my boyfriend and i have been planning this big trip through italy for many many months now and it’s coming to an end very soon. i wanted to give you 25 of our very favorite things to do, eat, drink and see…along with some tips about traveling through italy. it’s been so memorable and i’m so happy we decided to just go for it!

thank you to my friends who gave me recommendations and i hope this list helps plan your next trip. it can be kinda stressful planning a longer trip (we did 1 month) but it’s so incredible to immerse yourself into a culture.

we started with 5 days in rome…

1. roscioli was one of our top favorite meals in rome. make a reservation at la salumeria (it’s busy!) and order la gricia pasta and the burrata with sun dried cherry tomatoes. the cheese and meat plates are also insanely good.

2. forno campo de’ fiori is an awesome little bakery in a popular square. grab a few slices (wish i could try them all! my favorite was the ham) and a beer and enjoy on the street while people watching. cheap price and amazing taste.

3. meridionale is a cozy little restaurant with eclectic decor and good food. i also really enjoyed walking around that neighborhood. please get the squash pie with melted fontina. so unique!


it’s a little tricky to get to positano but not too bad. we knew that the pricy part of our trip was going to be in the south of italy. there’s so much tourism there and it feels like all the prices just go way up for hotels, food, and transportation. but it’s worth seeing for sure, so you gotta just let that part go. we chose 2 nights in positano and 2 nights in capri and ended up extending capri by two more days. it was definitely the right amount of time for us.

we took a train from rome to naples and then got a private car to drive us to the hotel. our hotel was gonna charge like 150 euros for the drive (around 1.5 hours) but we used this recommended driver that charged us 120 and she was really great. it’s gonna be your most expensive transportation probably. the roads are very windy with extreme cliffs, i am not sure i would recommend driving it yourself. but that’s just me.

you can email [email protected] and they wrote me back immediately. tell them what time you want to be picked up from the train and they handle it all from there.


4. la pergola. i can’t really speak for all of the food because we just got a snack but i was VERY into my fresh bruschetta. have a spritz and this snack with a great view. we also ate at chez black (not bad) and the three sisters restaurant next to it. i just don’t love the touristy vibe at them but the food was pretty good.

5. la bottega di brunella. there were two of these store locations in positano (the bigger one has an insane selection) i had so much fun browsing through all of the gorgeous linen jumpsuits, pants, dresses. i pretty much wore the three things i got over and over on the trip. definitely go!

6. le sirenuse hotel. we didn’t stay here because $$$$$ but it’s amazing for a glass of wine or cocktail on the patio. and the hotel def has gorgeous design details! later that night we had quite a few moscow mules at their bar next door, franco’s! it’s got a fun lively energy.

7. da adolfo. i am pretty bummed we didn’t get to go here. we were only in positano two days and i couldn’t reach them to make a reservation. soooo many people told me to spend the day swimming and eating and laying out here. i would definitely call and grab the boat over there for the afternoon. i’ll pretend i went with you.


we took a ferry from the main positano dock to capri. i think it was around 18 euro each and it was just under an hour to get there. we actually had a great time on that boat!

8. vintage fiat limo to anacapri. we were sadly kinda fighting on and off in positano. i think we were just exhausted and jetlagged and then the touristy/expensive vibe just threw us off. but once our boat got to capri it felt like a weight was lifted for us. we got off and there was a vintage fiat limo waiting there (definitely toursity to take it, but who cares sometimes, it’s fun!) he took us for 25 euros to the other side of the island, anacapri. the car was so cute, the weather and the views were incredible, it was a whole different vibe. we loved it!

ps. capri is pretty touristy still, but the little alleyways are still very charming. anacapri is muuuuch more chill and laid back. it depends on the vibe you’re going for. i would recommend doing both! the bus back and forth is really easy to jump on and it takes only 15-20 mins to get to the other side and feels like a fun adventure. take the limo once and the bus the rest of the time if you go around. or rent a scooter! that seemed like fun.

pps. we didn’t get to do the blue grotto because of the rain, and didn’t rent a boat because it’s a lot of money for just two people. but in a bigger group i would definitely do that.

9. buonocore gelateria in capri. get the gelato here, it was awesome. it’s popular for a reason. those homemade cones are SO yum. the pastries inside are also very worth it.


like i said, the buses are super easy to jump on and very cheap. they feel like little trolleys!

10. l’angolo del gusto – our favorite meal, maybe of the whole trip. that’s a lot of pressure to say that but everything just went right that night. the truffle mushroom risotto was out of this world. it’s a small and romantic spot next to this lovely white church. the wine, the caprese, the prosciutto and melon. please go there!

ps. capri is known for their mozzarella, so order it all the time! you won’t be sorry.

11. chair lift in anacapri. one of the most memorable activities for SURE. for a few euros you take this chair lift all the way up to the top of a mountain. the view is breathtaking, unlike any i’ve seen. you feel soooo high up, it’s relaxing and peaceful, and then the top you get even more views once you are on land. a must do. (it scares some people but i’m not afraid of heights. i promise it’s cool. it’s only about 12 minutes up and then you can take it back down or walk down. no thanks for me!)

12. casa rossa museum. it’s really nice to just roam around the little streets of anacapri. there’s no cars on a lot of the roads, and it sort of feels like greece with all of it’s white buildings and flowers. this red building stands out on your walk. it’s like 3 euros to get in and is pretty interesting to stroll through. it’s not a must, but if you walk by definitely pop in. i enjoyed the colors and details in there.


we actually had 5 unplanned days on our trip and decided to spontaneously hop on a plane to amsterdam. i really wanted justin to see it there and don’t regret it at all. we ended up taking the ferry from capri back to naples. (i would suggest doing capri last when you are down there because it was really easy to go back to naples by ferry and avoid the 120 euro fare from positano back to naples)

so if you don’t decide to randomly go to amsterdam, then just take the ferry (which is really nice and kinda fun) to naples, a cab to the train station about 15 mins away, and then take a train to florence. easy.

NOW, about florence. when you’re traveling you are going to have cities that steal your heart and cities that are just good. florence for me was pretty fancy/touristy. we stayed on the other side of the river (near here) which helped a lot…but it still just wasn’t my favorite. sorry florence!! happy to have seen it though and actually had one of our favorite meals of the trip there.

13. duomo – cattedrale di santa maria del fiore is one of the most intricate, gorgeous buildings i’ve ever seen. i’m not big on doing a bunch of history tours with lines and groups, we just spotted this place walking by. this place is worth checking out!!

14. this flagship gucci store (i’m a big fan of the brand) is so cool. pink velvet walls. inspiring dresses and shoes. it’s big and fun to walk through. they also have a gucci museum in florence that i’m sad we missed. i wonder if it’s awesome?

15. gusta pizza was right down the street from our airbnb. pretty awesome. i liked the meat pizza. you can ask them to add buffalo mozzarella and make it into a heart too! i ate the whole thing haha.

16. mercato centrale was cool to wander through. we didn’t actually eat there because we were so full from some other pasta dish we probably ate, but we liked looking at all the different stands and truffles and oils!

17. la ménagère. a little pricey but we had a wonderful lunch here. there’s a little cafe, a flower stand and a place to sit and eat in the back. pretty awesome space. try the gnocchi with green apple and have a glass of wine.

18. la buchetta. WOW i love this restaurant. everything we ate was spot on. but definitely, and i mean definitely, order a steak! you can see them preparing the giant steaks in the window. book a reservation and don’t miss this place. or the gnocchi and tiramisu! i know, a lot of gnocchi, but you gotta just go for it in italy, right?


from florence, we rented a car from avis (sorry i like telling all the little details because it’s HARD planning a big trip and i just want to make it easy on ya) and decided to drive the rest of the trip until venice. so happy we did! it was such an awesome way to see the countryside, the little towns, the wineries. and costs about the same as trains + taxis etc.

we drove about an hour and a half south to a lovely little town, siena. once you get out of florence it’s actually a pretty easy drive! the roundabouts can be kinda tricky (and cause some arguments) but you’ll get there. park here and walk all around! it feels like a muuuuch cooler medieval times there.

19. pizzicheria de miccoli. you can’t take any photos inside this charming little butcher shop. do yourself a favor and get a salami and cheese sandwich here on focaccia bread and be in heaven. when you walk through those red ropes you feel transported to another time!


after a few hours in siena, we drove about 45 minutes to meet up with some friends who were on their honeymoon. we were honeymoon crashers!! they invited us to stay with them two nights at their fancy hotel and we had a lot of fun wine tasting and spritzing around town. the air feels so good there, it’s wild. i love looking at the rolling hills and pretty sunsets. you feel like you are in a storybook.

20. boccon di vino. have lunch here, the view is just wow. and the food! the ricotta with herbs. the prawn carbonara pappardelle with coffee powder was out of this world. and again, the truffle gnocchi!

21. conti costanti – we wine tasted a few spots around where we had lunch. we loved this spot especially. pick the grapes off the vine and be happy.


then we drove all the way up to venice, about 4.5 hours. it was a very scenic drive and i suggest doing it. drop your car off at the airport, and take a boat to venice (or a bus + a boat. ask someone there) again, it all seems so overwhelming and unknown, but in reality it’s pretty easy. venice is incredible. best to go in september or october when it’s less touristy/hot…but even with the tourism it’s so incredible you just gotta go. mid september, it’s been the most perfect weather.

22. giant hands sculpture. so cool to see in person. read about them and their meaning here.

23. peggy guggenheim collection. my favorite museum. it’s in her house, and all cool art you wanna see. please go here, it’s so special.

24. cantina do mori. suuuuper old place with brass pots hanging from the ceiling. stop in for cicchetti (small snacks) and wine.

25. la zucca. def make a reservation here. and order the pumpkin flan and veggie lasagna, you will enjoy it. cute decor too! prob my fave in venice.

for a longer trip like this i think it’s cool if you can switch it up between hotels and airbnbs. because having the service, and restaurant, and clean sheets in a hotel is so nice…but also the feeling that you are actually living in the city in an apartment is very important too. i suggest doing both. here’s 40 bucks off if you want to book an airbnb!

italy, you are amazing! we have learned SO so much being here this long and we will never forget it. let me know if you have any questions, i’m happy to answer! xx, bri



Add your own

    Sophia Castano says:

    What an incredible trip. I have to say the bits that I liked the most from your post was when you said “this caused us to fight” or “I didn’t really like this as much as I wanted to.” To me, THAT is what everyone acts like doesn’t exists in vacations and it’s just not true. Going on trips can be so stressful, and you can do something you realize in the end you don’t like, but that’s part of what makes it special. Gotta say I will always be a huge fan of your travel writing, and hope you keep making them.

    Kelsey says:

    Always enjoy following you through your travels and most of all, your REAL thoughts, good or not! Esp delighted to run into you in Amsterdam.

    That dress you wore in Anacapri…please do tell!

    Emily Williams says:

    I’ve been dying to go to Italy and visit all the different places! Thank you so much for sharing all of yalls experiences! My husband and I definitely get fussy with each other when traveling and I love that you included those parts of what you did, didn’t like, and all the stresses that go into traveling. But I will definitely use this guide and your tips when planning a trip to Italy!

    Sirini says:

    In Praiano reading this planning our trip to positano tomorrow! Also bummed we couldn’t make reservations at da Adolfo because they’re super busy. Excellent tips though stealing parts of your trip xo

    Jess says:

    This post takes me back. I need to plan a return trip asap. Can I ask where you stayed in Venice? It looks beautiful! The Guggenheim really is the most amazing collection of art, and I love that she is buried there (with her dogs)!

    Stephanie says:

    Such an amazing trip! So lucky would love to go back to Italy and visit Positano and Florence, thanks for the tips and for sharing such beautiful inspiration photos!



    Jennifer says:

    Ive been watching your instastories like a hawk because we’re going to Italy end of oct > mid nov. My husband is half Italian and has been all over but I wanted another perspective for ideas on where to go and things to do. Thank you so much for taking time on your vacation to write this! Xoxo

    pe says:

    Your photos are always so extra and I love it!! Need to book an Italy trip now!!


    Marcella says:

    Lol, everytime my boyfriend and I go on vacation we always get annoyed with each other at some point because I’m hangry, or like this summer we were in Vancouver and I didn’t get off the bus in time so I had to ride to the next stop while he was waiting two blocks away, lol. We are so bad at public transit!!! But vacations are fun and worth it and seeing new things together is awesome.

    Fee says:

    Amazing photos Bri! You always have the best eye for photos and the best style, please let us know where you got that insanely cute straw bag! eep, so pretty!

    bri says:

    thanks girl! it’s from clare vivier

    Alexandra says:

    Your trip looks soooo good! I’m actually planning a trip to Italy next year with my cousin, she just graduated from high school and has never traveled to Europe.

    I was thinking Rome for a few days and then something more relaxing/beachy for the rest of the trip (about 8 days total). Do you have any recommendations on where we could go after Rome? I want to impress her and open her eyes! 😀

    Thanks Bri!!

    Ilaria says:

    I suggest to go up and visit Cinque Terre 😉

    Cortney says:

    Planning a trip to Italy currently and this was just insanely helpful! Loved your insight on what cities were your favorite and allllll the recs for food! One of our favorite journeys to virtually follow along with, for sure!

    paige says:

    this is amazing, i loved following along on your timeline of events–your insight is so great!


    Susan R says:

    We went to the Amalfi Coast for a friend’s wedding and like you, I fell in love with Positano – such a charming place!

    stephanie says:

    Bri, not sure if you’ve mentioned this in previous travel posts, but how do you find navigating language barriers, especially in less touristy areas?

    Gretchen Mason says:

    Definitely a bucket list trip for me! Thank you so much for all of the wonderful info and details!! I love how honest you are!

    Kristin says:

    Looks like such an amazing trip! I’m headed there in December, and this is all very helpful. I saw on your IG stories that you did a cooking class. Would you mind sharing info on that? Would love to do that.

    Thank you!

    Amanda says:

    Hi Bri,

    This trip looks it was amaze. I’ll be doing an abbreviated version in Spring 2018: Florence, Venice and Rome.

    I was curious… did you have to buy tickets in advance for Peggy’s museum or did you just walk up and purchase them in person?

    Also, did you by chance visit Michelangelo’s David in Florence? If so, any tips on how to reserve tickets in advance to skip lines? If not, that’s ok too. 🙂


    Dana says:

    I’m in Florence now and went to the David my first day- I booked tickets on the official website (ending in .it not .com or anything else!) for the opening time at 8:15. Then that morning you go to the ticket office to pick them up and walk on in! It’s not tourist season anymore so it was EMPTY when we went and everyone was taking solo shots with the statue. Hope this helps!!

    Taylor Karandos says:

    Where did you stay in Positano and Capri??

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