CLICK HERE TO VIEW ALL THE ESSENTIALS FOR YOUR NEXT WINE TASTING TRIP IN ITALY!

If you're planning a wine tasting trip to Italy, especially in the stunning region of Tuscany, you're in for a treat! From exploring charming boutique wineries to sipping the finest reds, whites, and roses, Tuscany offers some of the best wine-tasting experiences in the world. Whether you're a wine connoisseur or a casual enthusiast, the perfect trip to Italy pairs amazing wines with gorgeous scenery and rich history. To help you make the most of your adventure, I’ve put together a guide on the must-have items to pack and my top winery recommendations that you can't miss when touring Tuscany.

The Essentials for Your Wine Tasting Trip:

Tuscany's rolling hills, ancient vineyards, and picture-perfect villages deserve an equally stunning wardrobe. So let’s talk about what to wear and carry with you to make sure you’re stylish, comfortable, and ready for anything that comes your way.

A Fashionable Floral or Striped Dress
The Italian countryside is the perfect backdrop for a cute floral or striped dress. You want something breezy, easy to move in, and stylish enough to snap a few photos in front of the stunning views. I recommend a dress that’s light enough for the warm Tuscany sun, but with layers you can throw on for cooler evenings.
A Cozy, Yet Stylish Hat
You’re going to be outside in the sun for most of the day, so a chic wide-brimmed hat is a must. Not only will it protect your face, but it will add a touch of elegance to your outfit, making you look like you just stepped off a fashion runway in Milan.
Sunscreen and SPF Makeup
When you’re spending the day on wine tours in Tuscany, the last thing you want is to get sunburned. Pack a high-quality SPF sunscreen, and consider a tinted SPF foundation or a tinted moisturizer with SPF for added protection. I personally love using a light shimmer rose-colored blush palette, which gives a natural glow and works perfectly with the warm Tuscan light.
Comfortable Shoes for Walking
Tuscany is full of cobblestone streets and vineyard tours, so be sure to bring a pair of comfortable yet stylish shoes. Think sneakers or espadrilles that are easy to walk in but still look cute for your vineyard photos.
A Small Crossbody Bag
A compact, crossbody bag is perfect for holding essentials like your phone, camera, wallet, and sunscreen while leaving your hands free for wine glasses! Plus, a stylish bag can tie your entire look together.
Portable Charger
Between wine tasting, sightseeing, and photo ops, your phone will be in constant use. A portable charger will ensure you never miss a moment—and if you're like me, you'll want to document every sip!
Tuscany Travel Books
A good travel book or journal is an ideal way to record your thoughts, favorite wines, and memorable moments throughout your trip. I love bringing along a guidebook for hidden gems in Tuscany, or a personal journal to jot down everything I want to remember about my wine adventures.

Now, let's get to the fun part: Top 5 Wineries in Tuscany You Have to Visit!

1. Tenuta San Vicenti
If you’re looking for a unique, intimate wine tasting experience, Tenuta San Vicenti is a must-see. Owned by Dr. Marc Ronert and Jana Ronert, this winery offers a personal touch that makes it stand out from the rest. I was welcomed by the incredible winery manager, Benedetta, who provided us with a tour of the winery. It was amazing to hear directly from the winemaker, who walked us through their process of creating exceptional wines.

The wines at Tenuta San Vicenti are a true delight. Their light rose, a crisp champagne-like blend with refreshing apricot and vanilla notes, was perfect for a hot afternoon. The reds are bold and smooth, pairing beautifully with the spread of cheeses and bruschetta. Though it’s about 1.5 hours from Florence, the scenic drive alone is worth it. It’s an experience that blends amazing wine, incredible views, and warm hospitality—what more could you ask for?

2. Castello Vicchiomaggio
Welcome to the fairytale castle of Chianti! Castello Vicchiomaggio is one of the most charming wineries in Tuscany, offering a wine-tasting experience set in a beautiful medieval castle. The architecture is stunning, and the views of the rolling hills will make you feel like you’re in the pages of a romance novel. My favorite wine here? The Floreale rose—it quickly became my “rose all day” favorite. It's crisp, light, and non-sweet, perfect for sipping all afternoon.

But don't just take my word for it! Their bold Cabs and Sangiovese reds are outstanding, offering a depth of flavor you won't find anywhere else. The winery offers a decadent food spread for foodies, with options that pair perfectly with their wines. And the best part? You can stay in the castle! I highly recommend booking a reservation for both wine tasting and accommodations. It's an experience you won't forget.

3. Castello Di Brolio
A visit to Castello Di Brolio is like stepping into history. This World War II-era castle, home to the Ricasoli family, is the birthplace of Chianti Classico. The views from the castle are breathtaking, and the history surrounding the estate adds an extra layer of magic to the experience. While you’re there, make sure to visit the museum and garden.

The Chianti Classico wine is rich, smooth, and perfectly paired with the atmosphere of the castle. This is the place to enjoy wine and truly savor its deep connection to the land and history of the region. You won’t want to miss this incredible destination when in Tuscany.

4. Castello Verrazzano

Stop by this gorgeous castle only a few short miles from VicchioMaggio, enjoy the rich flavored Tuscana, pairs excellent with pork/beef dishes, an easy all occasion sipping red that has a warm seductive red fruit meets floral finish to satisfy any connoisseur’s palette. I loved the DOCG Chianti Classico for any red meat/pasta combo, and pairs well with a romantic view and sunset. Bought several bottles and still enjoying them, plus the wine tasting experience was so much fun, the Winetender poured as much as I liked, took all the time to walk me through the wine and the history of this beautiful castle, and I also bought several bottles of the rich and decadent olive oil! Still using this often to cook, and you can tell that quality is their main focus! Incredibly charming and memorable stop on the Tuscan tasting map!

5. La Pressura

Not just an airbnb, but a wine tasting experience and tour all in one! Free parking, great rooms, charming grounds with hiking trails, a beautiful poolside elegant setting, with a tour in the cellar and appetizers with tasting! This was truly one of the best experiences I’ve had with wine tasting, not just in Italy, but worldwide. The white wines and rose were clean, crisp, dry with a fruity undertone, and the reds ranged from afternoon delight to evenings by the fireplace! Had to take a few bottles to savor and a few for souvenirs, will definitely be back to stay and taste here at this quaint airbnb with a view and wonderful hospitality!!! Click here now to book your stay!

Final Thoughts:
A wine-tasting tour in Tuscany is an experience like no other. From charming wineries to breathtaking views, the region has so much to offer. Whether you’re sipping rose in a medieval castle or enjoying a crisp red on a scenic terrace, Tuscany never disappoints.

So, what are your must-have items for a Tuscany wine adventure? What wineries do you recommend? I’d love to hear your thoughts and recommendations to make my next Italian adventure even better!

Cheers to wine, great company, and unforgettable memories! 🍷

Pinkies Up!

-Erica Sunshine Lee