Five Days in Venice
October 27-31, 2026
This hybrid tour is ideal for independent travelers who also want to explore Venice during the very beginning of the off-season, when it might be raining, but no less beautiful. Venice is a moody and atmospheric experience, and late October is a gorgeous time to visit this singular city without the large crowds.
Over the course of five days, we'll delve into the Venetian Renaissance with a key visit to the Gallerie dell'Accademia for an in-depth exploration of Vittore Carpaccio's paintings of Saint Ursula and the 11,000 Virgins. We'll visit the Scuola di San Rocco, the Jewish Ghetto, and explore the northern lagoon, which is the soul of Venice. And we'll adore the Four Tetrarchs outside the Basilica of San Marco.
Our food and wine experiences will center around cichetti culture. As a preview to our visit to the Peggy Guggenheim Museum, I recommend watching Ripley on Netflix, so you can start to immerse yourself in the rich inner world through which I like to explore Venice.
The first group meeting is late afternoon on October 27th, and our last meeting is at 10 am on the 31st.
How it works
Join a 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 morning kicks off with an expert-guided walk that brings the city’s stories to life, then everyone gathers around the table for long, memorable lunches or dinners (four total) where the conversation is as rich as the food.
There's no required hotel package; stay wherever fits your vibe and budget. Venice is small and more expensive than other cities. You may prefer to book an Airbnb in Canareggio or splurge for a 5 star hotel because of all the cities in Italy, I think Venice is the best place to do that. (If you'd like to do that, get in touch, we can book it for you with upgrades and perks.) Otherwise, I like the H1 Canova or Madama Garden Retreat.
Expect to do a lot of walking, as there are no cars or bikes in Venice. Be comfortable with getting lost, letting the journey be the destination, and probablly save up a bit of money for shopping because there are so many beautiful things to purchase in Venice. This is perfect for anyone who loves art, hates selfies, and wants to admire Venice for the surreal, glimmering, improbably beautiful creation that it is.
$3,100 per person, due on July 1st. $500 non-refundable deposit to secure your spot.
