The Raymers Take Italy: Cortona

We spent two and a half weeks in Italy, and I’m going to let ya in on where we stayed, some local spots we found, and tips we picked up along the way!

We flew into Rome and headed straight to Tuscany because I wanted to be impeccably fresh for the wedding (read: drink wine). Catching the train in Roma is where we learned the first TIP! Get 360 degree luggage and only pack what you can carry! We got our sets from Costco and they were a great find.

360 Degree Luggage


Your arms will thank me after you have dragged your luggage across a multitude of cobblestone streets, moving from train to taxi, to gondola!

We used a travel agent to book our honeymoon and I wouldn’t recommend him, so I won’t disclose his name. But, I will tell you that travel agents can be a great way to go if it’s your first time to an area and you don’t want to do the leg work of researching and booking accommodations. He was free of charge because he receives commission from booking hotels, trains, tours, private transfers, etc. I wouldn’t suggest private transfers for vacation as they can get pricey, but they  were a nice touch of luxury since it was our honeymoon. The train system is extremely efficient in Europe and  you can get almost anywhere. Tickets are also easy to book on

Here is my second TIP! Take the Frecce (high-speed) trains when possible, especially on longer trips, and spring for 1st class! First class tickets are generally only €30 more than 2nd class and the difference is notable from the leather seats, more space, 1¢ wifi, and free wine & snacks!

le frecce

First Stop // Cortona

Cortona is in the Tuscan region of Italy and is well-known for being the backdrop to the movie, Under the Tuscan Sun. I basically got married in a town fitting for a big screen fairytale!


We stayed and got married at Tenimenti d’Alessandro. It’s home to the Borgo Syrah vineyard, and is located just outside of the Cortona walls.




Even if you don’t stay at Il Borgo, you should definitely look into visiting. They offer cooking classes, spa services, tastings, vineyard tours, and their food is amazing!

Make reservations at La Grotta. It is one of the oldest Tuscan restaurants in Cortona and it’s almost hidden location, in the city centre, makes it a pretty sweet find. And, I would be at risk of divorce if I didn’t advise you to leave room for just a little cup of Snoopy’s gelato.


If you’re visiting during the summer season, you can enjoy your gelato in Piazza Garibaldi, where the orchestra plays in the evening.


Every Saturday, a market fills Piazza Signorelli, where you will find a little bit of everything: food, clothes, gifts, jewelry, antiques and even household products. I found the best underwear I have ever owned for only 3/€10. Next trip, I will stock up!


If you’re interested in an intense hike with a stunning reward, then you need to check out the Basilica di Santa Margherita.

cortona church

And on that note, this is my final TIP! Ladies, bring a scarf everywhere you go! There are basilicas (important churches) everywhere, and you will want to go in all of them because they are stunning! But, you cannot go in with your slutty shoulders.



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Kenya Raymer is a writer, blogger, dancer and the hostess of the natural-hair meet up Curls & Cocktails. She is a self-love enthusiast who uses her natural-hair platform as a space to discuss hair and all things beautiful & real. She is loving in Nashville, TN, where she promotes the local eats, animal rescue, self-awareness, personal growth, happiness and finding comfort in your own skin.

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