“Italy with Spike!” Sept. 2026 TOUR #1

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ON SALE SEPT 30
From$8,135$5,690
ON SALE SEPT 30
From$8,135$5,690

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3020
7 or 10 days
Availability : September 2026
Min Age : 21+ (or 18+ with parent)

TOUR # 1 – September 2026!  Two different options:  

September 12-19, 2026
This 7-day, 7-night “Food & Wine Italy!” tour with Spike features immersive experiences in Rome and Tuscany, including a welcome dinner in the historic Theater of Pompey ruins, private tours of the Colosseum and Roman Forum, and a culinary walking tour with 15 tastings at iconic Roman food spots. In Tuscany, the group explores Montepulciano for wine tasting, stays in Val d’Orcia with its UNESCO-listed landscapes, sees film locations, and visits Pienza for architecture and artisanal pecorino cheese. The itinerary includes a hands-on cooking class and farm visit, an overnight in a medieval walled village, wine tasting along the Chianti Way, and other experiences… plus free time to explore some towns on your own if you wish. (You’ll even be able to add an early Vatican visit in Rome featuring exclusive entry to St. Peter’s Basilica and the Sistine Chapel. See Italy the way YOU want to with several options!)

September 12-22, 2026
The 10-day, 10-night “Complete Italy” tour with Spike option gives you the chance to extend your trip with a three-day Venice experience *or* to visit Cinque Terre, known for its picturesque multicolored houses and tiny harbor filled with fishing boats and Florence for its Renaissance masterpieces and stunning cathedral.

This is a small-group tour, limited to 14 travelers. Prices and Registration link below. If you’re viewing this page on a phone, the link to book your trip is at the bottom of the page. This tour is expected to sell out fast.

Tour Details

7-Day Option: 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. You’ll learn the history and legends of Roman food & wine on a strolling food tour. We will sample famous restaurant dishes which vary from neighborhood to neighborhood. We will also stop at the iconic food markets, groceries, coffee shops, and gelaterias along the way. You’ll get some of their recipes to take home!

Then, we board a private Mercedes Sprinter motorcoach and move on to the region of Tuscany and its 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 learn the different wine varieties of Montepulciano and neighboring villages. (Final stops in Tuscany TBD.) We will take a cooking class with a local chef showing us how to make three homemade dishes from scratch as well as a dessert – all of which we will enjoy with wine (or beverage of your choice). We will also visit Pienza, Siena, and several villages and towns in the Chianti Way of Northern Tuscany like Panzano and Greve. The tour ends in Florence unless you want to extend it with an optional 3 days in Venice…

10-Day Option: 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. The itinerary below is still flexible as I build out the perfect tour for my guests. I’m excited to take you back to some of my favorite places!

You will also have the option to arrive to Rome one day early for a private tour of Vatican City 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.

 

ON SALE NOW! BOOK YOUR VACATION:
 
7 days in Rome & Tuscany (Sept 12-19, 2026)
$5,690 per person (double occupancy, sharing a room)
$6,690 per person (single occupancy)
 
10 days in Rome, Tuscany & Venice (Sept 12-22, 2026)
$7,380 per person (double occupancy, sharing a room)
$9,290 per person (single occupancy)

 

 

How are is this tour different from Italy tour #2 ?
Both tours include the same incredible food & wine experiences.
Tour # 1 includes a visit to a local wine festival in Panzano and an overnight stay in Siena, while Tour # 2 includes a wine & charcuterie lunch at a legendary butcher shop in Greve and an overnight stay in San Gimignano. Otherwise, both tours are mostly the same and include a similar itinerary and two nights in Castellina in Chianti, a magical Tuscan village.

Possible Add-On Experiences:
You have the option to customize your tour by staying longer for an additional price. Each tour goes in a different direction for the final days:
Tour #1 gives you the chance to take a high-speed train to explore my favorite city Venice.
Tour # 2 gives you the chance to visit Florence and Cinque Terre in the Italian Riviera.

Why go in late September?
The crowds are gone and the weather is very pleasant with an average of around 77°F. 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!

Why go with Spike?
I plan a very well-researched custom tour that REALLY gives you the experience of Italy, not a tourist’s rushed itinerary. I’ve been to these places many times and I travel with you to ensure every detail is handled. Once you step off the plane, you don’t worry about a thing!

What else?
Lots of other discoveries for a first-time visit to Italy, especially if you wish to learn more about the history, culture, music, art and lifestyle of the Italians. So much is included to ensure you experience everything Italy has to offer! Plus there is free time built into our tours for you to explore what calls to you whether it be shopping, hiking or just relaxing with a cocktail!

Please Note: The Rome portion of 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 18+ with parent)

Photos

Price Includes

  • All Hotel Accommodations
  • Ground Transportation for tour
  • Welcome Dinner with open bar
  • Breakfast at all hotels
  • Many lunches & dinners including special food experiences (exact meals/itinerary TBA)
  • Fun, engaging & knowledgeable tour guides
  • Private tour of the Colosseum and Roman Forum
  • Walking Food Tour in Rome
  • 5 hour cooking class followed by a 4 course dinner with wine
  • Ticket to Panzano’s wine festival and collectible wine glass (tour #1 only)
  • Entrance to historical sites & churches in Rome (and Venice if applicable)
  • online & printed city guides and travel guides for places we will visit

Price Excludes

  • Flight to/from Italy (but I’ll help you find the best deal)
  • ETIAS travel visa if necessary (but we will help you get it)
  • Taxi/shuttle from airport to Rome hotel (or to Venice airport)
  • Lunches and dinners on some days (final itinerary with “explore on your own” days TBD)
  • Alcoholic beverages (other than where included like vineyards, wine tastings & food tours)
  • Room service fees, personal expenses and gratuities
  • Excess baggage charges
  • Travel Insurance
(Rough) Itinerary

Friday, September 11
Depart U.S. in evening

Saturday, September 12
Begin your Italian adventure in Rome, a city that seamlessly blends history, culture, and modern charm. Check in your hotel room and shake off the jet lag. I’ll provide a city guide for anyone who has energy to explore. We will meet for an early welcome dinner and tour orientation in a cave which is the 2,090 year-old remains of the Theater of Pompey. This is the famous spot where on 15 March 44 BC Julius Caesar was killed. Our hotel for two nights in Rome is located in Campo de’ Fiori, a vibrant open-air market in Rome, offering fresh produce, flowers, spices, and local goods from morning until early afternoon. At night, locals grab a bottle of wine and some cups when this square comes alive as a social hang out – a good slice of Roman life. In the 15th century, it served as a gathering spot for public executions. Today, it’s surrounded by lovely cafés and restaurants.Sunday, September 13 After breakfast, we will take a private tour of the Roman Forum and the Colosseum: One of the wonders of the world is also the largest ever amphitheater constructed in the 1st century to hold an estimated 70 thousand people. It was a real hub of entertainment in central Rome, with regular shows, animal hunts and gladiatorial battles to the death. The Roman Forum was the political and business center of ancient Rome, you’ll literally walk through a millennia of history. This is where the citizens came to listen to speeches from people like Julius Caesar, vote in elections, and witness both criminal trials and religious ceremonies. After a little time to rest or explore on your own, we will be joined this afternoon by a culinary expert who will give us a walking food tour of Rome. We will sample famous restaurant dishes and stop at iconic food markets, grocers, coffee shops, and gelaterias along the way. We will have 15 food samples in 5 different locations, plus free flowing wine at the two restaurant dining rooms we stop in. Only seasonal & fresh ingredients; you’ll learn the history and legends of Roman food & wine… and you’ll get some of their recipes to take home!

Monday, September 14
We leave Rome by private Mercedes Motorcoach and head north to Tuscany. Our first stop is to Montepulciano, a medieval and Renaissance town in southern Tuscany. It’s perched on a hill with stunning views and historic architecture. It is famous for its excellent wine production, particularly the Vino Nobile di Montepulciano, and you may recognize the Piazza Grande in the center of town if you’re a fan of “Twilight.” We will spend a few hours exploring the town and tasting the local wines before retiring to our comfortable 4-star hotel located in the most beautiful and unspoiled Tuscan setting known as the Val d’Orcia. Rolling hills, cypress-lined roads, and fertile farmland that has inspired countless artists and photographers. You can enjoy it from the jacuzzi on your terrace! We will stay here for 2 nights to explore Southern Tuscany.
 

Tuesday, September 15
In the morning, we’ll show you more of this area which is a UNESCO World Heritage Site, including spots where some of your favorite movies were filmed like “Gladiator” and “The English Patient.” Then we will explore another Renaissance hill town in Tuscany known as Pienza. It was famously transformed in the 15th century by Pope Pius II into an ideal city based on humanist urban planning principles and celebrated for its historical, cultural, and architectural significance. It’s also famous for its cheese! Pecorino cheese originated from Pienza and this renowned artisanal sheep’s milk cheese is celebrated for its unique flavors. We’ll sample some and pair it with local wines. Tonight, a 5 hour cooking class at one of my favorite restaurants in Tuscany, Podere il Casale. We will tour the farm and dairy, and then have a blast in a cooking class (with fresh pasta, meat, side dish, and dessert), with plenty of wine and cheese from the farm, of course. Take a look.

Wednesday, September 16
After breakfast, we will move on to the next town: Siena, Italy’s medieval heart and soul. This Tuscan hill town will transport you back to the Middle Ages. You will see the grand cathedral, Piazza del Campo and Siena’s narrow cobblestone streets. (This is the only difference in the two Tuscany tours… tour #2 visits San Gimignano instead.) Siena’s historic center was designated a UNESCO World Heritage Site for its extraordinary preservation and historical authenticity, representing one of the finest examples of a medieval and Renaissance Italian city. We will spend one night inside Siena’s heavily-fortified walls.

Thursday, September 17
Today, we drive up the famous “Chianti Way.” As we cross into North Tuscany, you’ll notice the landscape changes which of course also affects the vineyards. Here, Chianti Classico is produced – perhaps the most famous and heavily awarded wines. And today, we’ll stop to taste some at a winery. This afternoon, we arrive in the tiny village known as Castellina in Chianti. With origins dating back to the Etruscan era, this town was a constant battle site between rivals Florence and Siena. We’ll spend two nights here and you’ll have this evening to enjoy the vibrant main street filled with local shops, restaurants, and Renaissance architecture. Here’s some photos of the town.
 
Friday, September 18
Start your Friday wandering around Castellina in Chianti or just have a lazy day sipping an Aperol Spritz on the panoramic terrace or walk through the rose garden to the stunning swimming pool. In the afternoon, we will drive to the neighboring town of Panzano where their annual “Vino al Vino” wine festival will fill the streets with wine lovers sampling both old and new vintages of Chianti Classico and other local IGT wines. The festival also features live jazz music as the sun sets. Dinner will be the best steak you’ve had in your entire life (great vegetarian options too). Dario Cecchini is a culinary genius who I first discovered through Anthony Bourdain and then later on Chef’s Table and Top Chef. He’s an eighth-generation butcher and a true character! We will visit his home the week of his 71st birthday and he and his staff will prepare our 10 course dinner (!) above the butcher shop his family has owned for 250 years. A visit really gives you a sense of his reverence for history. Although I believe he is the first butcher in Panzano to to blast AC/DC and recite Shakespeare while chopping your XL T-bone Bistecca Fiorentina. Watch this if you want Dario to make you hungry.
 

Saturday, September 19
This morning, we pack up and head to the Florence airport to return home **OR** you can jump on the train with me and extend your vacation from 7 days to 10 days…

Optional Add-on Experience: Three days in Venice!
If you choose this option, we will board the high-speed train for a journey north to one of my favorite places in the world. Have you ever arrived to your hotel by boat? We step off the train and board a classic mahogany wood limousine boat which will take us on a cruise through Venice and along the Grand Canal – its “Main Street” since the 1700s. Our vintage Riva boats were the preferred choice for Princess Grace of Monaco, Bridgette Bardot and Elizabeth Taylor. Now they will take us on a leisurely cruise en route to our hotel in true Venetian style. Venice was founded a thousand years ago by Italian refugees sick of constant invasions by the Huns, Germans, Visigoths and basically everyone else. So they followed some fishermen out into the shallow lagoon where they could live in peace, and built their homes on stilts. Venice is now made up of around 126 small islands in a shallow lagoon that are connected by more than 470 bridges. It was one of Europe’s largest and most important financial powers and center of trade during the Middle Ages and Renaissance. It was a Republic for a thousand years and didn’t become part of Italy until 1866. Because of its long, deep history and culture, you’ll see its open piazzas, Gothic architecture, Baroque and Renaissance art and narrow canals… no wonder Venice is known as one of the most beautiful cities in the world.
 
Sunday, September 20 (Venice add-on experience only)
Italy invented espresso and coffee culture. So we start this morning at Cafe Florian, the oldest and most ornate cafe in Europe. Casanova, Marco Polo, Dickens, Queen Elizabeth, Scorsese, Clooney, Clark Gable, Elton John, Brad Pitt and 4 James Bonds have had espresso here since 1720… and now you will too! Then I’ll give you a tour of Venetian highlights including the 1,000 year old St. Mark’s Basilica Cathedral and the grand Piazza San Marco. Even if you’re not a music fan, your jaw will drop when we peek inside the Grand Teatro La Fenice opera house. It’s been in a bunch of movis including James Bond and The Talented Mr Ripley. If it doesn’t scare you, I’ll even take you into a church’s hidden flooded underground crypts which is the final resting place of many of Venice’s 15th century leaders. Haunted? Maybe. For dinner tonight, we will do as the locals: Aperitivo! This is a slow food experience similar to a relaxed happy hour bar crawl. This is a uniquely Venetian evening! We will eat “cicchetti” which are small finger foods and snacks served with wine, so you’re sure to eat something delicious you’ve never tried before. You’ll see a virtual buffet of finger foods under glass to choose from. Cicchetti are small flavor bombs, a complete recipe in the palm of your hand. They are a staple of Venetian way of life, and every traveler in Venice should have the experience!
 
Monday, September 21 (Venice add-on experience only)
More of Venice today, I’ll show you around some incredible sites like the Rialto Bridge and Market, the huge Gothic “Frari” and the oldest church in Italy (founded in 421 AD). But the afternoon and evening will be free for you to explore, shop or get lost wandering through Venice’s maze of narrow alleyways and bridges. Or take a romantic gondola ride through the quiet canals… And of course, you’re welcome to join me to some of my favorite spots on your final night in Italy.
 
Tuesday, September 22 (Venice add-on experience only)
It’s time to say goodbye… Arrivederci! Ciao! We head to the airport to return home.
 
Another Optional Add-on Experience: Arrive early to Rome and tour the Vatican! (price TBD)
If you depart the U.S. one day earlier on Sept. 10 and arrive Sept. 11, I’ll take you to my favorite Roman neighborhood for dinner. You’ll see the narrow cobblestone streets, colorful buildings, hidden squares and artisan shops as you wander through the picturesque Trastevere district. This is where the locals eat! And then on the morning of Sept 12, I’ll set you up on a guided tour of The Vatican. You’ll get to visit the smallest country in the world which contains the largest church in the world! In addition to St. Peter’s Basilica, you’ll see Michelangelo’s Sistine Chapel and Pieta, The Vatican Museums and more. Did I mention our guide takes you in the back door so you skip the line? The tour lasts 3-4 hours and you’ll have time to rest in your hotel before our group’s Welcome Dinner at night.
 
This is an early preview for you as I am still currently building this amazing trip. I’m in contact with my Italy partners to even include a few surprises not listed here. Because I am working to get you the best accommodations and food tasting experiences, some details of this informational itinerary could change. Please ask if you have any questions about details. I’ve offered variations of this Italy tour for years and I hope you and I get to experience it together!
 
Payment & Cancellation Policy
Payment schedule for Explore Italy 2026 (for 7 day tour)
PAYMENT 1: deposit to book your tour & reserve your spot  ($1,500)
PAYMENT 2: due November 15, 2025  ($2,000)
PAYMENT 3: due February 1, 2026  ($1,500)
PAYMENT 4: due May 1, 2026  (remaining balance)
 
Payment schedule for Explore Italy 2026 (for 10 to 12 day tours)
PAYMENT 1: deposit to book your tour & reserve your spot  ($1,500)
PAYMENT 2: due November 15, 2025  ($2,000)
PAYMENT 3: due February 1, 2026  ($2,000)
PAYMENT 4: due April 1, 2026  ($1,500 or remaining balance)
PAYMENT 5: due June 1, 2026  (remaining balance if any)
 

CANCELLATION NOTICE:  In the event that you have to cancel your “Explore With Spike” trip, we make every attempt to replace you with another paying traveler but if not, your payments are non-refundable. The best way to protect yourself against unforeseen changes in your travel plans is to purchase travel insurance.

Italy 2026 Cancellation Policy

Travel Insurance Recommendations

Questions? Email us! info@explorewithspike.com

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