A growing number of Canadians are turning to small-ship sailing trips to mark major life events, according to new data from G Adventures, which reports a 27% increase in marine travel bookings among Canadian travellers.
The trend points to a shift in how travellers are celebrating milestones. from proposals and anniversaries to birthdays and retirement, with many opting for more intimate, experience-driven settings at sea.
According to the company’s Skipper CEOs (Chief Experience Officers), requests tied to special occasions have risen significantly compared to three years ago. There has also been a notable increase in full-boat bookings, where groups of friends or families charter an entire yacht for private celebrations.
“Modern travellers are looking for moments that feel genuine rather than manufactured, which is why those special moments happen so naturally on sailing trips,” says Dave Hunter, Sailing Operations Manager and previous Skipper CEO at G Adventures.
“We’ve had travellers propose on the bow of the yacht, on remote islands atop a hill, in a caldera with the famous Santorini sunset, on a private beach with no public access, you name it. There’s a special magic in tucking into a hidden cove near Positano or the blue waters of the Cyclades where the only witnesses are a small group of new friends and your Skipper who knows exactly when the light hits the water to make a moment unforgettable. It creates the perfect environment for something meaningful and memorable without forcing it.”
Skippers often play a hands-on role in these moments, coordinating everything from proposal logistics to surprise celebrations.
“You’re a Skipper, but also a secret accomplice,” explains Hunter.
“I’ve run ‘covert operations’ at sea that involve specific ring-delivery timings, music cues, and distraction plans so the partner has no idea what’s coming. When everything comes together, the energy on the boat becomes electric. That’s the real difference on these trips. It’s not just two people, it becomes a shared, special moment with a built-in party.”
Skipper anecdotes highlight how personalized these experiences can be, from helping a guest safely hide an engagement ring to orchestrating private moments by steering the boat to secluded anchor points or arranging group distractions. In one case, a couple even followed up months later to share that their honeymoon sailing trip led to the conception of their child.
The company attributes the trend to several factors, including access to less crowded destinations, built-in social environments for celebrations, and the ability to tailor experiences using local knowledge. Unlike larger cruise ships, smaller vessels can reach remote coves and quieter beaches, offering a more private setting for milestone events.
The rise of what the company calls “sea-gagements”- engagements that take place early in a sailing trip followed by onboard celebrations, also reflects a growing demand for shared, immersive experiences.
At the same time, some travellers are seeking more purpose-driven travel, with itineraries that support local communities through visits to family-run marinas and sourcing food from local markets.
As the Mediterranean sailing season begins, G Adventures is highlighting a range of itineraries across Italy, Croatia, Greece and beyond, alongside routes in destinations including Montenegro, Thailand and Sri Lanka.
Mediterranean sailing highlights:
Sailing the Amalfi Coast: Capri, Positano & Coastal Bliss: Starting in Naples, this brand new seven-day journey balances adventure and relaxation, from soaking in the volcanic thermal springs of Ischia and visiting the legendary Blue Grotto in Capri, to navigating the pastel-hued, cliffside streets of Positano and Amalfi. Anchor in secluded turquoise coves for spontaneous swims, sunset limoncello tastings in Sorrento’s lemon groves, and private cooking classes to master regional flavors.
Sailing Croatia: Dubrovnik to Split: Departing from the medieval walls of Dubrovnik, this trip weaves through the sun-drenched islands of the Adriatic, offering the chance to hike through the lush, salt-lake landscapes of Mljet National Park and the Venetian-style marble alleyways of Korčula. Enjoy access to secluded beaches and quiet bays like Milna, where guests can swim directly off the deck or explore Roman ruins, and a special dinner in the UNESCO-listed streets of Trogir before arriving in Split.
Sailing Greece: Santorini to Mykonons: Setting sail from the breathtaking caldera of Santorini, this eight-day adventure offers a flexible itinerary that allows expert skippers to showcase hidden gems like the quiet trails of Folegandros, the secluded bays of Antiparos, and the authentic taverna-lined harbors of Naxos. Travellers can dive into crystal-clear waters for spontaneous snorkeling or explore ancient archaeological sites before enjoying a sunset cocktail overlooking Mykonos’ iconic windmills.
Sailing Italy to Croatia: Embarking from the canals of Venice, this 10-day cross-border voyage uncovers the hidden coastal gems of Italy, Slovenia, and Croatia. The journey traverses the Gulf of Trieste to the charming Slovenian city of Izola before hugging the Istrian Peninsula, with possible stops in the atmospheric seaside towns of Rovinj and Pula. Unlike traditional trans-Atlantic cruises, this small-vessel experience prioritizes island-hopping through the Kvarner Gulf, where travelers can swim in secluded bays before feasting on fresh local seafood.
Full G Adventures marine collection here: gadventures.com
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