Is there anything dreamier than a summer vacation in Italy? No, I don’t think there is and I’m certainly not the only one that thinks that, explaining the millions of visitors that Italy host every summer. The massive crowds are sure to distract that serene summer vacation you were envisioning…

How can you beat the crowds and get off the beaten path in Italy? Consider visiting Sicily! An under-rated Italian destination, Sicily a unique stop for travelers looking to see a different side of life in Italy. Sicily maintains a strong local culture that is distinct and different from mainland Italy, with a quarter of the tourist hoards than you might see in Venice or Pisa.

I traveled to Sicily as part of a heritage trip with my husband’s family in search of relatives and to reconnect with their family roots. We spent 2 weeks circumnavigating the island, exploring as many corners of Sicily as we could. Filled with beautiful sites, delicious food and wonderful beaches, there is so much to see and do in Sicily for 14 days.

Here is my ideal travel itinerary for 2 weeks in Sicily!

Day 1-2: Palermo

Palermo is the city where most of the international arrivals fly into, and it is usually the most logical place to begin your tour of Sicily, although there are an increasing number of flights to Catania. Of all the places we visited in Sicily, Palermo was probably my least favorite city because it is crowded, loud, and hectic. If you’re not into busy city culture, you might consider staying somewhere else. Nearby Terrasini is a nice alternative!

The streets of Palermo are pretty chaotic (think Rome but crammed into old city walls), so I would recommend waiting to rent a car until after you leave the city. But if you’re feeling wild, Palermo would be a fun place to rent a motorbike and scoot around for the day. Palermo is undoubtedly Sicilian and it has more than enough places to visit in 24 hours, but here are some of the most worthy stops

• • • Pretoria Square
    • Zisa Castle
    • Catacombs of the Capuchins
    • Jesus Palermo Church
    • Botanical Gardens

Day 3: Agrigento

Once you head out of Palermo, you will immediately feel more calm and relaxed. The rest of the island has a much more comfortable and laid back culture. Agrigento is a wonderful next stop to consider, although there are plenty of small towns along the way which might be worth stop depending on what you’re interested in, such as Selinunte, Segesta or Ribera.

Agrigento is a coastal city that is home to the amazing Valley of the Temples ruins. These are some of the best preserved Greek ruins in Europe and are deserving of at least a half day tour. Old town Agrigento is charming, located up on a bluff making for beautiful views and is a wonderful stop for a nice dinner and sunset. The beaches in southern Sicily are less picturesque than some on the North, but far less crowded, and I’m glad we checked them out!

Day 4: Ragusa & Modica

Known as sister cities, Ragusa and Modica are just plain beautiful. They are built on the top of cliffy scrags of jagged rock divided by deep valleys. Ragusa is even considered a UNESCO world heritage site!

The views are probably the most impressive parts of the city, but I also enjoyed the beautiful Cathedral of San Giorgio and the other Baroque churches in the cities. It’s easy to spend a day or two exploring around the old architecture and winding streets of these picturesque cities!

Day 5-7: Syracuse

Siracusa, also known as Syracuse to foreigners, is a picturesque and quintessentially Italian coastal city. It’s adorable charm makes this a must see on your 2 week vacation in Sicily. This was my favorite place in all of Sicily! One of my favorite things about Italian cities is walking around the streets. There are so many nooks and crannies! We spent one whole day in Siracusa doing a DIY walking tour along the coastal side of the peninsula of Ortigia.

The streets of Ortigia themselves are like works of art with small winding alley ways which turn a corner into a pallazzo and tiny plant lined balconies hanging over the streets as people dry their laundry across alleyways. There are lots of galleries, shops, restaurants and museums to check out, so leave yourself some free time!

After spending our entire first day exploring Ortigia, the next day we expanded out to explore other parts of Siracusa because greater Syracuse also has some great tourist attractions that I would recommend. Just on the north side of town, you can find ruins of a Roman amphitheater and Greek teatro. The Roman amphitheater was overgrown, but the Greek teatro is one of the best preserved in Europe. In its prime, the theatre could hold 15,000 people with a gorgeous ocean view.

Just the the east of the teatro at the archeological park, is a beautiful garden. Grown in what used to be the rock quarry, it is filled with native plants like lemon and citrus groves, as well as flowering trees and shrubs that were quite beautiful. At the end of gardens, is the ear of Dionisio. Dug out of the side of the rock bed, this cave was specifically designed for its acoustic properties. Over 150 feet tall, it’s sharp walls and curved ceiling enable you to hear someone talking at the back of the cave. It was amazing how well and clear the cave echoed.

Day 8: Mount Etna

The largest active volcano in Europe, Mt. Etna is visible from much of the Eastern coast of Sicily thanks to its high 9,000 feet of elevation. It is a famed staple of Italian life and provides abundant minerals and resources for the local agriculture and wine industries.

Depending on the time of year, you may be able to hike the volcano. You can opt for the 60 km hike from the base to the summit, or a simpler drive and hike for only 8 km. We opted for the drive, and drove up to the refugio where we hopped on the gondola to ride further up the volcano. The gondola ride is gorgeous because you can see both the city and ocean below. Plus it saves you some of the less scenic foothill hiking.

There is little scenery on the volcano itself, so you’re really just hiking for the views. If you have never hiked on a volcano before, be aware that it can be an unpleasant hiking experience thanks to the loose gravel and bald landscape. Pack lots of water since there aren’t any rest stops or shops on the volcano itself. I would say this is not a great hike for beginners, and it is good to be prepared for the experience.

Day 9 +10: Wine Region

The slopes of Mount Etna are well known for their vineyards and winery. The composition of the soil and terrain makes them ideal for grape growing, so we couldn’t pass up the chance to stop at a local winery to see the process in person. This is a natural next stop on your 2 week trip of Sicily!

There are plenty of hotels that specialize in a curated wine experience, offering half day or full day tours of the vineyards throughout the area. If you don’t want to stay at a wine hotel, I would definitely suggest visiting with a vineyard tour & tasting, so that you can get the full experience. There are lots of different winery options to check out, but my favorite was Gambino Winery and Tour. This was easily the most scenic winery tour I have ever been on. They have a brand new building on the slopes of Mount Etna, perfectly perched to see Taormina, Linguaglossa and a few smaller towns nearby. You can see the ocean, vineyards and mainland Italy all from their main winery building. Inside, the floor to ceiling windows and lovely main room make it feel airy and open.

Sadly, we arrived too late for a tour of the facilities, but thankfully, the gracious and friendly staff still let us sit down for a tasting. We started out with a Sicilian staple, a light and sweet summery Moscato followed by a seasonal red, similar to a pinot noir. This was my favorite of the wines, because it was a beautiful combination of sweet and dry, not common of reds. It had a notes of currant that were lovely. Next, was a heavy and dry merlot style wine. Hints of blackberry at first are followed by a dry, tart finish. To finish off our wine tasting, a sweet but bodacious red cabernet which is their most popular wine. The staff at Gambino Winery saw that the wine was going straight to our head, so they brought us a beautiful cheese and meat plate, as well as a traditional Sicilian vegetable plate, containing items like goat’s milk reggiano, sheep’s milk pistachio cheese, pork salami, pickled porcini mushrooms, sundried tomatoes soaked in local olive oil, and green & kalamata olives. 

Day 11: Taormina

Taormina is a beautiful cliffside town on the northeast side of Sicily, nestled into bays and bluffs on the downslopes of Mt Etna. It is one of the main tourist cities on this side of the island, thanks to the multitude of activities and stunning views. If you go all the way up to the Saracen Castle, you can get an incredible panoramic of the whole area!

The main archeological site in town is the ruins of the Roman-Greco theatre, which are well maintained with 360 views of beautiful scenery. If you’re not much of a history nut, opt for these ruins over the Siracusa ruins — it’s better preserved and still has its ancient façade. Comfortably situated on the bluffs overlooking the city, just to the east of the main area, you can easily access the ruins by foot. There is a small entrance fee and the best time to go is around sunset.

There is an upper city and lower city in Taormina. All of the beach access hotels and resorts are located on the lower portion of the city and are accessible by car, train or foot. The nightlife, restaurants and shopping are all located on the upper portion of Taormina. You can get in between the two by car if you’re not scared of driving on blind hairpin turns. If that isn’t your thing, there is a cheap and easy-to-use gondola that connects Taormina’s upper and lower cities.

The central town square is another great stop in Taormina and is definitely the hub of activity in the evenings. There are live musicians, delicious restaurants, touristic shops and great people watching to easily fill your evening. With copious wine bars and restaurants to choose from, let your nose lead the way and find the one that smells the best!

We spent our nights in Taormina a few miles outside the city at Hotel Lido Mediterreanee. We had such a wonderful stay at this hotel for a very affordable price. Our stay featured a delicious buffet breakfast daily with American style options, including scrambled eggs and bacon. This is a rarity in Italy, so we were so happy to see that! The best part, though, was easily the ocean views. We selected the standard ocean room thinking it would just be a room with a window view, but we were pleasantly surprised when we had a walk out balcony overlooking the ocean. The black sand beach is directly in front of the hotel with a private beach that you walk down to from the hotel patio terrace.

Day 12-13: Cefalu

Situated on Tyrrhenian Sea, Cefalu is a beautiful mountainside beach town that has lots of charm. Lots of European tourists visit Sicily for the beaches and Cefalu is one of the best on the island. I liked having Cefalu as our last stop on our 2 week itinerary in Sicily, because it was the perfect, relaxing way to end our vacation.

Cefalu is small and very manageable by foot; there is no need for a car here so we turned in our rental car and took the train from Taormina! The train ride up the coast offers lovely views of the beaches as well as a changing terrain from rocky and volcanic to soft white sand. Cefalu is quite popular with locals and visitors, so expect crowds. But you’ll find your little corner of paradise on the beach to soak in the stunning views and charming vibe.

Although we visited a few different beaches while in Sicily, the beach in Cefalu was my favorite. It falls in the shadow of a massive mountain, and is a sandy beach instead of rock, making it easy to swim and tan. With a long wide profile, you wade into the water comfortably and cool off in the water. There is also a lovely pier right in the middle of downtown Cefalu so you could run and jump into the deeper water and then swim into the beach. There is a lovely beach boardwalk the runs the length of the central Cefalu beach!

Cefalu is a major tourist attraction on the island and there are lots of shops and stores geared towards the needs of the tourist. But to me, it felt more sincere than Taormina. The streets are narrow cobble stone streets with bed and breakfasts scattered throughout the city. These sweet little balconies hang over almost every street with kids playing in them or laundry drying off the side.

We also stopped in the Plaza Duomo in the center of town. With several restaurants and gelateria’s lining the perimeter, this is the main social center in the city. There is live music playing at night with people dancing and singing along. The cathedral serves as the backdrop for the square and is very well preserved. It has Norman style architecture on the front and is from the early 1300s. There are beautiful arched entrances on the front and two tall towers on either side. We also stopped in front of the Church de St. Stefano, which has an adorable bell tower with a rusty old bell at the top and beautiful dual wrap staircases on either side of the entrance.

Day 14: Return to Palermo

While most people don’t think of Sicily for their first choice in Mediterranean stops, I think it is absolutely worth the stop. I loved my 2 weeks exploring this Italian island! The culture is markedly different than mainland Italy, and it offers many of the great beaches, scenery and unique history that you’d see in other parts of the Mediterranean.

This article was first published in August 2014 and was updated in July 2017 and April 2019.

Did I miss any of your favorite stops in Sicily? Comment below with your suggestions!