Apr 11–17, 2027 Naples to the Amalfi Coast Hosted by Derrick
A hosted group trip for gay men 40 and over. Pompeii, Capri, Positano and the best pizza on earth, with Derrick as your host and a table of like-minded men every night. Culture, not clubs. Come on your own and go home with friends.
Until the welcome dinner in Naples
April 2027 · Limited spots
Answer a few quick questions, then pick a time to meet Derrick. It is a relaxed call to get to know each other, talk through the week, and see whether this is your trip. Nothing is charged and nothing is held until you say so.
Who this is for
Almost everything sold to gay men is a party. And the older we get, the easier it is to end up at home, with the circle getting smaller. This is the other thing: a week of real places, good food and men you actually want to talk to.
01
Everyone on this trip is a gay man in his forties or older. Nobody has to explain himself, and nobody is the only one at the table.
02
Plenty of the group will be traveling solo. Some will bring a partner or a friend. Either way you have people to eat with, walk with and talk to all week.
03
This is not party travel. It is Pompeii, Capri, the food of Naples and the villages of the Amalfi Coast. The late nights are long dinners, not circuit parties.
04
Derrick spent 17 years living abroad, 12 of them in Madrid. He travels with you every day, from the welcome dinner to the last breakfast.
Your host
Derrick Fields founded Ursus Travel for gay men, bears, and those that love them. He left the US in 2009 and spent the next 17 years living abroad: the Peace Corps in Honduras, then Korea, China, Thailand and Vietnam, then 12 years in Madrid. He did not research southern Europe. He lived in it.
He built the group trips for a particular kind of traveler. In his words: men who broke up with their partner of twenty years, or lost their partner, and found the circle getting smaller. Ursus Travel exists to get them out of the house and into the world, with a group of men who get it.
On this trip he is with you every day. The welcome dinner, the ferry to Capri, the last night in Sorrento.
April 11 to 17, 2027
Day 1
Welcome to Naples
Meet the group in the hotel lobby at 5:30pm, then the welcome dinner.
Day 2
Naples, on foot and by the plate
A guided walk through the old city, then a food tour: markets, pizzerias, fritti, sfogliatella.
Day 3
Capri
The ferry across the bay, then the island, with time in Anacapri.
Day 4
Pompeii, then Sorrento
A private guided visit to the ruins, then on to Sorrento and a walk through town.
Day 5
Positano, Amalfi and Ravello
The Amalfi Coast in one day, by private van. Guided time and free time in each town.
Day 6
Sorrento, at your own pace
A free day. Marina Grande, Piazza Tasso, the cloister. Farewell dinner together that evening.
Day 7
Arrivederci
One last breakfast, then home via Naples airport.
On the itinerary
Ravello sits high above the coast, and the gardens of Villa Cimbrone end in a terrace over nothing but sea. It is on the itinerary, and it is the view people frame.
Positano, Amalfi and Ravello in a single day, by private van. In each one, an hour with a guide and then an hour on your own. Someone who knows the place, then time to make it yours.
A free day in Sorrento, spent however you want it. Then everyone back at one table for the farewell dinner. This is the one people remember.
The details
Three nights in Naples, three in Sorrento. The guided days are booked and paid for. The evenings and the free day are yours, and you will not be short of company.
Per person, sharing a room
$4,966
7 days, 6 nights · Apr 11–17, 2027
Not included: international flights, airport transfers, meals and drinks beyond the ones listed, travel insurance, tips for guides.
Traveling solo? A private room is available at an added cost. Ask Derrick on the call.
Before you ask
Yes. Derrick Fields hosts this trip and is with the group every day, from the welcome dinner in Naples to the last breakfast in Sorrento. TrovaTrip runs the logistics and provides a local guide throughout. Derrick is the reason the group is the group.
Gay men, 40 and over, from all over. Some traveling solo, some with a partner or a friend. The kind of men who would rather spend an evening over a long dinner than in a club. TrovaTrip caps this trip at 26 travelers.
It is a fair question, and Derrick asks it too. Italy has recognized same-sex civil unions since 2016, and Capri and the Amalfi Coast have welcomed gay visitors for generations. It is still a traditional country, and a lot of men feel easier arriving as part of a group than on their own. That is part of the point. You have a table of friends around you and a host who lived in southern Europe for 12 years.
It is the norm. 84% of people who travel with TrovaTrip book solo. The price you see is per person sharing a room. If you would rather have a room to yourself, a private room is available on most TrovaTrip trips at an added cost, and Derrick will give you the exact figure on the call.
No, and on purpose. Most travel marketed to gay men is built around nightlife. This is built around Pompeii, Capri, the food of Naples and the Amalfi Coast. You will have free time, and nobody will stop you going out. But the trip is the culture and the company.
Included: six nights in four-star hotels, three in Naples and three in Sorrento; six breakfasts, plus the welcome and farewell dinners; eight guided experiences, from Pompeii to Ravello; a local guide throughout, and Derrick with you the whole week. The eight experiences are Guided Naples walking tour, Naples food tour, Capri day trip, Pompeii guided visit, Sorrento walking tour, Positano, Amalfi, Ravello. Not included: international flights, airport transfers, meals and drinks beyond the ones listed, travel insurance, tips for guides.
Capodichino closes for runway resurfacing for a few weeks in late 2026. It is scheduled to reopen well before April 2027, and it is the airport TrovaTrip recommends for this trip, both in and out. Derrick can help you with flights on the call.
TrovaTrip rates it easy. Expect walking tours of about two hours on paved and cobbled streets, a ferry to Capri, and short van rides between the coast towns. Good walking shoes, a hat and sunscreen and you are set.
Nothing today. This is a conversation with Derrick, not a booking. When you do book, it is through TrovaTrip. While your spot is pending, it is 100% refundable. More than 90 days out, you get a partial refund plus future trip credit: your down payment less a $100 fee, and any further payments back to the card you paid with. Within 90 days of the trip, it is non-refundable, which is why TrovaTrip strongly recommends insurance with cancellation cover.
Apr 11–17, 2027 Limited spots
Register your interest, meet Derrick, and ask him anything. If it is not your trip, he will tell you. There is nothing to pay to have that conversation.