Exotic Italy: 2 weeks in Rome, Tuscany, Florence & Bologna

When Deepti Kshirsgar did a guest post for me about her love for Florentine sunsets, i honestly and smugly passed it off as naivety – sunsets happen every day, around the world, right?! Wrong! I was so wrong and she was so right.

My 2 week trip to Italy was conceived primarily due to ridiculously low air fare, so when i found a 28K INR return ticket Mumbai – Rome – Mumbai via Kuwait, i didn’t even blink and just booked it! Little did i know that it was about to change my entire perception about Italy and make me fall in love with it, as cliched as it may seem…

Having recovered from a very rough 2016, i was also looking forward to some fun solo travel after a long time.

My original plan was to cover Rome, Naples, Pompei, Capri and Florence, and possibly Pisa and Cinque Terre.

But I soon realized it was a crazy idea, and cut it down to just Rome, Florence (Tuscany), Bologna and San Marino – a whole country i found hiding inside Italy!! (more on that later).

Whenever i visit a new country, i’m always overzealous with energy and my strategy is to adapt to the new time zone and ‘push the day’, so my body gets naturally tired by night and resets the Circadian rhythm to the new time zone.

So without wasting ANY time, i went from the airport to the city center by train and got straight on to a ‘hop-on-hop-off’ bus without even checking in to my hostel!

Immigration was smooth, and my ‘buongiorno’ sounded so perfect to the officer that she though i was a native Italian speaker. Likewise with ordering my first espresso at the train station – it all came too naturally. That’s the beauty of Romance languages – when you speak one, the others are too easy to pick up!

Day 1 – Hop-On-Hop-Off Bus & Quick Recce

For the first 2 nights, i had booked an ‘artsy’ hostel in Rome, to go with the theme of the land – it was definitely a great choice, since it was a very nice hostel with a great rooftop, friendly staff, clean rooms and fun company as with most hostels. I even got to practice some Portuguese with my fellow Brazilian roomie and Spanish with Colombians 🙂


Day 2 – Walking around Rome’s Historical City Centre

Walking if my favorite way to soak in and understand a new place i visit, so here’s what i covered on Day 2 on foot in Rome: Trevi Fountain, Pizza Della Pilotta, Pantheon, Piazza Navona, Colosseum, a quick visit to the Vatican (took a Uber back to the hostel when it got too hot to walk) & Trastevere in the evening.

Day 3 – Quick Recap, Romun Forum & Imperial Forum

After acclimatizing to Rome in the first day and a half, i grabbed a local breakfast at the Mercato Centrale and then headed to explore the Roman Forum & Colosseum again. 

Day 4 – Train from Rome to Florence

I booked my train tickets to Florence and reached the wonderful Renaissance city. Post some laundry at the hostel, i walked around the historial city centre… 

Day 5 – Walking tour of Florence

Today i walked up to Ponte Vechchio & Piazzale Michelangelo followed by a paid walking tour of the city with Ciao Florence.

Day 6 – Wine tasting in Val D’Orca, Tuscany

The walking tour with Ciao Florence got me sold on doing a day trip to Tuscany with them the very next day, for around a 100 Euros. This included a bus trip to Montepulciano & Montalcino in the Val D’Orca Valley of Tuscany, along with wine and cheese tasting (lunch was to be paid separately)! Once again, it was 100% worth it and i had a terrific time!

Day 7 – Discovering Bologna

Scrapping my original plan to head South, i decided to skip the crazy heat and head north instead, and landed up in Bologna which honestly blew my mind for its surreal orange hues and staying in a private room in a fabulous hostel that i found… WeBologna. 

At this point, i have to mention what made me decide Bologna… while researching on places to escape the heat in mainland Italy, i discovered a whole new country i didn’t even knew existed:
San Marino

Day 10 – San Marino to Florence

After spending 2 days and 2 nights in the wonderful country of San Marino, i returned to Italy and headed back to Florence to meet a friend. This time, i chose to stay nearer to the historical city centre in a ‘poshtel’ called Plus Hostels.

Day 11 – Gardens of Florence

Me and my Canadian friend Harjeet explored the gardens of Florence today: Boboli & Bardini. In the evening, she did the walking tour that i had done earlier, while i dined on my own at the wonderful Buca Mario ristorante.

Day 12 – Walking in Florence

Harjeet had an idea of a few places she wanted to visit, inspired by Atlas Obscura, so we started the day with a quick breakfast with a view at Caffetteria delle Oblate followed by some walks where we explored Piazza di S. Pier Maggiore, Mercato St. Ambrogio, School of Leather, Basilica of Santa Croce, Mercato Centrale, the Piazza del Duomo, Piazza della Repubblica and Ponte Vecchio.

Day 13 – Day trip to Leaning Tower of Pisa

Although i used to shrug it off as ‘touristy’ earlier, i decided to make a quick last minute trip to Pisa to check out the world famous Leaning Tower of Pisa anyway. because… why not?!

What i loved about the city was how underrated the rest of the city is, and the amazing day trip options nearby, for those who extend the day trip into an overnight stay or more.

Day 14 – Local markets of Rome

Out of curiosity, i wanted to check out what the hyper-local markets in Rome looked like… where the locals shop their daily stuff. After a fun first half doing just that, spent the second half walking around the Trevi Fountain and the Roman Forum – my favorite parts of Rome!

Day 15 – Piazza del Popolo, Vatican City, Colosseum & Trastevere (Last day in Italy)

On the last day of my 2 week trip to Italy, San Marino & Vatican City, i went back to the Vatican for a quick visit but landed up getting absorbed in a crowd being addressed by The Pope himself!! Sometimes, amazing things happen even when you don’t have a plan.

Arrivederci, Italia!

The two weeks i spent in Italy were all about exploring with little planning, little research and just witnessing what it had to offer in terms of sights, sounds, tastes and experiences. Chancing upon San Marino was the cherry on the cake, but Italy surely stole my heart and i’m already itching to head back for more 🙂


Exotic Gringo (Kaushal Karkhanis)

Leading an experimental life as a digital nomad, I started traveling in 2007 while choosing to shuttle between Goa and Mumbai as 'home'. An epic life-changing trip to South America an year later gave birth to this blog, Exotic Gringo.