As you gals may know if you are following me on Instagram, Thomas and I are heading to Italy for two and half weeks in middle of May!  We are thrilled to check off this quintessential european destination off our bucket list.

Hi guys! I just came back from a two week Italy vacation, and I though it’ll be helpful for me to share my itinerary and plannings tips in this post.  I hope it helps you plan your perfect Italian vacation. If you have questions, I’d be happy to answer them in the comment box. Happy planning!


Throughout the planning process, I’ve come across a few golden nuggets of wisdom that really helped us plan our trip, and I’m passing  it on here to you gals. So let’s dive right in ! ( I understand the perfect itinerary will be different for everyone, so I’d like to say that this was the perfect itinerary for us, and I hope you use it as a helpful guide to plan your Italy vacation.)

  1.   Write down your must visit locations. For us it’s: Venice, Cinque Terra, Florence, Rome, Positano and the Amalfi Coast. There are so many other great city’s but since it was our first trip to Italy, I wanted to visit all the highlights first. There’s always a good reason to go back to Italy and explore some more right?
  2.   Get a good map of Italy. Visually mapping out your locations on an actual map will give you an idea of how to plan your trip, and it will make more sense when you start to look for flights. It saves you a lot of travel time in between if you book an open-leg flight ( flying in from one airport and flying out of another, for us it was flying into Venice, and flying out of Rome) Once you have an idea of where geographically the cities you want to visit are,  you can decide on which end of Italy you’d like to fly into. For us it is Venice. The country of Italy is about the same size of California, and since Venice it is on the top north point, it made the most sense for us to fly into Venice and fly out of Naples or Rome. We decide on Rome since Rome has a larger airport and therefore more frequent flights and less connections.
  3.  How many days where? With 14 previous days, how to divide your time? It will be different for everyone and depending on what your interests are, but you’ll want to stay at least 2 days in one location to get the highlight experience. 3-5 days to fully experience the city. If you love art and history Rome and Florence, Pompeii will be a good starting point. If you love scenery than the south of Italy may be great starting point. For us it meant starting in Venice for 2 days. The breakdown of our Itinerary is down, if you would like to see that scroll down gals.
  4. How to get to point A to point B? Luckily, Italy has great public transportation as many other european cities, they have the fast Italo trains as well many regional trains connecting all the major hubs and cities. To get an idea of the train schedules, go to their website: and see a date and time in the next few weeks, the schedules tend to be similar with very minor changes to schedules. The official train schedules don’t get released until 2-3 months prior to the date. I’d encourage you to plan on purchasing your major train rides in advance as you can save a lot of money, but be warned, the trains come early or late and if you miss the train, there are no refunds for super economy seats.  More on purchasing train rides and train codes in another post, stay tuned for that. I had to do a lot of research to find this out so that will save you some time.
  5. Accomodations: I would book accommodations at least 3 months in advance. A lot of the Airbnb fill up quick in the popular summer months so snagging up a charming place early is well worth it. A lot of Airbnb places have a lenient cancellation policy and will allow you to cancel for a full refund up to 30-60 days prior to your trip. Make sure to read the individual cancellation policy to be sure. We booked pretty much all Airbnbs for our stays. It in my opinion it’s one of the best ways to travel. Use my code to sign up and get a $40 credit on your first booking (first time signups only).


  1. Day 1 –  Venice Arrive in the morning. Sleep in Venice
  2. Day 2 – Venice. Sleep in Venice
  3. Day 3– On route to Cinque Terra, Sleep in Cinque Terra
  4. Day 4– Cinque Terra, Sleep in Cinque Terra
  5. Day 5– On route to Florence. Sleep in Florence (stop over in Pisa on the way)
  6. Day 6– Florence. Sleep in Florence
  7. Day 7– On Route to Rome, Sleep in Rome ( Meet our friends who fly in Rome today) (I would recommend going straight to Solerno instead)
  8. Day 8 – On Route to Positano, sleep in Positano ( Train stops in Naples, from Naples you’ll take the regional train or hire a private shuttle or take the ferry)
  9. Day 9 – Positano
  10. Day 10 – Positano (day trip to Capri)
  11. Day 11– Positano (day trip to Amalfi Coast)
  12. Day 12– On Route to Rome, sleep in Rome
  13. day 13–  Rome, sleep in Rome
  14. Day 14– Fly home from Rome.

This is a carbon copy of our itinerary. To some it may appear a bit ambitious and a lot of traveling, but I really don’t mind it. We will have a long break at the end in Positano before heading back. I’m excited to share that I’ll be Vlogging our trip in Italy and sharing that on Youtube and here on Darling Coco. In it will have all the details of our stay, activities, and places to eat.  Since I’m usually behind the camera (photographing) and now also in front of the camera with Darling Coco, it is a fun new endeavour. So I hope you tune in for that. Well, that’s all for the Itinerary and planning. I’ll be writing a more detailed posts on the train schedules and other tips and tricks. So stay tuned gals!




Comments are closed.

error: Copyrighted