90-minute small-group cruises aboard Kismet — craft beverages, scenic views, and private charters for up to 12 guests.
A curated lineup of Afternoon, Sunset, Mimosa, Happy Hour, Midday and Custom Charter experiences around Casco Bay.
boat-charters · Portland
Discover Portland’s coastal beauty on a private afternoon cruise with On the Rocks Cocktail Cruises. Enjoy scenic views, craft cocktails, and a personalized experience tailored just for you.
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.
“Every outing is organized with local river knowledge, basic safety instruction, and equipment checks before departure.”
Cozy, intimate groups for every cruise
Relaxing 90-minute cruises through Casco Bay
Scenic harbor, islands, lighthouse views
Bachelorette, proposals, corporate events accommodated
Open the individual experience guide to confirm current availability, pricing, policies, conditions, and inclusions before booking.
The operator provides clear meeting points, departure times, and destination coordinates for all outings.
Personal flotation devices, emergency protocols, equipment checks, and paddling orientations are provided before departure.
Recommended layering, water shoes, sunscreen, and dry bags are detailed in each experience guide.
Guides share rich knowledge of regional flora, fauna, scenic landmarks, and river navigation.
A glimpse into the experiences, natural landscapes, and adventures waiting on your next trip.
Images supplied on the current On the Rocks Cocktail Cruises listing.
On the Rocks Cocktail Cruises offers a variety of guided outdoor excursions, scenic routes, rentals, and custom itineraries tailored for families, couples, and adventure enthusiasts.
Yes. Most trips feature comprehensive safety orientations, equipment fittings, and calm routes suited for first-time adventurers. Check the details on individual experience guides for specific age and skill requirements.
Standard safety equipment (such as certified life vests and essential gear) is supplied for each booking. Detailed checklists regarding weather-appropriate attire and personal items are provided prior to departure.
Reserve a 90-minute cruise or design a private charter for proposals, bachelorettes, and corporate outings — limited to 12 guests.
Booze Cruise · Portland
Discover the beauty of Portland, Maine with a private Mimosa Cruise that combines scenic views, refreshing drinks, and intimate moments. Perfect for celebrations or peaceful escapes, this boat tour offers a truly special experience on the water.
water-activities · Portland
Discover stunning views and memorable moments on a private Portland Sunset Cruise with On the Rocks Cocktail Cruises. Perfect for romantic evenings, celebrations, or relaxing escapes, this boat tour offers a unique perspective of Maine’s beautiful coastline at sunset.
boat-charters · Portland
Set sail on a private, custom charter boat tour in Portland, Maine with On the Rocks Cocktail Cruises. Perfect for celebrations and corporate events, each cruise is uniquely tailored to you.
boat-charters · Portland
Set sail on a scenic 90-minute Happy Hour Cruise in Portland, Maine, enjoying craft beverages and stunning views of Casco Bay in an intimate setting. Perfect for relaxing and soaking in coastal beauty.
boat-charters · Portland
Discover Portland’s coastline with a 90-minute Midday Cruise aboard On the Rocks Cocktail Cruises. Small-group seating and craft beverages combine for an unmatched maritime experience in Casco Bay.
Click into any experience card above to view current dates, live availability, transparent pricing, cancellation policies, and booking details.