Watch Sailing & Boating Adventures Around the World
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Autopilot Failure at Sea PART 1 (Calico Skies Sailing Ep. 26)
In this episode we take you with us on our planned 12 day offshore sailing passage from the Bahamas, headed north. We begin by sailing off anchor and face calm conditions initially, though soon afterwards strong winds have us reefing down the mainsail. As we navigate the gulf stream we spend time co...
Offshore Passage Planning for our Sailboat (Calico Skies Sailing Ep. 25)
When you take big jumps offshore as opposed to a couple of nights here and there, overall travel time is reduced but preparing for the passage takes longer. To prepare for our planned 10 - 12 day sail north we’ll need to provision, get fuel, prepare meals, check the rig, research immigration policy ...
2018 Atlantic-Crossing Announcement
Ahoy crew! We’ve been saving this fun announcement for you. Many followers have asked our cruising plans this winter, and it’s likely not at all what you would have guessed. We’re going to complete our first Atlantic Circle! I mean ... life is very full for me and Phillip at HaveWind! We will b...
How to Provision & Prepare Your sailboat for Passage – Sailing to BERMUDA #1
After one year of living aboard our boat in a marina the time had finally come to take our sailboat, Britican, back out to sea. The plan was Charleston, SC to Bermuda, a five day sail. Read the full story about our preparations and the journey here: To see future videos, please subscribe to my ch...
#95: Historic Havana: Sail There with Me!
Mojitos at La Bodeguita del Medio, walk historic Cathedral Square, tour Hemingway's house, Finca Viega, dance at the Floradita and see inside the Casa Particular we rented for $40 CUCs/night. We take you all through Havana in this video with some very exciting news at the end. I'm going ...
#94: Clearing Customs and Exploring Cuba
Want to know exactly what it feels like to go through the customs process after sailing to Cuba? Come along. We'll walk you through. Show you exactly who boarded and what they wanted to know. We've included a lot of great tips in here for you as well to make the check-in process easy i...
#86: How to Provision & Prepare Your Boat for Passage
Provisioning for passage. Stowing goods on the boat (according to weight). Power conservation while underway. Watch schedules. Sleep arrangements. You name it. A ton of good, hopefully helpful info for you all while Phillip and I are preparing our boat to shove off for Cuba in just SEVEN days....
Gift #4: Sail with Us to the Miami Boat Show!
Very exciting video for you here guys. Our 4th Gift of Cruising will be a five-day offshore adventure sail from Pensacola to Miami with Phillip and I on s/v Libra to attend the Miami Boat Show, boat show tickets included. Super cool, right? We will depart February 10th and sail to the show. I wi...
Boat #12: 2013 Leopard 48 (Offshore Tour!)
Hey Crew! My first ever offshore boat tour! This was such a spur-of-the-moment, whirl-wind and might I say WINDY fun trip. I got invited last minute to join a yacht delivery crew taking this very nice 2013 Leopard 48 from Pensacola to Naples, FL. It was a fortuitous union of talents, good sailin...
Gift #3: Offshore with Andy Schell
Who wants to go offshore? If you said yes, then get on board with our 3rd Gift of Cruising -- an incredible offshore voyage giveaway with Andy Schell and Mia Karlsson at Here's the deal. Since this is SUCH a big gift, Phillip and I need your help. First, watch the video (particularly Andy&...
OFFICIAL TRAILER: “Trans-At on a Fast Cat”
At that's exactly what we do: Ride the wind and travel! This time, to France! Phillip and I recently completed our first trans-Atlantic passage crewing aboard a 46' catamaran and sailing 4,600 nautical miles across the Atlantic Ocean from Florida to France. It was an incredible adventu...
#76: How to Cross Oceans (My Trans-At Movie Trailer)
What do you need to cross an ocean? A level-head, an adventurous spirit and a sense of humor! Exciting news guys! I have completed the complete, 90+ minute movie from mine and Phillip's first trans-Atlantic this past June when we crewed aboard a 46' catamaran from Florida to France. It...
10. Exploring Tortola aboard Bella Luna (Swan 48 Sailboat)
After 10 days at sea aboard Bella Luna, Drake and Monique spend a couple of days exploring Tortola.