Naples Winter Wine Festival
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An ultimate one-of-a-kind custom songwriting experience with Troubadour 77 (Monty Powell and Anna Wilson)

If you have a song in your heart that’s yearning to come out, this lot is for you. Milestones is a unique service from Song Sessions (, facilitated by Billboard #1 and Grammy Award-winning singer/songwriters Monty Powell and Anna Wilson of Troubadour 77. 

An original song is the most powerful way to tell a story and capture memories, emotions, thoughts and wishes. With the help of Monty and Anna, you will create the ultimate “one-of-a-kind” gift to do just that. If you’ve never written a song before and have no idea how to go about it, they will guide you through every step of the process.

This experience can be done in person if you live in the Naples, FL area during the spring and fall seasons.  If you do not live in Naples, no worries: Anna and Monty can work to accomplish your milestone song virtually.

INSIDER’S INFOTo be scheduled for a mutually agreeable date. If winner lives in Naples, FL, session can be done in person (fall & spring sessions available). If winner lives out of state, songwriting experience will be completed virtually. Expires January 31, 2022.

DONORS: Anna Wilson & Monty Powell (Troubadour 77)