How To Plan A 10-Day Italian Vacation

How To Plan A 10-Day Italian Vacation

A European vacation can be daunting, but with the right planning and packing, a stress-free trip is possible! Today, our contributor, Carly Hill, is sharing her tips for planning a 10-day Italian vacation, including all the must-see sights, attractions, hotels and restaurants. Get ready for some major wanderlust!

OUR ROUTE

We flew out of Newark, New Jersey, with a layover in Paris before making it to Florence (3 days/3 nights). We then took the train to Salerno to catch the ferry to Positano (3 nights/3 days), and then took a private boat over to Capri to tour the island and stay one night. Our final stop was taking the ferry from Capri to Naples and then the train to Rome for two days/nights before flying back to New York.

What To Do

Florence

– Climb Giotto’s Bell Tower: We skipped the Duomo and decided to climb the Bell Tower instead (definitely a workout!), which resulted in the most incredible views of the city.
– Watch the sunset at the Ponte Vecchio:
This gorgeous bridge is the ideal spot to catch the sunset before heading to dinner. Bring a bottle of wine and watch the sky turn pastel over the famous bridge.
– Walk up to take in the views from Piazzale Michelangelo:
 This walk is steep, but the views from here are gorgeous and made for some pretty amazing photos. 
– Outlet shop at The Mall:
For those looking to shop, head to Florence’s luxury outlet called The Mall. You can catch a direct bus for about a 40-minute ride through the countryside to this insane outlet mall. From Gucci to Prada to Burberry, you’ll be able to find amazing deals on designer goods.
– Tour the Boboli Gardens at Palazzo Pitti:
Palazzo Pitti is a gorgeous palace that also has beautiful gardens in the back known as the Boboli Gardens. We bought tickets to tour those and we’re so glad we did. The gardens are lush and have incredible views of the country and countryside. We spent about an hour and a half walking through and it was a great afternoon activity, especially because we were able to be outside the whole time.
– Shop for leather goods at San Lorenzo Market:
Florence is known for its leather goods, so there’s no better place to pick up a gorgeous leather jacket or bag to bring back home.


Positano

Take a walk up to take in the incredible views: The mornings were a little chillier in Positano, so this made it a great time to go for long walks up the cliffs to take in the incredible views of the town. Everywhere you turn in Positano is swoon-worthy!
– Shop at the local boutiques for lemon souvenirs and pottery: Positano is known for its abundance of lemon products and gorgeous Italian pottery. We shopped in the local boutiques for lemon soaps, candies and candles to bring back with us. We also picked up some smaller pottery pieces, but most all of the stores ship back to the U.S. if you decide to buy any bigger pieces. I wish I could have bought it all!
– Take a cooking class: One of my favorite activities of the whole trip was our cooking class in Positano. We spent about three hours cooking and then the last hour or so enjoying the incredible meal we made!

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One-Piece Suit (c/o Everything But Water)

Capri

Take a boat tour of the island and visit the grottos: If you don’t have time to stay overnight in Capri, no worries. A day boat tour around the island is an absolute must to experience the turquoise waters and see all the grottos.
– Spend the day laying out at a beach club: Capri is all about relaxing, especially when it comes to its beach clubs. We spent the afternoon at La Fontelina laying out and sipping on Aperol Spritzes on the rocky beaches. Make sure to book a reservation through its website a few months in advance!

Rome

Walk around the Colosseum: It’s a historic staple that’s not to be missed.
– Make a wish in the Trevi Fountain: It’s overly crowded, but still a must-see when in Rome. Don’t forget to throw in a coin for good luck!
– Catch the sunset from the top of the Spanish Steps: This area of town is filled with designer boutiques, little cafes and flower shops, so explore around before heading to the top for a spectacular sunset view.
– Take a guided tour of the Vatican:
We bought tickets in advance for a three-hour guided tour of the Vatican, and we’re so glad we did, as it was packed inside! Our tour guide walked us through quickly, making sure we saw as much as we could inside.
– Relax in Villa Borghese:
Rome’s version of Central Park, take a breather and relax here after a busy morning of sightseeing.

Where to Eat

Florence

– I’Tuscani 2: When in Florence, you have to make sure to try a Florentian steak, and this is the place to do it! Make sure to come hungry as the portions are huge and meant to be shared at this cozy local spot.
All’antico Vinaio: The ultimate sandwich spot, there’s a reason everyone recommends this tiny panini shop for lunch. Whether choosing a favorite off the menu or making your own, you’ll be dreaming of these sandwiches from now on!
La Ménagère: The ultimate spot for cocktails and appetizers, this adorable flower shop/bar/restaurant/home goods store is the perfect place to sip on Aperol Spritzes and enjoy the beautiful cheese and meat board after a day of sightseeing.
Trattoria 13 Gobbi: Make reservations at this dinner spot so you can enjoy the famous rigatoni pasta dish. It’s an absolute must.
Gustapizza: A favorite spot in Florence, thanks to the adorable heart-shaped pizzas.
La Giostra: If there’s time for only one dinner in Florence, this restaurant has to be the one. Come for the pear ravioli (the most indulgent pasta dish you’ll ever eat!), but make sure to save room for the complimentary appetizers and other incredible dishes.
Locale: This super chic bar is a gorgeous spot near the Ponte Vecchico to enjoy a unique cocktail.

Wayf Dress, Cult Gaia Bag

Positano

– La Tagliata: This restaurant sits high on top of the town, so you get incredible views along with a tasting menu of six courses.
– Casa e Bottega: Our favorite breakfast spot (we went back both mornings!) for healthy smoothie bowls, juices and cinnamon pancakes.
Il Ritrovo: We took the most incredible cooking class here (a must while in Italy!) and can’t wait to come back to cook or eat again.
– Le Tre Sorelle: The ideal spot for people-watching and eating pizza before heading to the beach.
– Franco’s Bar: Our favorite cocktail spot of the whole trip, this place is a must to catch the sunset. It gets packed, so make sure to head there right at 5:30 p.m. when it opens!
– La Sponda at Le Sirenuse: For a special meal, there is no place more romantic or beautiful than dinner at Le Sirenuse. Make sure to save room for its famous lemon soufflé for dessert!

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Capri

– La Fontelina: Straight out of a Gray Malin photo, this famous beach club is a must to dine and relax at. Order the linguine and clams before soaking up the sun!
– Da Paolino: While in Capri, make sure to try as many lemon dishes as you can! At this gorgeous restaurant, there’s no shortage of that as you dine under the lemon trees and eat the restaurant’s famous lemon pasta. Save room for dessert in the dessert room as well!

Rome

Old Bridge Gelateria: Over toward Vatican City, this small gelato shop is life-changing! It’s the perfect treat after a long morning of touring the Vatican.
The Hassler: This famous luxe hotel also features a gorgeous backyard garden bar, the perfect place to relax after climbing the Spanish Steps.
– Il Corallo: This is the ultimate place to Instagram your meal thanks to the cacio e pepe inside a bowl made of parmesan!
Dillà: The most adorable spot for lunch thanks to the mismatched china, delicious pasta dishes and lots of rosé.
Giolitti: Considered one of the best gelato spots in the city, the long line is worth the wait for the extensive list of flavors.
– Taverna Trilussa: Known for its famous ravioli, this historic spot serves its delicious pasta dishes straight in the pan to your table.

Where To Stay

FlorencePalazzo della Stufa Residenza D’Epoca: This adorable bed and breakfast is located in perfect walking distance to great restaurants, shopping and historic landmarks. We couldn’t get enough of our spacious room, attentive staff and wonderful complimentary breakfast each morning.
PositanoHotel La Bougainville: Only a six-minute walk to the public beach and shops, this boutique hotel is on the top of our list in this beautiful city. 
CapriHotel La Palma: Located in the center of town, this hotel was the biggest hotel of our stay, and definitely felt the most luxe as well. It was right next to designer stores and tons of restaurants, so you didn’t have to walk far to find a place to stop in!
RomeAirbnb: We chose an Airbnb located in Vatican City for our stay in Rome. I loved the neighborhood we stayed in because it was quiet and filled with charming cafes and shops and not right in the busy area of the city.

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Author: Carly Hill

Raised in Northern Michigan, she now lives in NYC and splits her time working in social media, being a GG editor & exploring the city for the next best meal! Follow on Instagram

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