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Skip to main content
Adventure Collective Logo
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The Adventure Collective

The Adventure Collective Discover, plan, and share your outdoor adventures with our global community of explorers.

Add as a preferred

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Explore Adventures

  • All Adventures
  • Boat Charters
  • Water Activities
  • Fishing
  • Land Adventures
  • Motorized Land
  • Winter Sports

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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.

  1. Adventure Tour Operators
  2. On the Rocks Cocktail Cruises

Featured Cruises & Charters

A curated lineup of Afternoon, Sunset, Mimosa, Happy Hour, Midday and Custom Charter experiences around Casco Bay.

Afternoon Cruise
Portland

Afternoon Cruise

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.

Afternoon Cruise

Afternoon Cruise

boat charters
water activities
Portland, Maine
Mimosa Cruise
Portland

Mimosa Cruise

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.

Mimosa Cruise

Mimosa Cruise

Sunset Cruise
Portland

Sunset Cruise

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.

Sunset Cruise

Sunset Cruise

water activities
Custom Charter Boat Tours in Portland, Maine
Portland

Custom Charter Boat Tours in Portland, Maine

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.

Custom Charter Boat Tours in Portland, Maine

Custom Charter Boat Tours in Portland, Maine

boat charters
Relaxing Happy Hour Cruise in Portland, Maine
Portland

Relaxing Happy Hour Cruise in Portland, Maine

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.

Relaxing Happy Hour Cruise in Portland, Maine

Relaxing Happy Hour Cruise in Portland, Maine

boat charters
Casco Bay Midday Cruise with On the Rocks Cocktail Cruises
Portland

Casco Bay Midday Cruise with On the Rocks Cocktail Cruises

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.

Casco Bay Midday Cruise with On the Rocks Cocktail Cruises

Casco Bay Midday Cruise with On the Rocks Cocktail Cruises

boat charters

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.

On the Rocks Cocktail Cruises fleet
On the Rocks Cocktail Cruises team

On the Rocks Cocktail Cruises Casco Bay Cocktail Cruises

Experience Portland from the water with intimate, 90-minute cruises that highlight Casco Bay scenery, lighthouses, islands, and the city skyline. On the Rocks Cocktail Cruises runs Afternoon, Sunset, Mimosa, Happy Hour, Midday and customizable Private Charter experiences for groups up to 12 guests. These small-group cruises focus on comfort, local craft beverages, scenic photography, and relaxed social time aboard Kismet. Guests are encouraged to bring snacks and favorite drinks; glassware and mixers are available on request.

Why choose these Portland cocktail cruises?

  • Stunning waterfront views of Casco Bay, iconic lighthouses, and islands.
  • Small private groups max 12 for intimate, social experiences.
  • Flexible bookings and customizable charters for events like proposals, bachelorettes, and corporate outings.
  • Professional crew, safety briefings, and adherence to local maritime regulations.

Popular trips include a Sunset Cruise timed for golden-hour views, an Afternoon Cruise for relaxed daytime sightseeing, a Mimosa Cruise ideal for celebrations, and a Happy Hour Cruise focused on socializing with craft beverages. Custom Charter bookings let groups choose routes, timing, and onboard arrangements to match event goals, making the vessel a private venue for memorable moments. Safety and comfort are core priorities; life jackets, pre-departure briefings, and attentive crew support every trip.

Booking and planning

Reservations are available online with clear schedules, capacity limits, and pricing. Confirmation communications help coordinate arrivals and special requests. Ideal for tourists, locals, photographers, couples, and small groups, On the Rocks Cocktail Cruises delivers a distinctive Portland maritime experience centered on socializing and scenic discovery.

Keywords covered: Portland cocktail cruises, Casco Bay cruises, sunset cruise, mimosa cruise, private charter, happy hour cruise. These targeted keywords help guests find the right cruise for celebrations, photo sessions, proposals, and relaxed outings on Casco Bay.

Plan tips:

  • Arrive early for boarding and optimal seating for photos.
  • Bring snacks, a light cooler, and preferred drinks.
  • Check weather and sunset time for best lighting.
  • Communicate special requests in advance for custom charters.

Detailed trip descriptions

Afternoon Cruise: A relaxed 90-minute daytime route showcasing harbor islands, city views, and lighthouse panoramas—ideal for sightseeing and daytime photography.

Sunset Cruise: Timed to catch golden-hour light, this 90-minute outing emphasizes dramatic skies, reflective water, and romantic vistas perfect for couples and photographers.

Mimosa Cruise: A celebratory option for groups that want brunch-style vibes afloat; sparkling wine, lively conversation, and bright daylight views set the tone.

Happy Hour Cruise: A later-afternoon social cruise with craft beverages and relaxed atmosphere, designed for friends and colleagues winding down after a day.

Midday Cruise: Gentle pacing through calm waters, midday light, and easy conversation—great for families and mixed-age groups seeking a peaceful outing.

Custom Charter: Fully customizable for proposals, bachelorette parties, photo shoots, corporate events, and private celebrations. Routes, timing, and onboard details adapt to group needs.

What to bring

Pack layers, sun protection, a light jacket, camera gear, and any personal snacks or beverages. Small coolers and reusable containers are recommended.

Photography tips

Choose forward seating for unobstructed views, shoot during golden hour for the best light, and stabilize the camera for moving-boat conditions.

Accessibility & policies

The vessel supports calm-boarding protocols; guests with mobility concerns should contact the operator before booking to discuss assistance and arrangements.

Contact for availability, weather updates, and private charter inquiries today online.

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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.

Portland, Maine
Portland, Maine
water activities
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Portland, Maine
water activities
Portland, Maine
water activities
Portland, Maine

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