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81. AI’s Most-Asked Italy Travel Questions, Answered (Part One)

Release Date: 02/24/2025

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Join thousands of other listeners on our Substack, The Foodletter!

In this episode of That Was Delicious, host Brooke Eliason kicks off a multi-week series dedicated to all things Italy. She dives deep into the most frequently asked questions about traveling to Italy, offering valuable insights from her years of experience leading Female Foodie Tours. From the best time to visit and how to navigate transportation to must-visit locations and food recommendations, Brooke shares everything you need to plan an unforgettable trip. Whether you're joining one of her tours or venturing out on your own, this episode is packed with essential travel tips to help you explore Italy with confidence.

Key Takeaways

[10:10] Best Time to Visit Italy – If possible, avoid peak season (June-August). Shoulder seasons (spring and fall) offer better weather, fewer crowds, and easier reservations. Winter can be magical, especially in cities like Venice and Rome.
[13:00] How Long to Stay – A week is good, but two to three weeks allow for deeper exploration. Don’t try to cram too many cities into a short trip.
[17:00] Transportation Tips – Trains are the easiest way to get around, using Trainline.com for bookings. Renting a car is best for remote areas but can be challenging for first-time travelers.
[33:32] Accommodation Advice – Booking hotels or Airbnbs early is recommended, especially in a busy year like 2025 (Jubilee Year).
[34:59] Packing & Fashion – Italians dress well; avoid athleisure and opt for business casual styles. Comfortable shoes are a must due to extensive walking.
[46:02] Safety & Pickpockets – Naples has the most theft concerns. Always keep valuables in front of you, use a crossbody bag, and avoid distractions from potential pickpockets.
[50:47] Dining Culture & Food Tips – Meals follow a structured course order: Antipasti (appetizers), Primi (pasta), Secondi (meat), Contorni (sides), Dolci (desserts). Research regional specialties before visiting.
[52:03] Must-Try Italian Dishes – Rome is known for pasta (Cacio e Pepe, Carbonara, Amatriciana). Florence for Bistecca Fiorentina. Naples for pizza.

Notable Quotes

(10:19) “If you can only visit Italy in the summer, do it! But if you have flexibility, aim for spring or fall—it’s a completely different experience.”
(41:59) “You will be walking so much in Italy—comfortable shoes are the most important thing you’ll pack!”
(39:13) “Italians honor the seasons with their clothing, so don’t expect to see sandals in March, even if it’s warm outside.”
(28:56) “When picking your itinerary, don’t just visit Rome, Florence, and Venice. Mix in smaller towns for a richer experience.”

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