​

Hi Reader,

As the travel planner in my friend group, I've organized my fair share of trips over the years.

Girls' weekends. Family vacations. Friends’ getaways.

And they usually start the same way:

"This is going to be so much fun!"

Then, things start to get complicated…especially when you add a wine region to the mix.

Now you're coordinating winery reservations, transportation, tasting fees, and making sure nobody gets stranded at a winery because they stopped to buy a case of wine. 🤪

But some of my favorite travel memories have come from group wine trips.

The key is setting yourself up for success before anyone starts booking.

Here are a few tips that can make planning a group wine trip a whole lot smoother.

🗺️ Start with a Group-Friendly Region

Some wine regions are easier for groups than others.

Look for:

• Walkable tasting rooms or wineries clustered together
• Wine shuttles or private tours
• Group-friendly lodging options
• Restaurants that can handle larger parties

The right region won't solve every problem, but it can eliminate a lot of headaches.

👉 Need ideas? Check out some of my favorite wine destinations for group trips.

👥 Research Winery Group Policies

Not every winery is built for eight people showing up at once.

Look for ones designed for larger groups, with plenty of seating, outdoor space, and staff used to handling bigger parties.

Before you build your itinerary around a winery, check:

• Group size limits
• Reservation requirements
• Prepaid tasting policies
• Whether groups are only accepted at certain times

🚐 Simplify Transportation

Driving yourself can mean multiple designated drivers, and people getting separated or running late. The bigger the group, the more value you’ll get from hiring transportation.

Consider:

• A private driver
• A wine tour company
• A shuttle service
• One large vehicle instead of multiple cars

It's often more affordable than you expect once the cost is split.

⏱️ Build in More Time Than You Think

A wine tasting that takes 60 minutes for two people may take 90 minutes for a group.

There's always someone:

• Buying wine
• Taking photos
• Asking questions
• Running to the restroom

Plan fewer wineries and more breathing room than you think you need.

Remember: the goal is to spend time with people you enjoy, discover some great wines, and hopefully avoid any group-chat drama along the way. 😬

If that happens, nobody's going to care about the exact tasting schedule.

They'll just be asking, "When are we doing this again?" 🥂

Cheers,

Laura

⚙️ Travel Tools I'm Testing ​Doodle for agreeing on trip dates

🍷 Wine Finds I'm Loving ​A wine trivia game for the house

📸 Apps I'm Using ​This tool for sharing trip photos

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