Travel Agents Plan Incredible

Vacations to Italy

Sunset Travel & Cruise
Chicago IL, USA

From Chicago to…

Italy

We are specialists for planning vacations to Italy! We’ve been there dozens of times and know how to travel to Italy in style, and how to save you money with special insider travel deals.

From the beautiful artwork, crumbling ruins, and impressive palaces and castles that dot the horizon, we can help you see it all.

Whether you want to see the Leaning Tower of Pisa for the first time, taste wine in Chianti again, or simply eat the best food in the world, call the travel agents at Sunset Travel & Cruise in Chicago to help you understand all of your options and choose the best vacations, cruises, tours and more in Italy!

Italy Vacation Packages from Chicago's Best Travel Agency, Sunset Travel & Cruise - Sunset-Travel.com

First-timers visit Rome and Venice — and we can craft the perfect vacation there — but we can also take you further inside Italy to truly experience local culture in places you probably never even imagined exist.

Vibrant cities like Rome and Venice feature old and new mingling together seamlessly, but you can also enjoy the less-crowded coastal areas where you can relax on sandy beaches and swim in spectacular seas.

When you book your Italian vacation with Sunset Travel & Cruise, you’ll get a personal travel agent who has been there, done that, and can help you plan the perfect trip from start to finish.

“I will absolutely use Renee and Sunset Travel & Cruise for my next trip and highly recommend them to anyone looking for assistance planning a trip to Italy. They really know the country and how to ensure you have a once in a lifetime experience! Grazie Mille Renee and Team!” – Anne T.

Sunset Travel & Cruise

4.8

review us on

Luz Fernandez

00:05 31 Aug 24

Cabo was amazing. Thanks to Martha and booking with her she was great.

Linda Maman

11:12 21 Aug 24

Thank you Martha and Ryan for helping my husband and I celebrate our 10 year anniversary in Greece 🇬🇷. You both went above and beyond in putting the most amazing trip together for us.... Your expertise and recommendations were top notch!! I can’t wait to see what you will recommend next for us !! I highly recommend you bothread more

Cathy W

18:45 20 Aug 24

Just returned from a 4 night trip with my daughters to Punta Cana in the DR. Absolutely loved it and plan on returning. Martha was amazing! I will definitely be reaching out to Sunset Travel/Martha... to help plan future family vacations.read more

Elizabeth Perez

15:25 20 Aug 24

I went on my first solo trip to Punta Cana in the Dominican Republic. Martha was such a huge help, if it wasn't for her I'm not sure I would have done it. I would definitely recommend working with... Sunset Travel and Cruise, they're very helpful and accommodating.read more

Lolita Daniels

16:50 12 Aug 24

Martha Galvez is always wonderful when it comes to booking our all inclusive trips!! However, the resort we stayed at in Aruba was not to my liking this year! The check in clerk was not very... welcoming! Her uniform was filthy! There weren’t any entertainment shows on the resort! The food was not very appetizing! They didn’t have a wide selection of restaurants and stated they didn’t serve mimosa until after 12noon!! What!! Upon arrival to the room, Had to call room service to have the toilet seat replaced for as it was scarred and stained! The air conditioning was dripping water was all over the floor behind the lounge area leading towards my bed! Definitely a slip and fall hazard! No accommodations for the mini fridge, it was completely empty and hot! Wow! No complimentary soap everything glued to the walls as far as shower gel and soap! It’s almost as if they scaled back on all accommodations!! Definitely didn’t feel like all inclusive and I paid more for this trip than I’ve ever paid!! Will never stay at the Divi all inclusive Aruba again!!read more

NO ONE HELPS YOU LIKE A TRAVEL AGENT!

Experience Italy

Introduce Yourself to Italy
Rome
From the Sistine Chapel to the Colosseum, it’s a must-see item on your Italian bucket list.

Venice
Explore one of the most romantic cities in the world.

Florence

Milano
Go Back for More
Tuscany
No Italian experience is complete without seeing the Leaning Tower of Pisa.

Genoa

Bologna

The Lake Region

Naples and the Amalfi Coast

Puglia
Off the Beaten Path
Sicily
An entire trip in itself! Explore a culture all its own.

Marche
Take in nature reserves and a jazz festival, all in the same day.

Campania
See the Naples and Mount Vesuvius from an incredible helicopter ride.

Our Travel Agents Recommend

Top Destinations in Italy

Rome, Italy

Heading to Rome might be a little cliche, but it’s a bucket list destination for many people for a very good reason — it’s incredible. As one of the finest and oldest cities in the world, it has a history that spans over 2,500 years and it has been a hub of power, politics, culture, and development since it made its way onto the map.

There are various different accounts of how this majestic place was built, and various Roman emperors and Caesars have ruled the land — the place where the colossal Roman Empire grew from. Over the years, various monuments, palaces, and religious buildings have been constructed in the city, which are now beautiful tourist attractions and a reminder of the city’s glorious past.

Rome wasn’t built in a day — and can’t be seen in a day, either — but some of the most popular attractions to put on your itinerary include:

The Colosseum
St. Peter’s Square
The Pantheon
Trevi Fountain
Roman Forum
Sistine Chapel
Villa Borghese Gardens
Trastevere
Piazza del Popolo
Spanish Steps

Venice

Known as one of the most romantic destinations in the world, Venice is full of churches, buildings, old bridges, monuments and piazzas that create the artistic and cultural vivacity that marks the history of this city.

There are sandy beaches washed by the Adriatic Sea, and luxury resorts that offer vacationers every kind of comfort. You can walk the many paths traversing the green scenery, and take in peaceful rivers that pass through small towns that are rich in history and fascinating villas. Then of course, there’s the famous Venetian Lagoon, amazing cuisine, and a wine list that’s world-renowned.

From outdoor sports, nightlife in the many glamorous night spots, and shopping in the typical crafts workshops to buy souvenirs to simply relaxing with a glass of vino, there’s something for everyone in Venice.

Popular Venetian attractions include:

Saint Mark’s Basilica
Doge’s Palace
Academy Gallery
Historic Regatta
Venice Casino
St. Mark’s Square
Peggy Guggenheim Collection
Piazza San Marco
Ducal Palace
Teatro La Fenice

Call the Italian Travel experts at Sunset Travel & Cruise to take you from Chicago to anywhere in Italy, in style! We’ve traveled all over the country and can provide insights and tips to create a truly memorable vacation.

Florence

Florence is known as the “Cradle of the Renaissance” and begs for you to explore its monuments, churches and buildings, most of which were built during the period. It is considered one of the best-preserved Renaissance centers of art and architecture in the world.

Located just north of the Chianti region of Italy, Florence invites you to relax over a long dinner and a few glasses of a Super Tuscan Red, with schiacciata alla Fierentina for dessert.

Take time to do some shopping on the Via de’ Tornabouni, a street that’s home to many major fashion houses, dating back hundreds of years.

Or head to the center of town, the Centro Storico di Ferenze, which offers architecture and culture truly unique to the city.

Other attractions in Florencce include:

Santa Maria del Fiore
Ponte Vecchio
San Lorenzo
Palazzo della Signoria
Loggia dei Lanzi
Palazzo Medici Riccardi
Palazzo Davanzati
Vasari Corridor
Galleria dell’Accademia
Biubbe Rosse café

Call the Italian Travel experts at Sunset Travel & Cruise to take you from Chicago to anywhere in Italy, in style!

Milan

With its amazing, gothic architecture and vibrant arts culture, a visit to Milan should be on your list! Start with the third-largest church in the world, Santa Maria delle Grazie, then head over to Fiera Milano to lose yourself at one of the most important exhibition centers.

Located in Northern Italy, and the second largest city in the country, Milan is sure to wow your tastebuds. With unique flavors and ingredients, more rice than pasta and heavy on the butter, the city invites you to try some cotoletta alla Milanese, a breaded veal, or risottoa all Milanese with saffron and beef marrow.

Explore Milan’s museums and art galleries, which host some of the most important collections in the world. Or have your own night at the opera at the famed La Scala operahouse, one of the world most prestigious.

Popular Venetian attractions include:

Colonne di San Lorenzo
Sant’Ambrogio
Castello Sforzesco
Biblioteca Ambrosiana
Palazzo Belgioisos
Porta Ticinese
Sempione Park
Montanelli Gardens
Teatro degli Arcimbold

Call the Italian Travel experts at Sunset Travel & Cruise to arrange your trip to Milan!

Travel Agency Specializing in Italy Vacations - Sunset Travel & Cruise in Chicago

Our Travel Agents Recommend

Exploring More in Italy

Tuscany

Located in central Italy and stretching from the Apennines to the Tyrrhenian Sea, Tuscany is one of the most popular international tourist destinations. The landscape is spectacular, with a coast that alternates long and sandy beaches, like the Versilia beach, with mountains and rocky cliffs.

And the history? You can explore medieval villages, historical towns, castles and defense systems, and beautiful abbeys. Then there are dozens of spas that offer vacation relaxation thanks to their thermal waters and well-equipped facilities for all types of treatments.

You’re going to want to take in the tastes, as they have some of the best food on the planet — but yet they’re very simple. Sipping local wines and dipping bread into just-pressed smooth olive oil is one of our favorite things to do in Tuscany, and finding a winery will be no problem.

You’ll find typical appetizers of crostini and soup alongside main dishes of mullets, bistecca fiorentina (grilled T-bone steak) and guinea-fowl meat. For dessert? Castagnaccio (chestnut cake), buccellato (anise cake) and cantucci — and of course, wine.

The more popular attractions in Tuscany include:

The Leaning Tower of Pisa
Castello di Volpaia
Florence
Cinque Terre
Siena
Ciacci Piccolomini d’Aragona
Castello del Trebbio
Chianti
Monti dell’Uccellina
The Uffizi

Genoa

One of the busiest, and most important port cities on the Mediterranean Sea, Genoa, Italy is a sight to be seen!

With a redeveloped harbour area featuring Renaissance and Baroque architecture, palaces, museums and galleries, there is enough to do it fill an entire week with activities and sites.

Take in the dolphins and sharks at the aquarium or wander through Palazzi dei Rolli, a Word Heritage site of unique streets and palaces.

A boat ride will give you the most impressive view of this dramatic city, with its pastel buildings perched in the hills, overlooking the curved oceanfront. It’s truly a sight to be seen!

The more popular attractions in Genoa include:

Cattedrale di San Lorenzo
Palazzo Rosso
Musei di Strada Nuova
Porto Antico
Old Town
Caffe dei Musei
Piazza delle Erbe
Museum of Sant’Agostino
Belvedere Castelletto

Contact Sunset Travel & Cruise today for a Free Travel Consultation and complete arrangements to travel to Genoa, or anywhere in Italy!

Bologna

A crossroads between north and south, east and west, Bologna Italy is a lively city that’s easy to get to, and go anywhere from!

With it’s well-preserved historical center and one of the largest, permanent trade fairs in Europe, it’s definitely a city to be explored.

Start with the Piazza Maggiore, lined with arched colonnades, cafes and historic buildings while you take in the famed Fountain of Neptune. Walk through extensive, elegant porticoes while admiring the architecture protected from the hot sun.

Then, stop for some famous Bolognese sauce on your tagliatelle for lunch, or sample renowned proscuitto, mortadella and salumi with exquisite cheeses.

If you love music, Bologna not only has a deep history, but an evolution to its music that makes it a vibrant part of modern life.

Things to see and do in Bologna include:

University of Bologna (oldest university in the world)
Teatro Comunale di Bologna
Pignoletto dei Colli Bolognesi
Due Torri
San Petronio
Porta Saragozza
Sanctuary of the Madonna di San Luca
San Petronia Basilica

To see Bologna, or tour any part of Italy, contact the Italian travel experts at Sunset Travel & Cruise in Chicago. We’ve been there dozens of times and look forward to planning your Italian experience!

The Lake Region

The Lake Region of Italy, located in Lombardy, is a nature-lovers and adventurers paradise! It features gorgeous landscapes, ancient castles, villages lost in time and places rich in history and character.

If you’re the adventurous type, there is no shortage of activities. From swimming to canoeing, rock climbing, mountain biking, horseback riding and golfing, endless adventures await you!

Be sure to take the time to relax with an amazing meal of fish and seafood from the local lakes, exquisite olive oil, hand-harvested vegetables and of course, famous Italian wine.

From the largest lake to the smallest stream, the Lake Region of Italy is a must-see for water lovers of any age!

Contact Sunset Travel & Cruise to arrange your entire trip to Italy’s Lake Region and see a different side of this amazing country!

Lake Garda
With a 100-mile loop around the lake, Garda is the perfect outdoor playground! Visit its Botanic Garden on Mount Baldo, or the archaeological wonder known as Grotte di Catullo.

Lake Como
Known for its lavish villas and breathtaking views, Como is a paradise in itself. Take a cable car to Brunate, or hike it if your legs can withstand the walk!

Lake Maggiore
The most popular lake in the region, Maggiore is popular for weekenders and vacationers alike. Visit one of the islands or explore its many parks.

Lake Iseo
A ‘hidden gem’, Iseo’s features scenery of lush mountains and crystal blue waters. Explore medieval towns, or hike through a walnut grove to take in the view.

Naples

As one of the oldest, continually inhabited urban areas in the world, Naples Italy has an incredible story that should be on any history buff’s bucket list.

A UNESCO Word Heritage site, there is no lack of medieval castles, classical ruins and a large number of culturally and historically significant sites, including 448 historical churches.

The Naples National Archaeological Museum features one of the most extensive collections of artifacts from the Roman Empire, and of course there are the ruins of Pompeii and Herculaneum to explore.

Take a trip under Naples, to its series of caves and structures in the subterranean, including an unforgettable experience in the catacombs.

When you’re done exploring, you must experience pizza in Naples – where it all originated. Or choose from hundreds of fine eateries, as the city boasts more Michelin stars of any Italian city.

The more popular attractions in Naples include:

Centro Direzionale
Palace of Caserta
Pompeii
Herculaneum
Posillipo
Phlegraen Fields
Vesuvius
Palace of Caserta
Piazza del Plebiscito
Castel dell’Ovo
Villa Comunale

Contact the Italian travel agency experts! Sunset Travel & Cruise agents have explored the country dozens of times, and can create your perfect vacation from start to finish.

Puglia

An area in ‘the boot’ of Southern Italy, Puglia (also known as Apulia), is known for its whitewashed hill towns and hundreds of miles of coastline, the longest of the mainland.

Explore 2 national parks, go sightseeing and take in the amazing baroque architecture or sample exquisite olive oil from their 50-60 Million olive trees.

With ancient farmlands, fresh local produce such as artichokes, tomatoes, aubergine, asparagus and mushrooms are a staple of the local cuisine.

Puglia’s pristine beaches aren’t overly populated, and allow for soothing days soaking in the tropical sun. Or, take an unforgettable day trip to the Tremiti Islands.

For a truly authentic Italian experience, Puglia delivers, complete with long, relaxing afternoons where local shops are closed.

Sights to see in Puglia include:

Gargana Peninsula
San Giovanni Rotondo
Alberobello
Alta Murgia
Gargano
Iapygians
Salento
Terra d’Otranto

Vacation Packages to Campania Italy from Chicago's Best Travel Agency, Sunset Travel & Cruise - Sunset-Travel.com

Our Travel Agents Recommend

Other Destinations in Italy

Sicily

The largest island in the Mediterranean Sea, Sicily is worthy of an entire trip dedicated to exploring this unique region of Italy.

With a distinctive culture and important Archaeological and ancient sites, including the Valley of the Temples and Necropolis of Pantalica, Sicily is a melting pot of different influences. From ancient civilizations to French and Albanian inspired structures and food, discover something different here!

With fertile soil from its active volcanoes, and a pleasant climate, fruits and nuts flourish here. And then there’s the seafood! It’s out of this world paired with a local Marsala wine or world-famous limoncello.

Popular places in Sicily include:

Mount Etna
Zingaro Natural Reserve
Valle dei Templi
Villa Romana del Casale
Aeolian Islands
Syracuse
Soluntum
Piazza Armerina
Coastal Towers
Teatro Massimo

Campania

The mild climate, the beauty of the coasts, the richness of its art and history, and the love for food make Campania a must-see tourist destination for those journeying into Italy. As one of the regions of Southern Italy, it stretches along the Tyrrhenian Sea, from the mouth of the Garigliano River to the Gulf of Policastro. The seas boast intense colors and the coasts are flourishing Mediterranean vegetation.

And of course, there’s Mount Vesuvius, the only active volcano in Europe. And Naples, which is known for its liveliness and the splendid colors of the sea, but also for its history and old town center — the biggest in Europe, with an authentic museum under the open sky. Whether you want to take in the history, see the land by bike or foot, just relax in a thermal spa, or explore Capri, known for the social life and luxury, Campania can deliver.

Popular attractions include:

Ischia Spa
Mount Vesuvius
Pizzeria Capri Marano
Pompeii
Free Time Acquapark
Matese Regional Park
Agnano Crater
Caserta
Helicopter Tour over Naples
Ravello Festival

Contact Sunset Travel & Cruise for a personal travel agent who can create the perfect trip to anywhere in Italy.

Marche

If you’re looking to get away from the tourist crowds, a trip to this region of Central Italy is the solution. The winding landscape shows off ts multi-faceted beauty through cliffs and caves that overlook unforgettable beaches perfect for lazing out in the sun before jumping into the crystal clear waters of the seas. Then there are hills steeped in history and tradition, all set up against a backdrop of mountains and the greenery of its nature reserves.

You can enjoy birdwatching and spotting golden eagles and owls, while the more adventurous can take long walks through the woods and forests, or go horseback riding, canoeing and mountain biking.

For those who enjoy winter sports, the Apennines offer up over nine ski resorts, while ice skaters will enjoy the Ice Palace in Ussita.

Some of the most popular things to do in Marche include:

Frasassi Caverns
Furlo Gorge
Gradara Castle
San Bartolo Nature Park and Beach
Sea Turtle Sanctuary
Piazza del Popolo
Torre del Borgo Tower Museum
Conero Coast
Ancona Jazz
Palazzo Ducale

Vacation Packages to Italy

Sunset Travel & Cruise agents will guide you in making the best travel decisions!

Get the best options and the best deals on:

Flights & Hotels
Ground Transportation
Entertainment & Attractions
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We’re here to help you every step of the way!

Travel Agent

Insights…

“Rome is the most beautiful city!

Easy to walk, full of surprises and wonderful monuments. The biggest part of the city reminds you the ancient roman empire, so you think — especially in the night — that you soon you will meet a gladiator in the next corner! Excellent food, coffee and ice cream! Generally good weather, gentle people and nightlife. What else do you need?”

“It was an utter delight

to have all the arrangements for a week of wine tasting in Tuscany made for us and to have a driver/guide to manage our transportation and enhance our experiences through her knowledge as we visited various hill towns, attractions and wineries. The week was perfect, the borgo where we stayed was charming and traditionally Tuscan, the wines delightful and the scenery breathtaking.”

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TALK WITH EXPERT TRAVEL AGENTS!

773-929-8155

vacations@sunset-travel.com

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732 W Fullerton Ave.
Chicago, IL 60614

Located in Chicago’s Lincoln Park neighborhood and crafting amazing vacations since 1973, Sunset Travel & Cruise Agency is the travel agency to go to when you’re looking for more than just trip, but a life-changing travel experience.

We take the time to understand our clients, create amazing vacations all over the world and provide support for your entire journey!

Vacations to Italy

Italy

Experience Italy

Top Destinations in Italy

Rome, Italy

Venice

Florence

Milan

Exploring More in Italy

Tuscany

Genoa

Bologna

The Lake Region

Naples

Puglia

Other Destinations in Italy

Sicily

Campania

Marche

Vacation Packages to Italy

Preferred Travel Dates

Insights…

“Rome is the most beautiful city!

“It was an utter delight

Travel Stories…

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TALK WITH EXPERT TRAVEL AGENTS!