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  1. 15 Must-Try Outdoor Activities Cape Cod Has for Nature Lovers
  2. On the Rocks Cocktail Cruises

    On the Rocks Cocktail Cruises

    4.9 • 35 reviews
    Portland, ME

    Set sail with On the Rocks Cocktail Cruises for a relaxed spin through Portland’s postcard-perfect Casco Bay. At the helm is USCG-licensed Captain Jill Norwalk, whose lifetime on New England waters translates into easygoing expert...

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    Review summary

    4.9
    Excellent
    35 reviews•Google Maps
    28

    Book On the Rocks Cocktail Cruises

    Addon image

    Cruise Casco Bay on a Mimosa Charter From Portland

    1.5-hour Casco Bay mimosa cruise for up to 12 guests

    $788.64
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    Cruise Casco Bay at Sunset From Portland

    Relax on a Casco Bay sunset cruise with Portland views

    $73.14
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    Cruise Casco Bay on a Portland Happy Hour Charter

    Relax on a 1.5-hour Casco Bay happy hour cruise for up to 12 guests

    $62.54
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    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.

    What people are saying

    Review 1 of 5
    5/5

    Dale was so awesome! He made the trip so fun. We will definitely be back!!

    Photo of Nichole Brothers

    Nichole Brothers

    August 30, 2026

    Review 1 of 1
    5/5

    Dale was so awesome! He made the trip so fun. We will definitely be back!!

    Photo of Nichole Brothers

    Nichole Brothers

    August 30, 2026

    Addon image

    Cruise Casco Bay From Portland on a 1.5-Hour Charter

    Relax on a 1.5-hour Casco Bay cruise with views of Portland

    $674.16
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    Private Afternoon Cruise on Casco Bay

    Relax on a slow cruise for great views of Portland from the water

    $674.16