Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    1. Local experiences
    2. /Things to do in Portland…
    3. /Water Activities
    4. /Yacht Charters
    5. /Private Motoryacht Cruise in Portland
    Why travelers choose Greetwell

    Curated by our team

    Every experience is hand selected and approved by Greetwell.

    Personal concierge

    Real humans available to help before, during, and after your booking.

    Intimate & authentic

    Including unique in-home experiences you won't find anywhere else.

    Easy booking & cancellation

    Reserve in minutes with free cancellation on most experiences.

    Greetwell

    Experiences that stay with you long after the trip

    Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

    About

    • Our Story
    • For Experience Providers
    • For Hospitality Partners
    • For Developers

    Resources

    • Travel Guides
    • Help Center
    [email protected]1-877-GREET-WELL

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Product image 1
    Product image 2
    Product image 3
    Product image 4
    Gallery image
    Gallery image 2
    Gallery image 3
    Gallery image 4

    Private Motoryacht Cruise in Portland

    Cruise Maine's coast aboard the classic Calista Ann

    5.0 stars• 151 reviews

    Duration

    2 hours

    Ideal For

    Up to 12 people

    Includes

    Private boat, captain, crew

    Highlights

    Set out on the classic motor yacht Calista Ann for a private cruise along Maine's coastline. Coast Guard-certified professional captains and crew share local knowledge as you take in the bay.

    • Explore historic forts and picturesque lighthouses
    • Look for local wildlife such as seals and porpoises
    • Discover the area's history and the bay's significance
    • Take in views of the Maine coastline from the water

    Important details

    • Bring your own food, beverages, and water
    • Apply sunscreen and wear a hat and sunglasses for sun protection
    • Expect a customary 20% crew gratuity, not included in the listed price
    Split the cost with your group

    This booking is for the whole experience, which fits up to 12 guests.

    From$61per person
    Split with

    Cancellation Policy

    Trips run rain or shine. Cancel at least one week before your scheduled reservation for a refund. No refunds for cancellations less than one week before departure or for missed reservations. Full refund if the captain determines conditions are unsafe at the time of the sail.

    Product ID: K23FTQ

    FAQs

    Bring your own food, beverages, and water. Beer and wine are welcome aboard.

    Use the public restrooms in the Ocean Gateway Terminal or the restroom onboard.

    Experience provided by Sail Portland

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text 1-877-GREET-WELL

    Report an issue

    Calista Ann Private Charter

    from $742

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Nearby activities

    Portland Harbor Dinner Cruise with Oysters & Drinks
    Dinner Cruises

    Portland Harbor Dinner Cruise with Oysters & Drinks

    Sip local beer and wine and savor fresh Maine oysters during a scenic two-hour harbor cruise.

    Sip local beer and wine and savor fresh Maine oysters during a scenic two-hour harbor cruise.
    4.9 • 144 reviews
    $101/ person
    Wednesday Night Sunset Cruise With Live Music
    Sailing

    Wednesday Night Sunset Cruise With Live Music

    Sail Casco Bay at sunset with live music and a BYOB vibe

    Sail Casco Bay at sunset with live music and a BYOB vibe
    4.9 • 144 reviews
    $48/ person
    Sunset Cruise in Portland, Maine
    Boat Tours

    Sunset Cruise in Portland, Maine

    Cruise Casco Bay at sunset past lighthouses, forts, and islands

    Cruise Casco Bay at sunset past lighthouses, forts, and islands
    4.9 • 144 reviews
    $37/ person
    Scenic Cruise on Casco Bay From Portland
    Boat Tours

    Scenic Cruise on Casco Bay From Portland

    Cruise Casco Bay on the Joseph S. Kennedy with optional lobster roll add-ons

    Cruise Casco Bay on the Joseph S. Kennedy with optional lobster roll add-ons
    4.9 • 144 reviews
    $27/ person
    Private Afternoon Cruise on Casco Bay
    Private Boat ToursUp to 12

    Private Afternoon Cruise on Casco Bay

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

    Relax on a slow cruise for great views of Portland from the water
    4.9 • 31 reviews
    $674
    Cruise Casco Bay From Portland on a 1.5-Hour Charter
    Boat Tours

    Cruise Casco Bay From Portland on a 1.5-Hour Charter

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

    Relax on a 1.5-hour Casco Bay cruise with views of Portland
    4.9 • 31 reviews
    $674