​

Hi Reader,

Can I tell you one thing I’ve learned from planning a lot of wine trips?

It’s not about booking early.

It’s about booking the right thing early.

Because in wine country, it’s not always flights that disappear first.

Sometimes it’s the luxury winery retreat. Sometimes it’s the appointment-only tasting. Sometimes it’s the dinner reservation everyone else is trying to snag. 😬

So before you click “purchase,” here’s how I figure out what to book first.

✈️ Let’s Talk Flights

Flights are often the right first move, especially if:

• It’s an international trip
• You’re using points
• Your dates are fixed

For example, I’m heading to Chile next month and booked flights almost a year ago because I knew I wanted to use points.

But for Croatia last fall? I booked two months out and ended up scoring a great cash fare. So, flights aren’t one-size-fits-all.

If you’re flexible, check lodging and key experiences first. Flights may be easier to adjust than a sold-out wine festival you’ve been dreaming about. 🍷

🏨 Then Look at Lodging

Wine towns are often small, and inventory can be limited.

If you’re a mid-range traveler like me, waiting too long can mean choosing between sky-high pricing…or that one roadside motel that makes you reconsider your life choices. 😅

Or if your heart is set on a luxury winery retreat with six villas, that’s absolutely a reason to book lodging first.

Especially if you’re:

• Visiting during a harvest or festival weekend
• Traveling during peak season
• Trying to book on points

Because where you stay can shape your entire trip.

🍷 Next: Special Winery Experiences

Not every tasting needs to be booked months in advance. But certain experiences should be.

Like the winery I’m visiting in Chile that only offers private appointments. Meaning they can host like 6 people a day.

Lock in your top-priority experiences early, especially for:

• Appointment-only wineries
• Special pairing dinners
• Harvest events

Then you can fill in the gaps later and leave a little breathing room for spontaneity.

🚗 Don’t Forget the Rental Car

Once flights are set, book the car.

I once waited to book a rental for an island trip…and ended up with a clunker that I thought was going to break down at any minute. But hey, at least I got a car. 🤷‍♀️

Wine regions don’t always have deep rental inventory, especially near smaller airports.

Most rentals offer free cancellation. So, reserve it early and recheck pricing later.

🍽️ And Finally: Restaurants & Tours

I usually book these last. But in wine towns, some dinner reservations can be harder to get than Taylor Swift tickets. 🎟️

If you’ve ever scored a table at a place like Napa’s French Laundry, you know that sometimes the restaurant becomes the reason you plan the trip.

And the same goes for private drivers, special tours, and seasonal events. If you’d be disappointed to miss it, book it sooner rather than later.

Looking for a full step-by-step booking timeline? That’s exactly why I created this free wine trip planning checklist.

⬇️ DOWNLOAD THE CHECKLIST

It even includes when to handle passports, international driving permits, travel alerts, and week-of prep.

Cheers,

Laura

🚌 Tours I'm Loving ​My top picks for wine country tours

⚙️ Travel Tools I'm Using ​This site for the best car rental deals

🗞️ News I'm Following The new best day to book flights​

P.O. Box 44, Pinehurst, MA 01866
​Unsubscribe · Preferences​