In the coldest hour of the night, when even the gentlest north wind seems to have the power to penetrate every layer of clothing donned to protect against its insidious invasion the eye, attuned to minute alterations of light and shade after hours of night watch, becomes aware of a grey smudge on the eastern Read More …

The chilly crew of the When and If set sail from Cape Charles, VA this week and will be back in Key West before Thanksgiving – then we’ll be ready to take you out!

We’re laying up in Cape Charles, VA for a couple of weeks before we start our passage South…It’s going to be Christmas in the Keys so book your flight down to Key West and come join the party! When and If will be running private charters, daysails, and sunset sails and is also available for Read More …

We’ve had an amazing couple of weeks at the Newport Classics Regatta, New London Maritime Festival which involved an epic neck-and-neck with the brand spanking new schooner Columbia, a beautiful dockside cocktail party at Watch Hill Yacht Club and a fashion photoshoot at Sag Harbor, NY. Now we’re heading down to Philly to finish up Read More …

  We’re full steam ahead at Martha’s Vineyard from the 27th August till the 1st September – have a look at our schedule here or call 305 587 3915 about your private event on board!

Back for some of that frisky Hyannis sailing – come along for 3 hour daysails and sunset sails most days the next couple of weeks! Here’s our schedule for you!  

When and If is back at her adopted home in Vineyard Haven until the 2nd of August, running 4 hour Light Luncheon Daysails and Cheese Platter Sunset Sails for $79/head. We’re thrilled to be back and hope to see you here, book online come and join us for a beautiful sail! Take a turn at Read More …

We had a gorgeous Summer Sunset sail with Al from the Barnstable Patriot – take a look at his article and photos here!         Photos by kind permission of Alan Belanich

Hi everyone! We’ve just rocked up in beautiful Hyannis after an awesome tall ships festival in Philadelphia – we’re on the cape all summer long running charters and daysails every day so come by and say hi, give us a call and let’s get out in that sunshine!  

Check out our Summer 2015 logo – T shirts coming soon!   [powr-social-media-icons label=”Enter a Label”]

And foremast done! [powr-social-media-icons label=”Enter a Label”]

Mainmast in… [powr-social-media-icons label=”Enter a Label”]

Bringing her down the Hudson from Waterford to Albany to step the masts – keep checking for more video of our prep for a great season! [powr-social-media-icons label=”Enter a Label”]