Day01MAY 16
Palermo
Sicilian capital showcasing Byzantine mosaics, royal palaces, and authentic markets. This vibrant city blends Arab-Norman architecture with Mediterranean charm and rich cultural heritage.
May 16 — 25, 2028Land TripMediterranean
Sicily: Palermo to Taormina
Out Adventures
9Nights
9Locations
20Max Guests
Out Adventures
A Journey Worth Savoring
Greeks built it, Normans ruled it, Arabs perfumed it, and the Baroque dressed it up: Sicily is history's greatest collaboration! Cruise Palermo's storied lanes in classic Ape Calessinos, take in the golden glow of Monreale Cathedral's mosaics, then get delightfully lost in the tangled alleys of Caltabellotta, a hidden village few tourists ever find. Toast native wines at a historic estate, visit Godfather-famous Savoca, feel the centuries fall away inside Taormina's Ancient Greek Theater, and wrap up with a thrilling jeep ride up smoky Mount Etna.
Ancient theaters, terracotta villages, and smoldering Mount Etna collide on our gay tour through sultry Sicily.
Steven Krumholz
Steven Krumholz is the guy who actually picks up the phone — and the one who knows which cabin, which resort, and which party is worth your time. Decades of access, zero booking fees, all heart.
$0Booking FeeNEVER A FEE — HASSLE FREE.
A Journey Worth Savoring
Greeks built it, Normans ruled it, Arabs perfumed it, and the Baroque dressed it up: Sicily is history's greatest collaboration! Cruise Palermo's storied lanes in classic Ape Calessinos, take in the golden glow of Monreale Cathedral's mosaics, then get delightfully lost in the tangled alleys of Caltabellotta, a hidden village few tourists ever find. Toast native wines at a historic estate, visit Godfather-famous Savoca, feel the centuries fall away inside Taormina's Ancient Greek Theater, and wrap up with a thrilling jeep ride up smoky Mount Etna.
Ancient theaters, terracotta villages, and smoldering Mount Etna collide on our gay tour through sultry Sicily.
Steven Krumholz
Steven Krumholz is the guy who actually picks up the phone — and the one who knows which cabin, which resort, and which party is worth your time. Decades of access, zero booking fees, all heart.
Included
- Arrival & departure transfers to/from Out Adventures' joining/finishing point hotel
- An LGBTQ+ Out Adventures host and local guides throughout
- Daily breakfast, 7 lunches, 4 dinners
- All gratuities for drivers, day guides, included meals, and porters
- All activities mentioned in the itinerary
- All land transportation in comfortable, air-conditioned vehicles
- A $50 USD Rainbow Railroad donation to help resettle LGBTQ+ refugees
Not included
- International airfare
- Optional activities, meals and drinks not mentioned in the itinerary
- All items of a personal nature (laundry, souvenirs, etc.)
- Gratuities for your Out Adventures Host (budget approximately $70 – $100 USD)
- Travel insurance is mandatory for all travellers
Day02MAY 17
Palermo
Sicilian capital showcasing Byzantine mosaics, royal palaces, and authentic markets. This vibrant city blends Arab-Norman architecture with Mediterranean charm and rich cultural heritage.
Day03MAY 18
Monreale
Monreale is a hill town in Sicily, just southwest of Palermo, best known for its extraordinary 12th-century Norman-Arab-Byzantine cathedral. Its elevated position provides views across the Conca d’Oro and Palermo area. Monreale is well suited to a half-day or full-day cultural visit, with the cathedral complex, historic streets, and nearby scenic viewpoints as its principal draws.
Day04MAY 19
Erice/Mazara del Vallo
Erice and Mazara del Vallo form a useful western Sicily itinerary pairing a hilltop medieval town with a Mediterranean port city. Erice is known for its stone streets, Norman-era religious architecture, panoramic views and cable-car access from Trapani. Mazara del Vallo offers a multicultural historic center influenced by Sicily's Arab-Norman past, a fishing harbor, waterfront promenades and important archaeological collections. The locations are in Trapani province, approximately 45 km apart by road. The supplied LGBT sources discuss Sicily's broader LGBTQ+ travel scene, but do not identify specific venues in Erice or Mazara del Vallo.
Day05MAY 20
Caltabellotta
Caltabellotta is a hilltop town in Sicily’s Province of Agrigento, known for dramatic views across western Sicily, medieval and Norman-era heritage, and the rugged Monte San Pellegrino landscape. The town is associated with the Peace of Caltabellotta, the 1302 treaty that concluded a major phase of the War of the Sicilian Vespers. It is a suitable base for exploring historic villages, inland Sicilian scenery, and nearby archaeological and coastal attractions.
Day06MAY 21
Agrigento/Valley Of The Temples
Agrigento, on Sicily’s southern coast, is best known for the Valley of the Temples, an extensive archaeological park containing some of the best-preserved ancient Greek temples outside Greece. The site combines monumental ruins, Mediterranean landscapes, and views toward the coast, making it a major cultural destination for history-focused travelers. Agrigento’s historic center and nearby archaeological museum provide useful context for exploring the temples.
Day07MAY 22
Noto/Syracuse
Noto is a celebrated Baroque town in southeastern Sicily, about 35 km southwest of Syracuse. Rebuilt after the 1693 earthquake, its honey-colored historic center is a UNESCO World Heritage site known for grand churches, ornate palaces, and elegant streets. The wider Noto–Syracuse area combines Baroque architecture with ancient Greek and Roman sites, Mediterranean beaches, nature reserves, and the historic island of Ortigia.
Day08MAY 23
Motta Camastra/Savoca/Taormina
A scenic eastern Sicily itinerary linking Taormina’s historic center and Ionian Sea views with the hill villages of Savoca and Motta Camastra. Taormina is the primary base, known for its ancient theater, elegant pedestrian streets, and views toward Mount Etna. Savoca offers a preserved medieval setting associated with The Godfather films, while Motta Camastra provides access to the dramatic Alcantara River gorge and rural Sicilian landscapes.
Day09MAY 24
Mount Etna
Mount Etna is Europe’s highest active volcano and a major natural attraction in eastern Sicily. Visitors can explore lava landscapes and summit-area craters, hike on established trails, or take the cable car and guided 4x4 excursions from the southern access area near Rifugio Sapienza. The surrounding slopes are also known for vineyards, local food, and picturesque villages. Catania, Taormina, and other LGBTQ+-friendly Sicilian destinations are nearby, but Mount Etna itself is a dispersed natural area rather than a nightlife destination.
Day10MAY 25
Taormina
Taormina is a historic hilltop town on Sicily’s Ionian coast, celebrated for its panoramic views of Mount Etna and the sea, ancient Greek-Roman heritage, elegant streets, and proximity to beaches and natural attractions. It is widely described by LGBT travel sources as one of Sicily’s most gay-friendly destinations, although the supplied sources do not identify specific permanent LGBT venues in the town.