A Musical Sailing Adventure

Set sail with Tim on an unforgettable private charter experience blending epic cruising, original music, island exploration, and lifelong memories. Tim’s love of sailing and songwriting come together on these voyages that put you at the center of the experience. Where do you want to go?

About Sailing With Tim

Whether you’re a seasoned sailor or new to cruising yachts, this is more than a charter — it’s an adventure shaped by your dreams. Sail from one stunning anchorage to the next with Tim at the helm, sharing songs, stories, and sunsets that only a sailing vessel can deliver. From Caribbean beach bars to serene South Pacific lagoons, from ancient Mediterranean villages to isolated Baja islands, this journey becomes yours.

Why Sail With Tim?

Besides getting him to play your favorite songs from his vast catalogue, you get the benefit of seeing the places that inspire him through his eyes. He has 8 years of bareboat skippering experience on over 30 different boats in 7 countries.

Tim holds the following certificates:

• United States Coast Guard 25 Ton Master

• American Sailing Association 114 Bareboat Skipper and Certificate of Proficiency For Navigating in International Waters

• NauticEd Bareboat Charter Master

• National Outdoor Leadership School Wilderness First Responder

Start the Conversation

Availability is limited and charters are planned well in advance in the interest of securing the perfect vessel from the perfect point of departure. It is sometimes possible to include other musicians on the trip. Fill out the form and Tim will get in touch!