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

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

• Travel Dates:

  • Varies: Most JAN-MAR, AUG-NOV

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

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

2026 MILANO-CORTINA OLYMPICS GUIDE: 

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

UPDATES:  ITALY FARES ARE STILL REALLY LOW - MID $400s on several routes!  This sale won't last long - book fast! 

We're a little shocked to see these incredible fares to Italy during the Winter Olympics!   Flights to Milan and Venice put you right in the action - with events all over northern Italy.    And if the olympics aren't your think, the sale includes lots of dates JAN - MAR all over Italy (and a few AUG-NOV as well).   BOOK FAST if you find dates that work for you.  

🇮🇹 Why Visit Italy?

• THE 2026 WINTER OLYMPICS!

• 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.

   

What’s the Weather Like?

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

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

• January–March: Milder winter travel with highs in the 50s°F. 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.

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.}

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:

$441 MILAN, ITALY / JAN-APR, AUG-NOV

$458 VENICE, ITALY / JAN-MAR, AUG-NOV

$450 BOLOGNA, ITALY / JAN-MAR, AUG-NOV

$454 FLORENCE, ITALY / JAN-APR, AUG, NOV

$462 ROME, ITALY / JAN-MAR, AUG, NOV

$456 NAPLES, ITALY / JAN-MAR, AUG-NOV

$496 BARI, ITALY / JAN-MAR

LITTLE ROCK:

$441 MILAN, ITALY / JAN-MAR, AUG-NOV

$453 VENICE, ITALY / JAN-MAR, AUG-NOV

$447 BOLOGNA, ITALY / JAN-MAR, AUG-NOV

$471 FLORENCE, ITALY / JAN-APR, NOV

$467 ROME, ITALY / JAN-APR, NOV

$459 NAPLES, ITALY / JAN-MAR, AUG-NOV

$500 BARI, ITALY / JAN-MAR

FORT SMITH (FSM):

$459 MILAN, ITALY / JAN-MAR, AUG-NOV

$453 VENICE, ITALY / JAN-MAR

$447 BOLOGNA, ITALY / JAN-MAR, AUG-NOV

$473 ROME, ITALY / JAN-MAR

$456 NAPLES, ITALY / JAN-MAR

TEXARKANA (TXK):

$442 MILAN, ITALY / JAN-MAR, AUG-NOV

$453 VENICE, ITALY / JAN-MAR, AUG-NOV

$447 BOLOGNA, ITALY / JAN-MAR, AUG-NOV

$478 ROME, ITALY / JAN-MAR, AUG-NOV

$456 NAPLES, ITALY / JAN-MAR, AUG-NOV

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:

$433 MILAN, ITALY / JAN-MAR, AUG-NOV

AUSTIN: 

$441 MILAN, ITALY / JAN-MAR, AUG-NOV

$444 VENICE, ITALY / JAN-MAR, AUG-NOV

$436 BOLOGNA, ITALY / JAN-MAR, AUG-NOV

$467 FLORENCE, ITALY / JAN-APR, AUG-NOV

$461 ROME, ITALY / FEB-MAR, AUG-NOV

$448 NAPLES, ITALY / JAN-MAR, AUG-NOV

$459 CATANIA - SICILY, ITALY / JAN-MAR

HOUSTON:

$445 MILAN, ITALY / FEB-MAR, AUG-NOV

TEXARKANA (TXK):

$442 MILAN, ITALY / JAN-MAR, AUG-NOV

$453 VENICE, ITALY / JAN-MAR, AUG-NOV

$447 BOLOGNA, ITALY / JAN-MAR, AUG-NOV

$478 ROME, ITALY / JAN-MAR, AUG-NOV

$456 NAPLES, ITALY / JAN-MAR, AUG-NOV

MISSOURI DEPARTURES  /  AIRLINES: DELTA, AIR CANADA, UNITED

*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:

$439 MILAN, ITALY / JAN-MAR, AUG-NOV

$443 VENICE, ITALY / JAN-MAR, AUG-NOV

$447 BOLOGNA, ITALY / JAN-MAR, AUG-NOV

$454 FLORENCE, ITALY / JAN-APR, AUG-NOV

$457 ROME, ITALY / JAN-MAR, AUG-NOV

$448 NAPLES, ITALY / JAN-MAR, AUG-NOV

$496 BARI, ITALY / JAN-MAR, AUG-NOV

$459 CATANIA - SICILY, ITALY / JAN-MAR, AUG

KANSAS CITY:

$441 MILAN, ITALY / JAN-MAR, AUG-NOV

$452 VENICE, ITALY / JAN-MAR, AUG-NOV

$450 BOLOGNA, ITALY / JAN-MAR, AUG-NOV

$454 FLORENCE, ITALY / JAN-APR, AUG-NOV

$457 ROME, ITALY / JAN-MAR, AUG-NOV

$448 NAPLES, ITALY / JAN-MAR, AUG-NOV

$500 BARI, ITALY / JAN-MAR, AUG-NOV

$459 CATANIA - SICILY, ITALY / JAN-MAR, AUG

SPRINGFIELD:

$441 MILAN, ITALY / JAN-MAR, AUG-NOV

$452 VENICE, ITALY / JAN-MAR, AUG-NOV

$447 BOLOGNA, ITALY / JAN-MAR, AUG-NOV

$454 FLORENCE, ITALY / JAN-APR, AUG-NOV

$457 ROME, ITALY / JAN-MAR, AUG-NOV

$453 NAPLES, ITALY / JAN-MAR, AUG-NOV

$500 BARI, ITALY / JAN-MAR, AUG-NOV

$459 CATANIA - SICILY, ITALY / JAN-MAR, AUG

JOPLIN:

$489 MILAN, ITALY / JAN-MAR, AUG-NOV

$499 VENICE, ITALY / JAN-MAR, AUG-NOV

$494 BOLOGNA, ITALY / JAN-MAR, AUG-NOV

$498 FLORENCE, ITALY / JAN-APR, AUG-NOV

$501 ROME, ITALY / JAN-MAR, AUG-NOV

$509 NAPLES, ITALY / JAN-MAR, AUG-NOV 

OKLAHOMA DEPARTURES   /  AIRLINES: DELTA, AMERICAN, UNITED

*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:

$441 MILAN, ITALY / JAN-MAR, AUG-NOV

$453 VENICE, ITALY / JAN-MAR, AUG-NOV

$447 BOLOGNA, ITALY / JAN-MAR, AUG-NOV

$469 FLORENCE, ITALY / JAN-APR, AUG-NOV

$473 ROME, ITALY / JAN-MAR, AUG-NOV

$448 NAPLES, ITALY / JAN-MAR, AUG-NOV

$496 BARI, ITALY / JAN-MAR, AUG-NOV

$459 CATANIA - SICILY, ITALY / JAN-MAR, AUG

OKLAHOMA CITY

$441 MILAN, ITALY / JAN-MAR, AUG-NOV

$453 VENICE, ITALY / JAN-MAR, AUG-NOV

$447 BOLOGNA, ITALY / JAN-MAR, AUG-NOV

$450 FLORENCE, ITALY / JAN-APR, AUG-NOV

$477 ROME, ITALY / JAN-MAR, AUG-NOV

$466 NAPLES, ITALY / JAN-MAR, AUG-NOV

$496 BARI, ITALY / JAN-MAR, AUG-NOV

$459 CATANIA - SICILY, ITALY / JAN-MAR, AUG

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

$441 MILAN, ITALY / JAN-MAR, AUG-NOV

$453 VENICE, ITALY / JAN-MAR, AUG-NOV

$450 BOLOGNA, ITALY / JAN-MAR, AUG-NOV

$485 FLORENCE, ITALY / JAN-APR, AUG-NOV

$457 ROME, ITALY / JAN-MAR, AUG-NOV

$448 NAPLES, ITALY / JAN-MAR, AUG-NOV

$500 BARI, ITALY / JAN-MAR, AUG-NOV

$459 CATANIA - SICILY, ITALY / JAN-MAR, AUG

NASHVILLE:

$435 MILAN, ITALY / JAN-MAR, AUG-NOV

$443 VENICE, ITALY / JAN-MAR, AUG-NOV

$447 BOLOGNA, ITALY / JAN-MAR, AUG-NOV

$476 FLORENCE, ITALY / JAN-APR, AUG-NOV

$473 ROME, ITALY / JAN-MAR, AUG-NOV

$465 NAPLES, ITALY / JAN-MAR, AUG-NOV

$500 BARI, ITALY / JAN-MAR, AUG-NOV

$459 CATANIA - SICILY, ITALY / JAN-MAR, AUG

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:

$377 MILAN, ITALY / JAN-MAR, AUG-NOV

$443 VENICE, ITALY / JAN-MAR, AUG-NOV

$436 BOLOGNA, ITALY / JAN-MAR, AUG-NOV

$454 FLORENCE, ITALY / JAN-APR, AUG-NOV

$457 ROME, ITALY / JAN-MAR, AUG-NOV

$448 NAPLES, ITALY / JAN-MAR, AUG-NOV

$500 BARI, ITALY / JAN-MAR, AUG-NOV

$459 CATANIA - SICILY, ITALY / JAN-MAR, AUG

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

----------------------------------------

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!