


Relax on a slow cruise for great views of Portland from the water
1 Hour 30 Minutes
Up to 12 people
Bottled water
Relax on an afternoon cruise and take in Portland views from the water as you glide across Casco Bay. This slow-paced outing is ideal for an easy, scenic break.
Maximum of 12 guests per charter. There is no bathroom onboard the boat. Alcohol is available for purchase and you will need ID for purchases. A valid credit card must be presented at check-in and will remain on file. It may be used for incidental charges, including alcohol purchases, time overages, excessive cleaning, or damages to the property. Gratuity is included in the total price.
Cancellations seven days in advance will be refunded at no cost, minus any applicable service fees. If a trip is 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.
Please arrive 15+ minutes before departure and allow ample time for parking. If you are late, time cannot be added to the end of your cruise.
No. There is no bathroom onboard the boat.
There is a cooler onboard stocked with craft beer, wine, and canned cocktails for purchase. You will need ID for alcohol purchases.
Maine Wharf, 72 Commercial St, Portland, ME 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
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