Travel Inspiration: Insider Tips to Planning a Dream Trip to Italy

Let me start by saying….. ITALY is absolutely beautiful! Ever since my studies in art school, I’ve always been fascinated with Italy, especially Rome! It was extra special because:

1) My son who was 9-years old at the time, was able to experience it at such a young age 

2) We were spending it with my husband’s side of the family who resides in Finland (by the way his family is VERY LARGE! He has at least over 15 cousins, which includes his cousin’s children) Crazy right but awesome!

Italy was exactly what I thought it’d be, but even better! The food was absolutely delicious! Have you ever had fresh pasta? The variety of wine, olive oil, the plethora of Gelato, diverse people,  and lastly the culture. The museums, churches, and architecture are unexplainable! Italy is a splendid mix between noisy and quiet, too much and too little all at the same time!

If you are thinking of heading to Italy or just want to live vicariously through me then this post is for you. I want to share where we stayed, the cities we visited, what we did and what I wore because hey it’s one of the fashion capitals, right?


Can I just say? Rome reminds me of New York City except with Palm Trees! If you’ve never been to NYC then let me tell you, it’s stimulation overload, but I LOVE IT! Long avenues, lots of walking, crowds of people, street vendors, large buildings mixed with apartment complexes, underground express train station, museums, history and historic buildings with architecture that have been here for 100’s of years. People whizzing by on scooters as well as couples making out ~ definitely a romantic country.

We were lucky that we had a family friend who still keeps his childhood apartment in Rome which he let us stay there for a few nights so we could explore Rome before we went to meet the rest of the family at the Villa in Tuscany! Staying at the flat also helped our budget so that we could splurge when we went to dinner and museums. We ended up buying a few things for the kitchen so we could have breakfast in the flat before heading out for the day as well as some late-night snacks! Of course, Wine, Bread, and Cheese were the main staple!

There was so much to do and see that I can’t even fit it all but we definitely tried our best to visit all the famous tourist attractions such as the Spanish Steps, Colosseum, The Pantheon, Trevi Fountain, St. Peters Basilica in Vatican City.


After spending 3 nights in Rome, it was finally time to head off to Umbria to meet up with the rest of the family at the Villa near Chusi. My husband’s uncle found an agriturismo beautiful farmhouse villa that had been around since the 1700s by the Graziani family. The villa is located in the hilly countryside of Trasimeno Lake, on the border of Umbria and Tuscany. It’s a perfect place for an exclusive holiday of wellness and relaxation with family or friends.

I believe he chose this Villa because of the Finnish ties since the owner’s wife is from Finland. The name of the Villa is Case Graziani and to this day is still run by Graziani descendants. Set on many acres of land that are popular among tourists during the Summer for its Sunflower fields. Love Olive Oil? Then this is the place to be because Case Graziani produces and sells Olive right in their backyard. I know a lot of family members that shipped cases home!

This breathtaking villa is fully equipped with a Finnish Sauna, Pool, Jacuzzi, and Fitness Room and hosts up to 45 guests, and has 7 bedrooms. During our stay there, we traveled to the closest towns, Cortona and Siena, for sightseeing at Montepulciano and Arezzo, wine tasting at Contucci, shopping and to eat yummy lunch and dinner in the nearest town of Chusi. Below is just a sample of what you can expect from visiting these charming towns.


Cortona is a charming hilltop town in the province of Arezzo, Tuscany, and is known for its breathtaking views of Lake Trasimeno. It’s packed with ancient Etruscan history, historic churches, museums, tons of shopping,  art galleries, and delicious food. You can people-watch in the Piazza Della Republica as we did, or sit on the steps of the Palazzo Communale and catch a town flag demonstration in the Piazza Signorelli.

Looking for something to do outside of the above? Wander the town and look for charming details. The town’s steep and narrow little streets are packed with beautiful touches of decor such as colorful doorways, colorful plants in bright pottery, decorative fountains.


Siena is a small, romantic city in the central Tuscany region and is known for its gothic medieval architecture. The Piazza del Campo is the heart of Siena, aka the fan-shaped square, famous for the Palio, a horse race held twice a year and considered one of Europes greatest medieval squares. The city’s historic districts are home to artisanal boutiques, art galleries, local festivals, flea markets pastry shops, restaurants, and home to the famous Nino & Friends, a delicious candy and chocolate store that displays liquid chocolate fountains and delicious limoncello chocolate balls.

Besides the shopping and food, my most favorite part of visiting Siena was staring at the magnificent Duomo of Siena. The Gothic church is one of the most beautiful and impossible to miss treasures of the city. The exterior is nothing short of breathtaking with the heads of 172 popes peering down at you as you enter. The church interior features great art, including sculptures of Michelangelo and Bernini with mosaic tile floors



If you plan to make a trip to Rome in the summer, keep in mind that it gets extremely hot as the sun reflects off the cobblestones, which makes the city feel even hotter during the peak of summer. We visited in mid-September, and I was sweating bullets during the day (even with the many refreshing and yummy Gelato), but at night it cools off so you can carry a sweater or light scarf.


Umbria is warm during the day but tends to be on the cooler side as it’s near the coast. I packed a few light dresses, airy materials, and a lot of crop tops. I also packed a few light sweaters for those cooler days and nights. You will need a pair of shorts or pants if you plan on renting scooters or bikes to ride through the city. I love hats so I made sure to pack one that was light. And matched most if not all my outfits and could wear on the plane. Shoes included a pair of comfortable sneakers for walking and a few pairs of light sandals.

To sum it all, Italy was absolutely a dream, and there’s still so much that I haven’t seen or done! I plan to go back and fall in love with the country all over again. I hope you all enjoyed this post as much as I loved being there!

Ready to plan that dream trip to Italy? Check out all of Wild Bum’s Italy guides right here.

About the Author

Jaime Brown is a Boston based freelance wine and beauty writer, editor, and content creator. With a passion for all things Rosè and Red Lipstick. In addition to her role as Lead Content Creator at, she also contributes to Food & Wine, Apartment Therapy, SCOUTED by The Daily Beast, ThriveGlobal, and her blog 

Jaime Brown

Jaime Brown