Our hotel concierge connected us (my fiancé and me) with Craig for an island tour, and it was really the highlight of a wonderful weekend. Craig is a wealth of knowledge about Martha's Vineyard, with great stories of the island's history, celebrity guests, and his own adventures. He's friendly, easy to talk to, and a delight to listen to. Prior to taking off, Craig made a point to get to know us, how long we'd been in town, what we'd already done, and then gave an overview of where he planned to take us.
A fun bonus is Craig's professional photography background; he took photos of us at each stop on the tour (a welcome treat after many selfie attempts earlier in our trip). We were at Lucy Vincent Beach right around golden hour and got some amazing pictures.
In a tour full of great moments, Craig saves the best for last with a beach picnic and bottle of wine in Menemsha. The food (Menemsha Fish Market), view, and conversation with Craig made for a perfect cap on the experience. Along the way we noticed several locals chatted amiably with Craig, which underscored how well-liked he is around the island. His enthusiasm for Martha's Vineyard is contagious - we left the tour already talking about a next trip back.