Italy

SPRING/SUMMER           FALL/WINTER           WHAT TO DO
What to wear while vacationing in Italy, Italian fashion style on holiday. What to pack and how to organize your luggage, travel guide!
You may have the universe if I may have Italy.
— Giuseppe Verdi
 

Home to some of the world’s most incredible food, art, architecture and fashion, Italy is a glorious place of tradition that elates really like no other! 🍝 You may be escaping to Rome for a long weekend, driving a rental car through Tuscany, cruising from Florence to Venice on a Vespa, basking on the beaches in Positano, hiking Vesuvius in Sicily, wading through flooded streets in Venice, or photobombing the Leaning Tower of Pisa. Italy’s geography delights with extraordinary diversity — from the snowy Alps of the north to the volcanic craters of the south. Use these tips and lists to build your own packing list for your next Italian adventure!

The best luggage for Italy:

The best luggage for a trip to Italy is:

  • Nothing bigger than a carry on: If you’ve ever stepped off a train in Italy with a huge roller bag, a carry on, and your daypack, you know what we’re talking about. No. Just no. Big luggage is not for Italy. Travel lighter!

Travel to Italy with carry on luggage only if possible, either a roller bag or something without wheels if you’re up for carrying either a duffel bag on your shoulder or a travel backpack. Getting on and off of trains and navigating streets of very beautiful, but roughly paved, villages means the lighter you travel the better. At times, even if you have a roller bag you’ll need to pick it up to carry it up stone steps so be sure you’re able to do that! Also, many hotels in Italy don’t have elevators (or small, slow moving elevators) so lightweight luggage is important.

For more tips on how to travel light and only with a carry on, click here.


we recommend:

Voltage DLX 20" Spinner

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International Carry-On

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Carry On Spinner

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Platinum Elite 21” Carry On Spinner


Travel backpacks:

A travel backpack is really useful to have as part of your luggage while traveling in Italy. You’re going to be on and off of trains and wandering streets of very beautiful, but very roughly paved, villages. It’s important that your backpack is properly designed to make the weight you’re carrying comfortable and is weather-resistant. We don’t prefer the backpacks that look traditionally touristy, though. We think a cuter one keeps your outfit looking good and you enjoying using it. So get one that is both functional and stylish! And since pick-pocketing is always a concern during travel, make sure your backpack is one that cannot be unzipped/opened without you knowing!


we recommend:
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The Rowledge

A gorgeous larger sized pack with many compartments and a sleeve to slip over suitcase handles.

Ellie Leather Studded Backpack

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Mini Macaroon Colorblock Water Resistant Backpack

The cutest!

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Fjallraven Kanken Backpack

The beauty of Fjallraven backpacks is they pack down flat when not in use!


Italy packing tip: Leave room for SOUVENIRS

Visiting Italy is the time to buy souvenirs to bring home with you, even if you’re not typically a “souvenir” person! Why? Because Italy is amazing. Leave room in your bag for Italy to fill. Or bring a collapsible duffel in your suitcase to fill up with all your goodies for the trip home! Whether you buy pastas, chocolate, wine, coffee, olive oil, balsamic vinegar, Parmesan, handmade glass treasures, custom-made leather sandals, clothes, etc., trust us you’ll want to be able to bring it all home. If you don’t plan ahead for that you probably will end up leaving behind some of your own items to make room!

What to pack for Italy:

Here are a few non-negotiable items that should always find their way into your backpack for practically any Italian excursion.

Spoiler alert: You will be walking A LOT in Italy. Every day of your Italian vacation will be a different version of the following:

  • Wake up

  • Gather your camera, jacket, money, passport, and snacks into your day bag

  • Walk around for hours

  • Eat

  • Walk

  • Drink

  • Walk

  • Sit

  • Walk

  • Sleep


spring/summer

While you’re in Italy, take part in the la dolce vita by wearing fun accessories like printed head scarves, funky sunglasses, statement earrings, pops of rich red, and sweet dresses. In warm weather, you can dress pretty skimpy but note that signs outside many churches detail clothing that is not permitted: usually shorts, bare shoulders, and mini dresses for women. If you’re planning on wearing a lot of sleeveless dresses or tank tops, just be sure to bring a cardigan or scarf to layer and cover your arms!

Little dresses:

Traveling to Italy in warmer weather is so easy because you can wear easy, breezy, little dresses! They take up so little space to pack in your luggage and they look absolutely adorable on. There is nothing better to wear in Italy when it’s hot than a cute dress!


we recommend:

A hat:

Italy gets hot and sunny in the summer so packing a cute hat is a must! You’ll be outside in the sun so much you’ll definitely want to have one to protect yourself.

Cute separates:

A cute skirt and top, or pants and top, is a great choice for Italy in summer. These can also be lightweight and easy to pack like a dress but you can bring a couple tops and couple bottoms that all interchange with each other for a variety of awesome looks! Have at least one dressy combo for evening whether you’re going to a restaurant or bar.


we recommend:

Walkable shoes:

Remember, Italy involves A LOT of walking!! This doesn’t mean you need to wear athletic sneakers the whole time. Instead, choose fashionable sneakers, cute flats or sandals. Having two pairs of shoes is ideal for a trip up to 2 weeks long, 3 pairs if you add little flip flops for the beach.


we recommend:

Bathing suit:

If you’re going near the coast at all during your trip, you’ll want to definitely have a bathing suit! Take part in the gorgeous iconic Italian beach life.


fall/winter

A coat:

Italy gets pretty chilly in the winter, especially in the north! Be prepared with a good coat.


we recommend:

Jeans:

Jeans will probably be what you wear daily around Italy in cold weather!

Sweaters:

A couple sweaters are musts for Italy in the winter. Bring sweaters that can go with your jeans and your coat!


we recommend:

A Skirt or dress:

A skirt or dress can be great for day-wear but also can be dressed up for evenings. You want to have at least one killer dressed up look for evening whether you’re going to a restaurant or bar.

Boots:

Boots will be your staple footwear in Italy in winter. Have at least one pair and make sure it’s very comfortable for all the walking you’ll be doing!


we recommend:

A winter scarf or hat:

To keep the winter chill at bay, you’ll want a warm scarf and/or hat with you!


what to do

1. Explore Venice

Iconic Venice is a great place to visit even while not during Carnival! A bucket-list city, Venice is something out of a fantasy with mazes of the skinniest streets and waterways. It can be quite the ethereal backdrop for romance too, with gondola rides on the canals and candlelight dinners. There are even secret gardens to discover and prosecco at hip bars to be had!

2. See the Venice Carnival

In February about 2 weeks before Lent Venetians and visitors break out for masquerading party madness. It is one of the largest festivals in Italy and has been a tradition for centuries. Want an uber-festive experience? Pay to join a masquerade ball, a traditional and elegant affair! Just be sure to make all your plans and reservations early because the whole city gets packed during this time.

3. Discover Rome

One of the most romantic and inspiring cities, Rome is home to ancient world icons such as the Colosseum, Pantheon and Roman Forum. Rome once was the capital of the world and evidence of the city’s golden age can be witnessed at every turn. Check out the Trastevere neighborhood which is a student area west of the river — it’s a great place with affordable food, cool bars, and tiny streets frequented by locals instead of tourists!

4. Admire the Vatican Museums

It may have long lines but the Vatican boasts one of the world’s greatest art collections in a complex of museums. As you move through the extensively large grandeur, consider getting a guide to know what it all is you’re looking at! Some of what you’ll come across: rooms frescoed by Raphael, spectacular classical statuary, and the Michelangelo-decorated Sistine Chapel!

5. Wander through Pompeii

The once-thriving ancient Roman city was destroyed by the Mount Vesuvius volcano and preserved by thick ash. It’s frozen for all time for us to see. The remnants include a column-lined forum, a 5000-seat theater and beautiful, richly colored frescoes!

6. Hike the Cinque Terre

A cluster of five villages located along the west coast of Italy is called the Cinque Terre. The heavenly towns (each with its individual personality) are surrounded by vineyard-draped mountains. Hike between the towns on paths that range in difficulty (or hop from one village to the next by train). Stop at the different towns along your hike to enjoy the best seafood, pesto and local wine!

7. Explore the Amalfi Coast

Cinque Terre’s southern cousin, the Amalfi coast is less visited but equally as divine! Beautiful beaches can be seen from meandering footpaths flanked by orange groves, pine trees, wild orchids and crumbling ruins!

8. Shop in Milan

The financial and fashion capital of Italy offers sophisticated shopping! The cosmopolitan city contrasts the sleepiness of the south. Enjoy the vibrant cultural scene and check out some historic sights such as Leonardo da Vinci’s The Last Supper.

9. Take a photo in Pisa

You gotta do it. Get your goofy pic of the leaning tower which the entire town of Pisa has set itself up for tourists to do, then move onto other Italian adventures.

10. Visit Siena

Siena is a jewel in Tuscany. It is one of the best preserved medieval cities and famously is arranged around the Piazza del Campo arena (where horses race in the summer). It has a strong artistic community which shows in its cute shops of artisan products like artwork, rugs and chocolate!

11. Naples

While Naples does have a reputation for being unsafe, it also is a great place to experience some authentic Italian culture with winding stone streets, famous pizza, and even some enormous castles to visit and high-end shopping!

12. Relax on the lakes

The summer playground for the rich and famous like George Clooney and Italians themselves, are northern Italy’s beautiful lakes such as Lake Como. Come to play here in the lakes, go hiking and marvel at the gorgeous villas!

13. Explore Florence

Florence, once the medieval home of the wealthy and prominent Medidi family, is a special place. It’s a city laden with amazing food and wine bars, tantalizing gelato, charming streets, blockbuster museums, and ancient buildings and stunning churches. Try going on a few wine tours in the nearby countrysides to get more of a feel of the Tuscan region as well!

14. Tour “the Heel”

A drive around the southern heel of Italy’s “boot” gives a glimpse into rustic Italian life. It’s an area less traveled by tourists but it’s a beautiful place where most of the fruits and veggies in Italy come from!

15. Eat in Sicily

A foodie’s dream: there’s more to Sicily than its famous mafia! With a unique cooking style reflecting millennia of cross-cultural influences. It’s a complex, intriguing cuisine like no other in Italy. Indulge in fragrant couscous in Trapani, golden panelle (chickpea fritters) in Palermo and chili-spiked chocolate in Modica! There’s many local delicacies to discover in market stalls: briny olives, Bronte pistachios, nutty Canestrato cheese and glistening swordfish.

16. Take a cooking lesson

What better of a place to enroll in a cooking lesson than Italy? It’s a fun way to bring home a bit of Italian cuisine. Most classes cost between 75-300 EUR (for a 1-day class).

17. Day trip to Lucca

If you’re in Florence, take a quick jaunt over to relaxing Lucca to escape the tourists. It’s a wonderful city to explore by bicycle!

18. Take a professional tour

Both Walks of Italy and Context Travel offer incredible tours around the country. You will get your money’s worth and all the sites and history will come alive to you! If you are big into culture, history, or architecture these tours are for you. It’s a great way to gain a richer understanding of the country.

19. Explore Emilio-Romagna

The northeast picturesque region of Italy is worth a visit! It’s one of the richest regions in all of Europe, and though it attracts less tourists than Tuscany it boasts the same magnificence. Great medieval towns with fine wines, superb food and rich history!

 
 

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