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Hi Reader,

Most of my wine trips are pretty low-key. Usually just me and my husband, or maybe one or two friends.

Once the group gets bigger than that, things can get chaotic fast.

Suddenly, you’re coordinating reservations for eight people, someone’s always running late, and no one can agree on brunch. 🤷‍♀️

But I have learned there are some wine destinations that make group trips way easier than others.

The best ones have things like walkable tasting rooms, wine shuttles, great restaurants, and enough non-wine activities to keep everyone happy.

Here are five wine destinations that are especially fun with a group.

🌴 Santa Barbara, California
Santa Barbara makes group trips easy with beaches, seafood spots, and downtown tasting rooms in the Funk Zone and Presidio Neighborhoods.
👉 Santa Barbara Wine Tasting Guide​

🤠 Fredericksburg, Texas
Fredericksburg was basically made for wine weekends with friends. Wine shuttles, Main Street boutiques and bars, and plenty of Rhône and Tempranillo-filled tasting rooms.
👉 Fredericksburg Wineries Guide​
👉 Texas Hill Country Itinerary​

🌊 Hvar, Croatia
Hvar combines island wineries with boat days, beach clubs, and sunset drinks overlooking the Adriatic. Perfect for groups that want equal parts wine trip and summer vacay.
👉 Hvar Wineries Guide​

🍁 Southern Québec
Québec’s Eastern Townships are perfect for groups that want wine and variety. Think vineyard visits paired with spas, farm-to-table meals, and outdoor adventure.
👉 Southern Québec Guide ​

🏞️ Charlottesville, Virginia
With wineries clustered together, nearby cideries and breweries, and a lively downtown pedestrian mall, Charlottesville gives groups plenty of options for all tastes.
👉 Charlottesville Wineries Guide​
👉 Charlottesville Itinerary​

💡 One quick planning tip: if you’re traveling with a group, make sure to check winery websites ahead of time for reservation requirements and group policies.

Trust me, this is information you want before everyone gets in the car.

Cheers,

Laura

P.S. Which of these destinations would your group chat actually agree on?

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P.O. Box 44, Pinehurst, MA 01866
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