Many vacations abroad follow a familiar blueprint: make your list, make your way to the locations on that list, take photos to commemorate your time there, fly home and promptly start planning your next trip. But have you ever thought of swapping your phone camera and map app for a sketch pad and pencil? Or trading impossibly long lines and crowded lidos for serene open waters and warmly lit artists’ studios?
Consider a “hobbycation” (also sometimes referred to as a “skillcation”). These trips are designed to connect travelers with others who share a pastime — like cooking, writing, knitting, painting, swimming, or even ancestry deep dives — and they’re on the rise. According to one October 2025 survey by Marriott Bonvoy, the hotel chain’s global travel loyalty program, 68% of travelers say they have already taken — or plan to take — trips built around their personal passions. Among Gen Z, that number reaches around 82%.
If you’re ready to hone a skill (or learn a new one) on your next trip to Italy, here are some workshops, retreats and tours engineered to make new connections, spark curiosity and sharpen your knowledge.
Try convivial creativity in Tuscany
Set in the mountainous territory of Lunigiana and occupying a lovingly restored 17th-century mill beside the Rosaro River, The Watermill at Posara invites guests to immerse themselves in week-long, slow holidays built around convivial creativity — painting, cooking, knitting, Italian language learning and more.
Bill and Lois Breckon acquired the Watermill property in 1989, initially running it as a self-catering summer sojourn. But when a friend suggested they add painting classes to their itinerary, “courses became our mainstay,” Lois explains.
The retreat venue is surrounded by silvery olive groves and cypress-lined country roads that offer a warm and welcoming atmosphere where food and wine flows and everything is included, such as transportation, meals, post-lesson walks in the countryside, excursions to an outdoor market, picnicking at a nearby monastery, dining at a local gourmet restaurant, and even participating in a private tour of the marble quarries in Carrara.
The couple says they’re dedicated to fostering an easy, down-to-earth house party atmosphere “where guests feel they’re staying with good friends.”
Blow your writing wide open
If you think you have a manuscript in you (or just love putting pen to paper), Wide Open Writing (WOW)’s wordsmith workshops in Italy can help you get an old project over the finish line, or just get inspired to start a new one.
Led by facilitators Pam Dumlao, Dulcie Witman and Nancy Coleman, WOW’s Italy programs take place at Castelnuovo Tancredi, a nearly 1,500-acre olive oil and wine estate in the hills not far from Siena. The retreat is part literary vision quest, part blissful getaway — a place to escape the noise of daily life, to write and share stories in a supportive environment that fosters connections with other writers.
Wide Open Writing’s philosophy is a simple one: “Through our retreats and writing groups, we offer [participants] time and space and encouragement to focus on their craft,” says Dumloa.
“Our participants often tell us that the space we create for them, one of trust and openness and support, opens them up to write freely and to share without fear of judgment or criticism."
A typical day starts slowly, with gentle mind and body work like yoga or meditation, followed by a “silent breakfast” to help participants anchor themselves before diving into the first of two writing sessions.
There are two writing sessions each day — one in the morning and one in late afternoon — leaving the rest of the day open for participants to write on their own, take a nap, walk, swim, explore, or do whatever they need for themselves. Each day, there’s also a variety of opportunities for excursions, scenic hikes, walks on the beach and group field trips.
“As writers,” Dumloa emphasizes, “inspiration is everywhere.”
Swim like no one is watching
Dip more than your toes in Italy’s crystal-clear seas by signing up for SwimTrek’s small-group wild and open-water swim tours.
Since 2003, UK-based SwimTrek has been designing unforgettable trips tailored for swim enthusiasts who want to dive into the waters of Sardinia’s Emerald Coast, Sicily’s Egadi and Aeolian Islands, and the Tremiti four-island archipelago — the only Italian islands on the Adriatic Sea.
By day, swimmers splash around spectacular sea caves, gorges, cliff faces and sculptural rock formations. By night, they trade the briny deep for relaxing evening meals of local cuisine or enjoy whatever nightlife the destination has to offer.
SwimTrek’s tours are designed for anyone who can swim, regardless of experience level, but swimmers should have at least a basic understanding of open-water swimming. Tours are capped at 15 swimmers, divided into smaller swim teams based on speed. Every group is accompanied by a dedicated safety vessel and led by expert guides who offer encouragement and the occasional tips on technique.
Answer your Italian ancestry riddles
Digging into your ancestral roots no longer has to mean rifling through boxes in an attic or sitting for hours in a musty archive. With the rise of DNA testing that can accurately pinpoint “your people,” tracing family trees and hunting down one’s heritage have become hugely popular pastimes.
Companies like the Calabria-based My Bella Vita Travel have taken note. Their signature Small Group Heritage Tour invites those with southern Italian backgrounds to literally walk in the footsteps of their ancestors.
Founder Cherrye Moore has seen firsthand how travelers of Italian descent meticulously collect stories, documents and memories: “They research their ancestors the way others might study wine or pottery,” she says.
Moore’s signature tour allows participants to explore their lineage and histories in the places where they began — along village streets and among the folk traditions that shaped each family’s unique story. She says the experience is about “blending two things: the camaraderie and fun that happens naturally in a group, and the deeply personal experience of having time devoted entirely to your own family’s roots.”
Groups have stumbled upon long-lost family homes and uncovered a trail to an original baptismal font where a grandfather was christened generations ago. Mayors have been known to roll out the red carpet for groups; in one village, locals organized a communal cooking experience in the piazza, while another livestreamed an ancestor’s homecoming on the town’s social media page. “You never know what a town will reveal until you are standing inside it,” Moore says.
