Traveling Italy: Siena

September 10, 2013


Settle in, friends, and get ready for a bunch of posts about all things Italy and travel. Before I get to the specifics of our day in Siena, let’s talk a little bit about our trip in general. Joe and I have been thinking about taking a trip to Italy since we got married two years ago. Italy was the natural choice. I mean, what’s not to love? Amazing food, beautiful countryside, tons of history and super friendly people. Count us in!

I’m planning on covering the specifics of the costs of taking a trip like we did in another post, but for now, let’s talk about the fun stuff! With a little (okay, a lot) of help from Lauren over at Aspiring Kennedy, we planned our time in Italy accordingly:

Thursday, August 29th: Leave for Italy on the red eye flight
Friday, August 30th: Arrive in Rome at 4 p.m.
Saturday, August 31st: Full day of sightseeing in Rome
Sunday, September 1st: Travel by train from Rome to Florence (1.5 hour train ride) with afternoon sightseeing in Florence
Monday, September 2nd: Day trip to Siena (Tuscany region of Italy, 1.5 hour bus ride)
Tuesday, September 3rd: Day in Florence
Wednesday, September 4th: Travel by train from Florence to Cinque Terre (2.5 hour train ride)
Thursday, September 5th: Day on the beach in Cinque Terre
Friday, September 6th: Travel from Cinque Terre back to Rome (4.5 hour train ride)
Saturday, September 7th: Depart from Rome for home

Since I’m editing my photos out of order, these posts are probably going to come out of order. Let’s just overlook that, okay?


Joe and I agreed that our favorite day in Italy was our trip to Siena. Since we had three full days in Florence, we couldn’t pass up the opportunity to get a look at the Tuscan countryside and spend a day in a smaller town filled with a whole bunch of charm. We took the bus from Florence to Siena in the morning and took the last night bus back to Florence, giving us a full day there.

We didn’t really have an itinerary while we where in Siena, and I would suggest the same if you ever find yourself there. It’s a small town filled with a ton of adorable little clothing shops, cafes and places to stop and people watch. When we arrived in Siena, we each grabbed a slice of pizza and a Diet Coke and headed to the city center to people watch. There are no cars allowed in the center and people lounge around as if they are at the beach.




After lunch we did a little window shopping, then, at the advice of Rick Steves, we set out in search of the Tuscan Wine School to sign up for a class on Tuscan Wines. It was a little on the pricey side (40 euro per person) but totally worth every penny! The two-hour-long class gave a brief history of wine in Italy and Tuscany and then proceeded to let us taste six different wines grown in the area. The wines we sampled were high quality wines and we got generous pours of each wine, so I think that’s 40 euro well spent! My favorite wine? The vin santo, a sweet, straw-colored dessert wine.




We had a great group of people at our wine class, including a great couple from Switzerland (hello, Daniela and Fabian!) After our class wrapped up we grabbed dinner with our new friends at Zest Ristorante and Wine Bar. If you like good food and awesome ambiance, this is your place. Side note: Italy has now given me a true appreciation for the meaning of “al dente” pasta.


We hopped on the last bus out of town and found ourselves back in Florence by 10, full and happy from an amazing day. When I read about Siena, everyone had amazing things to say about the town. And now, you can add me to the list of those who have fallen head-over-heels about Siena. You better believe we’ll be back!


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  • Reply Julie Wunder @ Runninginaskirt September 10, 2013 at 11:51 am

    Hi Madison! I love your first Italy post and am looking forward to seeing the rest of your trip! My husband and I just took a similar trip in late May/June…. I posted the recaps on my blog as well, if you are interested. I’m curious about what you thought of Cinque Terre– we had a ton of rain and the trails were mainly closed when we were there!
    Your pictures are beautiful!!!

    • Reply MadisonMayberry September 11, 2013 at 1:07 am

      Hey Julie! I just had such a fun time reading through your Italy posts. It makes me want to go back to Italy asap! Especially now that I have a major jet lag hangover from the time change and going back to work.

      I have to say, I think we had the exact opposite experience in Cinque Terre! It was sunny and in the low 80’s the entire time we were there, so it was perfect for hiking and spending a full day on the beach in Monterosso (we also stayed in Monterosso, like you did!) Since the weather was so nice, the trails were open. But we only did the Monterosso-Vernazza hike and back to Monterosso. Holy difficult! But it was worth it for the views, right?! I think you should take another trip back to Italy just to enjoy Cinque Terre in the warmer months. šŸ™‚

      • Reply Julie Wunder @ RunninginaSkirt September 19, 2013 at 10:53 am

        Yes, the hike was totally worth it. I will never forget those views.
        I think we should go back too šŸ™‚ I’m also wanting to go back to France now too. I guess I have the travel bug.
        I thought our opinion of Cinque Terre might have been jaded by the weather. Good to know you liked it. I’m looking forward to the post.

  • Reply Rachel September 10, 2013 at 8:00 pm

    Gorgeous photos! Sounds like an amazing place I will need to make sure I make it to some day! That wine class also sounds amazing, what a fun experience šŸ™‚ Looking forward to your other posts!

    • Reply Madison Mayberry September 11, 2013 at 1:00 am

      Thanks, Rachel! You do need to make sure you visit sometime. It was truly a magical place and the whole country just won me over. I’m already thinking we need to go back! Now, if only airfare was cheaper… šŸ˜‰

  • Reply DessertForTwo September 11, 2013 at 12:32 pm

    I love this! I’m so excited for more of your Italy posts!

    I’m so glad you had a great trip! xo

  • Reply Kristin @ Iowa Girl Eats September 19, 2013 at 9:24 pm

    Your recaps are bring back such great memories of our trip to Rome and the Amalfi Coast a few years ago. Can’t wait to read more!! šŸ™‚

  • Reply Gabby Deitsch January 25, 2016 at 2:14 am

    We’re in the midst of planning a trip to Europe for this September and I can only find two posts of yours about Italy. Did you ever write the rest of your trip recaps or tips on packing, budgeting, etc.?

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