What It's Really Like on a Catamaran Sailing Vacation

"There are no strangers here; only friends you haven't yet met." 

— William Butler Yeats

Watching the coast go by. USVI

It was just sunrise in Milna’s harbor in Croatia.  Sitting with a guest drinking fresh brewed coffee while the town around us was waking up. She turned to me and said “I didn’t know travel could feel like this.” That’s the moment I wanted to share with you.

Before I tell you about the remaining cabins, here’s what people usually want to know before they book:  what is it actually like to spend a week aboard a catamaran?

More Space Than You'd Expect

Will it feel cramped? Will the seas be rough? Do I need sailing experience

The reality is almost always better than what people imagine. Modern catamarans have twin hulls and a wide beam, which means an exceptionally stable ride and surprisingly generous living space — indoors and out. Most guests are surprised the first time they step aboard.

Depending on your cabin, you'll have your own private space with an en suite bathroom, comfortable indoor and outdoor areas to relax, and the everyday conveniences you'd want for a week away.  There’s electricity, charging outlets, hot showers, comfortable beds and air conditioning.  Most guests arrive expecting to rough it a little. Instead, they find a relaxed, comfortable way to explore the coast — waking up in a new harbor each morning.

A Day Aboard

Mornings start quietly — coffee or tea on deck while the harbor comes to life. Our private chef prepares breakfast with fresh local ingredients, served in the shaded aft dining area.

From there, the day unfolds naturally:

• A few hours of sailing to a secluded cove for swimming, snorkeling, or paddle-boarding

• Lunch aboard

• An afternoon sail to a harbor or island village — time to wander, browse, sit by the water

• Dinner ashore, watching the light change over the coastline

There's no pressure to sail. Some guests like raising the sails or taking a turn at the helm; others are just as happy with a book and a glass of wine, watching the coast drift by.

And you only unpack once. No hotel changes, no repacking — your accommodations travel with you, and each morning brings a new destination.

Three catamarans of our Sicily crew.

The Joyride Difference

Keeping the trips small and personal is done on purpose.  You're never just another passenger in a large group — I host every journey myself, and I choose the destinations, restaurants, and local experiences that help you actually connect with a place, not just pass through it.

Some travelers arrive solo. Others come with a spouse, partner, or friend. It rarely stays that way for long — within a day or two, everyone is sharing meals, stories, and sunsets together.

That's the quiet magic of sailing: there's no packed sightseeing schedule, no rushing from place to place. People have time to actually get to know each other. A conversation that might last five minutes on land can stretch for hours on deck, walking through a village, or over a slow dinner as the sun goes down.

By the end of the week, guests who arrived as strangers often leave as real friends — many stay in touch long after, and more than a few have booked a trip together again.

I've had guests tell me, "I never knew this kind of travel existed." That's exactly what I hope people find — not just beautiful places, but a slower, richer way of experiencing them.

Typical catamarans we charter.

Croatia — This September

I have a couple of cabins left for our small-group September sailing week in Croatia. If you've been curious about this trip, just reply — ask me anything, or I'll send over the full itinerary and pricing. No pressure, just information.

And Croatia isn't the only place we go. We also sail Greece, the British Virgin Islands, Scotland, and a few destinations that never make it onto the website. If there's somewhere you've always wanted to sail, tell me — it might already be in the works.

I hope our paths cross aboard someday.

Warmly,Joy 💙