What Dream Plan Pack's Taste of Italy Trip Actually Includes And Why November Is the Right Time to Go

Italy keeps showing up on people's lists. Venice, Florence, Rome, the names feel like a given.

What stops most people isn't the wanting; it's the building. The flights, the hotels, the getting between cities, the figuring out which Colosseum tour isn't a waste of two hours.

Dream Plan Pack's Taste of Italy trip handles all of that. Eight days, six cities, November 1–8, 2026, hosted personally by Dionne Welsh.

Here's what the trip actually covers.

Day 1 and 2: Venice

The trip begins in Venice with arrival and a welcome dinner the first evening, no scrambling to find a restaurant after a long travel day.

Day 2 is built around Venice properly: a visit to the Murano glass factory on the island of Murano, a guided walking tour of the city, and a gondola ride. Country-expert guides lead every leg of this trip, meaning the person showing you around Venice actually grew up in and around Venice.

Day 3: Bologna and into Florence

Day 3 moves south from Venice toward Florence, with stops in Bologna along the way.

Bologna is one of those Italian cities that doesn't always make the highlight reel but absolutely should, it's the food capital of a country famous for food.

The day finishes with arrival in Florence for the evening.

Day 4: Florence and the Accademia Gallery

A full day in Florence with a guided walking tour and a visit to the Accademia Gallery, which is where Michelangelo's David lives.

The sculpture is 17 feet tall and has been standing in that building since 1873. Photos don't prepare you for the scale of it.

This is the kind of thing that belongs on the included itinerary rather than as an optional add-on, and it is.

Day 5: Orvieto and Rome

Day 5 makes a day-trip stop in Orvieto, a medieval hilltop city in Umbria that sits above everything around it on a volcanic plateau.

Then south to Rome, arriving in the evening with a guided tour of the Roman Colosseum.

The Colosseum after the day-trip crowds have thinned is a different experience from mid-afternoon.

Day 6: Independent Rome and the Vatican

Day 6 gives travelers the morning for independent exploration in Rome which means doing whatever didn't make it onto the group itinerary, or simply sitting in a piazza with an espresso.

The afternoon is the Vatican tour: St. Peter's Basilica, the Vatican Museums, and the Sistine Chapel with a guide who can tell you what you're actually looking at.

Days 7 and 8: Rome to home

A final morning in Rome before the trip wraps.

Flights home are booked separately, which means travelers can use frequent-flier miles or build in extra days in Rome or Venice if they want to extend.

What's included

Country-expert guides for every leg.

Daily breakfast and many additional meals.

All entrance fees to every attraction on the itinerary.

Luxury motorcoach, ferry, and shuttle transportation between cities with WiFi on the coaches.

Welcome drinks the first evening.

Comprehensive trip documents before departure.

And Dionne hosting personally throughout.

Flights to and from Italy are not included and are booked separately. Some meals are intentionally left open to give travelers flexibility.

Pricing

Double occupancy is $3,145 per person. A $250 deposit holds your seat, with the balance due closer to departure.

The single supplement is $1,395 for travelers who want their own room. Solo travelers participate in everything the same way, eat with the group, join every excursion, and have the option to step away when they want to.

Dream Plan Pack built this trip to work for solo travelers, not just accommodate them.

Why November

November in Italy means smaller crowds at the major sites, cooler weather that makes walking comfortable all day, and restaurants and neighborhoods that aren't operating at summer-peak capacity.

The Accademia Gallery, the Colosseum, the Vatican, all of them are better in November than in July.

Reserve your seat today.