Gay Sicily Tour 2027: Palermo, the Aeolian Islands & Mount Etna
8 Days, 7 Nights
September 5th-12th, 2027
About This Trip
Join SideQuests host Peter on this 8-day group adventure across Sicily, the sun-drenched island at the toe of Italy's boot. From Palermo's golden mosaics to a private boat day in the Aeolian Islands and a jeep ride up Europe's tallest active volcano, this one is la dolce vita with a little lava on the side.
September is the sweet spot in Sicily: the sea is still warm, the summer crowds have thinned out, and the evenings are made for long dinners and a spritz by the water. Come solo (most people do) and you won't be solo for long. Here's what you're in for:
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We start in Palermo, Sicily's loud, layered, gloriously chaotic capital, where Arab, Norman and Baroque history are all stacked on top of each other. We'll wander the old city with a local guide, weave through one of its historic street markets, stand under the glittering gold mosaics of the Palatine Chapel, and settle the great cannoli debate once and for all (spoiler: they're all good). Your first evening starts with a welcome dinner, and after that the city is yours.
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We follow the northern coast to Cefalù, a postcard-perfect seaside town with a Norman cathedral and a long sandy beach, and spend the afternoon doing absolutely nothing at a beach club. By evening we roll into Milazzo for a group dinner and an early night before the islands.
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A short ferry ride drops us in Lipari, the biggest of the Aeolian Islands, for two nights of island time. We spend a full day on our own private boat, swimming in clear water and cruising past volcanic cliffs and hidden coves, then head to a local winery to taste what grows in volcanic soil.
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Back on the mainland, we stop at the Gole dell'Alcantara, a gorge carved through ancient lava, then settle into Catania, a Baroque city built from black lava stone. Our final full day is the big one: a private jeep adventure up Mount Etna, Europe's highest active volcano, followed by a long Sicilian lunch together.
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This trip is a balance of city energy, beach days, island life and big-nature moments, with plenty of free time to explore Sicily at your own pace. Sicily is warm in every sense: the food is ridiculous, the people are generous, and the big cities have an easygoing, welcoming LGBTQ+ scene. And because every SideQuests trip starts in a group WhatsApp chat with monthly Zoom calls before departure, you walk into that welcome dinner feeling like you're meeting old friends, not strangers. The destination is just the container... the connection is the whole point. Come solo (most people do), with a partner or friend, and leave with a new group of friends and a camera roll full of memories.
Want the full lay of the land before you go? Read our Gay Sicily Travel Guide for where to eat, drink, and go out.
Just 10 earlybird spots left! Save $200
Deposit: $874 (just 25% down)
$3,695
$3,495
September 5th-12th, 2027
Palermo · Cefalù · Lipari · Catania · Mount Etna
Limited Spots Available
» Want to keep the adventure going? Add our Siracusa & Taormina extension after the trip!
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Kick things off in Sicily's capital with a guided walking tour through the old city, a wander through one of Palermo's historic food markets, a visit to the gold-mosaic Palatine Chapel, and a proper Sicilian cannoli tasting.
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Trade the city for the sea in Cefalù, one of Sicily's prettiest seaside towns, with a lazy afternoon at a beach club before a group dinner in Milazzo.
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Hop the ferry to Lipari, the largest of the volcanic Aeolian Islands, for two nights of island life, harbor-side drinks and wandering the old town's lanes.
Tour Highlights
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Spend the day on our own private boat, swimming in crystal-clear coves and cruising past dramatic volcanic coastline, then taste local wines at a Lipari winery.
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Head up Europe's highest active volcano on a private jeep adventure through lava fields and craters, with sweeping views across eastern Sicily, followed by a long Sicilian lunch.
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Travel with a small group of like-minded LGBTQ+ folks and a dedicated local trip leader from your first night in Palermo to your last morning in Catania, with private transportation and ferries handled for you.
What’s Included?
Pricing:
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Traveling solo and want the extra space? We get it, not everyone wants to share. Add a private individual room for the full trip. Not sure yet? This can be added or subtracted from your reservation up to 90-days pre-trip!
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Select "1" and reserve your accommodations for one night before your tour begins. (September 4th – 5th).
Select "2" and reserve your accommodations for two nights before your tour begins. (September 3rd – 5th).
Select "3" and reserve your accommodations for three nights before your tour begins. (September 2nd – 5th).
For ease, reserve your accommodations at our host hotel in Palermo (NH Hotel Palermo) before your trip starts. Your reservations will be linked so you don't have to check out and check in to a new room on the 5th. Rate INCLUDES complimentary breakfast for 1 or 2 people.
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Select "1" and reserve your accommodations for one night after your tour ends. (September 12th – 13th).
Select "2" and reserve your accommodations for two nights after your tour ends. (September 12th – 14th).
Select "3" and reserve your accommodations for three nights after your tour ends. (September 12th – 15th).
For ease, reserve your accommodations at our host hotel in Catania (NH Catania) after your tour wraps. Your reservations will be linked so you don't have to switch rooms, and you can take one more slow morning before you fly. Rate INCLUDES complimentary breakfast for 1 or 2 people. (Not doing the Siracusa extension? This is the easy way to buy yourself a little more Sicily, and a perfect base for a day trip to Taormina.)
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Not ready to leave? Tack on 3 nights exploring Sicily's southeast: the ancient island of Ortigia in Siracusa, the Baroque hill towns of Ragusa and Noto, and a day in glamorous Taormina with a private boat excursion around Isola Bella.
Not sure which add-ons you want? No worries! Add-ons can be added or subtracted from your reservation until 90-days before the start of the trip!
Not sure which add-ons you want? No worries! Add-ons can be added or subtracted from your reservation until 90-days before the start of the trip!
Add-Ons:
Only a 25% deposit is due to book. The remaining balance isn't due until 90 days pre-trip.
Your deposit is 100% refundable until the trip is confirmed (that's when 12 travelers have booked). Prefer monthly payments? Some guests use Affirm's virtual card at checkout.
See the full cancellation policy ↓
Navigation:
Tour Highlights — What’s Included — Pricing — Itinerary — Post Tour — Your Host — FAQ — About — Hotels
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You made it! Fly into Palermo Falcone Borsellino Airport (PMO) and make your way into the city, where Palermo starts showing off right away: palm-lined boulevards, domed churches with Arab-Norman flair, Vespas weaving through traffic, and the smell of something frying on every corner.
We'll get you checked in at our hotel on the Foro Italico seafront, and then the afternoon is yours to relax or explore! Nap off the flight, grab your first arancina (in Palermo it's arancina, not arancino, and locals will let you know), or wander over to the Quattro Canti and let it sink in that you're actually in Sicily.
Tonight is the one that sets the tone for the entire week: our welcome dinner, where a table of strangers turns into your people over Sicilian flavors and a glass or two of local wine. By dessert, it won't feel like strangers anymore. Exact meeting times land in our group WhatsApp chat ahead of the trip. -
Arrive at your leisure. Airport transfers aren't included, but taxis, the airport shuttle bus and the train all connect PMO with the city, and we'll share the easiest options in the group chat before you fly.
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Tonight we come together for a welcome dinner featuring the flavors of Sicily, the perfect place to meet everyone and kick off our island adventure in style.
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If the group's still got energy after dinner, Palermo's historic center comes alive late. No pressure, but it's an easy first taste of Sicilian nightlife.
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We'll spend our first two nights at NH Hotel Palermo (or similar), right on the seafront promenade and an easy walk into the historic center.
Day 1
Benvenuti! Palermo's First Toast & First Friends
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After an included breakfast, we hit the streets with a local guide for a walking tour of Palermo, a city that has been Phoenician, Arab, Norman and Spanish, and wears every layer proudly.
We'll dive into one of Palermo's historic street markets, where vendors shout their prices, stalls overflow with swordfish, citrus and olives, and street food is basically a competitive sport. Then we step inside the Palatine Chapel, where every inch of the walls and ceiling glows with gold Byzantine mosaics. It's the kind of room that makes the whole group go quiet.
Of course, no visit to Palermo is complete without a proper Sicilian cannoli tasting: crisp shells, fresh ricotta, zero regrets. The rest of the afternoon and evening are yours to shop, nap, or dig deeper into the city, on your own or with the group. -
Start the day with breakfast at the hotel before we head out.
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A relaxed guided stroll through Palermo's historic center, its grand piazzas and its extraordinary mix of architecture.
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A wander through one of Palermo's lively historic markets, loud, colorful and full of things you'll want to taste, plus entrance to the Palatine Chapel, covered floor to ceiling in shimmering gold mosaics.
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A proper cannoli tasting in the city that does it best. Then the rest of the day is yours.
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Our second and final night at NH Hotel Palermo (or similar).
Day 2
Markets, Mosaics & a Proper Cannoli
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After breakfast, we leave Palermo behind and follow the beautiful northern coast to Cefalù, one of Sicily's most picturesque seaside towns, all honey-colored stone, a Norman cathedral, and a rocky headland rising right behind the beach.
The afternoon has exactly one assignment: relax. We settle in at a fabulous beach club to soak up the Mediterranean sunshine, swim, and enjoy some well-deserved downtime by the sea. Every SideQuests trip needs a day like this, the exhale that keeps a big week from ever tipping into exhausting.
In the evening, we continue along the coast to Milazzo for a memorable group dinner before an early night ahead of our journey to the Aeolian Islands. -
Breakfast at the hotel before we hit the road.
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A private transfer along Sicily's northern coast to Cefalù.
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An afternoon of sun, sea and zero plans at a Cefalù beach club.
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A memorable group dinner in Milazzo, the gateway to the Aeolian Islands.
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One night at a 4-star hotel in Milazzo, right before our ferry to the islands.
Day 3
Cefalù Beach Club & the Road to Milazzo
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After breakfast, we board the ferry to Lipari, the largest of the spectacular Aeolian Islands, a volcanic archipelago off Sicily's north coast.
Once we arrive and check into our hotel, the island is yours. Wander the pastel lanes of Lipari town, climb up to the old citadel for the view, browse the boutiques and cafés, or grab a drink by the harbor and watch the boats come and go. Island time starts now. -
Breakfast at the hotel before we head to the port.
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A ferry ride from Milazzo out to Lipari in the Aeolian Islands.
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Explore the island at your own pace, from the old town and citadel to a harborside spritz.
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We'll spend the next two nights at the Arciduca Grand Hotel (or similar), a 4-star hotel in Lipari.
Day 4
Ciao, Aeolian Islands!
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Today is all about the sea! After breakfast, we set out on our own private boat to explore the Aeolian Islands from the water: secluded coves, dramatic volcanic cliffs and sea stacks, and water so clear you can see straight to the bottom. There will be plenty of chances to jump in, swim, float and soak up the scenery.
In the afternoon, we head back to Lipari for a visit to a local winery, where we'll taste wines grown in the islands' rich volcanic soil. Sea, scenery, wine and a whole lot of la dolce vita.
The evening is free for dinner and drinks by the harbor with your new favorite people. -
Breakfast at the hotel before we set sail.
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A private boat just for our group, with stops to swim in crystal-clear coves along the volcanic coastline. Swimming is always optional.
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A visit to a local Lipari winery to taste wines shaped by the island's volcanic landscape.
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Dinner and drinks on your own, or out with the group.
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Our second and final night at the Arciduca Grand Hotel (or similar).
Day 5
Private Boat Day & Volcanic Wine
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After breakfast, we say goodbye to Lipari and ride the ferry back to the Sicilian mainland.
Our journey continues to the Gole dell'Alcantara, a dramatic gorge where the river has carved through ancient lava flows, leaving towering walls of volcanic rock. Take your time with the views (and brace yourself if you dip a toe in, the river water is famously chilly).
In the afternoon, we arrive in Catania for a guided walking tour of its historic center. Catania was rebuilt after a massive earthquake in 1693 using the volcano's own black lava stone, and the result is a grand, moody Baroque city like nowhere else in Italy. Tonight is free to explore. -
Breakfast at the hotel before we leave the islands.
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Ferry back to the Sicilian mainland, then private transportation onward.
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A visit to the volcanic Alcantara gorge and its striking walls of lava rock.
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A guided stroll through Catania's Baroque center, its grand cathedral square and its lively streets. The evening is yours.
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We'll spend our final two nights at NH Catania (or similar), a 4-star hotel in central Catania.
Day 6
Lava Gorges & Baroque Catania
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Our final full day takes us high into the volcanic landscape of Mount Etna, Europe's highest active volcano. After breakfast, we climb aboard for a private jeep experience through lava fields, craters and otherworldly terrain, with panoramic views stretching across eastern Sicily and out to the sea.
After our adventure, we sit down together for a long, delicious Sicilian lunch, the kind that turns into toasts and stories and "wait, it's already 4pm?" It's our celebration of the week together.
Then it's back to Catania for your last evening in Sicily. Head out with the group for one last aperitivo, one last gelato and one last night out. -
Breakfast at the hotel before we head up the mountain.
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A private jeep adventure across Etna's volcanic terrain, with craters, lava landscapes and huge views. It's cooler up on the mountain, so bring a light layer and closed-toe shoes.
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A long Sicilian lunch together to celebrate the week.
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Our final evening is yours to spend together, from sunset drinks to a proper night out.
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Our last night at NH Catania (or similar).
Day 7
Mount Etna by Jeep & One Last Long Lunch
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After one last included breakfast, we pack up and trade hugs and goodbyes. Catania Fontanarossa Airport (CTA) is a short ride from the city center, so the send-off is easy.
Heading home? The post-trip blues are real, but it's a good sign. It means you experienced something amazing, and you're flying out with a camera roll you can't stop scrolling and a group chat that isn't going quiet anytime soon.
Not ready to let go of Sicily? Skip the airport and roll straight into our Siracusa & Taormina extension. -
One last breakfast at the hotel before departures.
Day 8
Arrivederci, Sicilia: Farewell (or Onward to Siracusa)
Join the post-tour adventure! Add this four-day, three-night journey through Sicily’s southeast, from ancient Ortigia to glamorous Taormina. The ultimate cap to an epic trip. See the details below!
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September 12th-15th | from ~$1,000Extend Your Trip: Siracusa, Ortigia & Taormina
September 12th–15th | from ~$1,000
Not ready for it to end? From Catania, we head south to Siracusa, once one of the most powerful cities of the ancient Greek world, and spend two nights near Ortigia, its gorgeous island old town of limestone lanes, seaside piazzas and sunset spritz spots. The next day, we explore the Baroque hill towns of Ragusa and Noto, finishing with dinner in Noto.
The grand finale: a day in Taormina with a private boat excursion around Naxos Bay and Isola Bella and a walking tour of the historic center, before a farewell dinner back in Catania. Departures are from Catania (CTA) on September 15th.
Pricing, hotels and single supplement details coming soon.
Meet Your Host
Peter brings years of experience in travel, community, and advocacy, from presidential campaigns to queer group tours. As a lifelong LGBTQ+ advocate, he's passionate about creating spaces that feel inclusive, intentional, and full of connection. Peter hosts SideQuests adventures across Italy, Japan and Colombia, and he knows how to turn a long Italian dinner table full of strangers into a group of friends by the time the espresso arrives.
Frequently Asked Questions
Have questions specific to this trip? Here are some common questions about our adventure.
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Our trips attract a diverse community, primarily LGBTQ+ travelers in their 20s-60s who are looking for meaningful connections and authentic experiences. We welcome allies and friends of all identities who share our values of inclusivity, curiosity, and openness.
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We keep our groups intentionally small, and this trip runs with 12 to 24 travelers, to foster genuine connections and allow for more intimate, authentic local experiences that wouldn't be possible with larger groups.
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Each trip is slightly different, but most SideQuests include:
Boutique accommodations
Some meals (with options, we’re happy to suit your dietary needs)
Excursions + guided activities
A local guide or trip leader
Private group transportation
Your hosts (hi, that’s us!)
On this Sicily trip, that means 4-star hotels, 7 breakfasts, 2 dinners and 1 lunch, private transportation and ferries, 9 included experiences, and a dedicated local trip leader. See What’s Included above for the full list. Airfare to and from Sicily and airport transfers are not included. You'll receive a detailed packing list and itinerary before departure.
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If your booking is still pending (meaning the trip hasn’t been confirmed yet), you’re eligible for a full refund — including your 25% deposit.
Once the trip is confirmed (after 12 travelers have booked), your deposit becomes non-refundable. If you need to cancel after confirmation, you’ll receive a Credit Voucher for the amount paid (minus a $100 cancellation fee). Your credit voucher is good to apply towards any SideQuests Travel tour booked within 1 year of your cancellation date.
At 90-days before the trip, all payments become non-refundable, since hotels, transportation, and activities have already been paid for. Any exceptions at that point are at the discretion of our local partners.
We always recommend purchasing travel insurance in case big life events unexpectedly occur— it’s really worth the peace of mind! There are a variety of carriers, our hosts personally have Allianz.
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You can reserve your spot with a 25% deposit and pay the rest in installments through Affirm. In order to do this, you must register a virtual card through Affirm.
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Yes! Most people do. Sicily's cities are social and easy to explore, and you won't actually be on your own: the moment you book, you're added to the trip's WhatsApp chat and invited to monthly Zoom calls, so by the time you land you already know your people. We design our trips to foster connection from day one, and many travelers arrive solo but leave with lifelong friends (and at least one new group chat). We create plenty of opportunities to bond with the group while also respecting everyone's need for personal space and independence.
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Not at all! Our trips are great for all experience levels. We’ve got you. Our trips are built with support and guidance baked in, from our group chats and Zoom intros to arrival instructions and packing tips. You don’t need to be a seasoned traveler, just someone ready to say yes.
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We offer both shared and private accommodation options. Many solo travelers choose to share rooms (with separate beds) to save on costs and enhance the community experience. If you prefer your own space, private rooms are available for an additional fee (listed during checkout). Private rooms are limited on this trip, so book early if you want one.
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Not at all! While our trips are centered around LGBTQ+ community, allies are absolutely welcome and a part of our greater community. As long as you’re here with respect, openness, and a good sense of humor, you’ll fit right in.
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Most trips include a mix of walking, light hikes, or outdoor activities, but we always include downtime, optional excursions, and flexible pacing. You do you, with a group that gets it.
This is a moderate trip rather than a strenuous one. Expect cobblestone streets and walking tours in Palermo and Catania, getting on and off ferries and a boat, uneven volcanic ground at the Alcantara gorge and on Mount Etna, and a bumpy (fun) jeep ride. Swimming on the boat day is optional. It's balanced with a beach club afternoon, island free time and plenty of downtime. Comfortable shoes are your best friend, and since we hop between islands, we recommend packing light. -
We strive to make our trips as accessible as possible and work with travelers on a case-by-case basis. Some destinations have inherent accessibility challenges, and this trip includes ferries, a boat day, cobblestone streets and uneven volcanic terrain at the Alcantara gorge and on Mount Etna, but we're committed to finding solutions whenever possible. Please contact us directly to discuss your specific needs.
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Palermo and Catania have Sicily's most active LGBTQ+ scenes, with welcoming bars, queer-friendly spots around their historic centers, and Pride celebrations that draw big crowds each year. The scene is smaller and more relaxed than in Rome or Milan, which makes it easy to slot into. Taormina, on the east coast, has welcomed gay travelers for well over a century. Our evenings in Palermo, Lipari and Catania are free, so there's room to explore with the group.
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Yes, especially in the cities. Italy has recognized same-sex civil unions since 2016 (same-sex marriage isn't legal yet), and Palermo and Catania are known for being open, warm and welcoming. As anywhere, smaller towns can be more traditional, but traveling as a group with a local trip leader who knows the island makes it easy to relax and be yourself.
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Yes. Most LGBTQ+ visitors find Sicily relaxed and welcoming, and our hotels, guides and partners are vetted through an LGBTQ+ lens. Like any popular destination, keep an eye on your bag in crowded markets and busy tourist spots, but beyond that you can expect a warm welcome.
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Fly into Palermo Falcone Borsellino Airport (PMO) at the start, and out of Catania Fontanarossa Airport (CTA) at the end. Because the trip runs one-way across the island, a "multi-city" or "open-jaw" ticket (into Palermo, home from Catania) is usually the smart booking. Airport transfers aren't included on this trip, but both airports are well connected to the city, and we'll share the easiest options in the group chat. Joining the extension? You'll still fly home from Catania.
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US, Canadian, UK, and Australian passport holders don't need a visa for tourism stays up to 90 days. Your passport should be valid for at least 3 months beyond your departure date and issued within the last 10 years. The EU's new ETIAS travel authorization (a quick online approval with a small fee, similar to the US ESTA, not a visa) is rolling out and is expected to be required by the time we travel. We'll share exact requirements with the group before departure. First-time visitors will also complete a quick biometric registration (photo and fingerprints) at the border under the EU's Entry/Exit System.
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Warm, sunny and one of the best months of the year to visit. Expect highs in the low-to-mid 80s Fahrenheit, a sea that's still warm enough for a long swim, and fewer crowds than in peak summer. It's noticeably cooler and windier up on Mount Etna, so bring a light layer and closed-toe shoes for jeep day.
About SideQuests Travel
Hi, I'm Matthew, co-founder of SideQuests Travel. I created SideQuests because I didn't want to just see the world, I wanted to make new friends and build-up my community while doing it. I wanted to see an amazing place in the world and come home feeling changed, so I started hosting trips for people who wanted the same.
SideQuests runs small-group adventures for LGBTQ+ travelers who want to see the world while actually connecting with others and themselves.
The moment you book, you're added to the trip's WhatsApp chat and invited to our monthly Zoom calls, so by the time you land, you already know a bit about each person embarking on the adventure with you. On most group tours, you finally click with the others right as everyone packs to leave,
but on our trips, that happens before anyone boards a plane.
We offer optional journal prompts and meditations for those that would like to participate, and a community workshop mid-trip where people share stories and truly get the opportunity to connect on a very real level.
Every hotel, guide, and operator is vetted through an LGBTQ+ lens ensuring that travel is not only safe, but enthusiastically welcoming.
Come solo, come with a friend, or a partner, and leave with a new group of friends and strengthened sense of community. We're not just building great experiences, we're building a supportive network of people you'll literally want to plan your next trip alongside.
Where You’ll Stay
We've chosen 4-star hotels in walkable, well-connected locations, keeping comfort front and center throughout.
In Palermo, we spend our first two nights at NH Hotel Palermo (or similar), right on the Foro Italico seafront promenade and an easy walk into the historic center, the markets and the nightlife.
In Milazzo, we stay one night at a 4-star hotel right before our ferry to the islands. In Lipari, we settle into the Arciduca Grand Hotel (or similar) for two nights of island time in the Aeolian Islands.
In Catania, we check into NH Catania (or similar) in the city center for our final two nights, perfectly placed for Baroque piazzas, late dinners and our Mount Etna adventure.
All accommodations feature private bathrooms and daily breakfast. Solo travelers can choose between a shared room (with another solo traveler, a partner, or a friend) or a fully private room for an additional supplement. If a friend or partner is coming but booking separately, no worries, we send a rooming questionnaire ahead of time to sort preferences.
Testimonials From Our Travelers
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![A man with tattoos and earrings standing at the beach during sunset, looking to his left.]()
“We felt like family just a day or two into the actual trip.”
David, Greece
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![A man standing on a sandy beach during sunset, smiling and looking to his right, wearing a pink short-sleeve shirt with a white leaf pattern.]()
"It’s wild how quickly a group of queer travelers became a little family. From late-night laughs to deep conversations, this trip gave me so much more than I expected."
JJ, Costa Rica
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![Two smiling men, one with blond hair and the other with brown hair and glasses, standing close together with their arms around each other, in front of a decorated building with colorful architecture.]()
"I’ve already signed up for three more trips! I’ve never felt more welcome in a group setting."
David, Thailand
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![Three young men standing on the beach with ocean in the background, smiling and enjoying the moment.]()
"He made sure everyone felt included and was enjoying themselves... He checked in with everyone to make sure we were all onboard with our schedules and feeling good about the trip overall.”
Thomas, Greece
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![A smiling man with dark, wavy hair and a beard, wearing a white shirt, standing in front of a stone wall during sunset.]()
"Matthew created an environment welcoming and safe for everyone (regardless of gender identity or sexuality) to have an amazing trip.”
Sam, Greece
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“Michael and Matt were great at breaking down barriers and helping all feel welcome.”
Kevin, Costa Rica
