Sip Casco Bay: Intimate Cocktail Cruises in Portland
90-minute small-group cruises aboard Kismet — craft beverages, scenic views, and private charters for up to 12 guests.
Featured Cruises & Charters
A curated lineup of Afternoon, Sunset, Mimosa, Happy Hour, Midday and Custom Charter experiences around Casco Bay.
About On the Rocks Cocktail Cruises
On the Rocks Cocktail Cruises offers intimate cocktail cruises around Portland's Casco Bay aboard Kismet. Specializing in small-group experiences, the company runs 90-minute Afternoon, Sunset, Mimosa, Happy Hour, Midday and custom charter cruises with a maximum of 12 guests per trip. Guests enjoy Maine’s craft beverages while taking in harbor skylines, lighthouses, and islands visible from the water.
Each cruise is designed for comfort, safety, and a relaxed social atmosphere. Skilled crew members maintain the vessel, provide local knowledge, and ensure a smooth, professional trip from boarding to disembarkation. On the Rocks encourages guests to bring preferred snacks and beverages to personalize the outing; the operation supplies glassware and optional mixers upon request.
On the Rocks accommodates private events such as bachelorette parties, proposals, and corporate outings through customizable charters. Custom Charter bookings include route flexibility, tailored timing, and onboard arrangements to match event needs. All trips follow local regulations and safety standards; life jackets and safety briefings are provided on every departure.
The company prioritizes clear communication, easy booking, and transparent pricing. Online scheduling shows available departures and guest limits, and staff confirm details before each cruise. Reviews highlight scenic views, attentive service, and memorable moments on the water. On the Rocks Cocktail Cruises is an ideal choice for small groups seeking a distinctive maritime experience in Portland with professional operation and a focus on local craft beverages. Seasonal routes showcase nearby islands like Peaks and Great Diamond; photographers and nature lovers frequently note wildlife sightings at golden-hour tide.
Book a Seat or Charter Kismet Today
Reserve a 90-minute cruise or design a private charter for proposals, bachelorettes, and corporate outings — limited to 12 guests.