Let’s talk about how late 2025 is the perfect time to think about your trip, before you start planning it.
A Rare Invitation: October 2025 Research Trip
Before diving into my trip-planning strategy, I have something special to announce:
Next month (yes, October!) I’m going on a research trip and I’d like to invite you to join me.
See the awe-inspiring temples of Paestum, where we will go deep into discussion rather than just “touring.”
Bake bread with Chef Mario Stellato and his grandmother.
Taste wine at my beloved Tempa di Zoe vineyard.
Geek out on medieval history with me in Salerno and go shopping.
You can also extend the adventure with two nights in Matera and a final night in Naples. Because it’s last-minute and at the magical end-of-season pricing, this is an opportunity I cannot repeat in another season. There are 4–5 spots filled, and I’m capping at 10.
Why You Should Dream NOW (Not Just Plan Later)
So many clients arrive to me stressed and glazed over. They’re paralyzed by too much information, and the most challenging part of planning an Italy trip is knowing how to sift through it all, but I can help you.
Why start now? Because dreaming early lets you clarify:
What do I want to FEEL on this trip?
What experiences genuinely matter most to me?
What can I afford to spend (and what’s realistic for 2026 Italy)?
Starting with intention and honesty is the secret to coming home fulfilled instead of overwhelmed or overspent.
Hard Truths: Logistics & Budget
Don’t overdo it: If you have 10 days, pick a maximum of three bases. Don’t be swayed by fast trains or bucket lists. Trenitalia won’t deliver you straight to the Amalfi Coast or Tuscan countryside—you’ll need transfers, ferry rides, or a car rental for rural adventures.
Timelines matter: The big cities (Rome, Florence, Venice) are best in the off-season (think February or early December). Prices drop and the crowds thin, which can be a dream for the right traveler.
Regional closures: Places like Amalfi and Puglia shut down after November 1st.
Budget-wise, don’t assume Italy is the cheap-and-cheerful destination it was in the days of the lira. The cost has shifted—especially for Americans. Get clear on your comfort zone and be upfront about your priorities: a great trip can be planned on any budget if you’re realistic from the start.
The Most Important Question: What Truly Inspires You?
Everyone always skips this step, so let me insist:
Do you crave outdoor adventure?
Dream of sitting in a Roman piazza like a Ripley character?
Want to reconnect with family or celebrate a milestone?
Clarifying how you want to feel will make all the difference.
My Four-Ingredient Recipe for a Great Italian Trip
Mix these in for the perfect adventure:
Plug In: See something iconic and take it in deeply—think Colosseum, Florence’s Duomo, or a UNESCO heritage marvel.
Unplug: Plan unstructured downtime—a wine tasting, a soak in thermal springs, or a two-hour people-watching session with a notebook in a piazza.
Indiana Jones Moments: Seek real adventure—ruins, archaeological wonders, challenging hikes, or a boat trip beneath ancient cliffs.
What You Love, Italian-Style: Bring your passion (cooking, fashion, sports, spirituality) and live it the Italian way for a fresh perspective.
Two Final Notes: Budget & Flight Myths
Be honest and up-front about your budget. Don’t feel guilty about your number—it’s your trip. Prioritize accordingly. If Venice is your dream, go all-in on one destination during the low season for a richer experience. It will likely be better than a three-city trip with a bigger budget.
And on flights? When you find a fare you’re satisfied with, book it and move on with your life.
For Paid Subscribers…
Sept 11th at 8 pm ET, I’m offering a live Zoom Destination Deep Dive on Matera (with replay available for three days).
Last month’s Florence Deep Dive, including a very detailed 5-day itinerary, is now available to purchase.
