OMG Dream Trip #1


Think about the most beautiful, inspiring, OMG place you’ve ever been to? What-do-you-got?

I’ve a place where the water is a prism of multiple shades of blue kissing ancient cliffside villages looking as they did hundreds of years ago. Narrow cobblestone streets lined by cafes, villas and authentic local restaurants. Churches older than most countries.

Then, imagine arriving at this Adriatic jewel via a luxurious, modern sailing ship with contemporary amenities and Michelin caliber chefs preparing decadent, fresh meals while port hopping. Think mega yacht meets small sailing ship.

I’ve just described a day in the week of a blissful experience aboard a Windstar sailing vessel going from Venice, around the boot stopping off at Capri, continuing to the Croatian ports of Split, Cotor, Rovinj, Montenegro and arriving in Venecia.

The pre-journey is magical unto itself…Roma. One of the five greatest cities of the world as it’s been for centuries. Once the center of the universe, today hub of culture, fashion, food, and of course history.

As a runner, how fortunate to pace myself through miles of piazzas, passing modern shopping alongside cathedrals and architecture dating back to the Renaissance. Jogging the grounds of the Vatican, stopping to read about the monuments around you or to hydrate with local gelato. Finish your run/bike ride at the Coloseseum. Give yourself at least two days to absorb the beauty of Roma.

Then, embark on your voyage from the Mediteranean’s port of Roma around Italy’s boot stopping off at Capri; then up the Aegean hopping the Croatian ports of Split, Cotor, Montenegro, and arriving a week later in Venecia…. Molto benne!

My ship of choice is Windstar’s Wind Surf, an elegant, modern five mast schooner. Think mega-yacht with all the amenities and a super attentive, professional crew…which far outnumber the 342 lucky guests. By the way, the Wind Surf has just completed a significant modernization!

I find walking the gangplank boarding a ship to be a sensation similar to the first turn on a roller coaster…. “Wow, am I really doing this” sort of feeling.

There are masts on this ship! And yes, the Wind Surf does actually cut its engines, raise its sails, and glide through the Med and Adriatic on its own power when the wind cooperates. There is an unfurling of the sails “ceremony” along with classical music accompanying the beautiful event.

During the 8 day voyage, it would take a lot to get me off this magnificent ship. Yet, each port towns’ historic elegance called out for exploration.

While cruise lines offer shore tours, I prefer exploring on my own. Running carefully along ancient cobblestone roads, and narrow pedestrian walkways. Occasionally, there are trail runs to the top of hills overlooking these centuries-old towns and the Dalmatian coast.

A benefit of a smaller ship is the ability to navigate into ports and fjords off-limits to larger vessels. Hence, appreciate the beauty of the narrow UNESCO site fjord near Kotor and the breathtaking medieval walls of Dubrovnik, also a UNESCO site difficult to reach on big ships.

The onboard experience was everything I’d hoped for and more. Delicious, fresh local food, spa treatments, full range of water sports, and a spacious, comfortable cabin which, the first thing you do waking up look at the take your breath away views.

Sailing the Windstar Wind Surf from Roma to Venecia is an experience I will always cherish. I hope you get to witness why!

Richard Shane

Founder and CEO The World’s Greatest Vacations