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A Wisconsin family company since 1995
March 30 - April 7, 2027 · Worldwide travel
Experience Italy through a premium, boutique small-group journey designed for fewer than 25 travelers. This carefully curated tour offers an elevated way to discover Rome, Florence, Tuscany, Siena, and the Italian countryside, combining iconic cultural landmarks with intimate local experiences that go beyond a standard group tour. Guests will enjoy private transportation, hand-selected hotel and countryside accommodations, expert local guides, included admissions to major sites such as the Vatican Museums, St. Peter’s Basilica, Siena Duomo, and the Colosseum, plus memorable culinary moments including a Tuscan winery lunch, hands-on cooking class, local restaurant dinners, and a gourmet agriturismo dining experience. With thoughtful pacing, premium inclusions, and a more personal group atmosphere, this one-of-a-kind Italian journey is designed for travelers who want comfort, connection, culture, and authentic beauty in every detail.
About
Experience Italy through a premium, boutique small-group journey designed for fewer than 25 travelers. This carefully curated tour offers an elevated way to discover Rome, Florence, Tuscany, Siena, and the Italian countryside, combining iconic cultural landmarks with intimate local experiences that go beyond a standard group tour. Guests will enjoy private transportation, hand-selected hotel and countryside accommodations, expert local guides, included admissions to major sites such as the Vatican Museums, St. Peter’s Basilica, Siena Duomo, and the Colosseum, plus memorable culinary moments including a Tuscan winery lunch, hands-on cooking class, local restaurant dinners, and a gourmet agriturismo dining experience. With thoughtful pacing, premium inclusions, and a more personal group atmosphere, this one-of-a-kind Italian journey is designed for travelers who want comfort, connection, culture, and authentic beauty in every detail.
Italy consistently ranks as one of the world’s top “dream trips” because it blends ancient history, Christian heritage, unforgettable food, and breathtaking scenery all in one experience. Rome and Tuscany are especially popular for travelers who want a slower, more meaningful pace rather than rushing city to city.
1. Explore the Eternal City of Rome
2. Scenic Tuscan Hill Towns and Countryside
3. Guided Touring Without the Stress of Independent European Travel
4. Christian Fellowship While Exploring Christian History
5. Bucket-List Italy Experience Without Feeling Exhausted
6. Wisconsin-Based Christian Tour Company Since 1995
120 or more days before departure: Full refund of everything you've paid, including your deposit.
119 to 90 days before departure: Refund of everything paid beyond your deposit. The deposit is non-refundable.
Fewer than 90 days before departure: No refund, unless your spot is resold or your travel insurance covers it.
We strongly recommend travel insurance.
Moderate activity A fuller day with regular walking and longer sightseeing. You should be comfortable walking over a mile a day at a steady pace to keep up with the group, and able to manage airports, stairs and occasional uneven ground independently. Best if you stay fairly active. Not sure if it suits you? Call us, or read what each pace means.
Your trip
Open any day to read it in full. Meal chips show what’s included that day. Timings are a guide — your final documents confirm the details.
Tuesday March 30
Our journey begins with the ease and comfort of traveling together from the very start. Guests will be picked up from designated locations in Wisconsin and transported as a group to Chicago for the international departure. From there, we’ll board our overnight flight to Italy, allowing the group to relax, settle in, and begin the experience together before arriving in Rome mid-day the following day.
Day 0Tuesday March 30
Our Italy adventure begins as we gather in Chicago for our overnight flight to Rome. Sit back, relax, and look forward to a memorable journey filled with ancient history, beautiful Tuscan countryside, delicious food, and wonderful fellowship.
Wednesday March 31Dinner
Ciao! Welcome to Rome. Once the heart of a vast empire, Rome is a city where ancient ruins, grand piazzas, Renaissance art and everyday Italian life blend seamlessly. Your adventure begins with a welcome meeting at 6 pm. After arrival and transport to the hotel, take the chance to explore at your own pace – wander through the historic centre, admire the Pantheon, or toss a coin into the Trevi Fountain to ensure a return to the Eternal City. You might also enjoy a stroll through lively streets lined with cafés and gelaterias, soaking up Rome’s timeless atmosphere.
Thursday April 1BreakfastLunch
This morning, enjoy a guided visit to the Vatican Museums and St Peter’s Basilica, walking through an extraordinary collection of artworks and galleries that span centuries of history, from classical sculptures to Renaissance masterpieces. The experience culminates in the breathtaking grandeur of St Peter’s Basilica, offering a profound insight into the artistic, cultural and spiritual heart of the Vatican. Following the visit, lunch is included at a local restaurant, featuring traditional Roman cuisine. The afternoon is free to explore Rome at your own pace.
Friday, April 2BreakfastLunch
This morning, travel by private transfer to Florence, breaking up the journey with a scenic stop in the Val d’Orcia, a postcard-perfect Tuscan landscape of rolling hills, cypress-lined roads and patchwork fields that has inspired artists for centuries. Continuing on to Montalcino, visit a local winery to learn about traditional wine-making in this renowned region, followed by a relaxed winery lunch showcasing local flavours. Later, stop in the charming Renaissance town of Pienza for a short orientation walk, then enjoy free time to wander its narrow lanes, take in sweeping countryside views or sample the area’s famous pecorino cheese. Arrive in Florence by late afternoon or early evening, with free time and free dinner to explore the city at your own pace and choose where to dine independently.
Saturday, April 3BreakfastDinner
Discover Florence, the birthplace of the Renaissance, on a walking tour with a local guide, delving into a city shaped by art, power and creativity. Wander through elegant piazzas and narrow historic streets, taking in landmark architecture, hidden details and stories of the artists, thinkers and families who defined Florence’s golden age. Along the way, gain local insight that brings the city’s layered past into focus, before enjoying free time to explore further, visit a gallery, or settle into a café and watch daily Florentine life unfold. In the evening, enjoy dinner at a local trattoria, sampling traditional Tuscan cuisine in a warm and authentic setting.
Sunday, April 4BreakfastLunch
Head out on a full-day experience in the Tuscan countryside, starting near San Gimignano. After some time to enjoy the area and its surroundings, take part in a hands-on cooking class at a local venue, followed by lunch and a tasting, where you’ll prepare and sample traditional Tuscan dishes using regional ingredients, paired with local wines. In the afternoon, continue with a transfer to an agriturismo in Monteriggioni, where you’ll have free time to relax, enjoy the peaceful rural setting, or stroll around the countryside at your own pace before returning.
Monday, April 5BreakfastDinner
This morning, discover this magnificent medieval city with a guided walking tour, exploring its atmospheric historic centre with narrow Gothic streets and elegant palazzi, all built around the iconic Piazza del Campo, famous for the Palio horse race. Continue with skip-the-line access to the Siena Duomo, one of Italy’s most extraordinary cathedrals, renowned for its striking black-and-white marble façade, intricate mosaics, sculpted pulpits, and richly decorated interiors showcasing masterpieces of Italian Gothic art. After the guided visit, enjoy free time for lunch and individual exploration, whether wandering through local shops, visiting hidden corners of the city, or relaxing in a café. In the afternoon, return to the agriturismo near Monteriggioni to unwind and enjoy the peaceful countryside. Round off the day with a gourmet group dinner at the agriturismo, featuring refined Tuscan cuisine made with local, seasonal ingredients.
Tuesday, April 6BreakfastDinner
This morning, depart Monteriggioni by private transfer to Rome. Upon arrival, enjoy free time for lunch, with the opportunity to explore or dine independently. In the afternoon, join a guided tour of the Colosseum, stepping inside one of the most iconic monuments of ancient Rome and learning about the history of gladiators, emperors, and the vast Roman Empire that once shaped the city. In the evening, come together for a special farewell dinner at a local restaurant, the perfect way to reflect on the journey and celebrate the end of the tour in Rome.
Wednesday April 7Breakfast
Your adventures come to an end today. There are no activities planned and you're free to depart the accommodation at any time after check-out. At the agreed time, a private transfer will take you to Rome Fiumicino airport.
Every day of Highlights of Italy (Rome and Tuscany) in one PDF, sent to your inbox. Print it, or share it with whoever is coming with you.
What’s included
✓International round-trip airfare from Chicago to Italy is included, making this a seamless start-to-finish travel experience.
✓Round-trip airport transportation from designated pickup locations in Wisconsin to the Chicago departure airport is included for added convenience.
✓Travel with an intimate group of fewer than 25 guests, offering a more personal, premium, and connected way to experience Italy.
✓Enjoy thoughtfully chosen hotel and countryside stays in Rome, Florence, and the Tuscan region, including boutique-style properties and an agriturismo experience.
✓9 breakfasts, 3 lunches, 4 Dinners
✓Travel comfortably by private vehicle during the land portion of the tour, including transfers between Rome, Florence, Tuscany, Siena, Monteriggioni, and return to Rome.
✓An English-speaking tour leader accompanies the group throughout the journey, with local expert guides included for select cultural and historical experiences.
✓Enjoy included group meals and premium food experiences, such as a welcome dinner, local restaurant lunches and dinners, a Tuscan winery lunch, a hands-on cooking class with wine tasting, etc.
✓Admission and guided experiences are included for major highlights such as the Vatican Museums, St. Peter’s Basilica, Florence, Siena, Siena Duomo, and the Colosseum.
Not included
—Tips for the tour host, tour leader, local guides, and drivers are not included and may be offered at each traveler’s discretion. Recommendations will be communicated.
—Any passport costs, visa fees, or required travel documentation are the responsibility of each traveler.
—Travel insurance is not included. The itinerary notes that insurance is required, and each traveler is responsible for securing appropriate coverage before departure.
—Meals outside the included itinerary meals are not included, including meals during free time or independent exploration.
—Drinks with included lunches and dinners are not included unless specifically noted.
—Any optional excursions, activities, museum visits, or entrance fees not specifically listed in the itinerary are not included.
—Round-trip airfare from Chicago is included, but optional airline extras such as seat upgrades, preferred seat assignments, baggage fees, or itinerary changes are not included unless specifically stat
What an incredible 11 days. Everything was perfectly planned. Scenery was amazing. I have told everyone there wasn’t one thing that I could give a negative review.
Before you travel
Three things people ask us before they book. Anything else, call (262) 290-1303.
Getting on board
Flights leave from Chicago. Exact times come with your final documents.
Who you'll travel with
Up to 25 travellers, more than half of whom have toured with us before, and one of our own directors with the group the whole way.
Solo travellers join every departure. Want to know who is already booked on this one? Call and ask — we are asked it every week.
Room options
Traveling alone? Tell us when you book and we will gladly try to match you with a same-gender roommate, so you avoid the single supplement.
Before you book
Completely normal. In fact, many of our guests say this trip was something they talked about for years before finally deciding to go. One of the biggest benefits of group travel is that you are never navigating airports, hotels, or transportation alone.
Tuscany is the slower, scenic side of Italy — rolling hills, vineyards, stone villages, quiet cafés, and countryside views that feel almost unreal. Many travelers say Tuscany becomes their favorite part of the trip because the pace allows them to truly soak in the experience.
Most guests are Midwest travelers, many from Wisconsin, who value Christian fellowship, comfortable pacing, and meaningful experiences over flashy luxury travel.
Yes. Especially in older parts of Rome and Tuscany. Comfortable walking shoes are essential, and guests should be prepared for uneven pavement and some stairs at historic sites.
Yes — many Tuscan towns are built on hills. The scenery is stunning, but guests should expect some inclines during sightseeing.
Yes, though like any major destination, travelers should stay aware in crowded tourist areas. One advantage of traveling with a group is having experienced tour leadership helping guide the experience.
That is exactly why we designed this trip to include the iconic highlights people most dream about — Rome, Tuscany, history, scenery, food, and fellowship — all at a comfortable pace.
Every day of Highlights of Italy (Rome and Tuscany) in one PDF, sent to your inbox. Print it, or share it with whoever is coming with you.
Ask a question
How much walking is there really? Can you accommodate a dietary need? Is there a roommate available? Ask us anything about Highlights of Italy (Rome and Tuscany) — a real person reads every message and replies within one business day.
from $6,950 / per person
Or call us directly: (262) 290-1303 · Monday–Friday, 9:00 a.m. – 4:30 p.m. CT
A real person reads every message and replies within one business day.
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