May 29 - June 5, 2027
Join us in 8 Days in Southern Sicily with Pride + Optional Amalfi Coast Sailing on
8 Days in Southern Sicily with Pride + Optional Amalfi Coast Sailing
Availability Note: Registration for this trip is expected to open approximately 12 months before departure and is currently planned to begin on May 29, 2026. To secure your place on the pre-departure interest list, click the Book Now link or request more information by filling out the trip form. We will add you to the list and contact you when registration officially opens.
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Discover the beauty of Southern Sicily with Pride Adventures as we travel from Catania to Palermo on an unforgettable journey shaped by ancient history, coastal landscapes, local traditions, and meaningful cultural experiences.
This hosted group trip blends the ease of small group travel with the warmth and connection of traveling with Pride Adventures. Along the way, we explore historic towns, archaeological wonders, and vibrant cities while sharing memorable moments, thoughtful inclusions, and special touches like our private welcome dinner and farewell dinner.
For those looking to extend the experience, there is also an optional Amalfi Coast sailing adventure, offering the chance to explore destinations like Capri and Positano from a completely different perspective.
Our Journey Through Southern Sicily Begins Here
Our route through Southern Sicily brings together some of the island’s most memorable destinations, each offering its own distinct character. From the coastal beauty of Syracuse to the baroque charm of Ragusa, the ancient wonders of Agrigento, and the vibrant energy of Palermo, this journey is designed to showcase a rich blend of history, culture, food, and connection.
Included experiences such as a hands-on arancini cooking class, a guided visit to the Valley of the Temples, and time to explore local towns and coastal landscapes help bring the heart of Sicily to life. Traveling together as a small LGBTQ+ group creates space for shared experiences, meaningful moments, and a welcoming community throughout the journey.
TRIP HOST
Kevin Smith - West Hollywood, CA
Kevin serves as Adventure Director | Customer Experience Officer, working closely with travelers before and during trips to support bookings, logistics, and the overall travel experience while staying connected to our community.
Kevin Smith - West Hollywood, CA Bio
Kevin is a trusted trip host and operations leader known for exceptional organization, meticulous planning, and a strong focus on traveler experience. He has hosted Pride Adventures and CGA trips to Costa Rica, South Africa, Lake Powell, along with numerous camping, hiking, and community adventures. In 2027, Kevin will be joining Pride Adventures full time, hosting and supporting several upcoming trips.
As Chris’s brother and a core member of the Pride Adventures leadership team, Kevin oversees sales and customer experience on the operations side, helping ensure every trip runs smoothly from the first inquiry through the journey home. He thrives on managing details, logistics, and behind-the-scenes coordination so travelers can focus on connection, adventure, and enjoyment.
Kevin’s background includes designing custom tours, curating private and small-group travel, and supporting a wide range of experiences, from adventure-focused itineraries to more complex, logistics-driven trips. His approach is thoughtful, calm, and highly detail-oriented, making him a steady and approachable presence for travelers.
Itinerary Overview
This eight day journey begins in Catania and ends in Palermo, with meaningful stops in Syracuse, Ragusa, and Agrigento along the way. Expect a well balanced mix of guided highlights, cultural experiences, scenic travel, and time to enjoy each destination.
From ancient ruins and historic streets to coastal views and local culinary traditions, this journey offers a deeper look at Southern Sicily while allowing time to relax, connect, and fully experience each stop.
For travelers who choose to continue, the journey can extend beyond Sicily with an optional Amalfi Coast sailing experience, adding a second chapter of coastal exploration and relaxation.
Days 1 and 2 | Catania and Syracuse
Your journey begins in Catania, where we arrive, settle in, and come together for the start of our Southern Sicily adventure. On our first evening, we gather for a welcome dinner, creating a warm and memorable start to the trip. The following day, we continue to Syracuse, one of Sicily’s most historic and atmospheric cities, where ancient layers of Greek and Roman influence meet elegant piazzas and coastal beauty. While here, we enjoy a hands on arancini cooking class, adding a fun and delicious introduction to Sicilian culture and cuisine.
Days 3 and 4 | Syracuse, Ragusa, and Agrigento
We spend additional time in Syracuse before continuing deeper into Southern Sicily. Along the way, we visit the baroque hill town of Ragusa, known for its striking setting and beautifully preserved architecture. From there, we travel onward through the countryside, with a visit to Villa Romana del Casale, home to one of the most extraordinary collections of ancient Roman mosaics in the world. By the end of the day, we arrive in Agrigento, where the island’s rich history continues to unfold. 
Days 5 and 6 | Agrigento and Trapani
This portion of the journey brings us to one of Sicily’s most iconic archaeological treasures: the Valley of the Temples in Agrigento. Walking among these remarkable ancient ruins is one of the defining experiences of the trip and offers an unforgettable glimpse into Sicily’s Greek past. We then continue west toward Trapani, with changing coastal scenery and time to enjoy a more relaxed rhythm. Here, there is space to soak in the charm of western Sicily and appreciate a side of the island shaped by sea, salt, and tradition.
Days 7 and 8 | Palermo
As we make our way toward Palermo, we stop to visit Monreale Cathedral, one of Sicily’s most breathtaking religious and artistic landmarks, famous for its dazzling mosaics. We then continue into Palermo, where the journey concludes with time to take in the city’s layered history, vibrant streets, and unmistakable energy. On our final evening, we gather for a farewell dinner to celebrate the experiences shared along the way. After breakfast on the final morning, the Southern Sicily journey comes to a close. 
Optional Extension | Amalfi Coast Sailing Adventure
For travelers who want to continue the experience, the adventure does not have to end in Palermo. After the main trip concludes on the morning of Day 8, you will have the option to fly from Palermo to Naples and begin an unforgettable sailing extension along the Amalfi Coast.
From there, we board our liveaboard sailboat and trade city streets for open water, sea breezes, and dramatic coastal views. This optional extension offers a completely different pace and perspective, with time to enjoy the beauty of southern Italy from the water while taking in legendary destinations such as Capri, Positano, and the Amalfi Coast. It is the perfect way to shift from a culturally rich land journey into a more intimate and scenic coastal escape.
Booking Options
Your Southern Sicily journey includes seven nights of accommodations as we travel from Catania to Palermo, with stays that support the pace, comfort, and character of the trip. Along the way, we experience a thoughtful mix of locally selected hotels that place us close to the history, culture, and atmosphere that make each stop so memorable.
From historic stays in Syracuse and Agrigento to the vibrant energy of Palermo, each accommodation is selected to complement the journey and give travelers a comfortable place to recharge after each day’s experiences.
We offer two rooming options for this trip:
Shared Room | We Can Match You
$3299
Stay in a comfortable shared room with one other traveler. Shared accommodations are a great option for those who enjoy the community aspect of group travel while keeping costs lower.
Traveling with a friend or partner? You are welcome to room together. Traveling solo? We can thoughtfully match you with another traveler on the trip. Shared rooms are ideal for guests who want a welcoming and social experience while enjoying all the highlights of this Southern Sicily journey.
Private Room | Your Own Space
$3999
Enjoy your own private room throughout the journey for added comfort, privacy, and personal space at the end of each day. This option is perfect for travelers who prefer a quieter retreat while still being fully part of the group experience.
Private rooms for this trip are limited to just 6 spaces and are offered on a first come, first served basis. If having your own room is important to you, we recommend booking early.
Adventure Activities
Get ready for an unforgettable journey through Southern Sicily. Below is a sampling of the memorable experiences we will share along the way, from ancient ruins and historic towns to local flavors, layered culture, and beautiful coastal settings. With thoughtfully chosen highlights and signature Sicilian moments, this trip blends discovery, connection, and meaningful time together in a way that feels both enriching and unforgettable. The itinerary specifically includes an arancini cooking class in Syracuse, visits to Ragusa, Villa Romana del Casale, the Valley of the Temples, and Monreale Cathedral, along with orientation walks in Syracuse and Palermo.
Arancini Cooking Class in Syracuse
Enjoy a hands on introduction to Sicilian cuisine with an included arancini cooking class in Syracuse. This experience adds a delicious local touch to the journey and offers a fun way to connect with the flavors and traditions that make Sicily so memorable.
Syracuse Orientation Walk
Get introduced to the charm and layout of Syracuse on an included orientation walk. This experience offers a first look at one of Southern Sicily’s most atmospheric cities and helps set the tone for the journey ahead.
Visit to Ragusa
Spend time in the beautiful hill town of Ragusa, known for its baroque beauty and dramatic setting. This is one of the itinerary’s named included stops and gives the trip one of its most visually distinctive cultural moments.
Villa Romana del Casale Visit
Explore Villa Romana del Casale, home to one of the most extraordinary collections of ancient Roman mosaics in the world. This included visit adds a fascinating archaeological and artistic layer to the journey through Sicily.
Valley of the Temples Guided Tour
Walk among the remarkable ruins of Agrigento’s Valley of the Temples on an included guided tour. This is one of the trip’s biggest headline experiences and one of the most iconic historic sites in all of Sicily.
Monreale Cathedral and Palermo Orientation
Near the end of the journey, visit the stunning Monreale Cathedral and continue on to Palermo for an included orientation walk. Together, these experiences bring in both Sicily’s artistic grandeur and the lively spirit of its capital city.
Optional Amalfi Coast Sailing Extension
For travelers who want to keep the experience going, our optional Amalfi Coast sailing extension offers an unforgettable second chapter after Southern Sicily. A small group of us will continue on from Palermo to Naples, where we will board a beautiful 54 foot sailing yacht and spend time exploring the coastline from the water. With only 5 cabins available, this extension is intentionally small, with space for approximately 6 to 10 travelers, creating a more intimate and immersive experience as we sail toward legendary destinations like Capri and Positano.
The video here is a general overview of G Adventures sailing experiences in the Mediterranean. While it does not show the Amalfi Coast specifically, it gives a strong sense of the sailing style, group atmosphere, and scenic beauty that make this add on such a memorable way to continue the journey.
Inclusions:
What's Included:
✓ 7 nights of accommodations in Catania, Syracuse, Agrigento, Trapani, and Palermo, or similar
✓ Breakfast at most accommodations
✓ Pride Adventures private Welcome Dinner in Catania and private Farewell Dinner in Palermo
✓ Transportation between destinations and to included activities, including private vehicle and local transfers
✓ G Adventures highlights, including:
• Arancini cooking class in Syracuse
• Visit to Ragusa
• Villa Romana del Casale visit
• Valley of the Temples guided tour
• Monreale Cathedral visit
✓ Guided visits and entrance fees for included activities, such as:
• Orientation walk in Syracuse
• Orientation walk in Palermo
• Archaeological and historic site visits throughout the itinerary
✓ Expert G Adventures Chief Experience Officer (CEO) throughout the journey, along with knowledgeable local guides at key sites
✓ Basic gratuities included for local guides, drivers, and included services, along with a base CEO tip of $5 per day
✓ Small group experience with Pride Adventures host and fellow travelers, with a maximum group size of approximately 15
What's Not Included:
✕ International flights, including your arrival into Catania, Italy and your departure from Palermo, Italy
✕ Transportation to and from airports
✕ Travel insurance, which is required for participation
✕ Meals not listed in the itinerary
✕ Optional activities and free time experiences not listed as included
✕ The optional Amalfi Coast sailing extension, which is offered as an additional add on experience at an extra cost
✕ Pre trip and post trip hotel nights, which may be available upon request but are not included in the base trip price
✕ Personal expenses such as souvenirs, beverages, snacks, laundry, and similar items
✕ Additional tips for hotel staff or personal services beyond what is already included
Physical Rating, Comfort, and Adventure:
Physical Rating: 2 Light
This journey is best for travelers who enjoy a comfortable pace with regular walking and sightseeing. Expect historic streets, some stairs, uneven surfaces, and full days that balance cultural exploration with scenic travel. Most days are more focused on discovery and movement between destinations than physical challenge, but you should be comfortable being on your feet throughout the day.
Service Level: Comfortable Adventure
This trip includes seven nights in comfortable, locally selected hotels across Southern Sicily, offering a mix of convenience, charm, and a welcoming place to recharge after each day. Accommodations are chosen to fit the pace and character of the itinerary, with some stays offering added touches such as beautiful settings, pools, or a more distinctive local atmosphere. The experience is designed to feel comfortable and enjoyable while staying true to the spirit of small group travel.
Travel Style: Cultural Discovery
This journey is designed for travelers who want to experience the highlights of Southern Sicily through history, culture, food, and meaningful local experiences. With several destinations packed into eight days, the trip keeps a steady pace while balancing iconic landmarks, scenic drives, and time to enjoy the character of each stop. It is a great fit for travelers who want a well rounded small group experience that feels immersive, social, and full of variety.
Important Documents & Links:
JoinCGA.com – California Gay Adventures
Documents containing personal information will be delivered privately to attendees via email and/or text as the trip dates approach. For any questions, please contact chris@prideat.com.
Important Documents & Links:
We’ve provided key resources to help you prepare for your Pride Adventures journey.
The Pride Adventures Trip Guide is your primary reference for itinerary details, accommodations, logistics, flight guidance, packing tips, and important updates. This guide also includes a dedicated section covering the optional Amalfi Coast sailing extension, so everything you need is in one place.
The G Adventures Trip Dossiers provide additional details directly from our tour partner, including day by day logistics, inclusions, and operational information for both the Southern Sicily journey and the sailing extension.
Adventure Updates
This section is reserved for important announcements and time sensitive updates.
For full details on flights, itinerary, packing, and trip logistics, please refer to the Pride Adventures Trip Guide, which includes both the Southern Sicily journey and a dedicated section for the optional Amalfi Coast sailing extension.
Questions? Contact tripsupport@prideadventures.com
🟡 Trip Status: NOT YET CONFIRMED
This trip requires a minimum of 8 travelers to confirm.
Please wait to book flights until we officially confirm the departure.
Once the minimum is reached, we will update this section right away and notify all registered travelers by email.
✈️ Flights
Please do not book flights until the trip is confirmed.
Arrival Airport: Catania, Italy (CTA)
Departure Airport: Palermo, Italy (PMO)
Please plan to arrive in Catania in time for the group start on May 30, 2027, and depart from Palermo on June 6, 2027.
Travelers joining the optional sailing extension will continue on to Naples after the main trip, with additional flight guidance provided in the Trip Guide.
If you would like help reviewing flight options before booking, contact tripsupport@prideadventures.com
💳 Deposits and Payments
Deposit: $500 due at registration
Flexible payment plans: Available
Final payment due: February 28, 2027
For travelers adding the optional Amalfi Coast sailing extension, payments for that portion will be made directly with the tour vendor. The Pride Adventures team will help facilitate the process and provide guidance along the way.
Questions about payment timing or payment plans? Contact tripsupport@prideadventures.com
🛡️ Travel Insurance
Travel insurance is required for participation once the trip is confirmed.
Your policy must include at least $200,000 total in combined coverage for emergency medical care, evacuation, and repatriation.
We also strongly recommend coverage for trip cancellation, interruption, baggage loss, and travel delays.
Please send proof of insurance to tripsupport@prideadventures.com before departure.
🩺 Travel Health
We recommend reviewing the CDC Travelers’ Health page for Italy before departure for the latest vaccine guidance, health recommendations, and travel updates:
Final health and entry reminders will also be included in the Trip Guide.
📘 Passports and Entry Requirements
Your passport should be valid for at least 6 months beyond your travel dates.
Entry requirements can vary by nationality, so please review the requirements for your passport country before travel. Final guidance will also be included in the Trip Guide.
⛵ Optional Amalfi Coast Sailing Extension
The Amalfi Coast sailing experience is offered as an optional extension following the Southern Sicily trip.
This small group sailing adventure takes place aboard a 54 foot yacht and is designed to be an intimate and flexible experience. Depending on cabin selections, our group will typically range from approximately 6 to 10 travelers.
Our goal is to fill the boat with Pride Adventures travelers so the experience feels more private and connected. If we fill the departure, the boat will be fully ours. If not, the sailing experience may also include a small number of additional travelers joining the same G Adventures departure. Either way, it remains a relaxed and memorable way to experience the Amalfi Coast from the water.
To include a Pride Adventures host, Kevin, on the sailing portion, we will need a minimum of 3 booked cabins on the extension. If fewer than 3 cabins are booked, the sailing experience can still move forward as an unhosted but fully supported G Adventures sailing trip.
👉 Full details, cabin options, pricing, and itinerary are included in the Pride Adventures Trip Guide.
🤝 Traveler Connections
• A live pre trip Zoom call will be held approximately 30 days before departure
• A private WhatsApp group will be created closer to departure
Details will be shared directly with registered travelers.
📬 Need Help?
For any questions about trip status, logistics, registration, or flights: