First Time to Napa Valley Itinerary Ultimate 5 Day Guide

First time to Napa Valley? I am so jealous. You get to experience one of my favorite destinations to visit in the world for the first time ever!

I moved to the San Francisco Bay Area in 2017, and remember how special and wonderful my first visit to wine country was. I couldn’t believe a place like this existed only an hour outside of San Francisco.

Since then, I have visited dozens of times! But Napa Valley has so many amazing this to uncover, so every trip, I still get to discover Napa as a traveler just like you.

Planning a trip to Napa Valley can feel overwhelming, which is why I created this first-timer’s itinerary, combining the perspective of a traveler and someone who’s been there before.

You’ll hit all the must-see spots, discover a few hidden gems, and get all the insider tips I wish I knew before my first visit to wine country.

First Time to Napa Itinerary Guide

This itinerary was thoughtfully curated for the first time visitor to Napa Valley. I have added a variety of tasting experiences, from tasting rooms, to small family owned wineries, and a quintessential Napa winery so you can get a well rounded trip to Napa Valley.

I have also added many options for wine tastings and things to do throughout this itinerary, so you can create the best itinerary for you based on your budget, level of wine knowledge, and vibe you are looking for.

Day 1: Arrive to Napa Valley

• Rent a car to get to Napa from airport
• Priest Ranch for lunch and wine tasting
• Check in to your hotel in Yountville
• Dinner in Yountville at Bistro Jeanty

Once you land in Northern California, you’ll pick up your rental car and head straight to Napa Valley, specifically to Yountville, where you’ll be staying in bliss for the next five days.

To make the most of your trip, try to book a flight that arrives in the mid- to late morning. And if possible, avoid arriving during rush hour; Bay Area traffic is no joke.

🍷 Wine Gal Tip: If you can find a direct flight, I recommend flying into Sacramento Airport.

Stop 1: Lunch at Kitchen Priest Ranch

You’re probably hungry after your travels, so kick off your Napa itinerary with a tasty stop at The Kitchen at Priest Ranch in downtown Yountville.

This casual spot serves American comfort food with a Midwest twist made with fresh, local ingredients. Order at the counter, then head up to the only rooftop patio in Yountville to enjoy your meal.

And don’t forget to save room for wine, Priest Ranch’s tasting room is right next door!

Stop 2: Priest Ranch’s BACON & Wine Tasting Or Chocolate & Wine Pairing

One favorite is the Bacon and Wine Experience, which features four wines paired with four uniquely flavored slices of bacon. It’s just as fun and delicious as it sounds.

If you’re craving something sweet instead, try the Taste and Terroir Experience, where you’ll be invited to “eat dirt,” in the form of handcrafted chocolate bites that resemble soil, each paired perfectly with wine.

🍷 Wine Gal Tip: Book one of Priest Ranch’s unique experiences here. The Kitchen is closed on Tuesdays.

Stop 3: Check in to Yountville Hotel

It is about that time to head to your hotel to check in for your stay in Napa Valley. There are plenty of incredible and luxurious hotels and B&B’s in Yountville. Two that I recommend for your stay are:

✅ North Block Hotel: A chic, Mediterranean-inspired boutique hotel located a short stroll from downtown Yountville. The North Block offers superior service, an excellent restaurant, and has received two Michelin Keys 🗝️

✅ Maison Fleurie: This charming French Country B&B in downtown Yountville is a true gem, featuring lush gardens, complimentary bikes, daily breakfast for two, fresh-baked cookies, and an afternoon wine and cheese happy hour.

Stop 4: Option #1 Dinner at Bistro Jeanty

🚶‍♀️short walk from your Yountville hotel

One must-visit restaurant in Napa Valley is Bistro Jeanty, an adorable French bistro nestled in downtown Yountville. With its cozy, charming atmosphere and elevated comfort food, it feels like a little slice of the French countryside.

The menu is packed with authentic French classics like Mussels au Vin Rouge, Cassoulet, and Escargot. But whatever you do, don’t skip the tomato soup. It’s famously delicious, served piping hot and topped with a flaky puff pastry, life changing.

Stop 4: Option #2 Dinner at The French Laundry

🚶‍♀️short walk from your Yountville hotel

You’re in Napa Valley for the first time and you are staying in Yountville, I HAVE to mention The iconic French Laundry Restaurant, a world-renowned, three-Michelin-starred restaurant.

If you are a foodie, this is the restaurant you are going to want to visit. It is pricey, and reservations are difficult to get, but dining here is a once-in-a-lifetime experience.

🍷 Wine Gal Tip: To snag a reservation at The French Laundry, book when they open on the first of each month for the following month. If you miss out, check the Facebook group where people trade, give away, or offer reservations.

Stop 5: Back to Your Hotel

It’s been a long day. Walk back to your hotel from dinner and get a good night’s sleep. You have a busy day of wine tasting and exploring Napa Valley tomorrow.

Day 2: Bubbles, Wine & Food Pairing, Views Oh My

• Breakfast at Bouchon Bakery
• Sparkling wine tasting at Schramsberg Vineyards
• Food & wine pairing at Davis Estates
• Wine tasting at Sterling Vineyards
• Dinner at Mustards Grill

Day 2 is packed with wine tastings in Calistoga (about a 30-minute drive from Yountville), so make sure you have a plan for getting around Napa for the day. Either driver yourself, book a designated or private driver, or consider skipping the third tasting.

Uber is available in Napa Valley, but with a busy day like this, the cost of multiple pickups can quickly add up. It’s often more convenient to hire a private driver so you stay on schedule and everyone can fully enjoy the wine experience.

Stop 1: Breakfast at Bouchon Bakery in Yountville at 9:00 am

Rule number one when wine tasting, don’t skip a meal. Start your day with breakfast at Bouchon Bakery in Yountville, just a short stroll from your hotel.

This beloved spot from renowned chef Thomas Keller (yes, the same culinary genius behind The French Laundry) is famous for its mouthwatering French pastries. The croissants are to die for, they also serve breakfast sandwiches and bagels.

✔️ Pro Tip: make sure to grab some extra snacks from Bouchon Bakery to enjoy in between your tastings.

🍷 Wine Gal Tip: If you are visiting Bouchon Bakery on a weekend, do yourself a favor and order online in advance, there is always a long line.

Stop 2: Schramsberg Vineyards for Sparkling Wine & Wine Caves at 10:00am

🚗 Yountville to Schramsberg, 30 minute drive

There’s no better way to start a day of wine tasting than with some bubbles, and Schramsberg has the best sparkling wine in town. This historic winery, tucked into the hills of Calistoga, has been producing sparkling wine since 1865.

I highly recommend booking their cave tour and tasting, which includes five sparkling wines. You’ll explore their incredible wine caves and get an inside look at the fascinating sparkling winemaking process, along with the rich history of the Schramsberg family.

🍷 Wine Gal Tip: Tastings at Schramsberg are available 7 days a week from 9:00 am to 3:00 pm

Stop 3: Davis Estates Food & Wine Pairing at 12 pm

🚗 Schramsberg to Davis Estates, less than 10 minute drive

One experience you absolutely shouldn’t miss on your first trip to Napa Valley is a food and wine pairing. Beyond the incredible wines, Napa is a foodie’s paradise and known for its farm to table dining.

A food and wine pairing makes for the perfect second stop of the day, and Davis Estates has one of the best in the valley. You’ll enjoy four beautifully crafted small plates, each thoughtfully paired with their current wine releases.

Also, Davis Estates has one of the most beautiful views in Calistoga. So you can’t go wrong here with fantastic bites, wonderful wine, breathtaking views, and it’s surprisingly affordable for Napa.

🍷 Wine Gal Tip: Davis Estates is open 7 days a week and reservations are required in advance.

Stop 4: Sterling Vineyards 2:30 pm

🚗 Davis Estates to Sterling Vineyards, 5 minute drive

One of the most popular wine-tasting experiences in Napa Valley is at Sterling Vineyards and its iconic gondola.

Your tasting begins with an aerial tram ride up to the hilltop winery, followed by the “Sterling Stroll,” a self-guided tour with five tastings (this is the tour that I’ve done twice).

It’s a relaxed walk through their winemaking facilities, ending on a patio with breathtaking panoramic views of the valley. The architecture is gorgeous, inspired by Mykonos’s famous white stucco houses.

Yes, it’s touristy and often pretty busy, but the views and gondola ride make it worth adding to your Napa itinerary, especially for a first-timer.

🍷 Wine Gal Tip: Sterling Vineyards is open 7 days a week, reservations are recommended, but walk-ins are welcome.

Stop 6: Refresh and Unwind at the Hotel

It’s been a long day, but I promise this next stop is worth it. After a quick cat nap and a freshen-up, head to your dinner reservation at Mustards Grill, just outside of downtown Yountville.

🍷 Wine Gal Tip: If you are looking for a more causal and low key dinner option, you can check out Gott’s Roadhouse or Pizzeria Tra Vigne in St. Helena

Stop 7: Dinner at Mustards Grill

🚗 Downtown Yountville to Mustards Grill, 5 minute drive

If you ask anyone for a recommendation for a Napa Valley restaurant, I guarantee Mustards Grill will be on that list.

As a Napa Valley staple for the last 40 years, Mustards Grill is that classic Napa restaurant with an old-school charm, and a local favorite.

A meal here never disappoints. Their signature dish is the mouthwatering Mongolian Pork Chop served with housemade mustard, definitely a must-try, and don’t forget a side of their shoe string onion rings!

Day 3: Big Bold Cabernets

• Mini Model Bakery in Yountville
• Wine tasting at Amizetta Vineyards
• Charter Oak for lunch
• AXR wine tasting
• Dinner in downtown Napa at Scala

If you are also a Cab lover like myself, today is your day. Both wineries on this itinerary have big, bold, and delicious Cabernet Sauvignons.

The first winery is at the top of Howell Mountain, it’s a back country road, that is windy and narrow. Uber will not pick you up here, so you will either have to drive yourself or book a private driver.

We drove ourselves, and it took us about 20 or so minutes to get to the top. However, if you plan on doing more than one tasting on Howell Mountain and you don’t have a DD, then I would hire a private driver to get you safely to your tastings.

For a second tasting on Howell Mountain, I recommend a tasting at Seavey Vineyard or Aonair, both small family-owned wineries with fabulous wines!

✅ 🚗 I recommend Designated Drivers Napa Sonoma for a tour because they offer an incredible wine country experience at a fraction of the cost of a private tour. They’ll drive your rental car & help you plan an itinerary, so you can sip, relax and soak up the day without stressing about directions or driving.

✨ ✨ And as a bonus, use code DDNS and mention me when you book to receive a free ​Unwined Gift Kit ​with your tour.

Stop 1: Mini Model Bakery in Yountville at 9:00 am

Today we are starting your day with a yummy breakfast at the Mini Model in downtown Yountville for breakfast, one of my personal favorites.

They are famous for their fluffy and buttery English Muffins. Smoother it with homemade strawberry jam, and it is the best English muffin you will ever taste!

🍷 Wine Gal Tip: On a tight schedule or visiting on the weekend, you can order ahead and pick it up. They are closed on Monday-Wednesday. They also have other locations in Napa Valley.

Stop 2: Amizetta Winery 10:30 am

🚗 Yountville to Amizetta Winery, 35 minute drive

If there’s one winery in this itinerary you absolutely can’t miss, it’s Amizetta Winery. I recently did a tasting here and had such a memorable experience, my husband and I already know we’ll be coming back.

What makes Amizetta stand out is that it’s a small, family-owned winery that offers a really warm and intimate tasting experience. Our host was fantastic, knowledgeable, personable, and genuinely interested in getting to know us.

The property is tucked into the foothills of Howell Mountain and offers breathtaking panoramic views of rolling vineyards and Lake Hennessey.

And the wine here is exceptional, some of my favorite in Napa, especially for the price point. They will even waive a tasting fee if you purchase three bottles.

🍷 Wine Gal Tip: Reservations are required, and wine tastings are available 7 days a week

Stop 3: Lunch at Charter Oak 12:45 pm

🚗 Amizetta Winery to Charter Oak, 20 minute drive

St. Helena is full of incredible dining options, but Charter Oak is the perfect lunch stop between wine tastings.

The vibe is casual yet upscale, with family-style dishes made from fresh, seasonal ingredients, most sourced from their own 3.5-acre farm. They’re famous for their burger, and after finally trying it, I can confirm: it’s next-level delicious.

Pro tip: Order the fermented soy dip (a.k.a. the best dip ever) for your fries, you’ll thank me later. We also loved the Aged Beef Chuck Tartare.

Stop 4: Wine Tasting at AXR Napa Winery at 3:00 pm

🚗 Charter Oak to AXR, 7 minute drive

AXR is a hidden gem just off Highway 29, surrounded by coastal redwoods that create a serene and magical atmosphere. My husband and I visited for our anniversary, and it was truly unforgettable.

The experience is intimate and private, your host guides you through the property’s history and a fairy circle of redwoods before settling into the charming front house for the tasting. And a fun surprise, we were served crispy kettle chips dusted with Cowgirl Creamery cheese, an unexpectedly delicious pairing.

The wine was exceptional, each pour was better than the last, truly showcasing the brilliance of winemaker Jean Hoefliger, an icon in Napa Valley.

🍷 Wine Gal Tip: Reservations are required, wine tastings are available 7 days a week

Stop 6: Relax at The Hotel

Head back to your hotel to get some rest before it is time to get some yummy dinner in downtown Napa.

Stop 7: Dinner at Scala in Downtown Napa

🚗 Yountville to Scala, 15 to 20 minute drive

For dinner tonight, treat yourself to an incredible Italian meal at Scala Osteria & Bar. It’s the sister spot to the iconic Don Giovanni’s (also in Napa), but with a focus on Southern Italian coastal cuisine, think lots of fresh seafood and handmade pasta!

The menu is packed with so many tempting dishes, it’s honestly hard to choose. I recommend ordering a bunch and sharing family-style so you can try a little bit of everything. And don’t skip dessert, the zeppoles are warm, fluffy donuts served with crème anglaise and chocolate sauce… absolutely worth saving room for.

If you’re in the mood to keep the night going, head to Sky & Vine Rooftop Bar at the Archer Hotel for drinks and views.

🍷 Wine Gal Tip: In downtown Napa, I also recommend Angele for French, Bistro Don Giovanni for Italian (same owners as Scala), and Zuzu for Spanish tapas.

Day 4: Treat Yourself

• Hot Air Balloon Ride or Spa Day
• Lunch at Oakville Grocery
• Stop at the Napa Valley Sign
• Wine Tasting at Quintessa or Tres Sabores
• Dinner at Charlie’s in St. Helena

There has been A LOT of wine tasting these last few days, so let’s start today a little differently and treat yourself to either an adventurous hot air balloon ride or a relaxing spa day.

Stop 1: Option #1 Hot Air Balloon Ride

🚶‍♀️Meeting point in downtown Yountville

For a bucket list experience, take flight on an unforgettable hot air balloon ride. Lifting off at sunrise, you’ll drift above the valley so you can soak in the panoramic views of rolling hills and sprawling vineyards in the morning light.

✅ I recommend Napa Valley Aloft for a hot air balloon ride, you can check their rates here!

Stop 1: Option #2 Mud Bath & Hot Springs in Calistoga

🚗 Yountville to Calistoga, 30 minute drive

If you’d rather stay on land and enjoy a morning of pampering, plan a relaxing spa day. You can book a treatment at the luxurious Bardessono Hotel and Spa in Yountville, or head up to Calistoga to unwind in one of its famous hot springs.

For the ultimate luxury experience, Solage is a top choice. But if you’re looking for something more affordable, check out Golden Haven Hot Springs. They offer a variety of options including hot springs, mud baths, massages, and several couples or friends packages.

Stop 2: Lunch at Oakville Grocery

🚗 Yountville to Oakville Grocery, 7 minute drive
🚗 Calistoga to Oakville Grocery, 20 minute drive

No trip to Napa Valley is complete without a stop at the Oakville Grocery along Highway 29. I love popping in for a coffee and sweet treat at breakfast or getting picnic supplies for the day.

The bustling market has everything, wood-fired pizza, artisan cheeses, sandwiches, salads, and a great selection of Napa wines by the glass or bottle. And it’s honestly just fun to browse and walk around.

Grab a seat outside or take your food for a picnic or winery visit. It’s a popular weekend spot, so expect crowds, or order your food ahead of time.

🍷 Wine Gal Tip: Depending on which winery you choose to go to next, you can bring your lunch to eat at the winery. Tres Sabores does allow picnics, Quintessa does not allow outside food.

Stop 3: Snap a Pic In Front of the Napa Valley Sign

🚗 Oakville Grocery to Napa sign, 1 minute drive

Since it’s your first time in Napa Valley, gather the crew and snap a photo in front of the iconic Welcome to Napa Valley sign along Highway 29. It’s super easy to pull off the road, there’s plenty of space to park and hop out for a quick picture. There is also the same Napa Valley sign in Calistoga as well.

Stop 4: Option #1 Quintessa

🚗 Napa Sign to Quintessa, 10-15 minute drive

If you’re looking for that WOW moment, that “I could totally live here” kind of feeling, then you need to visit Quintessa.

This is one of those iconic Napa Valley wineries you just have to experience in person. The estate is absolutely breathtaking, and their tastings are luxurious and intimate.

The private tasting takes place in an open-air pavilion with floor-to-ceiling glass windows, allowing you to soak in the sweeping vineyard views. It’s pure perfection.

The only con to Quintessa, it’s definitely a splurge. But if it fits your budget, I 100% recommend the experience.

🍷 Wine Gal Tip: Reservations are required, Quintessa is closed on Tuesdays & Wednesdays.

Stop 4: Option #2 Tres Sabores Winery

🚗 Napa Sign to Tres Sabores, 10 minute drive

Tres Sabores Winery has a completely different vibe from Quintessa, in the best way. It’s a small, woman-owned winery and one of the first California Certified Organic vineyards in Northern California.

I loved my experience at Tres Sabores. The tasting felt casual and down-to-earth, like the authentic wine country, no castles or gondolas, just great wine and good vibes.

Our tasting was held on a rustic patio tucked among the vines, creating an intimate and dreamy setting. It’s the perfect spot for a BYO picnic and is super welcoming to both kids and dogs. And bonus, you’ll meet some friendly ranch animals, including Golden Retrievers, Guinea fowl, and sheep!

🍷 Wine Gal Tip: Reservations are by appointment only, Tres Sabores is open 7 days a week.

Stop 5: Head Back to Hotel

After your tasting, take some time to relax in your hotel before dinner and drinks in St. Helena.

Stop 6: Downtown St. Helena for Dinner at Charlie’s

🚗 Yountville to Charlie’s, 20 minute drive

Your last dinner in Napa Valley is at Charlie’s, a cozy gem tucked just off the main street in downtown St. Helena. It’s quickly become the local hotspot everyone’s talking about. Behind it all is Chef Elliot Bell, a French Laundry alum with a résumé that includes some of the most prestigious kitchens in the world.

The menu is inventive and delicious, think elevated comfort food, like caviar served with mini potato skins and caramelized onion dip. So good! And, they can make almost any dish gluten-free.

🍷 Wine Gal Tip: Charlie’s also has a great happy hour and is the only spot in St. Helena serving a late-night menu, available until 11 PM. They are closed on Tuesdays and Wednesdays.

Day 5: Pizza, Wine Caves, & The Famous Oxbow Market

• Check out of hotel
• Wine tasting and pizza at Piazza del Dotto
• Oxbow Market

Today is a sad day, it’s your last day in Napa Valley, but before you get back to reality, there is one last tasting and thing to do on your itinerary.

Stop 1: Tasting at Piazza Del Dotto Winery & Caves

🚗 Yountville to Piazza del Dotto, 5 minute drive

After check-out, head to Piazza Del Dotto for their wine cave and pizza experience, a crowd favorite every time we’ve brought out-of-town friends.

The experience begins with a tour through their stunning marble wine caves, where you’ll taste wine thieved straight from the barrel. Then, settle in on the beautiful garden patio for a seated tasting paired with delicious house-made pizzas and vineyard views.

Make sure to wander the grounds afterward, the estate is home to lush gardens, a peacock, chickens, and turkeys.

🍷 Wine Gal Tip: Reservations are required, Piazza del Dotto is open 7 days a week.

Stop 2: Oxbow Market in Downtown Napa

🚗 Piazza del Dotto to Oxbow Market, 20 minute drive

So did I save the best for last? Before you make the journey home, make one last stop at the popular food hall, Oxbow Public Market in downtown Napa.

It’s fun to walk through the local vendors selling an array of local food and artisan products. There are artisan chocolates, olive oil, spices, a distillery, and plenty of options for lunch.

Before heading out, buy a coffee from Ritual Roasters or a yummy snack for later at Kara’s Cupcakes.

After Oxbow, take a walk along the Napa River for some views before you hit the road back to the airport.

Must Know Tips For Your First Time in Napa Valley

• Where to Stay: I recommend Yountville for a more central location or downtown Napa if you want a more lively nightlife and city vibe.
• How Many Wine Tasting to Book in a Day: I recommend a max of three, but two wine tastings offers a more relaxed and enjoyable experience
• Wine Tastings Reservations: Book all of your wine tastings in advance, and shoot for at least three months ahead of your visit. Book reservations at least two hours apart to allow for travel time.
• What to Wear Wine Tasting: Think wine country casual, and layer up! Mornings are usually chilly, the day is warm, and temperatures dip at night.

🙋‍♀️ Need more help planning? Join my FREE Napa Facebook Group!
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