Wines of Italy Travel Adventures

Italy, the way you've always wanted!

2025 Tours Now Open for Booking!

Join Us on a Tasting Journey Through Italy's Vineyards

Discover the rich history and traditions of Italian wine and culture by enjoying relaxing stays at luxury Italian wine estates, private tours of family-owned wineries led by vintners, and cultural excursions to Italy’s hidden gems. Experience Italy's sensual, rustic delights the way you've always wanted: in a small group (16-18 guests), led by people who love Italy, to off-the-beaten-path wineries where vintners focus artistically on the craft they love.

Wines of Italy Tours began in Trieste, Italy, over a glass of wine before dinner with  Andrea Garwood  and  Allison Fraiberg . Andie, Trieste-based owner of wine export company  DIVI srl , had long wanted to highlight treasured producers in the DIVI portfolio with eno-tourism; Allison, a professor of cultural studies in the U.S., had led educational travel programs for years with expert tour designer  Tessa Boyce  of  Tour Resource Consultants . A quick phone call (and another glass of wine) later, Wines of Italy was born.

We launched our tours with one guiding principal: To share our passion for Italy, wine, and culture with travelers who want to experience what big tour operators can’t deliver--an intimate and leisurely off the beaten path experience to family-run wineries we know well. “Hidden Gems” captures the true spirit of our tours and your experience will be entirely personal and customized. We are honored to provide our guests with a truly local, artisanal experience.


2025 Tuscany & Piedmont

Florence - Chianti - Monteriggioni - Langhe del Barolo - Milan

June 3-11, 2025 [$4,895] - OPEN FOR BOOKING!

Embark on a journey through Tuscany and Piemonte, Italy's most famous wine regions, offering unforgettable landscapes and iconic vineyards, where you’ll savor legendary wines like Chianti, Brunello, Barolo, and Barbera that capture the soul of Italian winemaking. Begin your adventure in Florence, where the city’s Renaissance charm reveals timeless treasures. From here, head into the sun-drenched hills of Chianti, where vineyards dotted with iconic cypress trees stretch as far as the eye can see and medieval villages beckon. Sip on bold Chianti Classico and discover rich Brunello di Montalcino as you wind through the picturesque countryside. Travel north into enchanting Piemonte, where the scenery shifts to the dramatic Langhe hills. Here, vineyards drape over the rolling terrain like a patchwork quilt, and ancient castles peer through on hazy, mist-covered mornings. Indulge in elegant Barolo, its tannins as powerful as the views, and vibrant Barbera, refreshing on your palate with its bright acidity. Conclude your dream journey in Milan, Italy’s bustling fashion capital. As the sun sets with a final toast, your journey through Tuscany and Piemonte lingers like the finest vintage—each sip, each view, a memory etched in the soul, whispering promises of return.

WINES: Barolo, Barbera, Barbaresco, Nebbiolo, Toscana Rosso IGT, Sangiovese, Brunello di Montalcino, Chianti Classico and more!

  • 9 days/8 nights of relaxing stays at luxury Italian wine estates & 4- and 5-star hotels (breakfasts included)
  • Deluxe private motorcoach transfer to and between all locations
  • 5 leisurely wine & food tasting experiences and tours led by vintners
  • 3+ dinners with wine pairings at local osterias & trattorias
  • Italian cooking class led by a local chef
  • Specialty Italian food & culture experience (e.g. olive oil tasting, truffle hunt, etc.)
  • Guided visits to Florence's famed Uffizi and Accademia galleries
  • Italian history & culture discovery talk presented by Professor Allison Fraiberg
  • Walking tours of local towns and villages led by expert local guides
  • Pastoral walks among the vineyards
  • Optional Activities: e-biking, yoga, spa, massage & more
  • Trawick trip interruption insurance

FEATURED ACCOMMODATIONS: In Florence, we will stay at the 4* boutique  Hotel Glance , just a short, convenient walk from the Santa Maria Novella train station, but nestled on a quiet street in the heart of the city by the San Lorenzo Central Market. And yes, that is a rooftop pool and lounge!

TUSCANY: Our journey takes us next into the glorious Tuscan hills, where we will relax and indulge at the 4*  Borgo San Luigi  country resort in Monteriggioni.

PIEDMONT: Blending old-world character with modern conveniences and Italian charm, 4*  Relais Almaranto  awaits us next and will be our perfect base from which to explore everything the UNESCO region of Piedmont has to offer!


2025 Southern Splendor: Puglia & Basilicata

Bari - Matera - Alberobello - Ostuni - Salento

June 20-29, 2025 [$4,995-$5,195] - OPEN FOR BOOKING!

Escape the Mediterranean crowds and embark on a dreamy journey through Puglia, the “heel” of Italy’s boot, a region steeped in ancient traditions and Mediterranean charm where wine and culture intertwine to create an unforgettable experience. In coastal gem Bari, the historic streets echo with the whispers of the past and seaside views welcome visitors and locals alike. A stay in UNESCO World Heritage site Matera takes you to ancient cave dwellings telling tales of millennia, and exquisite wines mirror the region’s storied history. The enchanting trulli houses of Alberobello transport you to a fairytale as you savor Primitivo and Negroamaro wines that capture the soul of the land. In Novoli, nestled in the heart of Puglia's wine country, indulge in exclusive tastings of bold Aglianico wines, set against the backdrop of sun-kissed vineyards. Discover the Salento region, where Lecce shines as the "Florence of the South," and baroque facades glow in the southern golden light. Here, the vibrant cultural scene is perfectly complemented by wines that celebrate Puglia’s rich terroir. Let the flavors of Puglia’s wines and the beauty of its landscapes linger in your memory, creating a truly magical experience.

WINES: Primitivo Riserva, Puglia IGP Moscato, Aglianico del Vulture DOC, Negroamaro, Salento IGP, Salice Salentino, Fiano del Salento IGP, Susumaniello, Squinzano

  • 10 days/9 nights of relaxing stays at luxury Italian wine estates & 4-star masserias & hotels (breakfasts included)
  • Deluxe private motorcoach to and between all locations
  • 5 private, leisurely wine & food tastings experiences and tours led by vintners
  • 3+ dinners with wine pairings at local osterias & trattorias
  • Italian cooking class led by a local chef
  • Specialty Italian food & culture experience (e.g. olive oil tasting, cheesemaker visit, taralli tasting, etc.)
  • Walking tours of local towns and villages led by expert local guides
  • Italian history & culture discovery talk presented by Professor Allison Fraiberg
  • Private boat excursion on the Adriatic Sea
  • Pastoral walks among the vineyards
  • Optional Activities: e-biking, yoga, spa, massage & more
  • Trawick trip interruption insurance

FEATURED ACCOMMODATIONS: We begin in Bari at the 4* Art Nouveau-styled  JR Hotels Oriente  near the historic center of the Apulian capital. Explore the Old Town, enjoy a seaside stroll, or enjoy a glass of wine on the rooftop garden!

SALENTO: Southern Puglia awaits, as we explore the Salento region from our luxe base at 4*  Borgo Mulino a Vento  resort. Set among an olive grove, with an underground oil mill dating back five centuries, this family-run borgo offers peace and tranquility near the sea and the quaint city of Otranto.

OSTUNI: In central Puglia, the 4*  Masseria Grieco Country Resort  will welcome us as we explore Ostuni, Alberobello, and other quintessential villages. Passionately family-run, this small ancient farmhouse has been lovingly restored and renovated to provide luxurious comfort to all guests.

MATERA: Our final stop takes us to the ancient city of Matera in Basilicata, where we will stay at one of the area's most luxurious hotels that just so happens to be built into the hillside caves! At  Sextantio La Grotta Della Civita , we will be in the center of the world famous Sassi quarters, a stunning and well preserved example of a village where hundreds of caves were turned into dwellings, churches and palaces. A UNESCO World Heritage site since 1993, the Sassi represent a unique hamlet throughout Italy: the earliest inhabitants date back to the stone and bronze age.

Puglia & Basilicata


2025 Dolomite Wine Trail: Alpine Peaks to Garda Riviera

Venice - Valdobbiadene - Dolomites - Lake Garda - Milan

September 4-13, 2025 [$4,995] - SOLD OUT!!!

Join us on an unforgettable adventure through the heart of Northern Italy, starting in the enchanting city of Venice with its dreamy canals. Journey into the hills of Valdobbiadene, renowned for its lush vineyards and bubbly Prosecco. Continue into the breathtaking Dolomites, where dramatic mountain landscapes create a stunning backdrop to the region's unique wines. Sample rich reds and crisp whites, each reflecting the distinctive terroir of the region, while taking in the towering mountain peaks and lush valleys. In the Veneto region, savor iconic Amarone wine, Ripasso della Valpolicella, and Valpolicella Superiore. Settle in on the serene shores of Lake Garda, where you can unwind and enjoy the region's refreshing Lugana and Bardolino wines while gazing wistfully at the lake’s crystal clear waters. Stroll through charming lakeside villages and savor local cuisine paired perfectly with the area's finest vintages. Conclude your tour in the vibrant city of Milan, Italy's fashion capital. This Dolomite Wine Trail tour promises an exquisite blend of culture, scenery, and unparalleled wine-tasting experiences.

WINES: Amarone, Lugana, Prosecco DOCG, Valpolicella Superiore, Ripasso della Valpolicella, Müller Thurgau, Lagrein, Gewürztraminer, Traminer, Pinot Grigio

  • 10 days/9 nights of relaxing stays at luxury Italian wine estates & 4-star hotels (breakfasts included)
  • Deluxe private motorcoach to and between all locations
  • 5 leisurely wine & food tasting experiences and tours led by vintners
  • 3 dinners with wine pairings at local osterias & trattorias
  • Italian cooking class or demonstration led by a local chef
  • Private boat excursion on Lake Garda
  • Guided hiking in the Dolomites (optional)
  • Walking tours of local towns and villages led by expert local guides
  • Italian history & culture discovery talk presented by Professor Allison Fraiberg
  • Behind the scenes visit to historical artisan silk atelier
  • Pastoral walks among the vineyards
  • Optional Activities: e-biking, yoga, spa, massage & more
  • Trawick trip interruption insurance


"From the boutique wineries to Italy's hidden cultural gems, every moment was an amazing blend of rich history, incredible wine, and mouthwatering food. It's the personal touches and intimate experiences that made this trip unforgettable. The memories made will last a lifetime!" - Latanya N.

Past Tour Highlights

Wines of Italy - Tuscany & Lake Garda 2023

"The organization was great--tours were awesome--food and wine excellent! Our tour leaders Allison, Tessa and Andie were fabulous. We look forward to the next U of R adventure!" - Gayle P.

Classic moments from our 2023 Wines of Italy Adventure in Tuscany & Lake Garda

"Every aspect of this trip was amazing! We traveled with a great group of people and everything was meticulously organized. My husband and I had been to Italy before, but we had never experienced it quite like this - great tours and hotel in Florence, magical Italian villas out in the vineyards of Tuscany, beautiful Lake Garda and the wine/food were incredible!" - Connie S.

Wines of Italy - Sicily June 2024

Don’t hesitate - do it, sign up for the trip. Do it for the life enrichment, the stories that have yet to be told, the lifelong friendships, and the profound ways these new places, experiences stir the soul. These trips have been the greatest investments of my life! - Rina D.

Wines of Italy - La Dolce Vita (June 2024)

If you'd like to receive updates about 2025 Wines of Italy tours directly to your inbox, click on the link below. You can also contact Allison Fraiberg directly at 949-444-8908 (voice/text) or WinesofItalyTours@gmail.com.

Meet Your Tour Leaders

Allison Fraiberg: I've been a professor at the University of Redlands since 1996 and started teaching travel courses (and collaborating with Tessa) more than a decade ago. I've guided students and alumni to South Africa, Vietnam, and all across Europe, but my heart belongs to Italy with its cobblestone cities and dreamy sun-drenched hillsides, all brought to life by the people who live there. Indeed, when I'm not teaching, you can usually find me enjoying a sunset aperitivo in Trieste, my home away from home. 

Andie Garwood: In 2015, I began exporting Italian wines all over the globe with my company, D.I.V.I. Srl. The connection between the producers and their creations is fascinating to me, and almost always circles back to the concept of family. The relationships I created became much more than business and allowed me to discover unique and off the beaten path locations. It just seemed wrong not to share them with wine lovers around the world! If I'm not selling wine, I'm probably sharing a glass with Allison in Trieste, my home since 1991.

Tessa Boyce: My passion lives in the world where travel and education intersect. In 2010, I studied abroad in Copenhagen and traveled on faculty-led trips. I learned more during that period than any other semester of college and discovered my ideal career! For the last decade, I've organized unique study abroad programs all over the world. I love building trips and experiences that cannot be replicated. I love traveling anywhere I can experience nature. My travels took me hut-hiking in the Dolomites and down the Ligurian Coast of Italy in 2021 and I am always thrilled to return to this magical country.

Which Wines of Italy travel adventure awaits you?