ITALY:  $500s Roundtrip!

• Destinations: Milan, Venice, Bologna, Florence, Rome, Naples, Catania (Sicily)

• Departures: AR, MO, KS, TX, OK, TN, NC

• Travel Dates:

  • Varies - OCT–March (including fall, winter holidays, and early spring 2025!)

• Airlines: American, United, Delta, British Airways, and partners

• Additional Highlights: Lodging tips for over 60 Italian cities and towns in the Travel Resources Guide!

PRICES:  These fares are $300 - $800 below usual for these cities / these dates! 

Introduction

Prices just dropped this afternoon!  We're seeing $500s RT on lots of routes to Italy!

With travel dates available from October through March, it’s the perfect time to plan an Italian escape for fall, winter holidays, or early spring—whether you’re picturing bustling piazzas, quiet coastal villages, or world-famous landmarks.

🇮🇹 Why Visit Italy?

• Milan: Italy’s fashion capital mixes historic cathedrals with chic urban energy—plus easy train access to Lake Como.

• Venice: Explore a floating city of winding canals, grand palaces, and timeless romance.

• Bologna: Food lovers rejoice—this medieval city is known for some of Italy’s best cuisine (and fewer tourists!).

• Florence: The cradle of the Renaissance—art, architecture, and incredible views from Piazzale Michelangelo.

• Rome: The Eternal City—wander from the Colosseum to Trastevere’s cobblestone alleys with espresso in hand.

• Naples: Vibrant street life, proximity to Pompeii, and the birthplace of true Neapolitan pizza.

• Catania (Sicily): A dramatic city on the slopes of Mount Etna—amazing seafood, history, and gateway to Sicily’s rugged beauty.

What’s the Weather Like?

• September–October: Warm, golden autumn days—highs in the 70s–80s°F (21–28°C). Perfect for sightseeing without summer crowds.

• November–December: Cooler, festive atmosphere with highs in the 50s–60s°F (10–18°C). Great for holiday lights, markets, and cozy trattorias.

• January–March: Milder winter travel with highs in the 50s°F (10–15°C). Fewer tourists, lower prices, and crisp, clear days—ideal for city walks and museum visits.

First-Timer’s Tips for Italy

• Move city-to-city by train. Italy’s rail system is fast, easy, and scenic—perfect for visiting multiple cities in one trip.

• Stay central. Book hotels or Airbnbs within walking distance of the city center—it’s worth every penny to be near the piazzas and sights.

• Plan meals later. Dinner typically starts after 7:30 p.m.—slow down, enjoy long meals, and embrace Italy’s relaxed rhythm.

• Cash still matters. Some smaller cafés and shops prefer cash, especially outside big tourist hubs.

• Embrace the pace. Italy isn't meant to be rushed—leave space in your days for lingering, wandering, and spontaneous discoveries.

If you love art, food, history, or just beautiful chaos, Italy will feel like home the moment you arrive.

Plan Your Italian Escape

With $500s–$600s fares and easy travel dates stretching into March 2025, now is the perfect time to lock in your Italian getaway.
From the gondolas of Venice to the trattorias of Rome, adventure—and espresso—awaits. 🇮🇹✈️🍝

Travel Lodging Guide

Our Airbnb Guide for Italy features curated lodging options in 64 cities and towns! From stylish apartments in Rome to hillside villas in Tuscany, these recommendations make planning your stay effortless.

_{*Click on flight links below to be directed to sample dates / flights.  This is a great starting place to start finding dates that work for you.  Prices were valid when this fare alert was assembled - but are subject to change at any moment.}

MISSOURI DEPARTURES

*Link takes you to a sample flight date on the google flights calendar.  To find a different date, simply click on the provided date in the top right - and google's calendar will open up for you.  Then, you can start your search. 

 ST LOUIS:

$575 MILAN, ITALY / UNITED, AMERICAN / AUG-MAR

$574 VENICE, ITALY / DELTA, AMERICAN, UNITED / OCT-MAR

$567 BOLOGNA, ITALY / AMERICAN, DELTA, UNITED / OCT-MAR

$652 FLORENCE, ITALY / AMERICAN, UNITED, DELTA / OCT-MAR

$572 ROME, ITALY / FINNAIR, DELTA, AIR FRANCE / OCT-MAR

$572 NAPLES, ITALY / AMERICAN, BRITISH / OCT-MAR

KANSAS CITY:

$599 MILAN, ITALY / UNITED, AMERICAN / OCT-MAR

$574 VENICE, ITALY / DELTA, AMERICAN, UNITED / OCT-MAR

$599 BOLOGNA, ITALY / AMERICAN, DELTA, UNITED / SEP-MAR

$606 FLORENCE, ITALY / AMERICAN, UNITED, DELTA / OCT-MAR

$585 ROME, ITALY / FINNAIR, DELTA, AIR FRANCE / OCT-MAR

$572 NAPLES, ITALY / AMERICAN, BRITISH / OCT-MAR

SPRINGFIELD:

$547 MILAN, ITALY / UNITED, AMERICAN / OCT-MAR

$574 VENICE, ITALY / DELTA, AMERICAN, UNITED / OCT-MAR

$567 BOLOGNA, ITALY / AMERICAN, DELTA, UNITED / SEP-MAR

$573 FLORENCE, ITALY / AMERICAN, UNITED, DELTA / OCT-MAR

$595 ROME, ITALY / FINNAIR, DELTA, AIR FRANCE / OCT-MAR

$572 NAPLES, ITALY / AMERICAN, BRITISH / OCT-MAR

JOPLIN:

$566 MILAN, ITALY / UNITED / OCT-MAR

$627 VENICE, ITALY / UNITED / OCT-MAR

$657 BOLOGNA, ITALY / UNITED / SEP-MAR

$661 FLORENCE, ITALY / UNITED / OCT-MAR

$644 ROME, ITALY / UNITED / OCT-MAR

TEXAS DEPARTURES

*Link takes you to a sample flight date on the google flights calendar.  To find a different date, simply click on the provided date in the top right - and google's calendar will open up for you.  Then, you can start your search.   

DALLAS:

$551 MILAN, ITALY / UNITED, AMERICAN / OCT-MAR

$606 VENICE, ITALY / DELTA, AMERICAN, UNITED / OCT-MAR

$571 BOLOGNA, ITALY / AMERICAN, DELTA, UNITED / SEP-MAR

$559 FLORENCE, ITALY / AMERICAN, UNITED, DELTA / OCT-MAR

$564 ROME, ITALY / FINNAIR, DELTA, AIR FRANCE / OCT-MAR

$550 NAPLES, ITALY / AMERICAN, BRITISH / SEP-MAR

AUSTIN:  DEC

$574 MILAN, ITALY / UNITED, AMERICAN / OCT-MAR

$574 VENICE, ITALY / DELTA, AMERICAN, UNITED / OCT-MAR

$589 BOLOGNA, ITALY / AMERICAN, DELTA, UNITED / SEP-MAR

$647 FLORENCE, ITALY / AMERICAN, UNITED, DELTA / OCT-MAR

$607 ROME, ITALY / FINNAIR, DELTA, AIR FRANCE / OCT-MAR

$572 NAPLES, ITALY / AMERICAN, BRITISH / OCT-MAR

HOUSTON:

$594 MILAN, ITALY / UNITED, AMERICAN / SEP-MAR

$602 VENICE, ITALY / DELTA, AMERICAN, UNITED / OCT-MAR

$595 BOLOGNA, ITALY / AMERICAN, DELTA, UNITED / SEP-MAR

$642 FLORENCE, ITALY / AMERICAN, UNITED, DELTA / OCT-MAR

$620 ROME, ITALY / FINNAIR, DELTA, AIR FRANCE / OCT-MAR

$655 NAPLES, ITALY / AMERICAN, BRITISH / OCT-MAR

ARKANSAS DEPARTURES

*Link takes you to a sample flight date on the google flights calendar.  To find a different date, simply click on the provided date in the top right - and google's calendar will open up for you.  Then, you can start your search. 

XNA:

$594 MILAN, ITALY / UNITED, AMERICAN / AUG-MAR

$599 VENICE, ITALY / DELTA, AMERICAN, UNITED / OCT-MAR

$587 BOLOGNA, ITALY / AMERICAN, DELTA, UNITED / SEP-MAR

$573 FLORENCE, ITALY / AMERICAN, UNITED, DELTA / OCT-MAR

$612 ROME, ITALY / FINNAIR, DELTA, AIR FRANCE / OCT-MAR

$572 NAPLES, ITALY / AMERICAN, BRITISH / OCT-MAR

$688 CATANIA, SICILY, ITALY / UINTED, AMERICAN, IBERIA / OCT-FEB

LITTLE ROCK:

$599 MILAN, ITALY / UNITED, AMERICAN / AUG-MAR

$574 VENICE, ITALY / DELTA, AMERICAN, UNITED / OCT-MAR

$598 BOLOGNA, ITALY / AMERICAN, DELTA, UNITED / SEP-MAR

$611 FLORENCE, ITALY / AMERICAN, UNITED, DELTA / OCT-MAR

$585 ROME, ITALY / FINNAIR, DELTA, AIR FRANCE / OCT-MAR

$572 NAPLES, ITALY / AMERICAN, BRITISH / OCT-MAR

OKLAHOMA DEPARTURES

*Link takes you to a sample flight date on the google flights calendar.  To find a different date, simply click on the provided date in the top right - and google's calendar will open up for you.  Then, you can start your search. 

TULSA:

$594 MILAN, ITALY / UNITED, AMERICAN / OCT-MAR

$594 VENICE, ITALY / DELTA, AMERICAN, UNITED / OCT-MAR

$587 BOLOGNA, ITALY / AMERICAN, DELTA, UNITED / OCT-MAR

$573 FLORENCE, ITALY / AMERICAN, UNITED, DELTA / OCT-MAR

$585 ROME, ITALY / FINNAIR, DELTA, AIR FRANCE / OCT-MAR

$572 NAPLES, ITALY / AMERICAN, BRITISH / OCT-MAR

OKLAHOMA CITY

$594 MILAN, ITALY / UNITED, AMERICAN / OCT-MAR

$574 VENICE, ITALY / DELTA, AMERICAN, UNITED / OCT-MAR

$567 BOLOGNA, ITALY / AMERICAN, DELTA, UNITED / OCT-MAR

$573 FLORENCE, ITALY / AMERICAN, UNITED, DELTA / OCT-MAR

$585 ROME, ITALY / AMERICAN, FINNAIR, DELTA, AIR FRANCE / OCT-MAR

$572 NAPLES, ITALY / AMERICAN, BRITISH / OCT-MAR

TENNESSEE DEPARTURES

*Link takes you to a sample flight date on the google flights calendar.  To find a different date, simply click on the provided date in the top right - and google's calendar will open up for you.  Then, you can start your search. 

MEMPHIS

$594 MILAN, ITALY / UNITED, AMERICAN / OCT-MAR

$594 VENICE, ITALY / DELTA, AMERICAN, UNITED / OCT-MAR

$599 BOLOGNA, ITALY / AMERICAN, DELTA, UNITED / SEP-MAR

$664 FLORENCE, ITALY / AMERICAN, UNITED, DELTA / OCT-MAR

$644 ROME, ITALY / FINNAIR, DELTA, AIR FRANCE / OCT-MAR

$572 NAPLES, ITALY / AMERICAN, BRITISH / OCT-MAR

NASHVILLE:

$594 MILAN, ITALY / UNITED, AMERICAN / OCT-MAR

$574 VENICE, ITALY / DELTA, AMERICAN, UNITED / OCT-MAR

$589 BOLOGNA, ITALY / AMERICAN, DELTA, UNITED / OCT-MAR

$647 FLORENCE, ITALY / AMERICAN, UNITED, DELTA / OCT-MAR

$603 ROME, ITALY / FINNAIR, DELTA, AIR FRANCE / OCT-MAR

$572 NAPLES, ITALY / AMERICAN, BRITISH / OCT-MAR

KANSAS DEPARTURES

*Link takes you to a sample flight date on the google flights calendar.  To find a different date, simply click on the provided date in the top right - and google's calendar will open up for you.  Then, you can start your search. 

WICHITA:

$599 MILAN, ITALY / UNITED, AMERICAN / OCT-MAR

$574 VENICE, ITALY / DELTA, AMERICAN, UNITED / OCT-MAR

$599 BOLOGNA, ITALY / AMERICAN, DELTA, UNITED / OCT-MAR

$573 FLORENCE, ITALY / AMERICAN, UNITED, DELTA / OCT-MAR

$633 ROME, ITALY / FINNAIR, DELTA, AIR FRANCE / OCT-MAR

$572 NAPLES, ITALY / AMERICAN, BRITISH / OCT-MAR

NORTH CAROLINA DEPARTURES

*Link takes you to a sample flight date on the google flights calendar.  To find a different date, simply click on the provided date in the top right - and google's calendar will open up for you.  Then, you can start your search. 

RALEIGH:

$551 MILAN, ITALY / UNITED, AMERICAN / MAY, OCT-MAR

$574 VENICE, ITALY / DELTA, AMERICAN, UNITED / OCT-MAR

$594 BOLOGNA, ITALY / AMERICAN, DELTA, UNITED / OCT-MAR

$647 FLORENCE, ITALY / AMERICAN, UNITED, DELTA / OCT-MAR

$619 ROME, ITALY / FINNAIR, DELTA, AIR FRANCE / OCT-MAR

$597 NAPLES, ITALY / AMERICAN, BRITISH / OCT-MAR

Here are some lists of recommended properties in Italy.   

 
Alberobello, Italy AirBNB List

Amalfi, Italy AirBNB List

Assisi, Italy AirBNB List:

Bari, Italy AirBNB List:

Bergamo, Italy AirBNB List

Bologna, Italy AirBNB List

Bolzano, Italy Air BNB List

Bonassola, Italy AirBNB List

Cagliari, Italy AirBNB List

Camogli, Italy AirBNB List

Capri, Italy AirBNB List

Catania Centro, Sicily, Italy AirBNB List

Como, Lombardy, Italy AirBNB List

Conca dei Marini, Italy AirBNB List

Corniglia, Cinque Terre, Italy AirBNB List

Florence 1, Italy AirBNB List

Genoa, Italy AirBNB List

Lecce, Apulia, Italy AirBNB List

Levanto, Liguria, Italy AirBNB List

Locorotondo, Italy AirBNB List

Lucca, Tuscany, Italy AirBNB List

Manarola, Cinque Terre, Italy AirBNB List

Mantua, Italy AirBNB List

Matera, Italy AirBNB List

Matera, Italy 2 AirBNB List

MIlan, Italy AirBNB List

Molfetta, Italy AirBNB List

Monopoli, Italy AirBNB List

Monterosso, Cinque Terre, Italy AirBNB List

Monticchiello, Italy AirBNB List

Naples, Italy AirBNB List

Ostuni, Italy AirBNB List

Palermo 1, Italy AirBNB List

Palermo 2, Italy AirBNB List

Pantelleria (island), AirBNB List

Parma, Emilia-Romagna, Italy AirBNB List

Perugia, Italy AirBNB List

Pienza, Italy AirBNB List

Polignano a Mare, Italy AirBNB List

Portofino, Italy AirBNB List

Portovenere, Italy AirBNB List

Positano, Italy AirBNB List

Praiano, Italy AirBNB List

Procida Island, Italy AirBNB List

Ravello, Italy AirBNB List

Riomaggiore, Cinque Terre, Italy AirBNB List

Santa Margherita, Italy AirBNB List

Taormina, Sicily, Italy AirBNB List

Tropea, Calabria Italy AirBNB List

Turin, Italy AirBNB List

Vicenza, Italy AirBNB List

Venice, Italy 1  AirBNB List

Venice, Italy 2 AirBNB List

Vernazza, Cinque Terre, Italy AirBNB List

Verona, Italy AirBNB List

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Castles of Italy, AirBNB List

The Dolomites, AirBNB List

 1. Reviews - Only units with and established rental record, and the very best reviews make the cut! 

2. Location:  This is the most important thing for travelers.  Only units in the best neighborhoods convenient to the sights make the list.  (rural rentals are exceptions)

3. Value:  We only recommend units that are decent to excellent values for what / where you’re renting. 

4. View:  We keep an eye out for units that have an excellent view!  

That's it.  We screen for great reviews, great locations, great views, and great prices.  This should give you some great options to start with whenever you're planning your next adventure!