Five Days in Rome
November 3-7, 2026
This hybrid tour is ideal for independent travelers who would also like to discover Rome in the short, quiet stretch between the end of high season and before Christmas. These 5 days will be filled with ancient Roman despots, Baroque drama, and plenty of Pecorino Romano.
We’ll do our best to scratch the surface of the extraordinary span of experiences to be had in Rome. Because I'm obsessed with Caravaggio, we'll hang out with him quite a bit, plus visit the Ara Pacis museum, the Baths of Caracalla, and do an after-hours tour of the Vatican Museum, not just for the Sistine Chapel, but to see Nero's bathtub made of imperial porphyry.
Between exploring neighborhoods and historical sites, we'll also discuss exactly why Bernini's St. Teresa is in ecstasy over Negronis at Dagnino and make sure to try pasta alla amatriciana, carbonara and norcia.
The first group meeting is late afternoon on November 3rd, and our last meeting is at 10 am on the 7th.
How it works
Join a small crew of curious, like-minded explorers for a five-day deep dive into one of Italy’s legendary cities—no cookie-cutter tours, just honest discovery and great company. Each day kicks off with an expert-guided walk that brings the city’s stories to life, followed by a gathering around the table for long, memorable lunches or dinners (four in total), where the conversation is as rich as the food.
There's no required hotel package; stay wherever suits your vibe and budget. If you want to stay in an Airbnb, I recommend the area around Campo di Fiori. If you want to stay in a 5-star, I like the Pantheon Iconic and can book that for you through my luxury hotel network. I will stay at Condominio Monti.
Expect lots of walking, plenty of unscripted moments, and an immersive city experience you can’t get from guidebooks—perfect for anyone who wants to dig deeper, eat well, and connect with Italy (and new friends) along the way. November can be cold, but it can also still be temperate and sunny.
$2,800 per person, due on July 1st. $500 non-refundable deposit to secure your spot right now.
Includes all tours and entrance tickets, and four shared meals.
