Before booking Yacht Week Sicily, I had one big question: Is it just a week-long party, or do you actually get to experience the destination?
My perception of Yacht Week came from visiting Croatia in 2017 where we saw the participants attending themed parties with DJs, partying and drinking champagne. It looked like fun, but I couldn’t help wondering if there was any time to truly explore the places you sailed to.
After spending a week cruising through Italy’s breathtaking Aeolian Islands, I can confidently say the answer is yes. While the parties are certainly part of the experience, they ended up being a much smaller part of my favorite memories than I ever expected.
Instead, I found myself riding scooters through charming villages, hiking an active volcano, sipping local wines while overlooking vineyards at sunset, snorkeling in crystal-clear water, and waking up every morning to a new island outside my cabin window. I’ve heard different destinations can have different vibes, the Yacht Week in Sicily was more mellow than some of other destinations.
If you’re considering Yacht Week Sicily, here’s what it’s really like.
What Is Yacht Week?
Despite the name, Yacht Week Sicily isn’t spent aboard luxury mega-yachts. Instead, groups travel on comfortable sailing catamarans, which become your home for the week.
Each boat includes a professional skipper who handles all the sailing, navigation, docking, and safety. If you’d rather not worry about grocery shopping or cooking, you can also hire a host, something our group decided to do, and one of the best decisions we made.
You sleep onboard every night, sailing between islands throughout the week. Our catamaran had surprisingly comfortable cabins, each with its own bathroom and shower. Storage was better than I expected, the beds were comfortable, and after the first night it genuinely felt like home.
Every day brings a new destination, optional activities, and organized Yacht Week events. The key word, though, is optional.
One of the biggest surprises of the trip was realizing you don’t have to attend every party or scheduled meetup. We skipped one of the large afternoon floatie gatherings simply because we wanted a peaceful afternoon relaxing on the water together. We never felt like we were missing out.
Yacht Week really becomes whatever you want it to be.
Before You Go: A Few Practical Tips
If you’re planning your own Yacht Week Sicily adventure, here are a few things I’d recommend packing and planning for.
- Bring motion sickness medication or patches, even if you’re only mildly prone to seasickness. I thought I’d be fine, but ended up putting on a motion sickness patch halfway through our first sailing day completely changed the rest of my experience.
- Pack light. While the cabins have enough storage, you’ll spend most of your days in swimsuits, cover-ups, and casual clothes.
- Bring a light jacket or sweatshirt. Even during the summer, evenings on the water and hikes like Stromboli can be cooler than expected.
- Rent scooters! Exploring the islands by scooter became one of the highlights of our trip.
- If your budget allows, hire a host. It was really nice having someone to cook amazing food for us while sailing around.
Day One: A Slow Start in Portorosa
Our trip began with a flight into Sicily followed by a private transfer to Marina di Portorosa, where we met the rest of our friends before boarding our catamaran.
Unfortunately, the start wasn’t quite what we’d imagined.
Due to delays and limited communication, we ended up waiting around three hours before we could finally board the boat. Between the long travel day and jet lag, everyone was running on fumes. We grabbed food and drinks while we waited, but at that point I couldn’t help wondering if the trip would live up to the hype.
Eventually we were able to bring our luggage aboard, unpack our cabins, and settle in before heading to dinner at Gradisca Portorosa, an upscale restaurant and lounge just a short walk from the marina.
Fresh seafood, homemade pasta, and a few drinks helped turn the day around, but we were simply too exhausted to stay for the opening party.
Looking back, I’m actually glad our first day wasn’t perfect, because every day after that just kept getting better.
Day Two: Finding My Sea Legs
The next morning, we finally set sail into the Aeolian Islands. Within minutes, I was reminded of something I’d conveniently forgotten—I get seasick.
The water wasn’t particularly rough, but there was just enough movement to make me feel less than wonderful. After hours of sailing, we stopped in Lipari. While we were there, I jumped onto the dock, put on a motion sickness patch, and hoped for the best.
It worked. From that point forward, I felt dramatically better and was finally able to enjoy what surrounded us. And what surrounded us was incredible.
Volcanic islands rose dramatically from the sea in every direction. The water was an impossible shade of blue, and every hour seemed to reveal another breathtaking stretch of coastline.
Later that afternoon we joined our first Yacht Week Sicily raft party.
I’ll admit, I expected warm Mediterranean water. Instead, it was a little cooler than I anticipated, especially later in the evening. Rather than staying in the water the entire time, our group found ourselves laughing as we had help getting ferried between catamarans on a stand-up paddleboard.
Sometimes the unplanned moments become the funniest memories.
After dancing with crews from neighboring boats and meeting people from around the world, we returned to our own catamaran for dinner before falling asleep to the gentle rocking of the sea.
Day Three: Lipari Quickly Became My Favorite Island
We’d settled into life aboard the boat, found our rhythm, and arrived at what would become my favorite stop of the entire trip: Lipari.
Half of our group rented scooters while the others explored town on foot. Choosing the scooter was easily one of the best decisions of the week. There was something incredibly freeing about winding along coastal roads with the Mediterranean stretching endlessly beside us. Every turn seemed to reveal another panoramic overlook or charming village.
We explored Lipari Castle and the Cathedral of Saint Bartholomew, both offering incredible views over the harbor before continuing around the island.
Next we found our way to Belvedere Quattrocchi. Standing at the overlook, we admired dramatic cliffs dropping into turquoise water with the neighboring island of Vulcano rising in the distance.
After returning our scooters, we headed to Tenuta di Castellaro, one of Lipari’s most beautiful wineries.
The afternoon included a guided tour of the vineyards and wine cellar followed by a tasting paired with local cheeses, cured meats, and regional specialties.
As the sun began setting over the vineyards and coastline, I remember thinking this was exactly the kind of experience I never expected to find on Yacht Week.
Before the trip, I imagined seven straight days of parties.
Instead, I found myself sipping locally produced Malvasia wine on a volcanic island while watching the golden light disappear over the Mediterranean.
That evening, we returned to the boat to celebrate our friend Loren’s 40th birthday. Our incredible host, Babi, surprised us with homemade desserts, making the celebration feel even more special.
Later, we headed to Turmalin Club for the Golden Era themed party, where we danced well into the evening before making our way back to the boat.
By the end of Day Three, I finally understood why so many people come back to Yacht Week year after year.
It wasn’t because of the parties. It was because every day felt completely different from the last.
Day Four: Hiking an Active Volcano on Stromboli
By the fourth day, I had settled into life aboard the catamaran, but I also knew my limits.
While the rest of our group sailed to Stromboli that morning, I decided to stay behind in Lipari with a few of the girls. After a couple of days on the water, I wasn’t quite ready for another long sail, so we opted for a slower morning exploring the town on foot.
We wandered through quiet streets, picked up pastries, enjoyed a leisurely lunch, and soaked in a different side of Lipari before catching the afternoon ferry over to Stromboli to meet everyone else.
One thing I appreciated throughout Yacht Week was that there wasn’t any pressure to participate in every activity exactly as planned. Whether you wanted to spend the morning sailing, exploring ashore, or simply relaxing on the boat, you could make the experience your own.
That evening, our entire crew set out on one of the adventures I’d been looking forward to most: hiking Stromboli, one of the world’s most active volcanoes.
As we climbed higher, the landscape changed dramatically. The lush greenery disappeared, replaced by black volcanic rock stretching in every direction. Steam drifted from the summit while the smell of sulfur lingered in the air, a constant reminder that this mountain is very much alive.
Every so often we’d catch a glimpse of glowing lava bursting from the crater before disappearing beneath the smoke. Standing on an active volcano was one of those surreal travel moments that almost doesn’t feel real.
If I could offer one piece of advice, it would be this: book one of the later hiking departures.
We reached the viewing area while it was still bright outside, and although the scenery was beautiful, the glowing lava is much more dramatic after dark. Waiting another hour or two in the afternoon heat simply wasn’t worth it for our group, so we made the decision to head back down. We were hot and hungry.
After the hike, we were covered in volcanic dust, sweaty, and absolutely starving.
We eventually found our dinner spot, ironically, a much nicer restaurant than our post-hike appearance probably deserved. We laughed about how filthy we looked while enjoying one of the best meals of the trip before heading back to the catamaran for a well-earned night’s sleep.
Day Five: Salina, Scooter Rides, and Crystal-Clear Water
I woke up to shouting, cheering, and music blasting directly above my cabin. Needless to say, I wasn’t thrilled.
Then I remembered. The Yacht Week Regatta had been moved because of the weather.
Within minutes I was dressed and out on deck joining dozens of catamarans sailing together while everyone danced in costumes, waved flags, and blasted music. Calling it a race would be generous, it was really just one giant floating celebration.
It turned out to be one of the funniest mornings of the entire trip.
As we continued sailing toward Salina, I looked back to see Stromboli still rising behind us, a plume of smoke drifting from the summit.
It’s not every day you can say you hiked an active volcano one evening and watched it erupt from a sailboat the next morning.
As we sat down to breakfast after the Yacht Week Regatta, we were treated to an incredible surprise. A pod of at least 20 dolphins appeared alongside our catamaran, swimming and playing in the crystal-clear water. Watching them leap out of the water was so special.
Before arriving in Salina, we stopped near Isola di Basiluzzo, and it was my favorite swim stop of the trip.
The water was unbelievably clear.
We spent the afternoon floating on inflatables, snorkeling around the rocky coastline, and simply enjoying being surrounded by the brilliant blue waters of the Tyrrhenian Sea.
Those peaceful moments ended up becoming just as memorable as the organized Yacht Week events.
Later that afternoon, we arrived in Salina and, naturally, rented scooters again.
Salina felt completely different from Lipari.
The island was greener, quieter, and somehow even more relaxed.
We cruised through Malfa, stopping to admire the coastal scenery before continuing into Leni, where we rewarded ourselves with gelato before making our way back toward town.
That evening everyone gathered for a relaxed dinner together.
Compared to the excitement of the volcano hike the night before, it was a quiet evening filled with good conversation, great food, and plenty of laughter.
Day Six: Panarea and the Perfect Ending
By our final full day together, it felt like we’d been traveling far longer than a week.
That morning, we woke up to one of my favorite breakfasts of the trip. Our host, Babi, had somehow managed to make homemade chicken and waffles aboard the catamaran. I still have no idea how she consistently created restaurant-quality meals from a tiny galley kitchen, but every single day she amazed us.
Hiring a host isn’t included with every Yacht Week charter, but if it’s within your budget, I can’t recommend it enough.
Instead of worrying about grocery shopping, meal planning, cooking, or cleaning, we were able to spend every minute enjoying the islands. More importantly, Babi never felt like someone working for us. She became part of our crew.
Our skipper, Bartol, was equally incredible.
Originally from Croatia and part of the official Yacht Week staff, he handled everything from navigating the catamaran to docking in busy marinas. He kept us safe, answered our endless sailing questions, and somehow always remained calm no matter what was happening around us.
Together, Bartol and Babi transformed our boat into a home.
As we sailed toward our final destination, someone had the brilliant idea of tying all of our inflatable floats together behind the boat.
We climbed aboard our floating train of unicorns, loungers, and tubes while the catamaran slowly towed us across the water.
We probably weren’t going more than a few miles per hour, but between the laughter, sunshine, and crystal-clear sea, it became one of those completely spontaneous moments I’ll never forget.
That afternoon we arrived in Panarea, the smallest of the Aeolian Islands.
While much of the group headed straight toward Raya Restaurant, Adam and I decided to explore first.
We wandered uphill through the narrow whitewashed streets until we reached one of the island’s scenic overlooks. It was a little sweaty getting there, but after spending days aboard the boat, it felt wonderful to stretch our legs and take in the views.
Eventually we met everyone at Raya Restaurant, and by pure luck we arrived before the Yacht Week crowd.
That meant we scored an incredible corner table overlooking the sea.
Watching the sunset with cocktails in hand was amazing.
Later that night we had our final dinner together, reminiscing about all the great moments, then joined everyone for Yacht Week’s final White Party.
Like every organized event throughout the week, there was a DJ, dancing, and crews from dozens of catamarans celebrating together one last time.
It was the perfect way to wrap up an unforgettable adventure.
Was Yacht Week What I Expected?
Honestly? Not even close.
Before booking Yacht Week, I assumed the parties would be the main event. Instead, they became the backdrop.
My favorite memories weren’t the late nights dancing. They were hiking Stromboli, riding scooters through Lipari and Salina, tasting local wines at Tenuta di Castellaro, snorkeling near Isola di Basiluzzo, watching sunsets in Panarea, and waking up every morning to another incredible island outside my window.
One afternoon we even skipped one of the organized floatie meetups altogether.
Instead of joining hundreds of people, we stayed back and enjoyed a peaceful afternoon on the water with our own group.
That was the beauty of Yacht Week.
You never felt obligated to do everything.
You could choose your own adventure.
Tips for Future Yacht Week Travelers
If you’re thinking about booking Yacht Week in Sicily, here are my biggest takeaways:
- Pack motion sickness patches or medication, even if you’re only mildly prone to seasickness.
- Rent scooters whenever you can, they were the best way to explore the islands.
- Book the Stromboli hike, but choose one of the later departures if possible so you can see it in the dark.
- Don’t skip the wine tasting at Tenuta di Castellaro.
- Bring a light jacket for evenings on the water.
- Remember that you’ll be sleeping aboard a catamaran for the week, not staying in hotels. Thankfully, the cabins were surprisingly comfortable, with private bathrooms, comfortable beds, and plenty of storage.
- If your budget allows, hire a host to plan your meals and cook them.
- Most importantly, don’t feel like you have to attend every Yacht Week event. Some of our favorite moments happened when we slowed down and enjoyed the islands at our own pace.
Final Thoughts
If you’d asked me how I felt on that first afternoon in Portorosa, I was jet-lagged, waiting three hours to board our catamaran, I probably would’ve given you a very different answer than I would today.
A week later, after sailing between volcanic islands, hiking one of the world’s most active volcanoes, exploring charming towns by scooter, tasting incredible Sicilian wines, and making lifelong memories with friends old and new, I realized something.
Yacht Week was never just about the parties.
It was about experiencing one of Italy’s most beautiful island chains from the sea.
The parties simply gave us another reason to celebrate getting there.
And that’s a trip I’ll never forget.
Continue Exploring Italy
One of the best parts about Yacht Week is that it’s easy to turn it into a longer Italian adventure. If you’re planning to spend more time exploring the country, check out my guides to Cinque Terre, Venice, the Amalfi Coast, and Genoa for even more inspiration.