September 2026: ITALY Food, Wine & History with Spike!

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1353
9 days, 9 nights
Availability : September 2026
Min Age : 21+ (or 16+ with parent)

This tour will be announced soon. Expected to sell out fast.

EARLY ACCESS: CLICK HERE to be notified before it goes on sale to the public!

Is Italy at the top of your bucket list? This 9-day, 9-night tour, led by Spike, is perfect for first-time visitors. You’ll journey through time exploring ancient Roman ruins, medieval streets, and Renaissance art in Rome, Florence, and Venice. The tour includes visits to Tuscany’s rolling hills, where you’ll explore the medieval walled cities of Siena, San Gimignano, and Montepulciano. We will indulge in authentic Italian cuisine and wine from local vineyards and wineries, experiencing the warm hospitality of the locals. You’ll also experience colorful markets, family-run pizzerias, and seaside trattorias, with opportunities to cook traditional dishes ourselves in a local farmhouse. This tour is timed to coincide with the peak harvest season for wine and Italy’s culinary specialties, offering a sensory journey through history, culture, and breathtaking beauty.

Did I mention the food? This tour has been extended from my previous Italy tours to take advantage of our arrival during peak harvest time. You’ll eat well! Few countries have mastered the fresh seasonal culinary craft that changes with each region we visit. We’ll visit colorful markets, family-run pizzerias, seaside trattorias, and maybe even do a little cooking ourselves.

With a group size of 13 people, you get an up close and personal tour. This trip is perfect for solo travelers, couples, family and friends. (In fact, two people save $ by sharing a room!)  Not designed specifically for photographers but you’ll come home with some amazing pictures and stories!

CLICK HERE to be notified before it goes on sale to the public!

Tour Details

Starting in the capital city of Rome, we will visit the “birthplace of Western Civilization” and wander through iconic landmarks of the once-mighty Roman Empire like the Colosseum, Roman Forum, Trevi Fountain and Pantheon… a literal millennia of history. We will also visit Vatican City for a private tour to marvel at St. Peter’s Basilica (the largest church in the world) along with the Renaissance art of the Vatican Museums, and of course Michelangelo’s Sistine Chapel. 

Then, we board a high speed train and move on to Florence, a city synonymous with Renaissance art and culture and home to masterpieces like Michelangelo’s David and Brunelleschi’s Duomo. Surrounding Florence, the region of Tuscany unfolds with rolling hills adorned by vineyards and olive groves, inviting travelers to savor world-class wines, indulge in delectable cuisine, and immerse themselves in the timeless beauty of this enchanting Italian landscape. We’ll visit Siena and the Medieval walled city of San Gimignano with lunch and wine samplings in a local farmhouse winery. Then further south to a completely different wine varieties of Montepulciano and neighboring villages. (Final stops in Tuscany TBD.) There will also be an option to take a cooking class with a local chef teaching us how to make three homemade dishes from scratch as well as a dessert – all of which we will enjoy with a glass of wine (or beverage of your choice).

Have you ever arrived to your hotel by boat? Venice is our last stop… a city of unparalleled beauty and one of my favorite places on Earth. We will wander its unique network of winding alleys and picturesque canals and get lost in a world of exquisite architecture on foot and by boat. You’ll enjoy the slow food experience known as “Cicchetti” as we walk through quiet neighborhoods to some of my favorite spots. You’ll see all of the historic palaces and landmarks, plus you’ll have the option of floating down the Grand Canal on an enchanting gondola. Venice remains an bucket-list destination where every corner holds a piece of the city’s rich cultural heritage… the perfect place to end our tour before returning home with incredible photos and memories.

ANNOUNCEMENT SOON: Sign up HERE to get early access.

Why September?
Summer in Italy is crowded, expensive and hot! But September is very pleasant with an average of around 77°F.  Arguably the best time to travel to Italy, the crowds thin out which mean less people in our photos! Plus, the harvest period begins, which in Italy, means the food scene explodes with everything from truffles to olives, grapes ripe on the vine and more!

Please Note: This tour will involve a lot of walking, you should be physically fit to be on your feet most of the day (and able to handle your own luggage to & from hotels).  We regret that this tour is not designed to accommodate guests with wheelchairs, mobility limitations, or strollers due to conditions beyond our control – some of the villages, ancient sites and old buildings we are visiting are not fully accessible.

Minimum Age: 21 (or age 16+ with parents)

Itinerary

Itinerary to be announced soon

Photos

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