Tuscany Villages, Castles & Vineyards

THE DREAM COMES TO LIFE …

Gaze down from the fortressed walls of this medieval Tuscan village over the meticulously tended vineyards and olive groves that pattern the gentle slopes below. This is classic Tuscany – the one that everyone yearns to see, and you’re experiencing it as an insider – as if you have a backstage pass. From walks to irresistible medieval hill towns – with locals waiting to welcome you like family – to private wine tastings and dinners in regal castles, your guide knows tucked away places the tourists have never heard of – after all, this has been his family’s home for longer than anyone can remember. Evocative historic sites, meandering countryside strade, and regal medieval castles await, and that’s just the beginning. From ancient abbeys to exceptional wine cantinas you’re experiencing this incredible region with all your senses – including evenings filled with friendly aperitivi, gourmet meals and romantic Tuscan sunsets.


TOUR DETAILS: Dates and Prices

  • 7 Days/6 Nights
  • Dates:
    • May 19-25, 2019
    • September 22-28, 2019
  • SAVE $500 through April 30th! Early-bird Tour Price: USD $3,795 [Regular Tour Price: USD $4,295], per person, based on double occupancy
  • 10 Month Payment Plan – available for a limited time
  • Single Supplement USD $695
  • BOOK NOW
  • WALKING RATING: Our walks are rated as easy to moderate, with durations on average of 1.5 – 3 hours and distances of 5-10 kilometers (3-7 miles). Although most routes are relatively short, you will encounter cobblestones, rugged pathways, uneven steps and steep ascents and descents in order to reach stunning views and hilltop villages. Our walks ideal for active travelers. No hiking experience is necessary, but we do recommend walking regularly before your trip, including up hills, whenever you can. Although non-walking options are provided throughout the tour, we caution that this trip is not the right fit for those who have difficulty walking or have a health-related condition that would limit participation and/or impede or inconvenience others.

THE UNEXPECTED IS PART OF THE JOURNEY

At Strada Toscana we weave amazing, authentic experiences into every trip, but sometimes unexpected things come up. If Mario calls to tell us they’re pressing olives at just this moment, off we go (I mean, we wouldn’t let you miss his newly pressed olive oil!), and if a site has an unscheduled closing, we improvise to include something equally as wonderful and interesting.

On that note, if our usual boutique hotels can’t accommodate us (which rarely happens), you can rest assured you’ll stay somewhere of an equal or higher level. The quality of our tours is never at risk, as our team is committed to excellence, along with our vast, local, Italian connections.

Day 1: Chianti

  • Welcome and trip orientation, vineyard walk, aperitivo, welcome dinner
  • Dinner

AFTERNOON: We meet up in Florence at the Peretola Airport and journey together to the rolling hills of Tuscany’s Chianti region – an area dotted with castles and striped with vineyards. Settle into your countryside accommodations and get acquitted with your friendly Tuscan trip leader, as you take an invigorating walk along the nearby countryside lanes and through stunning vineyards.

EVENING: Tuscan-style apertivo followed by a delectable welcome dinner

ACCOMMODATIONS: Hotel Villa Casalecchi (3 nights)

Hotel Villa Casalecchi – a classy 19th century Tuscan villa – exudes the authentic atmosphere of true Chianti amidst modern comforts and the peace and quiet of nature. Enjoy exceptional regional foods and top-notch Chianti wines by the pool’s edge at sunset with a caring, yet discreet, staff always at hand.

Day 2: Badia Coltibuono & Meleto

  • Scenic walk to Badia di Coltibuono, abby tour and wine tasting, tour of historic Castello Meleto
  • Breakfast and lunch

MORNING: After a delicious Tuscan-style breakfast, you’ll shuttle to the heart of the Chianti countryside for a splendid 2 hour walk to historic Badia Coltibuono, a monastery dating to the 11th century 

turned elegant, private family villa – with vast salons and frescoed rooms. Experience the atmosphere of centuries past in a fascinating tour, then indulge in a lunch of local salamis and cheeses while you sample the estate’s excellent wines.

LUNCH: at Badia Coltibuono with wine tasting

AFTERNOON: After your hearty walk and relaxing lunch at Badia Coltibuono, choose how you’d like to spend the afternoon.

  • Option 1: Continue to Castello Meleto for a tour that includes the castle’s ornately frescoes rooms and intimate private theater, as well as the castle’s gift shop where you’ll find handmade lavender-scented products and organic honeys.
  • Option 2: How about making some chocolate liquor? Return to our elegant countryside accommodations and take part in an oh-so-fun, one-hour liquor-making lesson.

EVENING: Shuttle to the village of Castellina for dinner on your own at one of the town’s inviting trattorie.

Day 3: Radda & Castello Brolio

  • Radda to Volpaia walk, Castellina village visit, VIP tour and wine tasting Castello Brolio
  • Breakfast and dinner

MORNING: Enjoy a hearty Tuscan style breakfast as you overlook the rolling hills of Chianti, then we shuttle to the charming hamlet of Volpaia for a panoramic countryside walk that begins in the in the historic center of the village and ends in the medieval hill town of Radda. This postcard-perfect route includes sweeping views of vineyards, olive groves and cool, green forests. For centuries this has been the land of wine, and as you walk with your expert guide the region’s fascinating history will come to life.

LUNCH: On your own in Radda

AFTERNOON: After lunch, choose how you’d like to spend your afternoon.

  • Option 1: Shuttle to the village of Castellina to explore the town’s winding alleys and browse the charming shops at your own pace.
  • Option 2: Return to our elegant countryside accommodations for some quiet time on your own.

LATE AFTERNOON: We shuttle to the extraordinary and regal Castello Brolio for a private VIP tour of the Ricasoli Collection, gardens and apartments of the Ricasoli family (closed to the public), followed by a tasting in the ancient Armory. Our visit culminates with a memorable gourmet dinner.

EVENING: Dinner at Castello Brolio

 

Day 4: Bagno Vignoni

  • Ring walk Bagno Vigoni
  • Breakfast and dinner

MORNING: After an early breakfast you’ll shuttle to the heart of Tuscany’s wine country and Bagno Vignoni, truly one of the most charming villages in Tuscany. Built upon an outcropping of tuff, and inhabited since Etruscan times, Bagno Vignoni sits upon springs of mineral-rich thermal waters routed through small channels and pools, eventually cascading gently over the cliffside on the edge of town. The effect is dramatic and breathtaking. After check-in you can explore the village shops and choose a place for lunch at your leisure.

LUNCH: On your own in Bagno Vignoni

LATE AFTERNOON: Few things are as gorgeous as a walk through Tuscany in late afternoon, as the sun turns the fields to gold. Take in the spectacular scenery of the Val d’Orcia as you expert guide leads you along the Anello di Bagno Vignoni, a trail that winds throughout the picturesque valley, nearby the impressive Castello Ripa d’Orcia, and finally back to Bagno Vignoni where you can enjoy a friendly apertivo alongside the town’s centuries-old thermal pool.

EVENING: Chef prepared dinner at our Tuscan accommodations

ACCOMMODATIONS: Relais dell’Orcia (3 nights)

The philosophy of the 4-star Relais dell’Orcia of Bagno Vignoni is to surround oneself with the beauty of Tuscany – its landscapes, nature, history and culture – and to enhance the art of hospitality with excellent products from local farms. With its elegant, yet inviting, rooms and proximity to historic walking trails, Relais dell’Orcia rates as our favorite accommodation in the Val d’Orcia for exploring Tuscany on foot.

 

Day 5: Pienza & Val d’Orcia

  • Pienza “passeggiata” ring walk, Chapel of the Madonna di Vitaleta, field of the gladiator, tour of Villa Le Foce
  • Breakfast

MORNING: After breakfast you’ll shuttle to the charming village of Pienza, dubbed Tuscany’s cheese capital, as this part of Tuscany is known for its sheep farms and outstanding pecorino cheese. You’ll begin with the scenic Pienza ring walk, alongside your expert guide – a walk that winds its way past the Chapel of the Madonna di Vitaleta and the “field of the gladiator” before looping back to the village itself with its panoramic views of the Val d’Orcia. Afterwards you’ll have free time to shop, explore and enjoy lunch on your own.

LUNCH: On your own in Pienza

AFTERNOON: We shuttle on to historic Villa Le Foce for a private guided tour of the manicured gardens that overlook the famous Val d’Orcia with its cypress-lined lanes and sweeping fields of grain. 

  • Option 1: Continue to the hill town of Montepulciano – the pearl of the Renaissance – for time on your own to explore, shop or cool your heels with a gelato (or glass of vino).
  • Option 2: Return to the Bagno Vignoni and our relaxing accommodations to enjoy some rest and relaxation on your own, or an afternoon walk into the village.

EVENING: Dinner on your own at the hotel or in Bagno Vignoni

Day 6: Montalcino & Sant’ Antimo 

  • MONTALCINO & SANT’ ANTIMO: Countryside walk to Abbazia di Sant’ Antimo, tour and brunello wine tasting, Montalcino historic center, thermal spa (optional/extra), special farewell dinner
  • Breakfast, lunch and dinner

MORNING: We shuttle this morning the steep hill town of Montalcino, ringed with meticulously maintained vineyards, with commanding views from the heart of Tuscany clear to the sea. This is brunello wine country and your day begins with a walk alongside stunning vineyards and ends with a tour of the ancient Abbazia di Sant’ Antimo. Afterwards you’ll continue to our friends’ brunello cantina for a light lunch and brunello wine tasting. What a treat!

LUNCH: At our friends’ outstanding winery near Montalcino

AFTERNOON:

  • Option 1: Continue by shuttle to Montalcino for shopping and exploring on your own.
  • Option 2: Return to Bagno Vignoni and the town’s chic, thermal spa to soak in the thermal, mineral waters – or perhaps to enjoy a massage or beauty treatment (optional/extra)

EVENING: Special farewell dinner at Osteria dell’Orcia

Day 7: Departure 

Transport to Florence Peretola Airport or Florence Santa Maria Novella Train Station.


DOWNLOAD THE ITINERARY

BOOK NOW

WHAT’S INCLUDED

  • Options and flexibility. You’re uniquely you, and we think that’s fabulous! That’s why we provide you options and flexibility each and every day. Prefer a bit of time on your own? Choose an explore-on-your-own option. Wanting more steps? Choose an optional, extra walk. Tailor each and every day to suit your unique desires.
  • Memorable accommodations for 6 nights in hand-selected boutique hotels
  • All breakfasts, 2 lunches and 4 dinners served with regional wines
  • Full-time experienced trip leader/walking guide, local guides and experts, behind-the-scenes support staff and support vehicle(s)
  • Tours, visits and hands-on experiences with local residents and artisans
  • Private land transportation throughout the trip
  • Daily guided walks, plus non-walking options: WALKING RATING: Easy to moderate, with durations on average of 1.5 – 3 hours and distances on average 5-10 kilometers (3-5 miles) – ideal for active travelers with or without hiking experience. You can expect hard cobblestones, uneven pavement, steps and steep hills. In addition, elevators are not available at our boutique hotel accommodations. Although non-walking options are provided throughout the tour, we caution that this trip is not the right fit for those who have difficulty walking or have a health-related condition that would limit participation and/or impede or inconvenience others.
  • Gratuities for hotels and meals

Not included: Airfare, ground or water transportation outside of that listed in the trip itinerary, alcoholic drinks, wines or meals ordered “on your own”, gratuities for drivers

The Unexpected is Part of the Journey: At Strada Toscana we weave amazing, authentic experiences into every trip, but sometimes unexpected things come up. If Mario calls to tell us they’re pressing olives at just this moment, off we go (I mean, we wouldn’t let you miss his newly pressed olive oil!), and if a site has an unscheduled closing, we improvise to include something equally as wonderful and interesting. On that note, if our usual boutique hotels or B&Bs can’t accommodate us (which rarely happens), you can rest assured you’ll stay somewhere of an equal or higher level. The quality of our tours is never at risk, as our team is committed to excellence, along with our vast, local, Italian connections.


DOWNLOAD THE ITINERARY

BOOK NOW

WHY CHOOSE a Strada Toscana Tour?

  • YOU’RE NOT JUST A NUMBER. We care deeply about our guests. In fact, we think of our small groups as a kind of family of like-minded travelers.
  • SMALL GROUP – BIG BENEFITS. Our maximum small-group size is 14, which means we’re able to stay in centrally located, boutique hotels (that often have limited rooms), eat in tucked away, family-run restaurants (that are always the best!) and use twin Mercedes Benz vans to reach restricted areas in historic villages.
  • WE’VE GOT YOUR BACK. Our support staff is always at hand to help you with everything from translating a menu to finding that special leather purse.
  • GORGEOUS & COMFY. You stay in upscale, boutique hotels with beautiful sleeping rooms, ensuite bathrooms and lovely touches that reflect the character of the region.
  • BEST VALUE. Because we’re destination experts and operate only in Italy, we know how to get the BEST quality for the very best price – that we then pass along to you. Our tours are an extraordinary value. Period.
  • YOU GET RIGHT TO IT. Spend less time transferring around in vans and more time experiencing. Your accommodations are in ideal locations for stepping outside to walk and explore.
  • PRIVATE DRIVERS. Strada Toscana teams up with exceptional drivers who own their own vans and their own businesses – and are really more like family. No conglomerates and no outside services.
  • AUTHENTICITY. Our trip leaders and guides are locals who are from the areas in which we tour. They know the region, the sites and the people like the back of their hand.
  • EXCEPTIONAL MEALS. The owner-run, top-notch restaurants on our tours are extraordinary, which means you enjoy delectable dinners in a welcoming, friendly atmosphere.

Learn more about our unique approach to traveling in Italy.