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.
More ways to explore the area's outdoor wonders
Hang tight — photos are loading
This usually takes just a second.
Difficulty
easy
Duration
2–4 hours
Fitness Level
No special fitness level required; this experience is relaxed and suitable for all ages.
Wildlife
History
Portland's harbor has been a key maritime hub since the 18th century, influencing regional trade and culture.
Conservation
Efforts in Portland focus on preserving water quality and protecting marine habitats to ensure sustainable tourism.
On the Rocks Cocktail Cruises
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.
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.
Max Guests
12
Cozy, intimate groups for every cruise
Trip Length
90 minutes
Relaxing 90-minute cruises through Casco Bay
Routes
Casco Bay
Scenic harbor, islands, lighthouse views
Private Charters
Customizable
Bachelorette, proposals, corporate events accommodated
Reserve a 90-minute cruise or design a private charter for proposals, bachelorettes, and corporate outings — limited to 12 guests.
Dress in layers
Coastal weather can shift quickly, so bring layers to stay comfortable on deck.
Bring seasickness remedies
If you're prone to motion sickness, pack or take remedies before boarding.
Book early for peak seasons
Popular dates fill fast; reserve your custom charter well in advance.
Respect crew guidelines
Follow all safety instructions and crew requests for a smooth, enjoyable cruise.
Windbreaker Jacket
Protects against spring coastal winds and sudden drizzle.
spring
Sunscreen
Important to prevent sunburn during long daylight cruising.
summer
Warm Hat
Keeps you warm as temperatures drop during fall evenings on the water.
fall
Gloves
Helpful for keeping hands warm during cold-weather cruises.
winter