Relax on a 1.5-hour Casco Bay happy hour cruise for up to 12 guests
1 Hour 30 Minutes
Up to 12 people
Bottled water, cooler onboard
Enjoy Portland views from the water on a 1 hour 30 minute happy hour cruise on Casco Bay. Relax onboard and purchase drinks from the cooler as you cruise.
There is no bathroom onboard the boat. All ages are welcome. Your credit card will remain on file and may be used for alcohol purchases, time overages, excessive cleaning, or damaged property.
Cancel 7 days in advance for a refund, minus any applicable service fees. If canceled due to weather, the trip will be rescheduled at your convenience or refunded. The captain may cancel at their discretion due to weather or unforeseen events.
No. There is no bathroom onboard the boat.
Bring your ID if you plan to purchase beer, wine, or cocktails onboard. You can also bring snacks and soft drinks, plus layers and sunscreen.
You get complimentary bottled water. Craft beer, wine, and canned cocktails are available for purchase from the onboard cooler.
72 Commercial St, Portland, ME US 04101
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