Expert Yacht Charter Advice ▪ Every Destination ▪ Every Option

At Sail Connections, you're not simply booking a yacht. You're drawing on the knowledge of experienced sailors who have spent lifetimes cruising both New Zealand waters and the world's leading charter destinations.

For more than 35 years we've been helping clients choose the right yacht, destination and operator through independent, personalised advice. We take the time to understand your sailing experience, holiday plans and expectations before recommending the charter options best suited to your needs.

Our clients return year after year because they value having a trusted, independent adviser who makes planning a sailing holiday easier, more enjoyable and more rewarding—all at no extra cost.

Independent Advice from Experienced Sailors

Sail Connections is led by Robert Cross, a lifelong sailor and yacht charter consultant with hands-on experience as a skipper, offshore sailor, boat owner and charter specialist. Together with a team of seasoned sailors, Robert helps clients choose the right yacht, destination and operator — not just the first available boat in a booking system.

Meet Robert

When you talk to Sail Connections, you'll be drawing on the knowledge of Robert Cross, a lifelong sailor and one of New Zealand's most experienced independent yacht charter consultants.

Robert has sailed since childhood, skippered charter yachts in the Greek Islands, completed offshore passages, raced yachts, built his own yacht, and spent decades exploring the world's leading charter destinations and working alongside trusted charter operators. Since buying the Sail Connections business 16 years ago, he has helped sailors of every experience level choose the right yacht, destination and operator for unforgettable sailing holidays.

Robert's goal is simple: to share practical, independent advice that gives you the confidence to make the right charter decisions and enjoy the very best sailing holiday possible.