Join Me for a 7-Day Wine Tour Through Tuscany
A Small-Group Wine Journey Through Boutique Vineyards, Medieval Towns, and Tuscan Cuisine
October 9-15, 2026 | 7 Days | Maximum 18 Guests - SOLD OUT
Hey there! I’m Lexi.
Tuscany is where I first fell in love with wine—and after leading two incredible trips here, I can't wait to share this amazing place with you.
I'm a WSET Level 3 Certified Wine Educator who's spent nearly a decade in the wine industry. I started Lexi's Wine List because I believe wine should feel accessible and joyful, not intimidating.
The best part about leading these trips is watching you fall in love with these places and people just like I did. I'll introduce you to family-owned wineries—the kind of hidden gems where the winemaker welcomes you into their home. You'll taste wines you can't find at home, share meals with new friends, and experience the kind of Italian hospitality that stays with you.
See our past adventures
Scenes from our previous small-group wine tours in Tuscany
Your 7-Day Itinerary
Every day is carefully curated to give you the perfect balance of wine, food, culture, and relaxation
Arrival in Tuscany
Upon arrival at the Rome airport, our private driver will transfer us to our boutique accommodation, a charming agriturismo in Umbria, just across the border from Tuscany. Di Colle in Colle features sweeping views of Lake Trasimeno, a vineyard, pool, and traditional restaurant with a private chef.
Once you settle in, we'll gather for a wine tasting with our villa owner, Giulio. He crafts delicious, boutique wines from the vineyards surrounding the property using organic farming. Dinner will include more of his wines paired with a comforting 3-course meal made by our private chef.
Nobile di Montepulciano
We'll enjoy a private historical tour of the iconic hilltop town of Montepulciano, known for its breathtaking views of the Val d'Orcia, well-preserved Renaissance architecture, and steep cobblestoned streets dotted with cozy wine enotecas and boutiques. You'll have free time to shop, explore, and enjoy a beautiful lunch.
Our afternoon winery visit is a special one — this family-owned winery in Montefollonico dates back 700 years. We'll tour the historic cellar and vinsantaia (where Vin Santo is made!) and enjoy a tasting of Vino Nobile di Montepulciano, Vin Santo, and more on the garden patio overlooking the Val d'Orcia.
Enjoy a sunset aperitivo of your choice (my go-to is an Aperol spritz) while taking in the stunning views of the lake. We'll gather around a cozy, candlelit dinner for our 3-course, chef-made meal and plenty of local wine.
Pienza & Brunello di Montalcino
Our day starts off with a private tour of Pienza, a quaint hilltop town with incredible history and Renaissance architecture. Pienza is known for its sheep's milk cheese, Pecorino, so a stop into a tiny, women-owned cheese shop for a tasting is a must. You'll have free time to explore, sit for lunch at one of my favorite osterias, or enjoy a coffee on a terrace with a view.
Brunello di Montalcino is one of the most prestigious wines in the world, and our private tour, visit, and tasting at this family-owned winery will show you exactly why.
Grab a cocktail or enjoy some downtime in your room before meeting at our usual dinner spot to feast on another delicious 3-course meal with wine pairings.
Truffle Hunting, Pasta Making, Olive Oil Tasting
We'll head to a nearby villa for a private truffle hunting experience with an expert dog as our guide — a light walk through the forest to grab some truffles followed by an educational truffle tasting.
Chef Elisa will lead us through a hands-on cooking lesson, where we'll learn to make fresh pasta. Then we'll enjoy our pasta for lunch on the patio, paired with local wine and followed by an olive oil tasting.
A sunset vineyard walk with Giulio is the best way to end the day. He'll walk us through the vineyard on property, admiring the vines and soaking up the lakeside views. We'll end the night with a 3-course dinner and more wine.
Siena & Chianti Classico
Our private historical tour of Siena will include a visit to the Basilica Cateriniana San Domenico to see one of the most important relics in Italy, as well as a stop in the iconic Piazza del Campo, where the famous Palio horse race takes place. You'll then have free time for lunch and shopping.
We'll visit the smallest winery in Chianti Classico - that's right, the smallest. This family-owned winery is run by the 6th, 7th, and 8th generations, who will welcome us into their home for a tasting and vineyard tour. With only about 2,000 bottles produced each year, they typically save these wines for family only, but they're kind enough to share a few with us (while making us feel like we're family).
We'll head back to the villa for our nightly routine of sunset spritzes followed by a 3-course meal.
Cortona
You might recognize the town of Cortona from the movie, Under the Tuscan Sun. Lizzy's guided tour here includes an insider's look into her hometown, with plenty of fun facts, interesting anecdotes, and recommendations along the way. You can then enjoy some free time shopping, savoring gelato, or sitting for lunch at one of our favorite local spots.
Cortona is a unique appellation in Tuscany that doesn't specialize in Sangiovese. We'll be welcomed into the home of a winemaking family who crafts wines from Syrah, Cabernet Sauvignon, and more international varieties. And a visit to see their sweet horse and ornery goat (Virus) is a must.
Our final dinner at the villa will include a tasting of the wines we enjoyed at each winery this week, thoughtfully paired with a multi-course meal by our chef. The perfect way to end a dreamy week in Tuscany!
Arrivederci!
Our English-speaking private drivers will transport us back to the Rome airport in time for your flight home. See you next time!
All-Inclusive Pricing
Everything you need for an unforgettable week in Tuscany
What's Included
- 6 nights at boutique vineyard accommodations
- Daily breakfast
- 6 dinners with wine pairings
- 5 family-owned, off-the-beaten path winery visits and tastings
- 5 private historical town tours
- Truffle hunting experience with educational truffle tasting
- Boutique olive oil farm visit and tasting
- Hands-on cooking class with local chef
- Wine experts at your disposal for the week
- Expert English-speaking local guides
- Private luxury minibus transportation throughout the week
- Transportation to/from Rome airport
- All entrance fees and activities
- Taxes
Not Included
- Flights
- Meals not mentioned in itinerary
- Alcoholic beverages outside of included tastings and meals
- Additional accommodations before/after trip dates
- Travel Insurance
- Gratuities
Secure your spot with a €1260 deposit
Common Questions
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Please click the “Reserve Your Spot” button to fill out a quick form. Shortly after, you will receive an email from me with further instructions on how to make your deposit and book your spot. If you don’t receive an email from me within 24 hours, please check your spam folder or “Promotions” tab. Reservations will be available on a first come, first served basis. Credit cards are accepted with no additional fees.
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October 9-15, 2026
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This retreat is perfect for wine lovers, food enthusiasts, and curious travelers who want a deeper taste of Tuscany — culturally and literally. You don’t need to be a wine expert, just someone who enjoys good company and beautiful places. Past travelers range from couples celebrating anniversaries to solo travelers seeking adventure to friends reconnecting over shared interests. If you appreciate quality over quantity and authentic experiences over tourist traps, you'll love this trip.
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€4200 per person for double occupancy (single occupancy: €1000)
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Boutique accommodations
All wine tastings and winery visits
Hands-on cooking experiences
Truffle hunting experience
Most meals (with wine, of course!)
Private transport during the retreat (and to/from the Rome airport)
Local guides and cultural experiences
A few surprise treats along the way
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Flights to/from Italy
Travel insurance (highly recommended)
A few meals on your own for flexibility
Personal purchases
Gratuities
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Expect a relaxed but full itinerary. There’s plenty of wine tasting and dining, but also time to explore, rest, or sip espresso in a sunny piazza. Some light walking is involved, especially in historic hill towns.
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Of course! Pricing for this trip is based on double occupancy, so there is just an additional fee of €1000 for solo travelers.
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October is a beautiful time to visit Tuscany, with mild and pleasant temperatures. You can expect daytime highs around 63-70°F (17-21°C) with cooler evenings of around 46-50°F (8-10°C).
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Your passport
Comfortable walking shoes
Layers for warm days and cooler evenings
Sun protection (hat, sunscreen, sunglasses)
An appetite for wine and delicious food
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A 30% per person deposit (€1260) is due upon booking. The final payment (€2940) is due by September 9, 2026. Credit cards are accepted with no additional fees.
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Deposits are non-refundable unless the trip is cancelled by us due to not meeting the minimum headcount. The final payment is non-refundable.
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Yes, we strongly recommend comprehensive travel insurance that covers trip cancellation, medical emergencies, and medical evacuation. We recommend TravelEx and we’d be happy to assist you with getting a quote and booking the insurance.
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You'll stay in boutique vineyard accommodations with private bathrooms. Our agriturismo in Umbria offers stunning lake views of Lago Trasimeno. All rooms are comfortable, clean, and charming—think authentic Tuscan style with modern amenities.
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The itinerary is thoughtfully paced with structured group activities balanced by free time. You'll have free time in each town we visit to wander, shop, or enjoy lunch.
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We can accommodate most dietary restrictions including vegetarian, gluten-free, and common allergies. Please let us know at the time of booking so we can coordinate with restaurants and our cooking class instructor.
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Our groups are typically small (maximum 18 guests) and attract wine-loving travelers of all ages, usually ranging from 30s-70s. What brings everyone together is a love of authentic experiences, good wine, and great food. Past travelers have made lasting friendships—the intimate group size makes it easy to connect.
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Absolutely! Many travelers choose to arrive a day early or stay longer to explore Tuscany or Rome independently. We're happy to provide recommendations for additional accommodations and things to do.
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We follow current Italian travel requirements and health guidelines. We recommend all travelers have comprehensive travel insurance that includes medical coverage. If you feel unwell during the trip, let us know immediately—your health and the group's safety are our priority.