10 Day Vacation visting Rome, Venice, Siena, & Positano

Ciao! I just got back from the trip of a lifetime to Italy with my family and I have been dying to share my itinerary with you! When I tell you I went IN on this itinerary, I truly went all in! I am giving you every single detail of our trip from places we stayed, activities we did, restaurants we tried and even what trains we took to get around from place to place! Without further ado, let’s get into it!

If you are interested in any of the outfits that I am wearing on the trip, I have every outfit linked on my LTK

Flight There

We opted to fly out of Chicago vs Indianapolis. We were able to find DIRECT flights for just $700 a piece! Flying from Indy would have been $1000+ for tickets and had multiple layovers so we opted for the Chicago option! A great travel hack is to look at flights from other airports in states near you if it isn’t a super far drive, sometimes you can get lucky and save $100s per person!

Flight Leaving Chicago at 4:10pm CST

Flight Lands in Rome at 8:20am Local Time


Day 1

Day 1 was really all about getting settled. Because our flight was getting in so early we had quite a bit of downtime before being able to check into our hotel. Because we had so much luggage we found a place called Rome Left Luggage right next to our airbnb that would store our luggage for around 2 euros per hour per bag! We were also able to arrange an airport pick up to the location through the same company which was convenient! I also want to note that this entire trip we never rented a car. There were 5 of us plus luggage and we wouldn’t have been able to rent a car to fit all of us. We opted for mainly travel by train and some Ubers when needed!

  • 10:30am- Went and saw the Pantheon
  • 1pm- Walked to the Altar of the Fatherland and Tomb of the Unknown Soldier
  • 2pm- Walked to the Coliseum
  • 3pm- Took an Uber to pick up our bags and check into our AirbnbThis Place had AMAZING views from it’s rooftop terrace. I will say we were slightly disappointed on the interior. One shower didn’t work and the other one had some drainage issues. We let the owner know and hopefully they will fix those issues because otherwise it was a great location!
  • 9pm- Drank wine and played card games on the terrace of our AirBnB


Day 2

The next day we headed off to Venice. We actually spent less than 24 hours in Venice because we had so many cities on the itinerary we wanted to Venice. I do wish we had some more time there but the time we did get there was AMAZING. It is such a unique city and we got to see so much!

7am- Woke up in Rome & got ready

8am- Breakfast and Cappuccinos at a local cafe- We just found something on a street corner near our AirBnb!

10:35am- High Speed Train to Venice (lunch on train)- We booked all our trains through italiarail.com These tickets cost us around $56 a piece. You can typically expect to pay around $20-$90 for your train tickets depending on where you are going!

2:35pm- Arrive in Venice and walk to AirBnB- Everything in Venice is walkable, there are no cars! You can use a water taxi but I recommend just walking unless you have too much luggage to carry. I had a 50lbs suitcase and was able to make it around fine though.

3:00pm- Check into AirBnB– This place was fantastic! Super cute, great view, very clean, and in a convenient location. Highly recommend this one!

3:30pm- Explored the Canals and got gelato

4:00pm- Went on a gondola ride on the canals- There are Gondolas everywhere. Drivers will be parked on the sides of the canals. To ride one, walk up to them and tell them you’d like to go on a gondola ride! We did 30 minutes and thought it was the perfect amount of time!

5:00pm- Went to a local spot to drink Aperol spritz & have bruchette during Happy Hour. I don’t know the name of the place we went but it was RIGHT next to the Conservatorio Benedetto Marcello where we took some amazing photos!

7pm- Ate dinner at San Trovaso Ristorante– This place is a hidden GEM!! Amazing seafood, drinks, and pasta. The atmosphere is gorgeous! If you are in Venice, you must stop here and be sure to dine on their patio!

9pm- Went to a wine bar by our Air BnB for a glass of wine


Day 3

Day 3 was mainly travel. Venice & Siena are quite far from another, It was nice to recoup and rest on the trains though. I was able to catch up on a lot of stuff and edit photos from the trip so far. Once we got to Siena we were absolutely taken back by it’s beauty! One thing I will mention- it is definitely easiest to get around Tuscany in a car. If you are able to rent one, do it! Since we were there for a short time and had so much luggage we opted out. Our Airbnb owner acted like we were crazy for not doing so which made us nervous. BUT… we had a fantastic time and if I did it over again I still don’t think I would have rented a car. We rented E-bikes for the day and traveled 14 miles and visited 3 wineries! The biking experience is my favorite memory from our ENTIRE trip. The views were breathtaking. The bikes are part electric so it only felt like I physically rode for about 3-4 miles in total which wasn’t bad at all!

8am- Wake up in Venice and Get Ready

8:30am- Ate breakfast at a local cafe nearby

11:26am- Board a train to Sienna- For this one we had to do a high speed train to Florence then take the local train to Siena

3:37pm- Train arrives in Sienna

4:00pm- Took a taxi to our AirBnb- Outside the train station there is a place to order a taxi, there is no Uber here!

5:00pm- Get fully checked into AirBnB– This place is straight out of a FAIRYTALE. My only regret is that we didn’t stay here longer!

6:00pm- Walk to local town Castelnuovo Berardenga (10 min walk) & Eat dinner at a local spot: Enoteca Bengodi

8:00pm- Hang out around the AirBnB and play cards

Day 4

Day 4 was our winery day which means it is the day of our 14+ mile bike ride on the e-bikes! This was everyones favorite memory from the trip and one of my favorite life experiences EVER. Even if you do have a rental car, I recommend renting an e-bike for the day to explore the tuscan countryside. SO WORTH IT!

8:00am- Wake up and have breakfast at our Air BnB- This place is an actual Bed & Breakfast and the host will make the breakfast for you!

9:00am- Walk into town to rent some E-Bikes at Chianti Bicycles

9:30am- Ride our E-Bikes 7 Miles through the rolling hills to Castello di Brolio

10:30am- Arrive at castle winery and tour the grounds

11:30am- Taste wines made at the castle

12:00pm- Ride another 3 miles to the next winery, Vineria San Felice– This place had our favorite wine that we tried on the trip, also the views were insane. They have a bed and breakfast on property. It would be a wonderful place to stay if you are coming to the area

12:30pm- Arrive at Vineria San Felice and do our next tasting

1:00pm- Ride back towards town 3 miles to our last winery, Felsina

1:30pm- Do our tasting at Felsina

2:00pm- Return our E-bikes and grab lunch at the local bar

3:00pm- Arrive back at our Air BnB and get ready for our dinner excursion- This was an experience to say the least lol. I wouldn’t recommend it so I am not including the link but there are so many excursions and things you can book online to do in the area, so definitely look into that if you are interested in something like this!

5:00pm- Take a taxi to Sienna to get picked up for our excursion

6:40pm- Our driver is 40min late but we eventually get picked up and taken to the excusion

7:00pm- Arrive at our excursion which is an Italian BBQ event at a winery- This entire experience felt extremely casual as if we were just hanging out in some random person’s backyard (which we were lol). It was actually a very fun time we got to me lots of people and the food was good but not worth $90 a person!

10:00pm- Arrive back in Sienna and take a taxi back to our Air BnB


Day 5

Another long travel day, but the destination is so worth it. A few years ago I discovered this Airbnb and knew I had to come back one day with my whole family! The airbnb is located one mountainside over from Positano in a town called Montepertuso. I prefer staying there because it is out of the crazy packed tourism in Positano and the views are breathtaking!

7:00am- Wake up and get ready

7:30am- Check out of our Air BnB and take a taxi to the train station

9:18am- Board our train to Naples

2:15pm- Arrive in Naples

2:30pm- Take a taxi to our AirBnB in Montepertuso- I booked our transfer through airportstaxitransfers.com. You have to drive into Positano, there is no way to take a train. I have rented a car before there as well and it was TERRIFYING. Lots of small windy roads on the edge of cliffs. Personally, I prefer having a driver take me in and then relying on their bus system once we get there!

4:00pm- Arrive at our AirBnB & are welcomed with limoncello and snacks brought by the host- This airbnb is my favorite place I have ever stayed. The hospitality of the family is unmatched.

5:00pm- Explore the ground and get ready for dinner

7:00pm- Dinner at La Tagliata If you ever visit Positano or anywhere on the Amalfi coast you MUST eat here. For $50 a person you get served family style & unlimited wine! There is no menu they just bring you out tons of things to try. Theres 4 courses Appetizers, Pastas, Meats, & Desserts! They bring you a limoncello shot to finish off as well! Stay for hours and enjoy amazing food with one of the best views in all of the Amalfi Coast!

10:30pm- Finish dinner and head back to our AirBnB- I forgot to mention that the restaurant is walkable from the airbnb and actually owned by the same people who own the airbnb we stay in!

11:00pm- Card games and fun on the rooftop terrace of our Air BnB


Day 6 was our day to Explore Positano & spend time at the beach!

8am- Wake up

8:30am- Homemade breakfast at our AirBnB- The owners are incredible and make the most delicious breakfast and cappuccinos!

10am- Hike down to Positano on the Path of the Gods- This is the beautiful picturesque path you see people taking photos at online! You can get on the path just a few feet from the airbnb!

11am- Arrive in Positano and explore some of the shops

12:30pm- Eat lunch at a local spot near beach

1:30pm- Hang out on the Positano beach and go for a swim- The beach was absolutely packed. If you can, I recommend going to Positano in early May. Once June hits, busy season starts and it is very touristy!

3:00pm- Take a taxi back to our AirBnB- They also have a bus system that will take you back to Montepertuso but the line was so packed that we called a taxi instead.

5:00pm- Get ready for dinner

6:30pm- Dinner in Montepurtuso at il Ritrovo, you MUST get the limoncello spritz here, SO GOOD!

9:00pm- Limoncello and games on the roof of the AirBnB


Day 7

Originally we wanted day 7 to be another day in Positano but our airbnb was not available that day and we couldn’t find any other places we wanted to stay in the area so we headed back to Rome where we would depart in a day and a half!

9am- Wake up and have homemade breakfast at our AirBnB

10am- Taxi picks us up to take us to our Rome AirBnB- Here we could have had them take us to Naples then took a train to Rome but the price was fairly similar and we were tried of having to taking so many trains so we opted for the 3 hour taxi ride to Rome instead!

2pm- Check into our Rome AirBnB

4pm- Go out and see the Spanish Steps and Borghese Gallery

6pm- Eat dinner at il Vero Alfredo

8:30pm- Head back to AirBnB and watch Stranger Things Finale

Day 8

This last day was super chill. We were resting and getting ready to head back home. We also took our COVID tests to get back into the US. We were able to do them virtually. I do believe they just lifted this requirement to return to the US but obviously that could change in the future so to be safe, make sure to check your travel requirements before you go!

9am- Wake up and get coffee from a local cafe

11am- Walk around the Mall near Trevi Fountain (Via del Tritone, 61, 00187, Roma RM, Italy) and look at the designer stores- We grabbed lunch inside at this salad & juice shop. At this point we were getting sick of Italian food and wanted a change of pace and this hit the spot!

2pm- Go and explore the Trevi Fountain

3pm- Head back to the Air BnB

6pm- Get ready and head out to dinner at the mall- I cannot for the life of me find the name to this restaurant. But it is located on the rooftop of the mall we visited earlier in the day. It has an Insane view of Rome and the food was incredible! To get there go to this address (Via del Tritone, 61, 00187, Roma RM, Italy) , enter the mall, and head to the top floor!

8pm: Head back to Air BnB and get ready to leave tomorrow

Day 9

6am- Uber picks us up to take us to Rome Train Station

6:30am- Board train to Rome Airport

7am- Arrive at Rome Airport

10am- Board flight back to Chicago

3pm CST- Land in Chicago

4pm CST- Start drive home from Chicago

8pm EST- Finally home

That’s all I got for ya! If you are looking to book a trip to Italy soon, I hope this helped! If you try out any of my recommendations, tag me on instagram @josie.bullard, I would love to follow along on your adventure!

Summer Italy Trip Itinerary