VanArnam Adventures – Tuscany, Italy, September 2026 Trip Overview
Join us in the heart of Tuscany for an unforgettable 8-day adventure from September 25th to October 2nd, 2026! Hosted by the experienced traveler Becki Trout (who has explored over 60 countries and holds a special love for Italy and Tuscany), this trip is crafted to blend relaxation with exhilarating days exploring Tuscany’s rolling hills, medieval villages, and world-class wineries. Becki knows the back roads, family-run wineries, and quiet hill towns that make Tuscany magical. Our home base is a stunning villa in Montefollonico, offering private suites with breathtaking views of the Tuscan countryside and Montepulciano. With a private chef preparing daily breakfasts, luxurious dinners at Tuscany’s finest restaurants, and a “leave your wallet at home” approach, every detail is designed for ease and indulgence. Expect ample walking opportunities, authentic local experiences, and plenty of free time for poolside relaxation. The group size is 15 people, consisting of 14 guests plus your host, Becki Trout (with Kent and Allison VanArnam providing behind–the-scenes support due to scouting commitments in Northern Italy). Cost: $6,000 per person, based on double occupancy (airfare not included).
Deposit: $1,000 per person to secure your spot. Email vanarnamadventures@gmail.com for booking details..
Highlights
Luxurious Villa Stay: Settle into a private suite at our Montefollonico villa with panoramic views, a pool, and personalized comfort.
Culinary Delights: Savor multi-course dinners celebrating Tuscany’s regional flavors at some of the area’s finest restaurants, plus daily chef-prepared breakfasts.
Wine & Local Experiences: Discover family-run wineries, hidden hill towns, and authentic Tuscan rhythms guided by someone who knows the region intimately.
Adventure & Exploration: Enjoy daily guided adventures through the countryside, with opportunities for walking and immersion in local culture.
Cultural Immersion: Wander medieval villages, soak in the landscapes, and experience the true essence of Tuscany with flexibility built in.
Day 1: September 25, 2026 – Arrival in Montefollonico
Our journey begins in Florence, where a private shuttle picks you up from your chosen location (airport or hotel) for a scenic 1.5-hour drive to our Montefollonico villa. Nestled on a sprawling estate with views of Montepulciano, this beloved villa offers private suites with dedicated bathrooms and customizable climate control. Upon arrival at 4:00 pm, enjoy a warm welcome reception, followed by a multi-course Tuscan dinner at 7:00 pm, prepared by our private chef team and paired with local wines.
Day 2: September 26, 2026 – Montepulciano & World-Class Wine at Contucci
Start with a chef-prepared breakfast at the villa, then we head straight into the medieval hill town of Montepulciano — the crown jewel of this part of Tuscany.
Our morning highlight is a private tour and tasting at Contucci Cantine one of our all-time favorite wineries in the world. Located in a Renaissance palace right on Montepulciano’s breathtaking main square, Contucci has been family-owned for over a thousand years. You’ll be welcomed (as friends of VanArnam Adventures) by Andrea Contucci himself — the 41st-generation owner — for an unforgettable walk through ancient underground cellars lined with massive oak barrels, followed by a guided tasting of their legendary Vino Nobile di Montepulciano and Rosso di Montepulciano wines. It’s intimate, magical, and a guest favorite every single trip.
At 1:00 pm we stroll just minutes through the cobblestone streets to Restaurant Romantico, perched on one of Montepulciano’s most dramatic lookout points. Lunch here is pure Tuscany: delicious regional dishes enjoyed with jaw-dropping panoramic views over the valleys and vineyards below.
After lunch you’ll have generous free time to explore this perfectly preserved walled medieval town at your own pace. Wander the labyrinth of charming alleys, pop into artisan workshops and enotecas, admire centuries-old architecture, people-watch from a café with a gelato in hand, or simply soak in the magic of one of Italy’s most beautiful hill towns.
We return to the villa mid-to-late afternoon for pool time and relaxation before heading out for tonight’s dinner at a beloved restaurant in a nearby medieval village. Another perfect VanArnam Tuscany day: great wine, great food, great views, and exactly the right amount of “choose your own adventure.”
Day 3: September 27, 2026 – Truffle Hunting Adventure & Legendary Steak Dinner
After a delicious chef-prepared breakfast at the villa, we depart for one of the most beloved experiences on every VanArnam Tuscany trip: truffle hunting at Podere Il Casale, just a short, scenic drive away.
We’ll meet a local truffle hunter and his expertly trained dogs for a fun, hands-on hunt through a nearby forest. Watch the dogs excitedly sniff out buried treasures, then dig them up together — whatever we find comes with us! The fresh truffles are handed straight to the chef, who works them into an incredible multi-course lunch served on Podere Il Casale’s elevated terrace with sweeping views over the Val d’Orcia hills. Each course is perfectly paired with their own organic wines. (Expect a moderate amount of easy walking on this magical morning — comfortable shoes recommended!)
Mid-afternoon we return to the villa for well-deserved free time: lounge by the pool with a book and a glass of wine, take a nap, or simply soak in the panoramic views from your private suite.
In the evening we head back to Montepulciano for a dinner that has become legendary among past guests: Osteria Acquacheta. This tiny, family-run temple of Tuscan beef is famous region-wide — reservations are nearly impossible, and part of the entertainment is watching hopeful walk-ins try (and usually fail) to charm the celebrity husband-and-wife owners. In the open kitchen they butcher enormous Chianina steaks to order, weigh them dramatically on a huge scale, then grill them to perfection right in front of you. (They also make one of the best eggplant parmigianas in Tuscany for non-meat eaters.) It’s loud, lively, authentic, and an absolute show — the perfect way to cap off a day of truffles and Tuscan countryside.
Return to the villa late evening, happily full and already planning how to tell the story of tonight’s steak spectacle when you get home.
Day 4: September 28, 2026 – Olive Oil Immersion & Magical Evening in Pienza
Enjoy a leisurely breakfast at the villa before we head out for a beautiful day in the Val d’Orcia.
In the afternoon we visit the historic Fattoria Fregoli in Pienza for an exclusive Olive Oil Tour, Tasting & Light Lunch. You’ll tour their 19th-century olive mill, walk among the groves, and learn the art of organic extra-virgin olive oil production—from hand-harvesting to cold extraction using sustainable modern techniques. The experience ends with a guided tasting of their superb oils made from classic Tuscan varieties (Frantoio, Leccino, Moraiolo), where you’ll discover notes of fresh grass, almond, and that signature peppery finish that defines top-tier Tuscan oil. A delightful light lunch featuring the estate’s oils is included.
After the tasting, we’re just minutes from the Renaissance jewel of Pienza — the “City of Light.” You’ll have free time to wander its golden-stone streets, browse artisan shops, taste the town’s famous pecorino cheese, take the optional self-guided audio tour of the palaces and Duomo, or simply soak in the panoramic views over the iconic Val d’Orcia landscape of cypress trees and rolling hills.
As the sun begins to set, we gather at Idyllium, one of Tuscany’s most spectacular restaurants. Perched high above the valley with a breathtaking terrace, we’ll start with artfully crafted cocktails while the landscape turns gold and rose, then enjoy an unforgettable multi-course dinner that blends traditional Tuscan recipes with modern flair — all while watching the sun dip behind the hills. This is the evening in Tuscany you’ll be talking about for years.
Day 5: September 29, 2026 – Michelin-Star Luxury at Baracchi Winery & Historic Dinner at La Chiusa
After breakfast at the villa, we depart for one of the most glamorous and delicious days of the trip: Baracchi Winery & Relais Il Falconiere.
The Baracchi family has been crafting exceptional wines here since 1860 across five generations, and today their estate is one of Tuscany’s most celebrated wine resorts. We’ll start with a private tour of their state-of-the-art winery, followed by a guided tasting of their acclaimed Brut Rosé sparkling, Sangiovese blends, and flagship Syrahs. Then we sit down in their gorgeous Michelin-starred restaurant Il Falconiere for what many guests call the most iconic lunch of the entire week — refined, seasonal Tuscan cuisine perfectly paired with Baracchi wines, all overlooking the vineyards and Cortona hillside.
Mid-afternoon we make the quick five-minute drive down to the enchanting hill town of Cortona (famous from Under the Tuscan Sun). You’ll have a couple of relaxed hours to explore its steep medieval streets, visit the Etruscan museum, browse leather shops and art galleries, or simply enjoy an aperitivo with panoramic views stretching across the Val di Chiana.
We return to the villa late afternoon for a short refresh before the shortest transfer of the trip — just three minutes out our driveway — to one of the most historic and soulful restaurants in all of Tuscany: Ristorante La Chiusa.
Dating back to Etruscan times (with tombs still on the property), La Chiusa has served as a Roman estate, medieval toll station, 18th-century olive mill, and hideout for the legendary “gentleman thief” Ghino di Tacco. Stones from a 700s abbey were used to build the dining room, and for the last 300 years the property has had only two owners — making it one of the best-preserved historic gems in the region. Tonight we’re welcomed like old friends for an intimate, unforgettable multi-course dinner that blends centuries of tradition with warm hospitality and exquisite flavors.
Return to the villa just minutes later, full of Michelin-star memories, Baracchi bubbles, and stories of Etruscans and Tuscan bandits. Another perfect day.
Day 6: September 30, 2026 – Wellness Spa Day & Village Wine Tasting
Today is all about you — our official “wellness day” at Spa Terme Sensoriali in Chianciano Terme, widely regarded as the best spa in Tuscany.
You’ll have the entire day to move freely between more than 20 rejuvenating sensory experiences: aromatic steam rooms, Finnish saunas, thermal pools (indoor and outdoor), hydromassages, mud therapies, chromotherapy showers, an ice cascade, a salt room, relaxing music zones, and the famous “river of senses” path. Professional massages and treatments are also available (pre-booking recommended). A delicious, healthy lunch is included at the spa’s restaurant overlooking the Val di Chiana.
In the late afternoon we return to the villa just long enough to freshen up before a five-minute walk (or one-minute drive) up the hill to the tiny, picturesque walled village of Montefollonico and Cantine Innocenti — the quintessential romantic, family-run winery you’d discover in a Tuscan novel.
Tucked away from the tourist crowds, this gem is literally steps above our villa. We’ll descend into their atmospheric underground barrel rooms lined with dusty, decades-old bottles, then taste their beautiful organic wines with the young owners Tommaso and Nancy — he’s the son of a philosophy professor who traded the classroom for the vineyard, and she’s a pharmaceutical chemist turned passionate winemaker. It feels like visiting old friends.
We cap the evening just a few doors down at 13 Gobbi, the village’s only restaurant and a perennial guest favorite. This cozy, authentic spot in the heart of quiet, perfectly preserved Montefollonico serves some of the most soul-satisfying food of the entire trip — think handmade pici with wild boar ragù, grilled Chianina steaks, and warm hospitality that makes you feel like a local.
A short ride back down to the villa under the stars ends a day of total relaxation, beautiful wine, and true Tuscan village magic..
Day 7: October 1, 2026 – Vintage Fiat Adventure & Farewell Cooking Class
It’s the day everyone talks about for years: Fiat Day!
After breakfast, step outside the villa to find a colorful lineup of restored vintage Fiat 500s gleaming in the Tuscan sun. Pair up, pick your favorite car, slip on the driving gloves, and let’s hit the road! We’ll caravan along some of the most beautiful back roads in Italy — winding through golden vineyards, past rows of cypress trees, over hills with postcard views in every direction, and through tiny hamlets where locals wave like we’re old friends. There will be plenty of pull-over spots for photos (because yes, you’ll want proof you drove a baby-blue Fiat through paradise).
Midday we park the convoy in a fairytale-perfect Tuscan village for a relaxed lunch — think long tables under a pergola, fresh pasta, local wines, and that perfect holiday feeling.
Back in the cars for one last glorious stretch of cruising before returning to the villa in the late afternoon for some well-earned pool time and prosecco.
Tonight we gather for our grand farewell: a hands-on cooking class with our beloved villa chef Sabrina. Roll up your sleeves and learn to make a full Tuscan dinner from scratch — fresh pici pasta, ribollita, tiramisù, the works — while sipping wine and laughing with your new friends. Everything you cook becomes tonight’s celebratory feast, served family-style under the stars. You’ll go home with a custom recipe booklet of everything we made all week (and the secrets to recreating Tuscan magic back home).
It’s the perfect, joyful, delicious send-off to an unforgettable week. Tears, toasts, and promises to do this again soon guaranteed.
Day 8: May 24, 2026 – Departure
Enjoy a final breakfast (7:30–9:30 am) before departing the villa for Florence, with drop-off at your chosen location (airport or hotel). Reflect on a week of Tuscan magic—vineyards, villages, and unforgettable moments with new friends.
What’s Included
7 nights in a private suite at our Montefollonico villa
All meals, snacks, drinks and all else you’d like
All activities, winery tours, and tastings
Private transportation throughout the trip
Vintage Fiat rentals, and spa day
24/7 support from Becki Trout as group leader and Kent and Allison VanArnam via digital communications
What’s Not Included
Airfare to/from Florence
Personal expenses
Travel insurance (highly recommended)
Why Book This Trip?
This Tuscany adventure offers a perfect balance of luxury, adventure, and relaxation, with a single villa base eliminating the hassle of packing and unpacking. From truffle hunting to driving vintage Fiats, every day brings new delights, complemented by world-class wines, exquisite meals, and the charm of Tuscany’s medieval villages. With Becki. Trout as your hosts you’ll enjoy a seamless, immersive experience in one of Italy’s most iconic regions. Ready to Book?
Secure your spot with a $1,000 deposit by emailing vanarnamadventures@gmail.com. Join us for a Tuscan journey you’ll never forget!