There are few trips I look forward to more than my annual girls trip with my best friend Emily. We live across the country from each other, so these trips have become our chance to catch up, drink really good wine, eat really good food, and spend uninterrupted time together somewhere beautiful.
This year, we chose California Wine Country and split five days between Healdsburg and St. Helena, with everything from casual walk-in tastings and morning hikes to one of the most incredible dining experiences I’ve ever attended.
And if there’s one thing I learned from this trip, it’s that you absolutely do not need to cram four wineries into every day to have an amazing Wine Country vacation.
We typically planned one or two tastings a day, left room for long dinners and slow mornings, and took advantage of some surprisingly good perks through our hotels.
Here is exactly how we spent five days in Wine Country — where we stayed, what we ate, the wineries I would absolutely return to, and a few things I’d do differently next time.
OUR 5-DAY WINE COUNTRY ITINERARY AT A GLANCE
DAY ONE | HEALDSBURG
Fly into SFO → Harmon Guest House → Marine Layer Wines → Marietta Cellars → Dinner in Healdsburg
DAY TWO | HEALDSBURG + DRY CREEK VALLEY
Quail & Condor → Healdsburg Ridge hike → Dry Creek General Store → Dry Creek Vineyard → Flowers → Dry Creek Kitchen
DAY THREE | HEALDSBURG TO ST. HELENA
Gott’s Roadside → The Station → Faust Haus → Harvest Inn → Cook St. Helena
DAY FOUR | ST. HELENA
Slow morning → massages → Outstanding in the Field at Robert Sinskey Vineyards
DAY FIVE | ST. HELENA + SFO
Sam’s General Store → Salvestrin → VGS Château Potelle → The Charter Oak → Grand Hyatt at SFO
WHERE WE STAYED
We split our Wine Country stay between two different areas, which I would absolutely do again.
HEALDSBURG | HARMON GUEST HOUSE
For the first half of our trip, we stayed at Harmon Guest House in downtown Healdsburg.
The location made it incredibly easy to explore town, but one of the biggest surprises was how much value was included with our hotel rate.
Our stay included a 20% discounted rate, a $50 dining credit, a welcome bottle of wine and complimentary wine-tasting perks for two.
Instead of immediately getting back in the car after arriving, we checked in and headed out for two complimentary tastings: Marine Layer Wines followed by Marietta Cellars.
Afterward, we used our hotel dining credit at the restaurant associated with the hotel and called it an early night.
After flying across the country and driving from San Francisco, this was exactly the kind of first day we needed.
WHY I’D STAY HERE AGAIN
Location, walkability and the included perks.
Wine Country gets expensive quickly. Having tastings and dining credits already attached to your hotel makes a meaningful difference — and gives you an easy itinerary for arrival day without needing to plan another major experience.
Where we stayed: Harmon Guest House
If we wanted to splurge: Hotel Healdsburg
ST. HELENA | HARVEST INN
For the second half of the trip, we moved to Harvest Inn in St. Helena.
This felt completely different from our Healdsburg stay and gave us another reason why I loved splitting the trip between the two areas. This propoerty was a bit older, but with that came lush landscaping, redwoods, and lots of seating areas. Our room was clean and the beds were comfortable, a win in my book.
Harvest Inn also had its own wine partnerships, with complimentary or discounted tastings available at several nearby wineries. Our planning materials included partners such as Whitehall Lane, V. Sattui, St. Supéry and Salvestrin, among others.
We ended up taking advantage of those partnerships later in our stay.
We also made it to the complimentary tasting happening on the property shortly after checking in.
WINE COUNTRY TIP
Before booking tastings separately, check your hotel's winery partnerships.
Between our two hotels, we were able to add several tasting experiences without paying full tasting fees. I would specifically look for this when comparing Wine Country hotels in the future.
DAY ONE | ARRIVE IN SAN FRANCISCO + HEALDSBURG
We flew into San Francisco International Airport, picked up our rental car and immediately started the drive north toward Healdsburg.
After checking into Harmon Guest House, we kept our first day intentionally easy.
MARINE LAYER WINES + MARIETTA CELLARS
Our first two tastings of the trip were both complimentary perks associated with our hotel stay.
We started at Marine Layer Wines and finished at Marietta Cellars.
It was such an easy way to ease into Wine Country after a travel day — no huge itinerary, no rushing from vineyard to vineyard, just a couple of tastings before dinner.
From there, we went to the Spoonbar the restaurant associated with the hotel and used our dining credit for dinner.
Then? Bed.
We had a much bigger day planned for tomorrow.
DAY TWO | HEALDSBURG + DRY CREEK VALLEY
This was our first true Wine Country day, but we started it with two things I love almost as much as wine: a great bakery and a hike.
BREAKFAST AT QUAIL & CONDOR
If you’re staying in Healdsburg, put Quail & Condor on your list.
We ordered espressos, a pistachio croissant, cinnamon roll and quiche, and it was one of those places where I immediately understood the hype.
Such an amazing bakery.
MORNING HIKE | HEALDSBURG RIDGE
After breakfast, we headed to Healdsburg Ridge to get some movement in before spending the afternoon wine tasting.
This has become one of my favorite ways to structure trips like this.
We weren't trying to turn Wine Country into a wellness retreat, but getting outside in the morning made those leisurely afternoons of wine and food feel so much better.
After our hike, we went back to the hotel, showered and got ready for our first full tasting day.
DRY CREEK GENERAL STORE
Before our first tasting, we stopped at Dry Creek General Store for provisions.
We picked out meats, cheeses and other things we could turn into a little charcuterie board at the winery.
Obviously, this was right up my alley.
DRY CREEK VINEYARD
This ended up being one of my favorite stops of the entire trip.
We brought everything we'd purchased at Dry Creek General Store with us and built our own charcuterie board while we tasted.
As someone who owns a charcuterie business, you know I was very happy here.
This was also the first winery I've personally visited that allowed us to bring food onto the property, which made the tasting feel especially relaxed.
The entire experience was phenomenal, but my favorite bottle was their Sauvignon Blanc.
If I were planning this trip again, Dry Creek Vineyard would absolutely make the itinerary.
MY PICK
Drink: Sauvignon Blanc
Bring: Picnic/charcuterie provisions from Dry Creek General Store
Would I go again? Absolutely.
FLOWERS VINEYARDS & WINERY
Our second tasting of the day was Flowers, where we booked the Sonoma Coast Journey.
This was a more structured experience and included a small food pairing alongside the wines.
Flowers is known for its Sonoma Coast wines, and after the relaxed picnic-style experience at Dry Creek, this felt like a completely different tasting — which is exactly why the two worked so well together.
We didn't try to squeeze another winery into the day.
Two was plenty.
DINNER | DRY CREEK KITCHEN
After Flowers, we went back to the hotel and gave ourselves time to relax before dinner at Dry Creek Kitchen.
They were offering a three-course dinner for $83, so we did the three courses and shared a bottle of wine.
It was such a nice ending to our first full day.
And then we did something that probably won't make most Napa itineraries:
We went back to the room, watched DCC and hung out.
Emily and I live so far apart that sometimes the best part of our girls trips isn't another reservation — it's getting to sit around in pajamas and do the things we'd probably be doing together all the time if we lived in the same city.
DAY THREE | HEALDSBURG TO ST. HELENA
The next morning, we packed up and started making our way toward St. Helena.
We didn't have a noteworthy breakfast planned and kept the morning leisurely before checking out.
And then it was time for something I had somehow never done before…
LUNCH AT GOTT'S ROADSIDE
Burgers and rosé in Wine Country?
Yes.
Gott's Roadside is one of those iconic Napa Valley stops I'd heard about forever but had never actually done.
It was cute, casual and exactly what we wanted between hotel check-out and our afternoon Cabernet tasting.
And because we knew what was coming next, this was also when I very intelligently remembered our ZBiotics.
Future Ali was grateful.
ESPRESSO AT THE STATION
Our next stop was The Station for espresso shots.
Because if you're about to spend the afternoon drinking Cabernet, hydration and caffeine feel like responsible planning.
Right?
FAUST HAUS
Then came Faust Haus.
Flowers and Faust are sister properties, but the experiences couldn't have felt more different.
Faust is very much Cabernet country, and we booked their Act II tasting, which our original itinerary described as a deeper exploration of estate, library and limited-production wines accompanied by cheeses, charcuterie and seasonal bites.
We had SUCH a good time here.
So good, actually, that we joined.
Faust Haus was also only moments from where we'd be staying that night, so instead of rushing away, we basically enjoyed the property until it was time to head over and check in.
WOULD I BOOK IT AGAIN?
100%.
This was one of those tastings where the wine, property and overall experience all came together.
CHECK-IN | HARVEST INN
We arrived at Harvest Inn just in time to catch one of the complimentary tastings being offered on property.
After getting settled, we decided to use the hotel shuttle and head into St. Helena for dinner.
Which led to one of our luckiest decisions of the trip.
DINNER | COOK ST. HELENA
We walked into Cook St. Helena without a reservation.
Apparently, we had no idea how lucky we were.
Everyone around us kept telling us they couldn't believe we'd managed to walk in and get a table.
And wow.
What an incredible meal.
We shared calamari, pasta and dessert, and it ended up being one of those spontaneous evenings that becomes a trip favorite.
This is also where traveling as a party of two really worked in our favor.
Throughout the trip, we found that two people could sometimes sneak into a tasting room, bar or restaurant where a larger group wouldn't have had a chance.
Would I rely on that for every dinner in Napa Valley?
Absolutely not.
But it was a very nice perk of traveling as a duo.
DAY FOUR | A SLOW ST. HELENA MORNING + OUTSTANDING IN THE FIELD
We intentionally kept this day light because we knew the evening would be the centerpiece of the entire trip.
We grabbed coffee, spent some time exploring St. Helena and wandered around the hotel before heading out for massages.
MASSAGES | HEALTH SPA NAPA VALLEY
We booked 80-minute massages at Health Spa Napa Valley that morning.
And here's something I wish I'd known beforehand:
I WOULD BUY THE DAY PASS.
Had I realized we could purchase a day pass, I would have planned the morning differently and spent more time lounging by the pool after our treatments.
If you're planning a massage here, I would absolutely ask about pool/day-pass access when booking.
After our massages, we headed back to Harvest Inn, relaxed and started getting ready for the event I had been looking forward to most.
OUTSTANDING IN THE FIELD AT ROBERT SINSKEY VINEYARDS
This was the experience of the trip.
Outstanding in the Field had been on my bucket list, and getting to experience it at Robert Sinskey Vineyards made it even more special.
Our event ran roughly 4:00–8:30 PM, and tickets were $420 per person.
If you've never heard of Outstanding in the Field, the concept is essentially a traveling long-table dinner series that brings people together around food in the place where that food and wine have a connection to the land.
And yes — it is every bit as beautiful in person as it looks in photos.
There were roughly 200 people gathered for our dinner.
The long table stretched through the property, dinner included lamb, and as the evening went on, the entire setting changed under the glow of the mason-jar lights.
It wasn't simply dinner.
It was one of those experiences where you look around and think, I can't believe we get to be here.
If you're building a Wine Country trip around Outstanding in the Field, my biggest advice would be:
Let this be the event.
Don't schedule three tastings beforehand.
We had coffee, massages, time at the hotel and plenty of time to get ready. By the time we arrived, we weren't exhausted from an entire day of drinking wine.
We could actually enjoy it.
THE BEST $150 WE SPENT: OUR NAPA DRIVER
This deserves its own section because transportation for the evening could have cost us hundreds more.
When I started looking at car and limousine services for Outstanding in the Field, we were getting quotes around $600.
Instead, we booked Bruno with My Local Driver.
Our original itinerary had him scheduled to pick us up in St. Helena at 3:15 PM and return us after the dinner around 8:30 PM.
Total cost?
$150 roundtrip.
He was fantastic, we felt safe, and I cannot recommend him enough.
Especially after a four-plus-hour wine dinner, having transportation already handled was non-negotiable for me.
BRUNO: www.MyLocalDrivers.com
DAY FIVE | ONE LAST DAY IN ST. HELENA
Our final morning started at another place I'd absolutely return to.
SAM'S GENERAL STORE
We grabbed coffee and croissants at Sam's General Store, walked around for a bit and enjoyed a very leisurely Sunday morning.
Fantastic coffee. Great pastries. Easy recommendation.
Then we went back to the hotel and looked at each other like…
Are we really leaving Wine Country without tasting any wine today?
Obviously not.
SALVESTRIN WINERY
Our first stop was Salvestrin, one of Harvest Inn's partner wineries and practically a stone's throw from the hotel.
The Harvest Inn partnership included a 2-for-1 Estate Tasting at Salvestrin.
Because it was a casual Sunday and we were only a party of two, they were able to accommodate us without much fuss.
Yet another reason I'd check hotel partnerships before independently booking every tasting on a Wine Country itinerary.
VGS CHÂTEAU POTELLE
Next, we headed to VGS Château Potelle.
This one was different for me because I had actually become a member during my previous Wine Country trip with Emily.
We were once again lucky enough to be accommodated fairly casually that Sunday, and it was such a fun winery to return to.
There's something really nice about mixing new discoveries with one place you already know and love.
ONE LAST BITE | THE CHARTER OAK
Before leaving St. Helena, we stopped at The Charter Oak for one final bite.
At this point, we were officially delaying the inevitable.
But eventually it was time to say goodbye to Wine Country and start the drive back toward San Francisco.
THE AIRPORT HOTEL HACK I WILL ABSOLUTELY DO AGAIN
Our flights home were around 6 AM the next morning.
Rather than waking up in Wine Country at an ungodly hour, driving all the way to San Francisco, returning a rental car and hoping nothing went wrong, we drove down the night before and stayed at the Grand Hyatt at SFO.
I booked our room using points — our original trip plan shows 27,205 points for the night.
And it was 100% worth it.
If you have an early SFO flight after visiting Napa or Sonoma, I cannot recommend doing this enough.
You're already at the airport.
You've removed a huge logistical headache from departure morning.
And after five days of wine tasting, dining and traveling, waking up and simply heading to your terminal feels like an absolute luxury.
HOW WE SAVED MONEY ON WINE TASTINGS
One of my biggest takeaways from this trip actually had nothing to do with finding cheaper wineries.
It was choosing hotels with wine partnerships.
At Harmon Guest House, our package included the discounted room rate, $50 dining credit, welcome wine and tasting benefits for two.
Harvest Inn offered another collection of complimentary and BOGO tastings through its winery partners.
Those perks allowed us to experience wineries we may not have otherwise added while keeping the trip from becoming an endless stack of tasting fees.
BEFORE YOU BOOK YOUR NAPA HOTEL:
Look beyond the nightly rate.
Ask:
Does the hotel include tasting partnerships?
Is there a food-and-beverage credit?
Do they offer a local shuttle?
Are any wineries walkable or just minutes away?
Are there complimentary tastings on property?
In Wine Country, those benefits can genuinely change the value of a stay.
WHAT I WOULD DO AGAIN
Looking back, there are a few decisions that made this trip work particularly well.
Split the trip between Healdsburg and St. Helena.
Instead of constantly driving back and forth, we got to experience two different parts of Wine Country.
Stick to one or two major tastings a day.
More isn't always better. I actually remembered the wines, enjoyed the properties and never felt like we were racing to the next reservation.
Start some mornings with movement.
Our Healdsburg Ridge hike was the perfect reset before a full afternoon of tastings.
Use your hotel's winery partnerships.
This is probably the most practical money-saving tip from the entire trip.
Leave room for spontaneity.
Cook, Salvestrin and Château Potelle all reinforced how much flexibility we had as a party of two.
Hire a driver when you actually need one.
We didn't need private transportation for five straight days. We did need it for Outstanding in the Field.
Stay at SFO before a very early flight.
I will die on this hill.
MY FAVORITES FROM THE TRIP
FAVORITE WINERY EXPERIENCE
Faust Haus
Beautiful property, great Cabernet and we loved it enough to become members.
FAVORITE RELAXED TASTING
Dry Creek Vineyard
Building our own charcuterie board and drinking Sauvignon Blanc in Wine Country? This was very me.
FAVORITE WINE
Dry Creek Vineyard Sauvignon Blanc
FAVORITE BREAKFAST
Quail & Condor
Espresso + pistachio croissant. Enough said.
FAVORITE SPONTANEOUS DINNER
Cook St. Helena
Still can't believe we walked in.
FAVORITE SPLURGE
Outstanding in the Field at Robert Sinskey Vineyards
Not even close.
BEST TRAVEL HACK
Grand Hyatt at SFO before our 6 AM flight
Future-you will be very grateful.
IF I WERE PLANNING THIS TRIP AGAIN…
I wouldn't add more.
That's probably the biggest compliment I can give this itinerary.
Five days gave us enough time to experience both Healdsburg and St. Helena without feeling like we were racing through Wine Country.
There were beautiful wineries and incredible dinners, but there were also croissants, a morning hike, massages, burgers and rosé, coffee runs, hotel-room TV and plenty of time to just sit with my best friend and catch up.
And really, that's what our annual girls trips are about.
Not checking the most wineries off a list.
Not trying to see everything.
Just choosing a beautiful place, planning a few things we're really excited about and leaving enough room to actually enjoy being there.
I would take this exact trip again.
Until the next Travel Edit. 🍷