Join SideQuests host Peter on an exciting tour of some of the best that southern Italy has to offer. We'll kick off the tour with dinner in Rome before heading down the coast to Naples and the greater Campania region, including the Amalfi Coast, Pompeii, Capri and Mount Vesuvius. With a mix of sunshine, stellar Italian wine and cuisine, historical sights, classic art, beautiful beaches and endless exploring of some of the most picturesque towns in the world; we think that this trip will be something you'll remember forever.

At SideQuests, we believe the best travel isn’t about rushing from highlight to highlight. It’s about creating space for connection, and making the kind of memories that stick with you long after you’re home. That's why we're excited to have this trip hosted by Peter, an Italian-American whose ancestors come from the region and who also has both a long professional history of LGBTQ+ community building and advocacy work and tourism/group travel experience. This trip will weave together culture, food, gorgeous scenery, and group connection in a way that feels intentional, welcoming, and deeply freeing.

If you’ve ever wanted to experience Italy without having to plan every detail, surrounded by a small group of like-minded gay travelers who are open, curious, and ready for something meaningful — this is the right tour for you!

What Airport Do I Fly Into?
For this tour we recommended flying into Rome (FCO) and departing out of either Naples (NAP) or Rome (FCO).

When Does the Tour Begin and End?

The first activity of this tour begins on September 20th at approximately 5pm. The tour concludes following your included breakfast at Grand Hotel Vesuvio in Sorrento, with choice of private transfers to Naples Airport (NAP) or Naples Central Train Station. From there, continue onward to Rome (FCO) or your next destination.

• Vibrant Naples – Immerse yourself in one of Italy’s most captivating coastal cities, renowned for its ancient history, sweeping Mediterranean views, world-famous pizza, and thriving LGBTQ+ nightlife scene.

• Exclusive Capri Island Adventure – Cruise in style on a private boat, marvel at the iconic Faraglioni sea stacks, and soak up the chic charm and breathtaking cliffs of this glamorous island.

• Magical Amalfi Coast – Explore the pastel-hued villages of Positano, Amalfi and Ravello, and Sorrento, discovering the romance, beauty, and coastal splendor that make this region world-famous.

• Authentic Cultural Tours – Discover the secrets of Southern Italy on private English-speaking walking tours led by our local gay guide Sergio, who brings the history and culture to life.

• Taste of Italy – Indulge in curated dining experiences, from traditional Neapolitan pizza dinners to gourmet meals, celebrating the rich culinary heritage of the region.

• Intimate Group Travel – Connect with like-minded LGBTQ+ travelers in a small-group setting (12–24 guests) designed for shared experiences, new friendships, and unforgettable memories.

• What Airport Do I Fly Into?
  For this tour we recommended flying into Rome (FCO) and departing out of either Naples (NAP) or Rome (FCO).

• When Does the Tour Begin and End?

  The first activity of this tour begins on September 20th at approximately 5pm. The tour concludes following your included breakfast at Grand Hotel Vesuvio in Sorrento, with choice of private transfers to Naples Airport (NAP) or Naples Central Train Station. From there, continue onward to Rome (FCO) or your next destination.

• What Is The Cancellation Policy?
  If your booking is still pending (meaning the trip has not been confirmed yet), you’re eligible for a full refund — including your 25% deposit.

  Once the trip is confirmed (after 10 travelers have booked), we will send you a confirmation notification and your deposit becomes non-refundable. If you need to cancel after confirmation, you’ll receive a Credit Voucher to be applied to a future trip within 1 year of cancellation, for the 25% deposit amount paid (minus a $100 cancellation fee). Optional Add-ons can be added and are fully refundable up to 60-days pre-trip.

  After the 90-day mark 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 strongly recommend purchasing travel insurance — it really is worth it.
  
  > For more FAQ, find your answers here.

Overview

Welcome to the Eternal City! If you’re arriving today, we recommend flying into FCO (Rome Fiumicino Airport). Today upon arrival, we will check-in at our Rome accommodation, Starhotels Metropole (or similar). This evening, we’ll meet in the lobby and head out together for a welcome cocktail reception followed by an included group dinner. Exact meeting times and locations will be shared closer to the trip date. Arriving early? You’re welcome to explore Rome at your own pace, and we’re happy to help arrange pre-trip nights at the same hotel if you’d like to extend your stay.

Welcome Aperitivo & Cocktail Reception

We’ll kick off the week with a relaxed welcome drink at a local spot near our accommodations or dinner location. This is a great time to meet your fellow travelers, ease into the Italian spirit, and toast the start of an unforgettable week in Italy.

Welcome Dinner – Included Meal

Our welcome dinner will take place at a highly rated local Roman restaurant and is included in your itinerary. You’ll enjoy a multi-course Italian meal featuring regional flavors, with shared appetizers, choice of main-course, and one non-alcoholic beverage + water included.

Overnight Accommodation at Starhotels Metropole (or similar)

Overview
After an included breakfast, we’ll check out and depart by high speed train for Naples (approximately 2–2.5 hours). We’ll arrive around midday, and after some free time to grab lunch, we'll head out on a guided walking tour through Naples’ historic center taking some time to be guided through some of the extraordinary architecture and art of this ancient city. Later we’ll return to the hotel to settle into our rooms before heading back out in the evening for a food and wine tasting experience together, to include some truly world famous pizza here in the city where pizza was invented.

Naples Introduction Walking Tour & Lunch

Our first taste of Naples comes via a relaxed orientation walk through the historic city center, offering context, character, and first impressions of this vibrant, bustling, and deeply beloved city. In addition to having time for a casual lunch, together we'll visit some key sites for short guided experiences that will have us marveling at the spectacular art and architecture; while also getting an orientation of this city that we'll be free to wander later. Our walk with end at the city's archeological museum where you'll have the option to visit the Pompeii exhibits and see some of the most important artifacts from the site that we'll visit the following day.

Food & Wine Walk & Taste Tour – Included Dinner

This evening, we’ll explore Naples through its food on a guided food and wine tasting walk featuring local specialties and neighborhood stops, we'll end with a classic Neapolitan pizza dinner at a locally beloved pizzeria. Dinner includes one pizza per person, one beer, wine, or non-alcoholic beverage, plus water for the table. Afterward, enjoy free time to continue exploring nightlife in Naples, or head back to the hotel for some well-deserved sleep.

Overnight Accommodation at Starhotels Terminus Naples.

Overview
After an included breakfast, we’ll check out and depart by private shuttle for Pompeii, kicking off a full day of history, landscapes, and iconic southern Italy experiences. From ancient ruins to volcanic views, we’ll end the day arriving in beautiful Sorrento, where we’ll settle in for the next four nights, at the precipice of the Amalfi coast.

Pompeii Guided Archaeological Tour

After arrival to Pompeii, we’ll explore the fabled city on a private guided tour led by a professional archaeologist, offering insight into daily life that was abrublty and dramatically frozen in time with the eruption of Mount Vesuvius in 79 AD. This immersive walk through remarkably preserved streets, homes, and public spaces brings one of the world’s most famous archaeological sites vividly to life.

Farm-to-Table Countryside Experience – Included Lunch

Following our visit to Pompeii, we’ll head to a local agriturismo countryside farm for a relaxed, garden-fresh lunch outside the city. This included meal features shared appetizers, a main course, water for the table, and one non-alcoholic beverage. This experience provides a perfect pause to refuel and soak in the slower pace of rural Italy with some carefully sourced ingredients sure to pleasure our palates.

Mount Vesuvius Crater Walk

Following lunch, we’ll travel by private charger to Mount Vesuvius for a guided crater walk, giving you the opportunity to stand on the rim of the infamous volcano and take in the sweeping views over the Bay of Naples. Comfortable walking shoes are recommended for this unique and incredibly memorable experience.

Arrival in Sorrento

After our guided visit and walk at Mount Vesuvius, we’ll continue on our private shuttle to Sorrento and check in at the Grand Hotel Vesuvio Sorrento. Settle into your room and enjoy a free evening to explore this quintessential coastal town. Enjoy dinner at your leisure with recommendations provided, of join your host at a local spot.

Overnight Accommodations at Grand Hotel Vesuvio Sorrento

Overview

Today is a (mostly) free day to enjoy Sorrento at your own pace. After an included breakfast, sleep in, wander the town, shop, café-hop, enjoy seaside walks, relax by the hotel pool or join some of your fellow travelers at a local beach club for an optional add-on. This is a day to lean into la dolce vita — the sweet, unhurried rhythm Italy is known for.

Day at Leisure

Spend the day however you’d like, whether that’s exploring Sorrento’s streets and viewpoints, lingering over long lunches, or taking a slow, restorative day. Your guide will be available with recommendations for shopping, scenic walks, and favorite local spots.

Optional Add-On: Beach Club Day (Additional Cost)

For those interested, you may join your host for an optional beach club day at a local seaside lido (additional cost). Expect private sun loungers, swimming, access to great food and refreshments, clear waters, coastal views, and a relaxed Mediterranean atmosphere — a classic way to experience the Amalfi Coast region.

Optional Add-On: Limoncello Tasting (Additional Cost)

Later in the afternoon, you can choose to participate in an optional limoncello tasting experience, offering a chance to sample this iconic local specialty while learning about its history and production.

Host-Led: LGBTQ+ Community & Connection Workshop

This evening, we’ll gather for an optional host-led LGBTQ+ community and connection workshop (approximately one hour). This facilitated space is designed for reflection, conversation, and meaningful connection — one of the most special and intentional elements of a SideQuests experience and typically a favorite moment for many of our travelers!

Evening at Leisure

Following the workshop, the evening is free for dinner on your own, with plenty of recommendations provided. For those who wish, your host will suggest an informal dinner location to continue the night together.

Overnight Accommodation at Grand Hotel Vesuvio Sorrento

Overview

After an included breakfast, we’ll set out for a full day exploring the iconic Amalfi Coast by land and sea. Traveling by private bus and public ferry, we’ll visit three of the coast’s most celebrated towns: Positano, Amalfi, and Ravello. After a super-adventurous day, we'll return to Sorrento in the evening with free time in the town for dinner.

Positano

Our day begins departing Sorrento by private bus. Arriving in Positano mid-morning, we'll enjoy time wandering its colorful lanes, browsing cute boutique shops, and taking in the towns iconic dramatic coastal views. Relax by the iconic beach, grab lunch at a charming cafe or ristorante, and enjoy. This is your chance to slow down, soak it all in, and live out your most cinematic Amalfi Coast fantasies.

Amalfi

Following lunch in the early afternoon, we’ll take the ferry together from Positano to the town of Amalfi, offering a beautiful perspective of the coastline from the water. Once we've arrived in Amalfi, we'll have free time to explore the historic town center, visit the cathedral, enjoy a gelato, or simply wander and people-watch. Plus, this is a fantastic time to get those iconic Amalfi coast photos and update that Instagram profile pic! ;)

Ravello

From Amalfi, we’ll travel by private transfer up the cliffs to Ravello, perched high above the sea and known for its sweeping views and peaceful atmosphere and beautiful flora. In Ravello we'll have more time to explore the town, stroll its scenic overlooks, and take in what are often considered some of the most beautiful vistas on the Amalfi Coast. Grab a snack, sit in the piazza with a mid-day espresso, wander the gardens and breathe in that salt air.

Evening at Leisure

Following time exploring Ravello, we'll return to Sorrento on a scenic drive by private bus. The evening is yours to enjoy with dinner on your own, or join your guides at a local recommended spot, and have a relaxed night after a full and unforgettable day along the coast.

Overnight Accommodation at Grand Hotel Vesuvio Sorrento

Overview

Wake up at our Sorrento hotel for an included breakfast, then board our private transfer to the marina in Sorrento for one of the most adventurous experiences yet. We'll set out for a full day exploring the legendary island of Capri by private boat. With time on the water, stopping to swim and cruising around the island, free time on the isle of Capri, and a celebratory farewell dinner in the evening, today brings together everything we love about this region.

Private Boat Tour of Capri

Following breakfast and our private transfer to Sorrento's marina, we’ll cruise around Capri’s dramatic coastline aboard small private boats (approximately 10 guests per boat), we'll be guided around with opportunities to take in the sea caves, rugged cliffs, and impossibly blue water. Weather permitting, we’ll make swimming stops along the way, giving you the chance to jump in and enjoy the warm Mediterranean around this gorgeous island.

Free Time on Capri

After docking at Capri’s marina, you’ll have several hours of free time to explore the island at your own pace. Stroll the iconic town, browse chic shopping streets, enjoy a long lunch, take in scenic viewpoints, relax at the beach, or ride the funicular to the top of Capri — the island is yours to experience however you choose.

Return to Sorrento
After a full day of soaking in the essence of Capri, in the late afternoon we’ll make our way back to Sorrento by private boat, giving you time to freshen up, relax, or take a short rest before our final evening together.

Farewell Dinner – Included Meal

Tonight, we’ll gather for a special group farewell dinner to celebrate an unforgettable week together. This included meal features shared appetizers, a main course, water for the table, and one non-alcoholic beverage (additional drinks available for purchase), the perfect capstone to our time on the Amalfi Coast.

Overnight Accommodation at Grand Hotel Vesuvio Sorrento

Overview

After one last included breakfast together in Sorrento, we’ll check out of the hotel and depart by private bus or sprinter van for Naples, with drop-off options at either Naples Airport (NAP) or Naples Central Train Station to make onward travel as easy as possible. A couple different times will be provided throughout the day (exact timing of transfers to be announced). Some from our group may choose to stay longer in Sorrento, others may continue by train from Naples to another destination in Italy or Europe, and the rest of us will return home via Rome (FCO) or Naples (NAP).

Departures & Onward Travel

From Naples, you can fly out directly from NAP, or take the train onward from Naples Central Train Station — including back to Rome if you’re connecting for an international flight from FCO, or continuing your trip elsewhere in Italy. Your host will provide guidance on timing and the best option for your specific plans so you can get where you need to go smoothly.