostie

Healdsburg, CA Itinerary - Winery, MacRostie

Healdsburg, CA Itinerary - Winery, MacRostie

Healdsburg, CA Itinerary - Winery, MacRostie

Healdsburg, CA Itinerary - Winery, MacRostie

Healdsburg, CA Itinerary - Winery, MacRostie

Healdsburg, CA Itinerary - Winery, MacRostie

 

Gary Farrell Winery

Tucked up above, a visit at Gary Farrell is truly an elevated experience. While at the property we were able to walk the stunning grounds, visit the full facility where the grapes are sorted/stored, and learn about the personalization behind their craft.

After the tour, our tasting was held in a private room with the most decadent cheese pairing. A beautifully unique experience, and once we concluded we made our way to the terrace to enjoy the stunning view you see below. Named a Top 100 Winery in 2019 by Food & Spirits, proof alone that this destination should be the cornerstone to your next Healdsburg visit.

Healdsburg, CA Itinerary - Winery, Gary Farrell

Healdsburg, CA Itinerary - Winery, Gary Farrell

Healdsburg, CA Itinerary - Winery, Gary Farrell

Healdsburg, CA Itinerary - Winery, Gary Farrell

Healdsburg, CA Itinerary - Winery, Gary Farrell

Healdsburg, CA Itinerary - Winery, Gary Farrell

Valette

If there is anything I love more than wine, it’s food. I can vividly remember my top five favorite dining experiences, and a visit to Valette has now made it’s mark on that list.

I’m not even sure where to begin, but let me start by saying, come with a serious appetite.

Conveniently located in the heart of Healdsburg Square, Valette’s changing menu will not disappoint. I personally loved their Hawaiian Ahi ‘Poke’ Style dish and House Made Semolina Pasta in their goat cheese mornay with olive oil poached cherry tomatoes. I don’t know how I was able to consume dessert, but I believe dessert is for a second stomach. While I was blown away by their ItsNotA ‘Snickers Bar’ dish (the table’s favorite), I still dream of their Bread, Butter & Jam — a brioche loaf soaked in condensed milk, toasted, and then given jam and ice cream on the side. It was unlike anything I’ve ever had, and truly mind-blowing.

Healdsburg, CA Itinerary - Winery, best restaurant, fine-dining

Healdsburg, CA Itinerary - Winery, best restaurant, fine-dining

Healdsburg, CA Itinerary - Winery, best restaurant, fine-dining

Healdsburg, CA Itinerary - Winery, best restaurant, fine-dining

Healdsburg, CA Itinerary - Winery, best restaurant, fine-dining

Healdsburg, CA Itinerary - Winery, best restaurant, fine-dining

JourneyMan Meat Co.

If you follow me on Instagram, you’ve seen me rave about Journeyman. Fun fact, I’ve started to take on a more vegan/vegetarian lifestyle in the last year for a variety of reasons. Exceptions to the rule are when I know how the meat was sourced, treated, and if it’s local. So for someone that has adopted a mainly vegetarian lifestyle, I’m now a proud member of their salumi club based on the quality and curation of their meats.

I dream of the breakfast sandwich, burger and pizza we sampled during our experience. I’m a sucker for detail, and the taste of everything on their menu is truly praise-worthy. If you don’t think a salumeria can impress you, you’ve met your match.

Healdsburg, CA Itinerary - Sonoma, Salumeria, JourneyMan Meat Co

Healdsburg, CA Itinerary - Sonoma, Salumeria, JourneyMan Meat Co

Healdsburg, CA Itinerary - Sonoma, Salumeria, JourneyMan Meat Co

Healdsburg, CA Itinerary - Sonoma, Salumeria, JourneyMan Meat Co

Healdsburg, CA Itinerary - Sonoma, Salumeria, JourneyMan Meat Co

Healdsburg, CA Itinerary - Sonoma, Salumeria, JourneyMan Meat Co

Williams Selyem

Last, but certainly not least, Williams Selyem. Such unique grounds with beautiful modern buildings. Nestled off a windy road, so removed we lost service part of the way there. Rolling hills with vineyards as far as the eye could see made for a tasting in the owner’s home even more exceptional.

Interesting thing I learned this weekend, is that most wineries will bring in a service to bottle their wines on site since the equipment is costly. This location truly does everything on-site, with such delicacy and detail. During harvest they hand pick their grapes in the middle of the night as it’s the peak time to remove the grapes from the vines. It’s all an art, and it’s some delicious art if I do say so myself.

Healdsburg, CA Itinerary - Winery, Williams Selyem

Healdsburg, CA Itinerary - Winery, Williams Selyem

Healdsburg, CA Itinerary - Winery, Williams Selyem

Healdsburg, CA Itinerary - Winery, Williams Selyem

Healdsburg, CA Itinerary - Winery, Williams Selyem

235 Luxury Suites

If Airbnb and a luxe hotel had a baby, it would be 235 Luxury Suites. With multiple suites, each suite includes three large bedrooms each with a private bath that all connect to a large common room, living room, and beautiful balcony.

The prime location of the property can’t be beat. With Healdsburg Square on one side, and large trees and the sound of running water on the other — it’s the perfect spot to host a girls weekend or a group of friends. The rooms are sound-proof and equipped with the most incredible pillows (they have soft, medium and firm options to delight all guests). It was truly one of the best night’s rest I’ve had in a long time.

Healdsburg, CA Itinerary - Winery Options and Dinner, 235 Luxury Suites

Healdsburg, CA Itinerary - Winery Options and Dinner, 235 Luxury Suites

Healdsburg, CA Itinerary - Winery Options and Dinner, 235 Luxury Suites

Pure Luxury Transportation

Justin and I always error on the side of caution, and hands-down prefer a driving service when visiting wine country. First of all, it’s common sense. Second, Justin as a firefighter-paramedic has been on enough tragic calls, we just always believe it’s worth the investment to not have to worry about who is driving.

Pure Luxury was professional, clean, comfortable, and equipped with all the luxurious amenities that make the service extra special.

Healdsburg, CA Itinerary - Winery, Napa, Sonoma, Driver, Pure Luxury Transportation

Healdsburg, CA Itinerary - Winery, Napa, Sonoma, Driver, Pure Luxury Transportation

Healdsburg, CA Itinerary - Winery, Napa, Sonoma, Driver, Pure Luxury Transportation

Oakville Grocery

This place is a no-brainer. We have a soft spot for Oakville Grocery as they treated Justin and the other first responders so well during the Napa-Sonoma fires in 2017. Their food is high quality, flavorful, and includes enough options to get your greens in between decadent wine tasting and fine-dining experiences.

We often stop at their locations to grab a delicious local bottle, a charcuterie spread and picnic between tasting visits.

Healdsburg, CA Itinerary - Winery, Artisan Lunch, Oakville Grocer

 

 

 

 

 

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