Schooner Captain Outdoors: Schooner Timberwind, Rockport, ME   Book This Career Mentorship   Watch the Video

Do you live for your weekends on the water? Do you have a favorite “Sail Away” song? Maybe the one by Enya, STYX, The Little River Band, Randy Newman, David Gray, Sister Hazel or Neil Young, who have all recorded title songs with dreams of sailing away in mind?

So many sailing and boating enthusiasts dream of throwing their day job overboard and living their life on the high seas. Does this sound like you? Then Bob Tassi, Captain of the Schooner Timberwind, is ready to mentor you in your dream job!

Bob worked for many years as a music producer in Nashville with artists such as Dolly Parton, DC Talk and Patty Loveless. But Bob’s true love was always sailing, and he took every opportunity to get on the water. In 1998 he quit his music career and moved his family to Maine to begin working aboard the Stephen Taber as a deckhand for a $125 per week. From deckhand, he got promoted to mate and then to Captain in the Maine Windjammer Fleet until he ultimately purchased the Timberwind. He created the Vocationing lifestyle of his dreams!

Bob’s whole family works on the schooner. His wife, Dawn, a nurse in her previous life, is the head chef. Their children, Emily and Will, entertain the other kids and swab the deck. Bob guides the Timberwind on her journeys, plotting and charting the course. In the evenings, he brings out his guitar or accordion to entertain his guests. In the schooner business you have to be both a great mariner and a wonderful host.

While on your VocationVacations® dream job holiday, Bob will mentor you in some or all of the following activities:

• Live and work aboard as a member of the crew
• Be involved in all aspects of operations while underway
• Haul anchor, sails, and tender boats
• Wash down, polish, coil and flemish all lines
• Galley prep and service
• Touch up paint as necessary
• Re-supply schooner during turn around, with wood water, food and ice
• Receive an overview of coastal navigation
• Learn about the schooner business from Captain Bob
• Q&A with Captain, cook and mate

The Schooner Captain VocationVacations® holiday includes:

• Three to six days of one-on-one mentorship in your dream job
• The opportunity to participate in a total of one hour of pre- and post-VocationVacation career coaching from an accredited, affiliated VocationVacations career coach
• A pocket-size VocationVacations journal so you can document your dream job becoming a reality
• Breakfast, lunches and dinners while on the Schooner Timberwind

Available: June through September, based on Mentor's availability with exception of holidays

Price: $1049 and up Per Person

Book This Career Mentorship

(The purchase of a 3, 4 or 6 night Schooner Timberwind sailing cruise is required, but not included in the price of your VocationVacations holiday. To book please click through to Schooner Timberwind.com)

Country Inn Maine	Trade Winds Inn
Other activities and tourist destinations while on your VocationVacations adventure: Maine Office of Tourism Rockport, Maine Maine's Mid Coast Full payment of the VocationVacations dream job holiday is required to make a reservation. A $100 non-refundable fee is assessed if a VocationVacations experience is cancelled or rescheduled prior to 14-days of the scheduled VocationVacations holiday, based on the approved availability of the mentor to reschedule. A VocationVacations adventure cannot be rescheduled and is non-refundable if cancelled within 14 days of the scheduled VocationVacations holiday. Written notification of cancellation or rescheduling is required in all cases. In the US, Grounded Nomads, LLC and VocationVacations holidays encourage all customers to acquire travel insurance to cover any unforeseen expenses due to cancellation or rescheduling. In the UK, Grounded Nomads, Ltd and VocationVacations holidays must require all customers to acquire travel insurance to cover any unforeseen expenses due to cancellation or rescheduling and provide verification of such travel insurance to Grounded Nomads, Ltd.