Friends in Italy
Guided By Margaret Cassady
Italy—such a beautiful place to meet.
Three nights each in Rome, Tuscany, Bologna, and Venice.
Friends in Italy
13 Days / 12 Nights / 12—15 Travelers
$5980 per person (double occupancy)
+$1600 single supplement
$1000 deposit reserves each spot
“I can’t wait to introduce you to some of my favorite Italian places and people.” —Margaret
April 7—19, 2025
(Mon—Sat)
Highlights
Rome
Borghese Gallery Tour, Rome
“Many travelers don’t make it to this incredible small museum. The palace itself is stunning, and it’s filled with jaw-dropping sculptures. You won’t believe how Bernini made marble look like fabric and flesh.”
San Brizio Chapel & Orvieto Duomo
“Before you even get in the door, this hilltown-topping cathedral will amaze you, with the whole history of the world carved into the front. Its San Brizio Chapel is a masterpiece of Renaissance painting, with realistic bodies and 3D illusion.”
Charming Accommodations
“You’re going to love the hotels! They’re all very comfortable, charming, unique places in the best possible locations. Our fortrezza hotel in Sorano will be a highlight, with its peaceful countryside setting, heavy old stone walls, and delicious restaurant serving local food and wine.”
Siena Contrada & Palio Tour, Siena
“I love hearing travelers audibly gasp when they emerge onto Siena’s main square, the Campo. My local guide friend will help us picture it transformed into a track for the famous Palio horse races.”
Food Tours in Rome & Bologna
“Bologna is a perfect city for strolling, with miles of covered sidewalks; and it’s the home of Europe’s oldest university, so it’s got a fun, lively college vibe. Best of all, it’s considered the food capital of Italy!
Backstreets Walk, Venice
“Most tourists in Venice stick to a few overcrowded areas. Let’s be explorers instead of tourists! One of my favorite experiences is strolling the uncrowded side streets, squares, and islands, showing my tour members how the locals really live.”
Itinerary
Tuscany Day Trip
Day 1—Meet at our Rome hotel in the afternoon to get acquainted, then we’ll stroll to some of my favorite squares and monuments, and kick off our trip with delicious Roman specialties for dinner. (Dinner included, sleep in Rome)
Day 2—With my dear friend, one of the best local Roman guides, we’ll visit the Borghese Gallery's incredible sculptures. Then we’ll discover stunning city views, "secret" ruins, and gorgeous churches with museum-worthy art. (Lunch and dinner on your own, sleep in Rome.)
Day 3— It’s your choice this morning: free time for your own sightseeing (or sleeping in)....or, learn all about Roman food as we taste our way through the Testaccio food market with a local expert (optional, extra fee). This afternoon we’ll join my guide friend again to explore Rome's ancient seaport, Ostia Antica. (Lunch on your own, dinner on your own)
Day 4—Drive to Orvieto; we’ll tour its incredible cathedral, Etruscan well and wine cellars with a local guide. Then continue to our "agriturismo," a countryside hotel in a medieval fortress. We’ll have dinner together at its local food and wine inspired restaurant. (Lunch on your own, dinner included, sleep in Sorano)
Day 5—With a local guide we’ll make a day-trip loop to explore mysterious Etruscan remains and the ancient healing hot springs of Saturnia, with many classic Tuscan photo ops—picture lots of rolling hills and rows of cypresses. (Lunch on your own, dinner included, sleep in Sorano)
Day 6—Enjoy a “vacation from your vacation” with a relaxing day at our agriturismo, capped off with a cooking class where we’ll learn to prepare an Italian feast. (Lunch and cooking class dinner included, sleep in Sorano)
Day 7—Today is our biggest driving day, but the roads are lovely and it’s split with a long stop in Siena en route. My local guide friend will explain the fiercely loyal Siena neighborhoods which compete in the Palio horse race, and show us some of the city’s masterpieces of art and architecture. Afterward, we’ll continue to Bologna, where students at the world's oldest university give a youthful vibe. (Lunch on your own, dinner included, sleep in Bologna)
Day 8—Bologna is the food capital of Italy, so our “progressive lunch” is a gourmet walking/tasting tour with a local specialist. Your afternoon is free to stroll the arcaded sidewalks and discover the beautiful medieval towers and Renaissance churches. (Lunch included, dinner on your own, sleep in Bologna)
Day 9—With a local expert, we’ll explore some of the amazing and untouristed WWII sites near Bologna—German bunkers, cemeteries, and memorials to the resistance fighters. (Lunch and dinner on your own, sleep in Bologna)
Day 10—Drive to Venice; I'll take you on an orientation walk to teach you how to navigate this maze of a city, and we'll share a bar-hopping "progressive dinner" with the locals. (Lunch on your own, bar munchies supper included, sleep in Venice)
Day 11—Explore Venice's artisan workshops (perhaps Carnival masks, blown glass, gondola builders....) and hidden corners with my local friend. You’ll have the afternoon free to discover more sights…or just people-watch on the piazza with a glass of prosecco in hand. (Lunch and dinner on your own, sleep in Venice)
Day 12—A day in the Venetian lagoon, exploring the islands by boat. Each has its specialty: there are islands famous for glassblowing, lacemaking, artichokes, the cemetery—even some where plague victims quarantined. Over a Venetian feast tonight, we’ll toast our adventure and our travel friends. (Lunch on your own, dinner together, sleep in Venice)
Day 13—Tour over after breakfast. It’s easy to get to Venice’s airport, or to catch a train to Milan, Florence, or elsewhere to extend your vacation.
Tour itinerary subject to change.
What’s Included
Bologna
Included:
A small group experience of 10-15 people
Twelve nights accommodation, including breakfasts
Six group dinners & two group lunches, drinks included (reasonable limits)
All group sightseeing activity entrances and local guides
Transport by private bus between cities; train tickets to & from group stops
All tips for guides, hotels, restaurants, and drivers.
Pre-tour travel consultation with Margaret
Flexible reservation and cancellation policy
Not Included:
Airfare & airport transportation
Activities not included with the tour
Hotel extras and room service
Extra wine at group meals
Travel insurance
Conditions:
Tour itinerary and What’s Included details subject to change. Future substitutions will be approximately equal or better in value.
This tour requires a minimum of 12 travelers booked by April 1, 2024 to be viable.
FAQ
Siena
Where will this tour stay?
No generic high-rise business hotels on this tour--we stay in small, charming three- and four-star hotels right in the heart of the towns we visit. They’re all in historic structures, so each room may be different (and you may have to climb stairs!).
How much walking will there be on this tour?
There is some kind of walking tour each day, and you’ll certainly be walking more in your free time. Figure several miles a day, often on uneven cobblestones or on dirt paths around archaeological sites. Lots of standing on city sidewalks and marble floors can sometimes be equally tiring—make sure your back and knees can handle this. We’ll definitely work off our pasta and gelati!
What’s the balance between group time and free time?
This tour is designed to strike a balance between group time and your own free time to explore or just relax. I will be on hand to help you plan your activities during free time.
When should I plan to arrive in Rome for this tour?
Some travelers like to arrive a day or more early and book a hotel on their own, to start adjusting to the time change and to explore Rome sights we won’t be visiting as a group. You can also fly directly into Rome from all European hubs. If you arrive the day the tour starts, plan to get there before lunch to get settled before our start time.
What will we eat?
Of course we all know pasta and gelato—and we’ll certainly have our share!--but many Americans don’t realize how much variety Italian food has between regions. There are cream-stuffed buns and cheese-stuffed rice balls in Rome…truffles and wild boar in the Tuscany/Lazio countryside…the original “bologna” in Bologna (it’s 100% better than your elementary-school sandwich meat!)…and risotto in Venice. We will definitely taste our way through Italy on this tour!