48 Hours in Healdsburg, CA


Healdsburg is a small town located in the heart of wine country, just 70 miles North of San Francisco.  It is surrounded by rolling hills of vineyards and is home to amazing restaurants, shops and events.

There is so much to experience when visiting Healdsburg, and it can become very overwhelming when deciding where to go, what to see, and most importantly what to eat and drink!  Whether you are visiting for a wedding, a girl’s trip, or a romantic getaway, it is always nice to have a plan.  I have put together a helpful guide of suggestions for where to stay, restaurants to eat at, events and wineries to go to during your quick trip. Cheers!

Where To Stay?

Depending on your budget or style, there are many options to choose from to rest your head at night.  Make sure to make reservations as soon as you know when you’ll be visiting wine country as hotels are usually pretty full year round.

891 Grove St, Healdsburg, CA 95448


198 Dry Creek Rd, Healdsburg, CA 95448


1001 Westside Rd, Healdsburg, CA


219 Healdsburg Ave, Healdsburg, CA


Day 1:

Assuming you are arriving to town around the time of check in at a hotel or bed & breakfast (3pm), you must be ready for a refreshment! Head on over to Hawley Winery. It is right off the square of Healdsburg, the tasting room is open until 6pm and they have a variety of wines to enjoy. Not into wine? Check out Bear Republic Brewing Co. for one of their many craft beers or their delicious homebrewed root beer.

If you are visiting on a weekend, you might want to make reservations for dinner at either Zin Restaurant or for a more upscale dining experience, Dry Creek Kitchen. If you’re looking for something a little more laid back try Healdsburg Bar & Grill where you can enjoy dining outside if it’s a warm evening. 

Day 2:

Good morning! If you’re searching for a breakfast option or just some delicious coffee, Healdsburg has you covered. If you’re wanting to fuel up for the day make your way to Costeaux Bakery where there are plenty of breakfast options. They also sell “boxed lunches” if you plan on snacking at a winery later on in the day. If you’re more of a coffee & bagel morning person, check out Flying Goat Coffee.

Now onto the wineries! If you would like to plan out your own day, The Wine Road has all the information you will need to do so. I would suggest visiting no more than four wineries so that you can truly experience each winery to its fullest and not overdo it with too much alcohol. Plan on electing a designated driver, or hire someone to drive you from a licensed group such as Beau Wine Tours.

Wineries To Visit:

Lunch Options:

If you are planning on taking a lunch and snacks with you for the day I suggest stopping at Big John’s Market or grabbing one of those boxed lunches from Costeaux. The Dry Creek General Store is also an extremely popular lunch stop for locals and visitors combined. Whatever your choice may be, don’t skip lunch while wine tasting!

Depending on the time of year and days that you are visiting Healdsburg, you can take part of some popular events as well:


  • Annual Winter Wineland, January
  • Annual Barrel Tasting, March
  • West Wines Guided Vineyard Walk & Tasting, 10:30am (repeats every Saturday in the summer until August 31st)
  • Tuesday in the Plaza, 6pm-8pm May-August
  • Saturday Farmer’s Market, 9am-12pm May-November
  • Wednesday Farmer’s Market, 3:30-6pm June-October
  • Annual A Wine & Food Affair, November

Day 3:

On your last day I suggest not going overboard with wine tasting, leave that to your second day. Since you are probably leaving early-mid afternoon, I highly suggest a one-stop shop, Partake by Kendall Jackson is a wonderful experience where you can indulge in a food and wine pairing and relax in the lounge until you have to leave town.

I know that you will have an amazing time whenever you decide to visit Healdsburg; these are just suggestions on how to plan your escape to the wine country. Enjoy!