Personally Sicily was not on my radar until a good friend, who has family roots there, proposed a trip. Upon some deeper research, I wondered why it was the first time this angelic Italian island had been in my travel consideration set.

Sitting on the map as the soccer ball of Italy’s boot, Sicily is an interesting cultural convergence. After the fall of the Roman Empire ruling often changed hands which led to a rich and diverse cultural, architectural and archeological landscape with influence from the Greeks, Romans, Byzantines, Arabs, Normans and Spaniards. As such, it’s a magical cultural mashup unlike anywhere else in the world.


We began our adventure on the island of Ortygia, the historic walled old city of Siracuse. Home base was a fantastic apartment within the old town walls which boasted a 360 degree views of the fortress from the roof patio. Ortygia itself, is a fantastic little island. Perfect for a few days of exploring, swimming and relaxing as you can see we definitely indulged in. Man I love a good swimming platform! It’s just so quintessential Europe.

imageIMG_0001IMG_0038imageimage imageIMG_0099IMG_0096imageNext we ventured north to the Aeolian Islands, specifically Lipari. Sitting just off the Northern Coast of Sicily, the Aeolian Islands are absolutely stunning. Each seem to just pop out of the sea, two of which are still active volcanoes. Lipari used to be a pumice mine which makes for the most beautifully clear and blue water I have ever seen. We stayed in a quant little boutique hotel, La Settima Luna, which had a roof top soaking pool and a personal bartender for your aperitif. Seriously, at your service! The town of Lipari, itself was just adorable and a short local bus ride away on the other side of the island.imageimageimageimageimageimageimageOur last stop was Taormina, which sits on eastern coast in the shadow of Mt. Etna, Europe’s largest volcano. Built up a hill, the views of the Ionian Sea are unmatched. We splurged and got a room at the amazing Villa Carlotta. Sitting mid way up, in walking distance to the town center at the top of the hill and just a short shuttle down to the beach, Villa Carlotta is a master of service. From the champagne welcome to the Etro robes their service is unmatched. Taormina was lively, rich in food, culture and shopping. Definitely the most touristy destination on our trip but well worth it as the last stop in our adventure. If for the views alone!imageimageimageimageimageimageimage

Insider Tips:

» Make sure to check out, or rather eat your way through, the fish and produce market on Orytiga Island. It’s small but has just about everything you could want to see, including a swordfish if you’re lucky! Walk all the way to the end for the most amazing tapas platter you’ve ever had.

» On Lipari, you have to do two things: 1) Rent a moped and circumnavigate the Island. You will be offered the most stunning views and possibly the best photo ops of the trip. 2) Hire a private boat, aka Bubu Rizzo (any local will know who you’re talking about) to take you to your own private pumice beach. There’s really nothing quite like having white sands and crystal blue water all to yourself.

» If you’re going to try and travel around as much as we did, hire a van with driver to get from destination to destination. If you have 4 or more people it’s worth the money because of the time it saves.

» I would highly recommend splurging at one of your accommodations. The high/low approach is a favourite of mine. Villa Carlotta Taormina for example was the perfect end to our trip. Welcome champagne and all!

If you’ve ever thought, or more importantly not though, of Sicily as a travel destination, book it without hesitation. I promise it will not disappoint!

All images via She The Huntress.