Set sail with On the Rocks Cocktail Cruises for a relaxed spin through Portland’s postcard-perfect Casco Bay. At the helm is USCG-licensed Captain Jill Norwalk, whose lifetime on New England waters translates into easygoing expert...
Sunset cruises on Casco Bay with Captain Vinny, Jill, Dale, and the rest of the crew have earned a serious reputation for delivering memorable evenings on the water. The boat holds just 12 people, which keeps things intimate and personal rather than feeling like a crowded tour. Captains come prepared with local history, fun facts, and a solid knowledge of where to find the best sights, including lighthouses, seals, and osprey. Drinks are a genuine highlight, with an impressive selection of local options that guests consistently rave about. Owner Jill is frequently praised for her communication and responsiveness when booking, and the crew overall gets high marks for being warm and hospitable. Private charters seem particularly popular for special occasions like bachelorette parties, and guests have even brought food on board to make a full evening of it. The no BYOB policy is worth knowing ahead of time, but reviewers note the onboard selection more than makes up for it.
We thoroughly enjoy working with the team at On the Rocks! We've worked with Captains Jill & Dale on multiple charters and it has been fantastic each time! They keep it easy - with drinks for sale for your trip, cold ice and a speaker on board!
Alicia Gaiero
June 22, 2026
We thoroughly enjoy working with the team at On the Rocks! We've worked with Captains Jill & Dale on multiple charters and it has been fantastic each time! They keep it easy - with drinks for sale for your trip, cold ice and a speaker on board!
Alicia Gaiero
June 22, 2026