The Napa Mistakes I See Every Single Time

I’ve been to Napa more times than I can count at this point, and no matter how many groups I plan trips for, the same four mistakes come up again and again. If you’re heading to wine country soon, here’s what to avoid — and how to actually do it right.

​1. Not Booking Tastings Ahead of Time

Most wineries in Napa are reservation-only now, especially the ones worth visiting. Walking in without a booking usually means getting turned away, or waiting around hoping for a cancellation. If you’re planning a weekend or a full trip, book your tastings 2-3 months out — especially if you’re going on a weekend, when availability disappears fast.

​2. Not Booking a Driver

Here’s the thing about a tasting day: you’re tasting all day, not sipping. If you’re the one driving, you’re either skipping pours or white-knuckling it between stops. A private driver means everyone in your group actually gets to enjoy the wine, worry-free, without watching the clock or counting glasses.

​3. Flying Into San Francisco

This one surprises people. Flying into SFO adds an extra 1.5-2 hours of driving each way once you factor in traffic through the city and over the bridge. Fly into Sacramento or Oakland instead — both are closer to the valley, and you’ll spend less time in the car and more time actually in Napa.

​4. Too Many Tastings in a Day

More is not more when it comes to wine tasting. 1-2 wineries is the real sweet spot for a day — any more than that and it stops being enjoyable and starts feeling like a checklist. Treat it like a meal, not a race. Slow down, actually taste what’s in the glass, and let the day breathe.

Planning your own Napa trip? This is exactly the kind of thing I handle so you don’t have to guess — from booking the right tastings to arranging a driver to building a pace that actually feels like a vacation. DM me or reach out below to start planning.

xo, Bailey