One Week in Italy! Tips for planning your Italy Vacation

Italy. One of those dream destinations that you see on postcards, in movies, and on every travel influencer’s website. I’ve been to many beautiful places in my life, but Italy truly tops them all. From the scenery, to the people, the architecture, it is truly a magical country that I would love to spend MUCH more time in. Today I wanted to give you an overview of what a week in Italy could look like, including what something like this typically costs. If you’re planning a trip to Italy, I hope you find these tips helpful and they are a great resource for you to have the best trip ever. As always, I am happy to answer any additional questions so please feel free to comment below or send me a message for more information! Now, let’s dive in!

Our trip to Italy was VERY fast paced and we truly only got a little taste of the country. If you have the time, I would really recommend trying to allow yourself two weeks to really experience the country. However, it is possible to have a great trip in only one week, you just have to set expectations accordingly. I plan on creating more posts in the future to expand on some specific locations and details, but for now I am sharing a general overview of our week. Enjoy!

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Day 1-3 – Lake Como

Our trip started out in the beautiful area of Lake Como! We arrived in Milan (the closest airport to Como) at around 7pm on Monday evening. From Milan to Como, you have the option of taking the train or hiring private transportation. For a variety of reasons, I highly recommend splurging on the private driver. It is about a 60-90 minute drive depending on which village you stay in. While the train is a much cheaper option, nobody wants to lug heavy bags around a train after traveling for 24 hours, and then have to get off the train and find another mode of transport to get to your actual lodging. The door to door service of a private driver is well worth the money. The private driver costs us 165 euros, but that was a tad lower than other drivers in the area. I saw some quotes closer to 200.

After being picked up from Milan, our driver Lamberto dropped us off at our INCREDIBLE bed and breakfast, Cherry En Rose. I could go on and on about how amazing this stay was, but I will let the photos do most of the talking. From the moment I stepped in our room I was BLOWN AWAY by the view of the lake. The owners of this place were incredibly welcoming, breakfast was so peaceful every morning, and the price was very reasonable. At the time of our trip (Mid-April 2023) this room was $513 for 3 nights. For this kind of view and breakfast, I found that to be a great deal.

After we checked in and dropped our bags, we walked down to Hotel Villa Aurora for dinner, and decided we were going to have every possible meal we could at this place while we were in town. We still dream about the lasagna and Tiramisu. The pricing was also extremely reasonable. We spent around 65 euros on a dinner for two, including dessert. The view here was also incredible.

Then it was time for some well deserved rest before Day 2.

Day Two – Lezzeno and Varenna

After a great night of sleep, we got up and had breakfast downstairs in the adorable seating area, served by our lovely host. We then walked down the road to the ferry. It was a quick easy 10 minute walk, and purchasing ferry tickets was very straightforward. Ferry tickets were just a couple of dollars each time. This was the view of the Lake from where we boarded the ferry.

The ferry ride was about 20 minutes if my memory serves me correctly. We then hopped off and spent a few hours exploring Bellagio. We had lunch at Bilacus (wonderful lunch spot!), explored the different shops with beautiful clothes, leather goods, etc, and then took the ferry to Varenna. In Varenna, we did more shopping and explored Villa Monastero, which was 10 euros per person. After this we completed our day by yet another dinner at Hotel Villa Aurora.

Day Three – Elopement Day

If you had told me 7 years ago that my career would allow me to travel to Italy and photograph a couple on Lake Como, I would have thought you were crazy. I still have to pinch myself sometimes looking at these photos. Our whole reason for traveling to Italy was to capture Tiffany and Stephen’s elopement, and it was truly the most incredible day. We started out with a vow exchange at Villa Balbianello, and then hopped on a boat tour of the Lake where we took more couples portraits. I won’t disclose pricing details of the wedding here, but as far as the boat tour goes, if you wanted to do a similar tour of the lake on your visit, you can plan to spend anywhere from a few hundred to a few thousand for this experience. It truly varies widely, so it’s best to do your research about which one suits your needs. If you want a private tour that is several hours, on the most picturesque boat, it will be on the higher end. But there are options for other boats and shorter tours that won’t set you back nearly as much. We went with Como Classic Boats and I truly can’t recommend them enough. We had a wonderful experience.

Day Four – An unplanned trip to Venice!

On day four, we got up before the sun and started our traveling for the day. Our wonderful host Linda, from the bed and breakfast, called us a cab and he drove us to the train station in Como. We had train tickets from Como to Florence, but when we got to our connecting station in Milan, we realized there had been a train derailment in Florence, cancelling all trains in and out of the area. 🙁 We were sad, but this is where back-up plans come in! On our itinerary I had already created a “plan B” for each day, so we quickly changed our plans, bought tickets to Venice, and we were off!

P.S. Things like this are why I HIGHLY recommend getting a Eurail Pass if you plan on using the trains on your european trip. A 7 day pass is currently running around $300 per person. If you are planning on staying in one local area, this may not be necessary. But if you plan on using high speed trains that go through different areas of a country, it is a good investment for these types of situations. While you may be able to purchase individual train tickets cheaper, if you find yourself in a situation where you miss your train or need last minute tickets for some reason, you have that flexibility with the pass. Without the pass, you would have to buy tickets last minute which can be very expensive. Buying train tickets earlier is always cheaper. They can double (or more) in price if you buy them last minute.

So back to Venice. As soon as we stepped out of the train station I knew this place was going to be special. THIS is the view that you get as soon as you leave the station. Pretty incredible, right?

One of my dreams for a long time has been to take a gondola ride in Venice, so after dropping our suitcases off at Stow Your Bags, that was our very first stop! We decided to just hire a random gondola on a side street that we passed, thinking all gondolas were created equal. We were WRONG. Haha. Here are some tips for taking a Gondola ride in Venice.

  1. Pre-book your gondola trip. This will allow you to ensure you get the best tour for your group, and you may be able to find a gondolier that will sing. Ours did not, so that was a bit disappointing.
  2. Get a gondola close to the grand canal. While you don’t want your entire tour to be through the grand canal, you don’t want to be in the “back streets” the whole time like we were. To be honest, the 30 minute tour got a bit boring in the quiet back alleys. We only got to see the grand canal for a few minutes. Basically what I am saying is research the best routes, don’t just take any gondola
  3. Bring cash! Many gondoliers do not take card. In our situation, he told us he would take card, then we came to find out that he spoke absolutely zero english, didn’t understand our question, and therefore we had to pay cash. We were 2 euros short of payment because of the miscommunication. Don’t put yourself in that awkward position.
  4. Don’t “shop around”. The gondola system in Venice is highly regulated, and they will all charge the same, unless someone is trying to scam you. A 30 minute tour during the day is 80 euros. It goes up to 120 in the evening.

While the gondola tour could have been better, it was still an awesome bucket list item to check off!

Other tips for Visiting Venice, Italy

  1. Watch for pickpockets!! This is one of the worst cities for pickpocketing. Do not, I repeat DO NOT leave anything valuable in jacket pockets, backpacks, back pockets, etc. I am 90% sure someone actually tried to pickpocket me on the jam-packed water taxi, but thankfully I know much better than that. Whenever you are traveling, you should always have a crossbody bag that hangs in front of your body to prevent issues like this. Don’t rely on the zipper of your pockets to protect from thieves. My friend got her phone and wallet stolen in Venice under 2 jackets. It can happen. Here are some of my recommendations for travel bags. If you are looking for a great bag to travel with, there are some recommendations on my Travel Favorites List

2. Utilize the water taxi. I have traveled all over the world, and I consider myself to be very good at navigating maps, but Venice is incredibly confusing. The set-up of the city with all of the canals and side streets makes it incredibly difficult to navigate. You are much better off using the water taxi. (the cost from the train station to St Marks Square is between 10-15 euros at the time of writing) Don’t try to to rush through Venice. It is a city that can take a bit longer to navigate, so I recommend planning a more slow paced day here without too many set plans. We truly enjoyed just walking around, exploring, taking photos, and listening to the instrumentalists in St Marks Square.

After our day in Venice, we had to head straight to Florence, as we had already booked a non-refundable hotel. We got to Florence around 8pm and walked to our hotel, Croce Di Malta. This hotel normally would have cost us $358. I have personally never spent that on a hotel. My husband had earned a great incentive through work where we got a hotels.com gift card that covered our stay. The only reason I chose this hotel was because of the proximity to the Duomo. You can definitely find more affordable places to stay in Florence, but everything within walking distance of the square is going to be expensive, so it depends on how much you want to travel.

After checking in, we had dinner across the street at the only restaurant that was still open, and then decided to take a late night stroll to the Duomo. I would have loved to see this in the daylight, but it was just as gorgeous at night! I never take my professional camera out late at night, so cell phone photos will have to suffice for this destination 🙂

Honestly, I’m not sure why everyone says gelato is better than ice cream. We searched for the perfect gelato all week, I wasn’t really impressed. Maybe we just chose all the worst places, haha!

Day 5 – When In Rome

Day 5 consisted of another early wake up call to head down to Rome! If you can’t tell, we like to get up early when we travel and pack in as much sight-seeing as possible!

We boarded the first train to Rome in the morning, and arrived around 9:30 or 10 in the morning. We then got a taxi (they sit right outside of the train station) and checked our bags at our hotel, Florio Luxury Rooms. This hotel ran us $215 per night, for a total of $430. Honestly, this place was worth every penny! It is a boutique hotel with only 3 rooms, but it was extremely clean, quiet, and they truly went above and beyond to make the rooms nice. It is also within an easy walk to all the main sights, so you save money on transportation. The walk is also safe, which is a big thing to consider in Rome. The location of this hotel could not have been better.

After dropping off our bags, we walked to the Colosseum where we had a tour that we booked through airbnb experiences. The tour was $50 per person and included the colosseum, roman forum, and palatine hill. The total length was 3 hours. I have mixed feelings about the tour. The main benefit to booking a tour of the colosseum is that you skip the line of people waiting to get in. However, for someone who isn’t deeply interested in all of the historical details, it was a long tour. Our guide was great and I did find it interesting, but I think it would have been better to do the self-guided tour and skip over parts that didn’t interest us. Nonetheless, we got to see the colosseum 🙂 We left the tour after palatine hill because it was extremely hot and we wanted to explore other parts of the city.

I really want to go back to Rome and see the Colloseum at sunset/night time!

Side Note – I’m not sure if you’ve noticed yet, but I don’t recommend too many places to eat, because we hardly choose specific places to eat when we travel. We would rather spend the majority of our time and money walking around and exploring, so most of the time we just pop in somewhere that looks good, or grab a quick snack and keep going. Honestly, there’s not too many bad food choices in Italy, and we always feel like the big touristy restaurants are over-hyped anyway.

Anyway, back to our day in Rome. After exploring the city and relaxing a bit, we had a night time tour that led us through some of the lesser known city streets and told us the “dark side” of roman history. This is one of my FAVORITE things we did!! This tour was only $27 each! I highly recommend this tour to anyone visiting rome. I felt like I truly got to know the city in a different way than the typical sights you see by other tourists. Book Benjamin for your tour HERE!

Day Six – Lemons Everywhere!

For our last full day, we took a day trip from Rome to the Amalfi Coast. Let me just say, this place was like another world. It was insanely beautiful, there were lemons EVERYWHERE, and the coastal views were absolutely insane. We took a tour that left Rome at 7 am on a bus, and took us to Positano and Amalfi. If I had it to do over, I would do not do this with a tour company. Essentially, all the company did was drive us to Salerno (our guide did do a wonderful job telling us the history and interesting facts about the area) and facilitated the ticket purchase for the ferry. I was not aware that we would then be put onto a ferry full of hundreds of people. It was very chaotic. The day that we went, there were lots of factors working against us crowd-wise, but if you want to visit Amalfi and have one day, just take a train to Salerno and buy ferry tickets to Amalfi and/or Positano. Super easy! I would personally recommend just staying in Amalfi though. There was much more to do and see in my opinion. Positano is best for someone with very expensive taste, which is not us 😉

Day Seven – Delta Saves The Day

After our jam-packed day in Amalfi, we went back to our hotel in Rome, and set our alarms to be up by 6 AM so we could walk to the Trevi fountain to end our trip. This was truly a Lizzie Mcquire moment for me, haha. It was a sentimental way to end the trip, because tossing a coin in the Trevi fountain has been another long time dream of mine. So many bucket list moments checked off during this trip! After the fountain, we grabbed a coffee at L’Antico Forno, and it was time to head back to the airport.

I also want to take this opportunity to sing the praises of Delta airlines. We had planned to spend another day in Italy, as we were supposed to make our way back to Milan and fly out from there a day later, but unfortunately we had a death in the family and needed to come home early. I was dreading the conversation with Delta, and the money it was going to cost us. Delta not only changed our airport from Milan to Rome, but they even dropped the entire change fee and saved us $1200. I cannot thank them enough for getting us home early and going the extra mile to help us. This is why Delta will always be #1 in my book.

We truly had an INCREDIBLE week in Italy, but there are so many things I still want to do and see there! I would love to visit the Starbucks Roastery in Milan, take a cooking class in Florence, visit Blue Grotto in Capri, and so many other things! Maybe we will be back sometime soon! Hey, if you know anyone getting married in Italy, I know a girl who would love to take their photos! 😉 I hope this post has been helpful and inspiring, and gives you some insight into what a week in italy can look like! Below, I am going to post a summary of what it would normally cost for this itinerary. Keep in mind, some of this was comped for us as we were there for work, and we also used gift certificates for some things, but this should give you an idea of pricing for your own trip.

Two Flights from Jax to Milan – $2100

Private Transport from Milan to Lake Como – $165

Hotel in Lake Como (3 nights) – $513

Villa Monastero Tickets – $10 Each

Ferry tickets – Roughly $50-$60 total

Hotel in Florence – $358. You can find options closer to 200-250

Hotel in Rome – $430 (2 nights)

Eurail Passes for 2 – $600

Gondola Ride – $80

Day trip to Amalfi – $400

Dark Side of Rome Tour – $27 Each

Colosseum Tour – $50 each

Boat Tour – Budget $500

Budget around $200 for various transportation like busses, local trains, ferries, etc.

With all of that said, if you want to hit all of these places and do all of the tours we did I would budget around $5000 with flights included. This does not include food costs, as that really depends on the experience you’re looking for. However, we rarely pay for flights anymore. We put all of our daily expenses on credit cards that we pay off every month, and utilize the points for travel. Between our credit card points, gift cards, etc, we are able to have these incredible experiences for much less.

If you have any questions about traveling to Italy (or anywhere!) please leave them below! I am happy to answer anything!

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