“Italy with Spike!” Sept. 2026 TOUR #2

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2885
7 or 11 days
Availability : Sept-Oct 2026
Min Age : 21+ (or 18+ with parent)

TOUR # 2 – Sept./Oct. 2026!  Two different options:  

September 25 – October 2, 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 25 – October 6, 2026
The 11-day, 11-night “Complete Italy” tour with Spike option gives you the chance to extend your trip with a 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. More details below.

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…

11-Day Option: Continue on to the famous Italian Riviera, walk the famous Cinque Terre trails past gravity-defying vineyards, colorful rock-perched villages, and the deep blue Mediterranean Sea. The pastel houses clinging to the cliffs in villages like Manarola, Vernazza and Monterosso al Mare are spectacular. And to stay overnight when the tourists are gone and you have the whole village to yourself with a starry sky overhead as you hear the waves crashing against the rocks… it’s magical! Finally, we end in Florence, a city synonymous with Renaissance art and culture and home to masterpieces like Michelangelo’s David and Brunelleschi’s Duomo.

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 25-Oct 2, 2026)
$5,690 per person (double occupancy, sharing a room)
$6,690 per person (single occupancy)
 
11 days in Rome, Tuscany, Florence & Cinque Terre (Sept 25-Oct 6, 2026)
$7,480 per person (double occupancy, sharing a room)
$9,275 per person (single occupancy)

 

 

How are is this tour different from Italy tour #1 ?
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. The Cinque Terre roads and paths on the 11-Day tour have steep inclines – the villages are built on the side of hills and cliffs.

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
  • Entrance to historical sites & churches in Rome (and Florence 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

Thursday, September 24
Depart U.S. in evening

Friday, September 25
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.

Saturday, September 26
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!

Sunday, September 27
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.

Monday, September 28
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 while we learn what gives Pecorino its unique flavors. 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.

Tuesday, September 29
After breakfast, we will move on to San Gimignano, a small walled medieval hill town that is both visually striking and perfectly preserved. Google photos of San Gimignano to see how you will travel back in time while spending a night in a quiet town up on a hill under the stars with a glass of local wine in hand! (This is the only major difference in the two Tuscany tours… tour #1 visits Siena while tour #2 may do San Gimignano instead. TBD.)

Wednesday, September 30
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. For lunch, we may visit Antica Macelleria Falorni in the village of Greve. This artisan butcher & charcuterie opened in 1806. You can step into the 15th century cave to see how they have been slow-curing their meats and aging their pecorino cheeses with the same ancient traditions for over 200 years and nine generations. For lunch, we will taste all the specialities of this classic family-run shop, enjoying panini sandwiches, coldcut platters, Tuscan soups and wine overlooking the picturesque setting of one of Italy’s most beautiful piazzas. (Plenty of vegetarian choices too!) I love their wine vending machines!  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

Thursday, October 1
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). Bistecca alla Fiorentina is a famous Tuscan dish: a massive, thick-cut T-bone steak, traditionally from Chianina cattle which is highly-coveted. It’s seasoned simply with course salt and olive oil then grilled over a wood fire. It’s a signature dish you’ll never forget!

Friday, October 2
This morning, we pack up and head to the Florence airport to return home **OR** you can join me and extend your vacation from 7 days to 11 days as we visit the Italian Riviera & Florence!

Optional Add-on Experience: two nights in Cinque Terre and two nights in Florence!
Stay in Manarola tonight  (Cinque Terre add-on experience only)
Known for its picturesque multicolored houses and tiny harbor filled with fishing boats, Manarola is famous for its historic Gothic church of San Lorenzo, scenic vineyards, and culinary delights such as its renowned local wine Sciacchetrà, olive oil, and fresh-caught seafood, making it a romantic and tranquil destination favored by visitors for both its natural beauty and traditional Ligurian culture

Saturday, October 3  (Cinque Terre add-on experience only)
Explore Cinque Terre today! Cinque Terre is a stunning coastal area in northwest Italy, composed of five ancient fishing villages—Monterosso al Mare, Vernazza, Corniglia, Manarola, and Riomaggiore. All five of the villages are perched dramatically on cliffs overlooking the Ligurian Sea. The villages are connected by scenic hiking trails, trains, and boats, and the entire region is part of a national park and UNESCO World Heritage Site renowned for its colorful houses, terraced vineyards, and rugged natural beauty. You’ll be amazed by its charming narrow streets, picturesque harbors, beautiful sea views, and local specialties like olive oil and wine, with Monterosso offering sandy beaches and Vernazza known for its photogenic waterfront. All of them have been unchanged for centuries! Stay in Manarola again tonight

Sunday, October 4  (Cinque Terre add-on experience only)
Return to Florence by train midday. Florence is the cradle of the Renaissance. There’s so much to experience here and a quick walking tour will put it all in perspective for you. Stay in Florence tonight

Monday, October 5  (Cinque Terre add-on experience only)
Explore more of Florence today/tonight. The city is famous for its stunning landmarks like the Duomo (Santa Maria del Fiore) with its breathtaking Brunelleschi dome, the Uffizi Gallery housing masterpieces by Botticelli and Michelangelo, and the iconic Ponte Vecchio bridge over the Arno River. In one day, you can explore the Duomo complex, stroll through Piazza della Signoria to see Palazzo Vecchio and Loggia dei Lanzi, visit the Accademia Gallery to marvel at Michelangelo’s David, and enjoy stunning city views from Piazzale Michelangelo. Other highlights include wandering the historic streets, visiting the Basilica di Santa Croce, and sampling Tuscan cuisine at the vibrant Mercato Centrale food hall. It’s one of my favorite cradles of history and art and together we can explore the highlights that interest you most. Stay in Florence again tonight.

Tuesday, October 6  (Cinque Terre add-on experience only)
Fly out today

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