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Italian Summer: A Two Week Italy Itinerary

Get this…I get a call this past summer from an old (partial) friend from Orlando, Florida. We catch up for a little while and then she drops a bomb.

“So, I know we haven’t talked that much…or like hardly ever ((we hung out with mutual friends at a pool in our neighborhood)) but I was wondering if you would want to go with me to Italy in August? Most things are paid for you just have to buy a plane ticket etc. Oh, and I’m going because my friend is getting married at a castle in Bolzano…the countryside of Italy.”


SPEECHLESS. I promised myself earlier this year that I wouldn’t go back to Europe because my experience was way different from what I had hoped…but how the fuck do you pass this up? Not just the going to Italy part, or even the money that’s already been paid…but A WEDDING AT A CASTLE. I would let you push me off a flaming bridge into the depths of hell if I said no. Of course, I didn’t say no. I SAID FUCK YEAH.

One month and lots of planning/excitement/shopping later…we were off for 2 weeks to explore the beautiful country of Italy…here’s our  Italy itinerary.


Rome wasn’t built in a day. Literally the first words I uttered when I landed because I waited my whole life to say that haha. ANYWHOOO, the city of Rome, the first stop on our trip. We landed early, had an amazing espresso with our Airbnb hosts, primped from the long plane flight and hit the town. Ice cream at 11 am? DUH!

The gelato was just as good as I expected…but wanna know what I didn’t expect? As we were strolling along, I noticed that the Colosseum was in the middle of the city. WHAT??? Okay, call me crazy but holy shit I had no idea. This is something that people drive past every single day.

For some reason, I thought it was in the outskirts of Rome in some majestic fucking field. My mind was blown. I mean, people don’t just drive past the Grand Canyon on a daily basis…there were taxis honking and hundreds of people swarming it. My feelings were mixed.

After seeing a long line, some guy talked us into a group tour to get us in there faster…all I can say is, underwhelmed. Eh, it was okay. Moving on…

After we sat down and had lunch at this cute cafe, of course, me not being able to keep my mouth shut ever, I overhear the table next to us was American so I spark up a conversation. LOW AND BEHOLD, the girl at the table went to the same college as I did!! WHAT?

We instantly became friends, got each others number and I thought I would never see her again. Well, that night after exploring all day, we all meet up, have the best dinner filled with a shit ton of pasta and Prosecco that’s when the real fun began. Weird outdoor carnival anyone? After we left the creepy carnival, for the life of me I can’t remember the place we went, but I just know it was awesome. Some indoor/outdoor beach club. Let’s just say I get more than blackout.

The next morning I wake up only to realize we missed the Vatican tour. UGHHHH why do I do this to myself? Long story short, we rally, I throw up from being so hungover outside the Vatican, I die a slow and painful death waiting for the group tour and then somehow feel a tiny bit better enough to enjoy everything.


Wanna know a not so fun fact?

Rome’s restaurant and bar scene pretty much close down by 10-11pm. The only place you can go out late and have fun are clubs that are usually open until 3-4am.

Sure, we visited the Trevi Fountain, completely submerged with tourists, and saw some main attractions, but just as I expected, Rome was not the best start to this wonderful Italian vacation. This is why I love traveling though, it really makes a difference in your trip more so with the people you meet sometimes rather than the things you see.


This is more like it. Wow, what a city. Away from the crazy hustle and bustle of Rome, Florence was like a little hidden gem. Known for its Italian leather and rich culture but I came to love it strictly for the food. Not to say it was better food, but the vibe of the city was way more intimate and relaxing, exactly how I pictured Italy to be. We stayed here longer so we could visit Tuscany, you know, the wine region? It took my breath away. The rolling hills, beautiful landscapes and of course lots of wine.

But Florence wasn’t all about the wine…okay maybe 90% of it was 😉 but I felt so much more from this amazing little city. This was the turning point for our trip, and although it had only been a couple of days since we set foot in Italy, we realized the touristy stuff just wasn’t for us. A Duomo we wanted to see, a museum we wanted to enter, but everything was packed. JAM PACKED, and the more we got to thinking, the more we realized we didn’t want to do any of that.

Shopping, eating, drinking, wandering, socializing. Those were the things we wanted to experience, so that’s what we did.


Oh Venice, how beautiful you are. Or so I thought. You hear about and see pictures from this colorful, vibrant city all over the internet. But just like all things on the internet, it was a mirage. Okay, don’t get me wrong…the city was definitely how it looked. Bright houses lined the canals, the architecture and the sheer essence of the place was pretty magical…BUTTT (there is always a but) it was dirty. The canals were disgusting, it smelled bad and the gondola ride for being $100 Euro did not seem worth it to me. It’s not you and your significant other romantically riding around being serenaded by the guy in the striped shirt…it was gondolas bumping into one another and canals filled with 6 boats at a time.

I feel like I am always rambling about the let downs but I was definitely let down. Now, this might have something to do with the fact I was there during peak season, so I can’t speak for any other time. All I know is the gondola ride at the Venetian in Las Vegas looked better than that.

I think the highlight of Venice was getting stuck in a terrible rain storm while sitting at a restaurant on the canal. It was us and one other table that braved the winds and vicious rain. It was also both tables that got free Limoncello for waiting it out. Seems like I had a lot of luck with this throughout my trip haha.

If all else was to fail, the food was delicious every single place we went. Italy never let me down on food.



By far my favorite city of the entire trip! I am a sucker for those countryside mountains and views that go on for miles. If you think about it, the other cities were just concrete slabs, but this was heaven.

See what I mean?? Imagine seeing nothing but the city and then driving into this!

So, as much as I want to give you the full rundown of the wedding we attended here, I think it deserves a post in its own. There was just so much detail and exciting things that happened that I don’t want to get off track. Let’s just say that it leaves you speechless…in a good way of course. Here’s a sneak!

Maybe one day ::cough cough SINA cough::

Bolzano was strictly for the 2-day festivities so we didn’t get to explore much, but I need to add that the people we rented the room from in our B&B were the friendliest people ever. So welcoming and made the entire experience more than enjoyable. Despite there being no AC in the room …us Americans are spoiled.



Fashion capital and that it was. There were men dressed to the 9’s and women just struttin’ their stuff like the entire sidewalk was a runway. I was so ecstatic to be here since I have the worst shopping addiction. No really, it’s bad. At this point in the trip though I was just ready to be home and didn’t care too much about doing anything. We hit up a few shops; Europe seems to have amazing shopping, and cheap too! I had to purchase another carry-on bag to bring home because I bought so many clothes and presents!

Since this was the last stop on our trip, somehow (not sure how) we were tired of Italian food. I know it sounds like the worst kind of sin but we just were. I was pizzaed out! Probably because I ate it so much for breakfast…oops. We pretty much just hung out that day and then took a day trip to Genoa!!



You know, like the salami? Ha, so this wasn’t supposed to be on my list, but a friend of mine from Florida was doing a European trip same time as us! Since this was the first time we were close in proximity, we decided to meet up! I needed some greenery and beach in my life, so what better place than the coast of Italy?

We met her and her friends in Genoa and took a train to the beautiful beach of Bogliasco. I’ll be honest, the water was unreal, but the beach itself was literally ROCKS. Big ass rocks too. Not the nicest thing to plop your ass on to catch some rays. We endured the pain for a little while before getting a table near the bar. DUH.


That’s me barely being able to walk out to the ocean. So worth it though, look at the blue ombre! After sitting down at the table, we literally just drank bottles and bottles of champagne. Relaxing, enjoying the view and good company. Exactly what we all needed after weeks of fast travel!

the coast


Is a place ever really as you expect? I feel like some places can blow your socks off and some can be complete duds. Italy has both of those feelings! As always, the very popular tourist destinations took a plunge to the bottom of my mental list considering a number of people visiting and overrated sites to see.

Bolzano was at the top, showing me that the countryside can sometimes be way more exhilarating than any big city. Overall, I would LOVE to visit more parts of Italy in the future! Making my way to some islands and doing a little more research the next time I go!

Each and every person has their own path they like to explore and that is perfectly fine! Always remember to stay true to who you are and what you love. If you do this, you are (almost) always guaranteed a great time! Have you been to Italy before? If so, what did you love AND hate about it? Let me know in the comments but until our next adventure…

xo Bonvoyage Babes

  1. Monika says:

    From what you-ve described, Florence would be my favorite city! I love the ambience and the photos! And I am quite surprised that bars in Rome close that early, I thought people there liked to hang out more

  2. Blair villanueva says:

    OMG you’ve got my dream! I love it 🙂 Italy is my dream place because I find it always romantic and my boyfriend is an Italian 🙂

    • Tatum Skipper says:

      I wish I could have experienced it with my boyfriend!! I would love to go back and explore more. I am half Italian actually!!

  3. Italy is amazing! (Even though it’s so popular with hordes of tourists) I loved every place in Italy I went to (maybe with the exception of Milan, but it’s probably because I’m not into fashion 😉 I love the fact that you also visited small villages, the countryside and the coast. Bolzano is unbelievable! The photos are amazing and I envy you cuz I wanna go back there! And if you loved Italy, try also Albania across the Adriatic sea! 🙂

    • Tatum Skipper says:

      I really wanna go back to and explore more of the coastal area! I will definitely look into Albania also to see everything it has to offer! Thanks for the tip.

  4. Joy Generoso says:

    I miss Italy including the Pizza, Pasta and Gelato. Spent 5 days in Italy (Florence, Rome and Venice) and haven’t gotten enough of it. Would love to go back and explore more. 🙂

  5. I just got back from Italy too! I’ve just been writing up a post about it too! I absolutely fell in love with it. I preferred Rome to Florence though! If you go again, try go to Cinque Terre too, that was probably a highlight for me!

    • Tatum Skipper says:

      Really? I feel complete opposite but every person is different!! I wanted to go soooooo bad! But I was with another girl who wasn’t fond of my suggestions so definitely next time!

  6. Bhusha says:

    Whoa! You managed to cover so much! That’s one spectacular offer that no one could resist. I can understand your feeling about colosseo being in the middle of city. Many other places like Stonehenge are so far away. I was feeling bad that I missed Venice. But in the last couole weeks, this is the 2nd time I’m reading about the crowd there.

    • Tatum Skipper says:

      Yeah it gave me a lot of mixed feelings!! I will be back to explore other parts though for sure. The crowd is insane in Venice so go in the off season!!

  7. Alice Chen says:

    I have been dying to visit Italy! It looks so amazing and I’m glad you enjoyed the gelato as much as I would imagine! It’s crazy you had that coincidence meeting your friend. Too bad about the hangover though! Haha

    • Tatum Skipper says:

      The food is worth it in itself to go honestly!! Right?? How insane is that whole story?? Haha yeah the hangover was the worst!!

  8. Natasha says:

    I really liked Rome. We did a lot of drinking at the restaurants but not in bars so much. We did go to one awesome bar called Druids Den. Thanks for sharing your experience with us

    • Tatum Skipper says:

      Yeah the little bistros here and there were so much fun! I will definitely check it out next time I go! Thanks for the tip 😉

  9. I love Italy! I didn’t hate any part of it because I always have a positive attitude when I travel. It seems like you visited a great list of places. Rome and the Colosseum are definitely my favorites. It’s so exciting to be in a city that’s been such a major part of history.

    • Tatum Skipper says:

      Yeah I try to but I guess since I am not fond of all the history, I just love adventure so it wasn’t my favorite.

  10. I was shocked to find the Colosseum in the middle of the city too. I was just walking around alone with tourist map. I turn a corner and bang. There it is. It was really overwhelming, even swarmed by tourists.

  11. Oh Italy, Yes sometimes when things get so popular they become so jam packed, we know EXACTLY what you mean! We had the same feeling when Climbing the Great Wall! How did you choose your AirBnB? Did you manage to see the statue of David on Florence?

    • Tatum Skipper says:

      Yeah I know! Oh wow at the Great Wall too?? That’s crazy, but believable! She picked them since she had already booked everything!! Yes I did get to see it!!

  12. Ariane says:

    Italy is such a beautiful country. So many different places to visit. And yes, when I went to Rome the first time I couldn’t believe it was reality, soooo gorgeous!

  13. Veronica P. says:

    hahaha first I read 14-hour itinerary and thought: “hmm I am not the only one lol”
    I just spent 14 hours in Bergamo recently on the way to Morocco
    Love your pictures, especially the ones from Florence. And hat swimming pool is so amazing!

    • Tatum Skipper says:

      Hahaha I would have to be super sonic to do it in 14 hours haha. That’s awesome!! I definitely wanna explore more.

  14. Natalie says:

    The offer of a lifetime! What a lucky lady you ARE!!! LOL! We love Italy. It is so vibrant and full of history and art and wonderful warm people. I was caught off guard by the ancient colosseum rising out of the middle of the modern city, too!

    • Tatum Skipper says:

      Right??? I got super lucky!! Yeah I wish I could have explored more of the coast but it was definitely beautiful. Right?? I thought I was the only one who was weirded out by that!!

  15. Italy is certainly a lovely place to visit and you did OK to see as much of it as you did in just 2 weeks! As someone who loves nature, I would tend to agree with you that Bolzano would have been the highlight. Shame you missed seeing the Vatican while you were there. Perhaps another time. Would be interested to check out the wedding post. Nice photos!

    • Tatum Skipper says:

      No no, I did see the Vatican and the Sistine Chapel! I just accidentally made up miss our first visit so we had to go at a later time haha. After the fact that I threw up outside of it. Oops.

  16. Jean says:

    Oh wow! Italy has also been high on my list of places to see. Your itinerary makes me so jealous that I’m not there right now. Eating all the gelato, marvelling at the buildings. Ah well I’ll have to be content gushing over your photos.

  17. Ana Ojha says:

    I loved the way how you’ve described your experience about all touristy places. They are nothing but a herd of crowd acting like cattle. I too prefer countryside and Bolzano looks absolutely splendid!

  18. What a great and action packed Itinerary! What I wouldn’t give for someone just to call me and say “fancy a trip to Italy?” I hadn’t heard of Bolzano before reading this so i’ll make sure to check out a little more about it.

  19. Only By Land says:

    Wow, I wish I had a friend like that, you must appreciate that! The picture of the chocolate ice-cream goes well with your nails! I was underwhelmed by the Colloseum too, it looks a lot better from the outside than inside, but the movie history here is incredible! I’m going to Florence and Venice this fall so it’s good to hear your thoughts on them, I guess Florence is the one to enjoy! Even if Venice is dirty and smelly I’ll still get an Instagram image making it look beautiful and colourful!

    • Tatum Skipper says:

      Yeah it was a really cool experience. Haha it does match my nails!! Yeah I will not be going back to Rome but toally Florence you will love.

  20. Melissa says:

    I’ve had similar experiences when I’ve felt completely underwhelmed by a place. I think at times we built a place up in our minds, so that when we finally visit reality doesn’t measure up to our expectations. With that said, I found Italy abosolutely magical. Milan didn’t wow me, but the rest of Italy did.

    • Tatum Skipper says:

      I felt like that with some parts of Italy and not with others exactly like you said!! I hate having expectations but it’s so hard not to!

  21. 14 days itinerary? Now that’s pretty long. Over the years I have been attracted to the idea of long term, slow travel. I would have devoted most of my time in Italy in Rome and Venice, my childhood dream. Glad it is on your list.

  22. Arnav Mathur says:

    You are one lucky lady, to go on a fully sponsored trip for 17 days in Italy and that too to attend a wedding in a castle. I can only imagine, about the awesome time you must have had at all the places you mentioned in the itinerary.

  23. Indrani says:

    Like you I was also shocked to find the Colosseum right in the middle of the city!!! Locals must be lucky to see it everyday or they may be even bored… who knows! Loved seeing the cathedral of Milan, you got a great shot! Missed visiting Genoa. Seems like a great place!

  24. Everything about Italy is amazing. We loved Florence for its historic aura teeming with art and architecture inspite of the touristy crowd. Venice has a completely different charm we love walking along those canals taking in the bright and rickety houses along the canals. You have covered pretty much of Italy we did miss the countryside part the Tuscany and the beautiful Bolzano.

  25. Cat says:

    Your post makes me want to go to Italy now!! You have visited so many places in just 14 days! I am a food lover so I would spend probably spend much of my time in Florence, but Genoa looks like a great place to have fun and relax as well!

    • Tatum Skipper says:

      The food is worth the whole trip in itself. I ate pizza for breakfast so much because it was sooooo good!

  26. Italy is one of my favourites – I was lucky enough to live there for a while (Pisa) so have traveled to a lot of the same places that you did. It’s tough in the peak summer season as it’s just heaving with people, but there are still some hidden gems! Glad that you enjoyed bits of it 🙂

    • Tatum Skipper says:

      Yeah I wanna go back and explore more of the coastal areas and during NOT peak season haha. That’s awesome you lived there.

  27. lau says:

    wow this is great! I can never get tired of visiting Italy, espepcially Rome, my fav city! 🙂


  28. Merryl says:

    I really wanna visit Italy! My sister’s been there a couple years ago and says it’s amazing. Love your pics!!


  29. Lyndsay says:

    Genoa looks incredible! I’ve been to Rome & Venice, but I’d love to take a road trip all over Italy!

    Great itinerary!

  30. Shane Prather says:

    I wish I would’ve made it past the classics of Venice, Florence and Rome. I can see there are gems beyond off the beaten path of Italy. Fabulous guide!

    • Tatum Skipper says:

      Yeah definitely have to go on the road less traveled sometimes…you have more time though!!

  31. Monika says:

    Florence is definitely my number one from the above! I would love to visit all though. Spend onky a couple of hours in Italy, Verona.

  32. The pictures are absolutely amazing. They ooze out fun, thrill and adventure.
    Venice for me for sure but I want to do all of them!!

  33. Ami says:

    Sounds like a perfect way to explore Italy. The one place that I missed out was Florence. Did not get enough time there . And for that alone, I want to go back

  34. Tarah says:

    Ahh this is perfect!! Literally everything I want to do all in one place. I am heading to Europe on Sunday and am definitely looking to do a long Italy trip while I’m there!

  35. Suruchi says:

    You seem to had an awesome time girl. Even I run away from the concrete jungles and love to hover over countryside, mountains, meadows and beaches. Bolzano and Genoa seemed like my type of places. I loved them.

  36. Rachelle says:

    Isn’t that just the dream? Having someone call us out of the blue to go on an amazing trip? I’m glad this jaunt to Europe turned out better than your last one!

  37. Derek says:

    Loving all the great pictures. My wife and I are planning to go to Italy one day. It looks so awesome!

  38. Eric says:

    I am taking off to Italy/Switzerland/Croatia/Slovenia for 3+ weeks this October. Reading this has given me some good insight :). My goal also is to avoid most of the big cities and wind up in more of the smaller regions. Seems like its a good thing to do if you are opposed to the larger crowds. The Dolomites are calling my name!

    • Tatum Skipper says:

      Ugh I am in love with Italy AND Switzerland!!! Never been to Croatia but always wanted to go…I would suggest Interlaken, Switzerland and Bolzano, Italy if you are looking for amazing places that aren’t super touristy!! Try out the RoutePerfect app it might really help you.

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