How to plan the best Sicily holiday

Going to Sicily is better than going to the moon.” -Gabriel Garcìa Màrquez, Spanish author and playwright.

Jessica in Marzamemi

It seems like Sicily is a place that people aren’t too sure about…they don’t know what to expect or why they should go. I can’t even give a quick summary of why you should visit Sicily because the list is sooooo long! And there are plenty of ways to take a Sicily holiday (or vacation for my fellow Americans!).

Maybe it’s 2020 being 2020 with all of its uncertainty, but our travel style has evolved to include a little help. Our trip to Sicily was our second Italy trip where we had help, and let me tell you, it’s a huge weight lifted off my shoulders.

I love planning, don’t get me wrong. But sometimes it’s all too much. Planning a trip takes so much effort and is exhausting…even for someone who does it all the time. That’s why, for our 10-year wedding anniversary trip, we decided to work with a company to make our Sicily trip as smooth as possible.

Sean and Jessica in Taormina Theatre

This trip was gifted so that we could share our experience with you. All opinions are my own.

I researched a lot (as I do) and discovered Sicily Activities — a small, professional company run by Alex and Massimo. I’m always completely honest with you, so I’ll be honest in saying that it partially stuck out to me because the website was well-done and in English. I know, I know! That is not always a sign of quality or even a good company. Don’t worry, though. I dug deep, talked to them, and researched more. It’s just that first impressions mean a lot, and fewer hurdles is appealing, especially for such an important trip.

We clicked instantly. I felt good about putting our very special anniversary trip in their hands. I was starting to get more excited and less nervous about completely blowing it.

Isola Bella

How to plan the best Sicily holiday

Planning a trip can be high-stress, and while using a company like Sicily Activities significantly reduces that stress, there’s still a bit of work you have to do. That’s what we’ll cover first because it’s really what will get you excited for your trip!

Know what you want from Sicily

First of all, know generally what you want out of your trip. There is so much to Sicily that it can be overwhelming. We figure we need to go back at least 2-3 more times for 1-2 weeks each to feel like we’ve “seen” Sicily properly. But you may not be like us and just want a taste of everything the island has to offer.

We went for a foodie tour on the east coast of Sicily with Sicily Activities. (Our full itinerary is below). But you can choose a general tour with a ton of sightseeing. Are you a fan of the Godfather? They have special tours for that, too. If it’s a romantic anniversary, they’ve figured out the perfect itinerary for you to celebrate properly. And yes, there are many more ideas.

The beauty of working with Sicily Activities is that, while they have suggested tours (small group and private), you can create your own. Let them know what you’re interested in, and they will create the perfect multi-day adventure for you with transfers and incredible guides. They make it easy to relax.

Jessica in winery

Know your vacation style

You decide if you want mid-range or luxury accommodations (this is a good time to splurge a little, I promise you). Think about if you want your days packed with activities or want some time in the evening for yourself. This is so important. You have to understand your own travel personality a bit. While the company does a great job of building the itinerary with great adventures and booking knowledgeable guides, it has to work for YOU. So, make it as busy or as calm and you need it to be.

They also act like a vacation concierge as well. So, outside of the planned activities, if you’re looking for a good place for dinner, need help getting tickets for something, or just have questions, they are there to help. Anyone would be happy to have that service.

Our 7-day Sicily Itinerary

Sicily Activities offered to pick us up from the airport and get started right away, but we had some unfinished business with Catania, so we stayed the night in the main city in the east (it has an international airport, too). If you want to learn more about our Sicily trip that was cut short, I wrote a pretty raw and emotional post about it that you can read. So, we started with them the day after we arrived.

Day 1 in Syracuse

We were picked up from our hotel in Catania and driven to the island of Ortigia in Syracuse. The landscape in Sicily is always epic, so the drive goes by pretty quickly. Then we hopped out of the luxury van and listened to the waves of the sea.

After we dropped off our luggage at our hotel (which is in a perfect spot to walk around and take it all in), we took a walking tour with our super knowledgeable guide who grew up here, Valeria.

It was on this tour that the weight of the history of Sicily really hit me. When you come from a country that is less than 300 years old, it’s so hard to understand how there are structures still standing in Sicily that are hundreds or a thousand years older than your country.

Seafood in Ortigia

We learned so much and did our best to take in our surroundings. But since we were on a little foodie adventure, Sicily Activities had scheduled a couple of stops so we could taste the local food and wine…and I tried my first octopus! It wasn’t bad at all. Sean loves the stuff and will order it about once a day in Sicily.

What a day! Ortigia makes a great first impression for anyone when visiting Sicily.

Jessica in Noto

Day 2 in Noto and Marzamemi

Our guide/driver, Elena, picked us up from the hotel and took us to Noto. This little town makes a big impression with its baroque architecture. Because the original town was destroyed in the 1693 earthquake (yep, still before the USA was its own country), they decided to rebuild just a few kilometers away.

Our first stop in town was to try a special kind of local chocolate. It’s so interesting…and we bought 4 bars. I may be eating one as I type this. 😉 Then we walked the main street (Corso) and learned about why some of the doors to the buildings were about 5 feet off the ground.

If you like churches and palazzos, this is a great place to spend a few hours. It’s an easy walk that boosts lots to see!


Once we were ready, Elena drove us a little farther to Marzamemi — a cute little fishing village. While walking on the wall and climbing on rocks by the water was fun, the square for the town might be the cutest one I have EVER seen.

It’s surrounded by shops and restaurants with the coolest signs and colorful tables and chairs. Many of these restaurants have seating with a view of the sea. Is there anything better than a sea breeze on a hot day while eating lunch? No. No there isn’t. That’s how we enjoyed lunch!

Jessica with tour guide in Taormina

Day 3 in Taormina

It was time to go to Taormina, so Elena (our guide/driver from yesterday) picked us back up and took us to our hotel in Taormina where we dropped off our bags and started a foodie walking tour!

This town is amazing. It’s a bit hilly, so be prepared, but my goodness. Just look around and you’ll think “whoa!”. And that will happen again and again.

Sicilian treats

I love that Sicily Activities had included food elements into the walking tour…and then we added some more because we’re us :-P. Our guide was so flexible and I’m pretty sure she was having fun, too! We learned about the ancient portas (gates), the imposing churches, the history of the town, and of course about the food.

Everywhere was photogenic, and she would help us find the perfect spots. I’m also grateful to her for asking if we wanted a picture together. We always forget to do that!

Jessica in theatre

We rounded our day together off with a visit to the ancient Taormina theatre. I was in awe. This place is mindblowing and I can’t imagine anything more spectacular. The theatre is perched on the hill (our hotel was directly below it) and so the view from the seats were of the stage, the columns, and the sea. Magical is the only way I can describe it. It was the PERFECT end for the Taormina tour.

Sicilian cooking class

Day 4 with a cooking class

We got hands-on in our Sicilian cooking class. We’ve had good cooking classes and meh cooking classes, so we never really know what we’re getting into. But luckily, this was a good one!

We started by meeting our chef and heading to the market to buy the ingredients. Of course, it’s only a couple minutes walk away and he knows everyone along the way. Ah…you gotta love small Italian towns.

Just after that brief interaction, Sean whispered to me, “I already have a good feeling about this one.”. He was so right. I smiled and laughed so much during the whole process. Our chef set everything up for us, and while he would do that for each course, we were given a table with food and wine. Let’s just say, you’ll not go hungry here!

Stuffed Sardines

We made a feast! It started with shaping dough into various shapes of bread, then we made pasta, covered a fish in salt, stuffed sardines, layered the eggplant parmesan, breaded and wrapped the swordfish, then fried the sardines and zucchini flowers. We tried but couldn’t eat it all! Luckily, they happily wrapped it up and we had it for dinner that night, too. A second chance to eat all of that deliciousness? Yeah, we were happy with that!

Mt Etna winery

Day 5 in the Mt. Etna countryside

We’re in the car again and this time we are headed to the countryside of Mt. Etna. I can’t express how excited we were to finally get a bit closer to the famous volcano.

Our first stop of the day was at a winery with insane views and the nicest staff. That’s one thing I experienced everywhere, everyone was SO NICE. I don’t know why, but I wasn’t expecting that.

When we arrived, we were given a nice chilled glass of white wine (it was a HOT day, so this was appreciated) and were welcomed with some history of the vineyard. After giving us plenty of time for photos and video, we went in to start our tasting with the perfect view in front of us.

We tried a couple of whites and a couple of reds and ended up buying 4 bottles of wine and a bottle of their olive oil. It was that good! And they had a nice deal when you ship it home…so guess what arrived TODAY!! The doorbell rang and Sean yelled down, “Is that the wine?!” Shipping it home made it even better because we didn’t have to figure out how to pack it all into the suitcase.

Our next stop was a lovely farmhouse for lunch. While our lunch was great with an impressive antipasti and the kind of pasta that reminds you that you really are in Italy, the atmosphere stole the show. It was so lovely and just felt good, you know what I mean?

After we ate, our guide Salvo took us around the property a little bit to see the animals, the grapes, and the many places that seemed like little peaceful hiding spots.

lava flow

Day 6 on the slopes of Mt. Etna

The last day was an epic one. We were picked up at our hotel and taken straight to Mt. Etna and we couldn’t have been happier!

As we started to ascend the volcano, we noticed different kinds of plants. I had no idea there were plants on the side of the volcano. I’ve known how good volcanic soil can be but never pictured what that really meant. Our guide, Rosario, was so flexible with us because we wanted to keep stopping to take it all in (and take some pictures!)

Jessica on Mt Etna

There’s a stop at one point with a shop, cafe, and restroom. This is important information because it’s nice to know you have a place to use the bathroom! It’s near the easiest crater to get to and one of the most incredible views I’ve ever seen.

I was in awe. I couldn’t stop smiling, but it was so windy that keeping your mouth closed is a good idea. Also, a mask and glass/goggles aren’t a bad idea either! This is simply an experience you have to have.

View of vineyards

Our last stop before heading back to our hotel was at a winery overlooking the vineyards and the coast. Sean and I sat there talking about how absolutely perfect everything felt. We were sitting at a winery that was hundreds of years old, with the best view I could think of, eating autumn-inspired Sicilian dishes and drinking delicious wine under a canopy of trees on a day with the perfect temperature.

It felt fitting to have such a perfect lunch experience to end our time with Sicily Activities. I can’t think of a better way to end the week of exploring, learning, eating, and drinking our way around the east coast of Sicily, Italy. I’m tearing up just thinking about it. We do these kinds of things and work with these kinds of companies because it’s fun for us, but also so we can inspire you to do the same so that you can have epic memories, too.

Jessica in Mt Etna Crater

Read more on Sicily: Foods to try in Catania, Sicily

My favorite parts of our Sicily Tour

While the whole trip was amazingly well-organized and we enjoyed every bit, there’s bound to be parts that made us go “wow!”. These are the memories that will stick out the most for us and we’d consider must-do with Sicily Activities.

Take the foodie tour of Taormina. There is so much to learn and this town is a treat to walk up and down (we did it MANY times!). You’ll get a taste of Sicily while getting a city tour of Taormina and a better understanding of Sicily in general.

Cook your little heart out at the cooking school. We had such a blast during our cooking class. It was actually fun (sometimes they are just stressful!) and our chef was amazing. It didn’t hurt that we were constantly fed and given wine 🙂

What topped it all was the Mt. Etna day trip with lunch at a winery. Sounds simple, straight-forward, but really it was fantastic and created a lasting memory that I’ve struggled to put into words. I did my best above but it was all about the feeling it gave me and a lot of that came from the guide who knew everything there is to know about Mt. Etna. He also stopped at all the spots he thought we would love. I couldn’t stop talking about the vegetation so he made it a point to not just stop at lookouts but also places with different plants. Then, lunch at the winery just made the day that much better.

Obviously, we’ll all love different things, but that’s the great thing about booking with Sicily Activities. You know what you like, and they know how to take that information and create a perfect Sicilian vacation.

Jessica with Mt Etna Guide

Why book with Sicily Activities

First, they are nice people with a passion of helping others create the perfect holiday to Sicily. But they also have won a 2020 Traveller’s Choice Award from TripAdvisor and have been accepted as a XO Private member which are considered destination masters. Their guides are locals and fully certified as tour guides which is very important in many parts of Italy.

Communication is key in trip planning. You don’t want to be left hanging with some of your plans hinge on other parts of your plans. Luckily, while in Sicily, you work with one person and they are there to help you at every turn!

As I mentioned before, the big thing for me was less stress. It was evident in the beginning that I could depend on them and I didn’t have to worry. Here’s an example of them having their stuff together. Our trip got postponed from March to September. Before our March date I mentioned my allergies to animals and it wasn’t a problem but I had to know ahead of time. The day before we went to the farmhouse in September, Alex sent me a message letting me know that we would be around animals the next day. I had forgotten about that…and she remembered!

They are also there to help every step of the way and are always available. I was thrilled they were able to get us a table at a restaurant who declined us (I still don’t know why). I asked a question about it and 10 minutes later I got a reply from Alex saying it was completely okay to make a reservation and asked what time we would like. It’s things like that and attention to detail (like letting a hotel know it’s our anniversary) that make a big difference to a trip.

While you can book day trips with Sicily Activities, I highly recommend making your life easier and putting at least a few days in their hands. Book directly with them and let them know we sent you to them — it’s like a little hug from us to you to them. And it always helps a business to know it was worth working with someone like me!

Sean and Jessica in Taormina

If you’ve made it to the bottom, HIGH-FIVES to you!! I can get a little long-winded when it comes to epic trips, but I wanted you to have alllllll the information.

I hope you enjoyed this trip to Sicily and I know Sicily Activities can’t wait to welcome you whenever you are able to visit. It’s truly a hidden gem for many and that’s the most fun part of our job…helping you discover places like this.

Wishing you joy and travels!

Jessica Cutrufello wearing a green floral dress, glasses and pink lipstick

Hi! I’m Jessica, an American who made Amsterdam her home in 2014. I share European gems through food and memorable experiences. Want to know more? Head to my about page or check out my YouTube channel.