When Victoria travel advisor Maksym Shkurupii designed a 32-day Mediterranean journey for a couple aged 80 and 86, he proved that the only real requirement for a grand adventure is simply wanting one.
At a Glance
A 32-day Italy and Sicily itinerary for an 80 and 86-year-old couple costs approximately $11,000 CAD for two and eliminates backtracking through strategic routing: Rome and Amalfi Coast by train, Sicily by rental car in a counter-clockwise loop, and a positioning night near Naples that makes the next morning's flight effortless. The design prioritizes depth over speed, using the right tool—driver, guide, or train—for each leg.
There is a particular kind of travel professional who treats a route not as a list of destinations but as a piece of engineering. Maksym Shkurupii is that kind of advisor. When a Victoria couple, aged 80 and 86, came to him with a simple wish — an unhurried month in Italy, the parts most visitors never reach — Shkurupii didn't hand them a brochure. He designed something bespoke: 32 days, 3 countries, the whole of Sicily by car, and approximately $11,000 CAD for two, with zero backtracking from start to finish.
The philosophy behind the trip is disarmingly straightforward. As Shkurupii puts it, "this trip is proof that the only real requirement for a grand adventure is wanting one." His clients were 80 and 86 years old. The trip was a month long. And every single leg of it was built around the right tool for the right moment.
The Architecture of a Month
The journey opened in Rome, where three nights at a boutique hotel near Termini gave the couple time to ease in. A skip-the-line guided tour of the Colosseum, the Roman Forum, and Palatine Hill anchored the visit, while the rest of the days were left gloriously unscheduled: piazzas, carbonara, and the particular pleasure of wandering a city without a clock. From Rome, the train carried them south through Naples and around the bay on the Circumvesuviana to Sorrento, the clifftop town Shkurupii chose as the ideal Amalfi Coast base.
The Amalfi day itself was handled with precision. Rather than putting his octogenarian clients behind a wheel on one of the world's most vertiginous roads, Shkurupii booked a full-day air-conditioned minivan with a driver, reasoning that "the world's most beautiful road is best enjoyed when neither of you is gripping a steering wheel above a 300-metre drop." It is a small decision that reveals a larger truth about his approach: expertise is often most visible in the disasters that never happen.
The move from Sorrento to Sicily was orchestrated across a single day that quietly did three jobs at once. The couple checked out of Sorrento, rode the bay around to Pompeii, and at 2:30 in the afternoon met a professional archaeologist for a three-hour small-group tour of the ruins and the Villa of the Mysteries, timed deliberately for after the cruise crowds had left. One night beside Napoli Centrale followed, a placement that looked like an odd one-nighter on paper but made the next morning's flight to Catania entirely effortless.
Sicily, Taken Slowly
A compact automatic, collected at Catania Airport with Zero Excess coverage included, became the vehicle for eight days and the grand counter-clockwise circle of the island. Taormina came first, a family-run villa with sea views and Mount Etna looming behind the ancient Greek theatre, granita in the morning air. Then Ortigia in Siracusa, a tiny baroque island that once rivalled Athens, where a balcony room let the golden stone glow at all hours. Agrigento followed, a ground-floor garden B&B ten minutes from the Valley of the Temples, best visited at sunset. Then Marsala, a countryside casita between salt pans and vineyards, the deep-west Sicily that almost nobody sees.
For the finale, Shkurupii secured three nights at Butera28, guest apartments inside Palazzo Lanza Tomasi, the last home of Giuseppe Tomasi di Lampedusa, author of The Leopard, hosted by the Duchess of Palma herself at around €130 a night. Every major booking site had shown no availability for his clients' dates. Shkurupii was unbothered. "Sold out online is often just the beginning of the search," he notes. The palazzo's own direct booking channel still had a room. The OTAs had simply exhausted their allotment. Within those walls, the couple could join "A Day Cooking with the Duchess": market shopping at Il Capo, cooking in the palazzo kitchen, their dishes served by white-gloved waiters, and, in a glass case nearby, the original handwritten manuscript of the novel itself.
The Invisible Work
A two-hour easyJet hop from Palermo to London, €261 for both in seats 3A and 3B, replaced what would otherwise have been a long and expensive backtrack across Europe. Two nights at The Clermont in Victoria, a grand railway hotel beside the station, provided what Shkurupii calls the "elegant decompression chapter" after a month of gelato and temples. Then came eleven days on an art tour the couple had arranged independently through their local gallery. Shkurupii booked nothing for it, and he was emphatic that this was entirely intentional. "A good advisor knows which parts of a trip aren't his," he says. The entire month had been engineered to hand the couple off, rested and on schedule, to a chapter that was theirs alone.
That restraint is as much a part of the design as the positioning night beside Napoli Centrale or the Zero Excess rental coverage that prevented any number of classic Sicilian parking disputes. Three airlines crossed the itinerary without a shred of brand loyalty: WestJet open-jaw across the Atlantic, Ryanair across the strait, easyJet out of Sicily. "The routing logic is the luxury," Shkurupii explains. "The airline brand is irrelevant." Total airfare for two, for a 32-day trip, came in at around $4,100 CAD.
Who This Trip Is For
The itinerary suits anyone who values depth over speed, people who want to understand a place rather than collect it. It rewards those comfortable sitting with a sea view for two nights, those willing to let an archaeologist lead rather than following a guidebook, those who find more pleasure in a terrace at dusk than in a checked box on a bucket list. It is not a trip for travellers who measure success in cities visited per day, nor for those who believe that the internet's first search result is the final word on availability.
The broader lesson Shkurupii takes from the journey is one he applies across every itinerary he builds. Each leg should earn its place using the right tool: trains and guides on the mainland, a car only where it delivers freedom, cheap positioning nights that protect expensive days and the energy to enjoy them. The routing logic, not the brand name or the star rating, is where the real value lives.
What Comes Next
For a travel advisor who has just proven that 32 days, two octogenarians, and an entire island can be choreographed without a single backward step, the next horizon is already taking shape. Shkurupii has his sights set on Japan and South Korea, two destinations where the same philosophy of deliberate, tool-matched, client-first design will no doubt produce something just as quietly extraordinary. The planning, one suspects, has already begun.
