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First visit to Napa? How to have the best day ever.

No time to be intimidated by California’s classiest wine region—you’ve got too much to see and do.

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Ostentatiousness with zero sense of humor is possibly one of the most puzzling mash-ups you could ever encounter in a destination—Las Vegas, which has the first bit down pat, works wonderfully well because everyone laughs at it, starting with the people who built the place. Awash in often rather comical displays of wealth and yet predisposed toward pretense, the Napa Valley can overwhelm—it really doesn’t matter how many times you’ve been here before. Napa is, by many measures, a wholly ridiculous place, a product of a long-ago time when being fabulously rich in America made you cool. (The ’90’s sure were fun, weren’t they.)

Oh, well. We could sit here all day discussing its flaws, but in the end, we’d likely come to agree that none of these flaws are anything close to fatal. This narrow little (for California) valley will probably always be one of the most beautiful places on the continent, no matter what time throws at it. Slow down, take a few deep breaths, taste the right wine in the right setting, check into one of the country’s most luxurious hotels, stop in for dinner at one of many good restaurants, where everything tastes like it was harvested or butchered barely an hour ago, and all you’ll be able to think of, when all’s said and done, is how dearly you’d love to be able to repeat the experience. (Over and over and over again.)

It is foolish to come here for the first time intending to try everything. First of all, a very few could afford it. For your premier engagement, one is best off not overloading one’s itinerary, or clogging up the day with restaurant reservations and appointment-only tastings. Avoid the tour bus magnets. Bypass the busiest of the tourist towns. Be stingy with your dining dollars. Truth is, a day in the valley can be a relatively simple and affordable affair—you just have to know how. Here’s a quick tip sheet that’ll have you feeling good in no time.

Stop for breakfast. The best way to arrive from San Francisco is via the magical Carneros region, straddling the Napa and Sonoma boundary. You’re not just here to admire the postcard-ready vistas and the miles of vineyards, you’ve also come this way in order to stop for breakfast at the Boon Fly Café. This Napa-fancy interpretation of a roadside diner is worth a stop for tasty homemade donuts and an exceedingly proper eggs benedict. 4048 Sonoma Highway

Head up the hill. It’s amazing, really, how many wineries there are—start, however, with a stop at one of the better-known tasting rooms that relatively few people seem to visit. The Hess Estate, located up atop Mount Veeder on the valley’s west side, is one of those places you try once and then forever find yourself returning to—the brand may be familiar, but the wines served in the tasting room are a whole lot more upmarket than what you’d find on the shelf around the country. The main reason to come here, however, is the welcome—you’d never know you were just up the hill from so many tourist traps; for $25 you get a thorough tasting; the staff are often quite amiable and ready to talk with anyone genuinely interested in wine. Upstairs, you’ll find the other reason to come up here—a sizeable showing of the Hess family’s well-regarded modern art collection. Galleries are always open to the public, whether you taste or not. 4411 Redwood Road

Play the market. The city of Napa used to be the last place visitors might end up when visiting the valley; these days, it’s almost enough to keep you busy for a full day. There are a few reasons for this, but none quite as compelling as the outstanding Oxbow Public Market. This covered public market that runs every day, year-round, features some of the Bay Area’s best-loved food—oysters at Hog Island, charcuterie at The Fatted Calf, ahi tuna burgers at Gott’s, local veggies spun into great dishes at Kitchen Door, microbrews at Fieldwork Brewing, pizza at Ca’Momi—the list goes on. For dessert, hit up Three Twins Ice Cream or Kara’s Cupcakes, followed by coffee at Ritual. Seriously—come hungry. Need an eating break? Across the parking lot, check out the recently-arrived Culinary Institute of America satellite campus, breathing new life (thank goodness, finally) into the spectacular failure that was the Center for the Wine, Food & the Arts (COPIA) complex. Check out the gardens, book a table in the school restaurant, attend a cooking demo or even sign up for, say, a pastry short-course. 610 First Street + 500 First Street

Get a taste of the town. Since you’re in the neighborhood, walk the few blocks to The Vintner’s Collective, which showcases the work of a group of small area wineries that don’t have their own tasting rooms. It’s housed in a historic stone building on Main Street; you may never have heard of most or all of these wineries, but this is Napa—they’re all going to be interesting. Tastings start at $10 and you don’t have to make an appointment (1245 Main Street). Afterwards, take a stroll along the Napa River—either park at the foot of Main Street and hook into the nicely manicured Riverwalk, which takes you back up towards the First Street Bridge, or go for a longer jaunt down a completed piece of what will eventually be the 47-mile Napa Valley Vine Trail. A popular, riverfront segment can be accessed just south of the intersection of Third and Soscol; serious walkers should hook a left at Streblow Drive and join the River to Ridge Trail, which leads into the hills. (During the cool, wet winter months, it’s particularly green and beautiful up here. Just plan on getting your shoes muddy.)

Ready, set, cruise. Ready to take a leisurely drive? Good, because in spite of how busy the roads get here, a sunny afternoon of motoring through the vineyards remains a highlight of the Napa experience. One of the best things about the valley is how, as in many busy tourist destinations, people tend to follow each other around—almost religiously, in fact. As a result, there are a few very crowded wineries and a few very crowded towns. Route 29, which goes north-south on the west side of the valley, is very busy, to the point where driving it is rarely much fun, anymore. The Silverado Trail, which does the same thing just a mile or two to the east (yes, the valley is that narrow) is often less busy. North of Trancas Street in the city of Napa, all the way up to the top of the valley at Calistoga, the Trail is all you need to be using; you can cut across whenever you have to. Take it all the way to the top, then turn around and stop at everything that caught your eye along the way.

Sneak into the valley’s top hotel. You won’t have seen it from the road, but one of the best stops along the Trail is another famous spot that hasn’t given into mass tourism—when you see it again, pop up Rutherford Hill Road for one of the valley’s finest views. People pay a great deal of money to eat dinner out on the patio at Auberge du Soleil, and there’s a reason they do this—the setting is perfect. (Also, the food is solid, if traditional.) This isn’t just a restaurant, however—this is one of California’s most exclusive hotels, in one of the best locations you could ask for, anywhere—good job then, that for the price of a cocktail, you can sneak onto the bar’s small but pleasant patio, claiming the same view as the restaurant next door. 180 Rutherford Hill Road.

Go eat in the valley’s tastiest town. Is it dinner time already? Cut across the valley to the town of Yountville, a sometimes surprisingly normal place, for being smack in the middle of the valley. Well, normal until you start paying attention—the heart of this quaint burg has over the years evolved to become one of the continent’s culinary capitals, with what seems like more Michelin stars than drug stores. Ask two people who know Yountville for advice on where to eat first and you’ll likely find yourself in a spirited discussion, but there’s something about Redd that just won’t quit—it’s simple, it’s modern, it’s elegant and so is the California-fresh New American cooking. The wine list is a thing of beauty. Ready to eat a little earlier? They’ve got a great bar menu as well. 6480 Washington Street

BookingBuddy

Booking a trip?
If you’re looking for the lowest airfares to the San Francisco Bay Area, start by noodling around on CheapFlights or BookingBuddy—both will compare multiple sites at once, saving you a lot of running around. When you’re ready to book, we recommend Orbitz or Expedia—both offer 24-hour cancellation policies, allowing you to lock in the lowest fare while you finalize your plans. (As always, read the fine print first.) Just on here looking for the best Napa Valley hotel deals? Start by searching TripAdvisor, or Hotels.com, but don’t book anything without a stop at Priceline, where you can save up to 60% on any given night by taking advantage of their Express Deals feature. (This simple tool has probably saved us—no joke—thousands of dollars, over the years.). Finally, if you need a rental car, begin your search by swinging wide to get a sense of the market—BookingBuddy lets you check pretty much every site worth knowing, with just a couple of clicks.

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