A Guide to the Ultimate Guys’ Getaway in Napa Valley

Day 1

Arrive, Eat, and Begin Your Tasting Odyssey

Before the trip gets rolling, you’ll need to decide where your group will call home during your stay. Harvest Inn in St Helena puts you at the geographic heart of the valley, offering eight lush acres of property, vineyard views, fire pits, and direct access to Harvest Table's farm-to-table kitchen. And, if you time your trip well, you could attend one of the Inn’s monthly cigar dinners, which feature live music and cigar pairings. If the crew prefers to be downtown at the center of the action, the Archer Hotel puts bars, restaurants, and live music venues all within walking distance. For a full splurge, Carneros Resort and Spa offers private cottage suites that sleep groups, a heated adults-only hilltop pool with cabanas, and three on-site restaurants.

Once you arrive and settle into your hotel, kick things off with a casual visit to the Oxbow Public Market, a marketplace of local shops perched right next to the Napa River. Grab a coffee, browse the local vendors, and snag a bite to eat before the day truly starts. Here, you’ll find many different food counters with a wide variety of options, so everyone in your group can get exactly what they’re craving, whether it’s wood-fired pizza from Live Fire, gourmet hot dogs from Sumo Dog, or grilled oysters from Hog Island.

Now that you’ve all fueled up, it’s time to hit your first winery of the trip. For architecture and engineering geeks, Napa Valley has plenty of striking properties worth exploring. Start at Artesa Vineyard & Winery, a Spanish-owned winery that almost appears to have sprouted directly out of the Carneros hillside. Stroll the sculpted grounds, enjoy the view from the terrace, then sit down for a serious tasting. Most of the wines available here are exclusive to Artesa — as in, you won’t find them on any restaurant’s by-the-glass list — so you can be sure you’re in for an exclusive kind of treat.

From there, you should have time to squeeze in one more tasting before the afternoon winds to a close. You'll see your next stop from the Silverado Trail and your first thought will be that you've taken a wrong turn toward ancient Shiraz. Darioush is one of the most architecturally audacious buildings in all of wine country — 16 freestanding columns, hand-carved stone details, and a dramatic portico that evokes the palaces of Persepolis. Owner Darioush Khaledi grew up in Shiraz, Iran's wine-producing heartland, and the design is a direct expression of that heritage. Inside, you’ll be greeted with the warm grace of traditional Persian hospitality, and by the time you leave, you’ll feel like family.

At this point, the sun should be sinking toward the horizon, and you’ll want to think about dinner. If you have a bit of extra time to kill, head first to ArBARetum, Napa Distillery’s art deco-inspired craft cocktail bar, to enjoy what will likely be the most creative drink you’ve ever encountered. You can also pop next door to Napa Cigars to browse a large selection of premium tobacco products while you sip on premium whiskeys.

For dinner, keep heading down First Street to Oenotri, which is the kind of Italian restaurant the whole crew will be still talking about the next day. House-made pastas, wood-fired Neapolitan pizzas, and a wine list that takes regional Southern Italian seriously. Loud enough to have a real conversation, good enough to slow down and pay attention, this is the perfect way to end your first night in Napa Valley.

Day 2

Supercars, Artful Tastings, & a Cigar Dinner

Rise and shine! If you did Day 1 right, you should be well-rested and ready to take the valley by storm today. But first, you’ll need some caffeine. Head to Ohm Coffee Roasters, a cool, rock-and-roll inspired coffee shop with excellent roasts and homemade pastries. Now that you’re fully energized, it’s time to get behind the wheel.

Napa Valley Car Club is the valley’s leading destination for exotic sports car tours. Whether you’re a well-seasoned driver or you’ve simply always dreamed of sailing across vineyard-lined roads in a McLaren, the Car Club has you covered. You can book private group tours, so that your whole crew can participate in a high-octane sports car rally, or you can rent one of their cars for a longer stretch of time, and cruise through the rest of your trip in style. You can also check out Napa Valley Supercars, another premier supercar rental spot that runs in a road rally format — the whole group drives together in convoy through the Valley following a lead vehicle through some of the most cinematic wine-country roads in North America.

If you choose a half-day supercar tour, you should have enough time left in the afternoon to taste a few more wines. Head up-valley to St Helena, where HALL Wines awaits. HALL is what happens when a serious art collection meets world-class winemaking. The St. Helena property is anchored by a 35-foot stainless steel bunny sculpture at the entrance and surrounded by works from more than 25 established artists. You’ll spend your time there exploring incredible original artworks, taking in the view, and of course, sampling some of the most distinctive and well-regarded wines in the valley.

End Day 2 with a splash, and reserve a spot at Harvest Inn for one of the valley’s finest dinner events, their legendary cigar dinner. Intimate, fire-lit evenings on the terrace, pairing premium cigars with wines from the Inn's curated cellar and fare from the minds of culinary geniuses? Sounds like this will be the highlight of the trip. Check the Harvest Inn's current schedule and book as early as possible. If a scheduled dinner isn't available during your visit, the Inn's private event team can arrange a bespoke experience for groups.

Day 3

Flavors & Fore!

Nothing says “guys’ trip” like spending the day on the green. Wake up bright and early, and head to one of Napa Valley’s many top-notch golf courses, such as the award-winning (and host to the PGA Tour!) Silverado Resort & Spa. The resort’s two different golf courses mean that you can cater your day to every golfer in your group, no matter the skill level — the North Course features challenging obstacles and is ideal for more seasoned players, while the South Course is great for groups that want to take the day at a relaxed pace. Silverado’s onsite golf shop has you covered for club rentals, too, so no one needs to be left out. While you’re at the resort, be sure to check out the other extensive offerings available, from spa treatments to racquetball courts.

We’ve been packing in quite a few activities over the last few days, and a long afternoon on the golf course is sure to leave you a little tired. Take this opportunity for a quick midday break. Head back to the hotel, get changed, and relax — perhaps this is the perfect time to grab a beer at your hotel’s bar and enjoy some solo patio time. Once you’ve all had a moment to reset, though, it’s back at it. It should be nearing dinner time, and we bet you’ll be starved for a hearty meal after so much exercise earlier in the day. This evening, head to Calistoga for a meal at Fleetwood Restaurant, which focuses on wood-fired cuisine and a relaxed, warm atmosphere. Enjoy a selection of dishes sourced from fresh, local produce, as well as handcrafted cocktails, all while you’re surrounded by the breathtaking views of the Calistoga hillsides.

Before the evening wraps up, why not catch a show? On any given evening, Napa Valley has a full roster of fun events, including live music, comedy shows, and more. Places such as Wilfred’s Lounge serve as both music venues and fun late-night bar spots — perfect for closing your last full day with a bang.

Day 4

Castles, Caves &, One Last Stop

Even though you’re heading back today, the adventure isn’t quite over. First, squeeze in one more wine tasting at a place with mindblowing architecture. Drive north to Calistoga and prepare to feel genuinely confused about what country you're in. The only authentically built 13th-century Tuscan-style castle and winery in America, Castello di Amorosa took fourth-generation Italian winemaker Dario Sattui more than three decades to construct. The result: 141,000 square feet across eight levels, 107 rooms, 8,000 tons of hand-chiseled stone, a working drawbridge, a dungeon, a torture chamber, a medieval church, and a 15,000 sq. ft. wine cave. Walk every inch of it, then taste the wines in the Great Hall under the Tuscan frescoes.

Before you head out, stop for one last lunch at Calistoga’s House of Better, a wellness-focused casual restaurant emphasizing foods that taste good and feel good. It’s exactly what you guys will need after a few days of letting loose.