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.

• Round-Trip Airfare

International round-trip airfare from Chicago to Italy is included, making this a seamless start-to-finish travel experience.

• Airport Pickup

Round-trip airport transportation from designated pickup locations in Wisconsin to the Chicago departure airport is included for added convenience.

• Boutique Experience

Travel with an intimate group of fewer than 25 guests, offering a more personal, premium, and connected way to experience Italy.

• 7 Nights Accommodations

Enjoy thoughtfully chosen hotel and countryside stays in Rome, Florence, and the Tuscan region, including boutique-style properties and an agriturismo experience.

• Meals

9 breakfasts, 3 lunches, 4 Dinners

• Private Transportation

Travel comfortably by private vehicle during the land portion of the tour, including transfers between Rome, Florence, Tuscany, Siena, Monteriggioni, and return to Rome.

• Expert Tour Leadership

An English-speaking tour leader accompanies the group throughout the journey, with local expert guides included for select cultural and historical experiences.

• Curated 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.

• Sightseeing & Admission

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.

• Guide, Host & Driver Tip

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.

• Travel Documentation

Any passport costs, visa fees, or required travel documentation are the responsibility of each traveler.

• Travel Insurance

Travel insurance is not included. The itinerary notes that insurance is required, and each traveler is responsible for securing appropriate coverage before departure.

• Meals Not Listed

Meals outside the included itinerary meals are not included, including meals during free time or independent exploration.

• Beverages

Drinks with included lunches and dinners are not included unless specifically noted.

• Optional Activities

Any optional excursions, activities, museum visits, or entrance fees not specifically listed in the itinerary are not included.

• Airline Extras

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