Red Lips & Wine Sips Tuscan Wine Escape

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Red Lips and Wine Sips Tuscan Wine Escape


Bring your passion for wine and join Tanja and Annika in Tuscany, Italy, for a wine-enthusiasts journey like no other! Learn the complex and fabulous world of Italian wines, how to pair wines with just the right foods and tips and techniques for choosing and enjoying wines wherever you are in the world. From your 17th century villa accommodations, surrounded by the spectacular Tuscan countryside, you’ll enjoy excursions to medieval hill towns, wine tastings in historic cantinas and delectable regional meals. 

Although Tanja and Annika have been in the industry for a long time, they love the opportunity to share their knowledge and engage new wine lovers. Their focus is on creating memorable experiences, while using the opportunity to share something new and exciting with their guests. 

ABOUT Tanja and Annika

Tanja is an experienced and passionate wine consultant with over 7 years of experience in the Okanagan Valley as both a wine tour guide, Assistant Manager at Sandhill Winery, and Special Events Coordinator for Cedar Creek Estate Winery. With WSET 3 certification and extensive knowledge of international wine regions, Tanja provides comprehensive and informative wine tastings from our Okanagan’s world-renowned vineyards to the world.

From wine lover to wine connoisseur, Annika has been working in the industry for over 7 years with experience from the Niagara Region in Ontario, and the Okanagan. Her varied background includes working in the restaurant industry for 10 years, before switching to a more wine focused career in the retail setting. With WSET 3 Certification, Annika loves sharing her knowledge and passion for wine, in hopes to ignite the same in others.


  • How to explore the Italian wine world, while indulging in traditional fare and immersing yourself in the Tuscan lifestyle
  • The simple approach to Italian wine tasting and techniques
  • The ancient history of wines and wine-making in both Tuscany and Umbria
  • The meaning of IGT, DOC and DOCG wines
  • How to understand wines under the IGT, DOC and DOCG designation
  • Ways to familiarize yourself with Italian grape varietals
  • Insider approaches to regional, small-production wineries
  • How to read an Italian wine label
  • Hands-on grape harvest experience!
  • How wine is made at a family-run cantina (winery)
  • The step-by-step winemaking process for both white and red wines
  • How to compare and contrast Italian wines to North American wines
  • How to expand your palate by tasting a variety of Italian wines
  • Simple ways to detect aromas and flavors in wines
  • The surprising basics to Italian wine and food pairing
  • The process of making natural wines – an up-and-coming wine-making approach in Tuscany and Umbria
  • The art of the aperitivo in Italy
  • How and why Prosecco wine is a part of Italian culture
  • The important differences between commercial and small production wineries

Not included: Airfare, meals, alcoholic drinks, buses, trains or boat transportation outside of that which is specifically listed in the trip package, gratuities for villa staff and drivers

The Unexpected is Part of the Journey: Although we are weaving amazing, authentic experiences into this trip, sometimes unexpected things come up. If a site has an unscheduled closing, we improvise to include something equally as wonderful and interesting. The quality of the trip is never at risk, as our hosts at Strada Toscana are committed to excellence, along with their vast Italian connections.


Sunday, September 27: Arrival

  • Tour of Villa Poggio alla Trese, trip orientation, intro to Italian wine regions
  • Aperitivo, dinner

Benvenuti in Italia! Upon arrival at Chiusi-Chianciano train station, enjoy a short taxi ride to Poggio alla Trese, your 17th century villa accommodations near the Tuscan town of Chiusi. After check-in you’ll have the opportunity to explore your surroundings and learn some of the fascinating history of the both the house and the area, as well as a trip orientation session with Annika and Tanja.

Then it’s time for an informative introduction to Italian wine regions, Annika and Tanja, along with comparisons between Italian and Canadian producers. Learn the key wine regions of Italy and how to identify the grapes grown in those regions. Find out what IGT, DOC and DOCG stand for, and learn how to spot the indicators of quality on wine labels.

A friendly aperitivo follows, hosted by sommelier, Paola, featuring a mini-lesson on Prosecco (the classic wine for Italian aperitivo), and a delicious, regional-style dinner paired with local wines.

Monday, September 28: Parrano & Cantina Murogrosso

  • Tour of family-owned winery, participation in the grape harvest, tasting of Umbrian wines, olive oil tasting
  • Breakfast, lunch and dinner

This morning, after an abundant breakfast at the villa, featuring organic, sheep’s milk yogurt, breads & torte from the local pasticceria, fruits, marmalades and cornetti, along with made-to-order Italian coffees it’s off to Cantina Murogrosso, near the Umbrian hill town of Parrano. Be sure to wear your best walking shoes, as you’ll enjoy a guided tour of some of the estate’s vineyards, plus you’ll also be taking part in “la vendemmia” (grape harvest) right along with the winery’s workers. Learn step by step the process from vine to vat, and why small production wineries that continue to pick by hand produce Italy’s finest wines.

Afterwards you’ll take part in a delightful tasting of several of the estate’s wines, led by sommelier, Paola, who brings a fresh, sensible approach to wine tasting. A light lunch is included.

In afternoon we head back to the villa for some time on your own to relax and refresh before gathering together for an oh-so-fun olive oil tasting lesson, followed by bruschetta-making over wood coals at the villa’s outdoor fireplace. Delicious!

This evening you’ll enjoy a regionally inspired dinner, paired with estate wine.

Tuesday, September 29: Montepulciano & Cantina Crociani

  • Montepulciano, wine tasting in 15th century cantina, shopping, pairing wine and food
  • Breakfast, lunch and dinner

This morning, after breakfast at the villa, it’s off to the Renaissance hill town of Montepulciano where you’ll start your visit in regal Piazza Grande. Montepulciano is considered the pearl of the Renaissance, as the nobility of Florence have had homes here for centuries – plus Montepulciano produces one of Italy’s finest wines: Vino Nobile di Montepulciano. After a look around the historic center, you’ll continue to Cantina Crociani – and its 15th century wine cellar – for a tour and tasting of their exceptional wines. Learn about types of Sangiovese, one of Italy’s most important grapes, and enjoy an informative wine tasting accompanied by a classic Tuscan lunch.

Afterwards there will be some time to explore and shop on your own before heading back to the villa.

Following apertivo, today’s evening session accompanies a Tuscan-inspired dinner menu. Learn simple rules for Italian food pairings with local wines, plus basic tips and tricks to creating perfect pairings at home. Learn how wine should compliment – not compete – with food.

Wednesday, September 30: Montegiove & Cantina Castello di Montegiove

  • Truffle hunt, tour and wine tasting at Castello di Montegiove
  • Breakfast, lunch and dinner

This morning after another abundant breakfast, it’s off the medieval castle village of Montegiove, where you’ll meet up with tartufaio, Alessio, to hunt for truffles along with his adorable dogs, Luna and Chico. Then it’s on to the castle itself for a private, invitation-only tour  with our friend Lorenzo – including a visit of his medieval cantina. Talk about special! Then make yourself at home for a private wine tasting, along with a light lunch, featuring several of the estate’s excellent wines – including a delightful rosato and an exceptional Sagratino – along with crostini topped with shaved truffles.

This evening you’ll enjoy a special aperitivo, followed by a farewell dinner featuring local specialties.

Thursday, October 1: Departure

This morning our drivers will be transporting you to Chiusi-Chianciano train station.


Your accommodations are beautiful Poggio alle Trese, a 17th century villa, nestled along the border of Tuscany and Umbria, near the town of Chiusi (Tuscany). The villa boasts sweeping terraces for dining or lounging, swimming pool, elegant breakfast room, grand dining hall and numerous sitting rooms. Sleeping rooms are furnished with family antiques and offer either an ensuite bathroom or a shared bathroom (max 2 guests of the same gender per bathroom). Rooms options are made available upon booking. View photos of Villa Poggio alle Trese here.


  • 5 days/4 nights at elegant Villa Poggio alla Trese, situated in the picturesque countryside near the charming Tuscan hill town of Chiusi.
  • Taxi transportation to/from Chiusi-Chianciano train station on arrival and departure days
  • Private van service to/from all cities, towns and sites included in the itinerary
  • All abundant breakfasts, featuring fresh-baked Tuscan pastries, organic sheeps’ milk yogurt, local cheeses, seasonal fruits, organic cereal, & fresh eggs, plus Italian caffè, cappuccino and herbal teas.
  • All lunches  
  • All regionally inspired dinners with local wines
  • Daily wine tastings featuring regional IGT, DOC and DOCG wines
  • Private castle visit
  • Visit of 15th century wine cantina
  • Participation in the grape harvest
  • Wine and food pairings
  • Vineyard tour
  • Advice from Italian wine experts on how to enjoy Italian wines
  • Truffle hunt
  • Olive oil tastings and bruschetta-making lesson
  • Daily sessions with Tanja and Annika

Red Lips and Wine Sips Tuscan Wine Escape



  • 5 Days/4 Nights
  • Dates:
    • September 27 – October 1, 2020
    • A $500 deposit is required to book your space on this trip.
  • Trip Price (choose your room configuration upon booking):
    • $3,085 USD per person – single occupancy room with ensuite bathroom
    • $2,985 USD per person – single occupancy room with shared bathroom (no more than 2 people per bathroom)