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    1. Local experiences/
    2. All experiences/
    3. Water Activities/
    4. Sailing

    Best results for Sailing in Portland, ME

    Showing 1-16 of 16 results
    Sail Saco Bay on a 4-Hour Cruise
    Sailing

    Sail Saco Bay on a 4-Hour Cruise

    Sail longer and see more of Saco Bay on a half-day trip

    Sail longer and see more of Saco Bay on a half-day trip
    5.0 • 376 reviews
    $256/ person
    Sail a 2-Hour Sunset Cruise in Kennebunkport
    Sailing

    Sail a 2-Hour Sunset Cruise in Kennebunkport

    Sail into the evening with a small-group sunset cruise

    Sail into the evening with a small-group sunset cruise
    5.0 • 376 reviews
    $138/ person
    Cruise the Saco River & Saco Bay on a 2-Hour Sail
    Sailing

    Cruise the Saco River & Saco Bay on a 2-Hour Sail

    Sail Maine’s coast in a small group of 6 or fewer

    Sail Maine’s coast in a small group of 6 or fewer
    5.0 • 376 reviews
    $127/ person
    Sail on a Private 2-Hour Charter in Maine
    Sailing

    Sail on a Private 2-Hour Charter in Maine

    Reserve a private sail for up to 6 on the Saco River and Saco Bay

    Reserve a private sail for up to 6 on the Saco River and Saco Bay
    5.0 • 376 reviews
    $694& up
    4-Hour Sunset Sailing Cruise in Kennebunkport
    Sailing

    4-Hour Sunset Sailing Cruise in Kennebunkport

    Sail for 4 hours at sunset with room to spread out

    Sail for 4 hours at sunset with room to spread out
    5.0 • 376 reviews
    $299/ person
    Take a Private 2-Hour Sailing Lesson in Maine
    Sailing

    Take a Private 2-Hour Sailing Lesson in Maine

    Private sailing lesson for up to 6 with a customized focus

    Private sailing lesson for up to 6 with a customized focus
    5.0 • 376 reviews
    $801& up
    3-Hour Private Sail in Kennebunkport
    Sailing

    3-Hour Private Sail in Kennebunkport

    Charter your own sailboat for up to 6 on the Saco River and Saco Bay

    Charter your own sailboat for up to 6 on the Saco River and Saco Bay
    5.0 • 376 reviews
    $941& up
    3-Hour Guided Sailing Cruise in Kennebunkport
    Sailing

    3-Hour Guided Sailing Cruise in Kennebunkport

    Sail the Saco River and Saco Bay in a small group

    Sail the Saco River and Saco Bay in a small group
    5.0 • 376 reviews
    $192/ person
    Private 2-Hour Sunset Sailing Charter in Kennebunkport
    Sailing

    Private 2-Hour Sunset Sailing Charter in Kennebunkport

    Reserve a private 2-hour sunset sail for up to 6 guests

    Reserve a private 2-hour sunset sail for up to 6 guests
    5.0 • 376 reviews
    $801& up
    4-Hour Private Sailing Lesson in Kennebunkport
    Sailing

    4-Hour Private Sailing Lesson in Kennebunkport

    Learn to sail with a private instructor on a 42-foot boat

    Learn to sail with a private instructor on a 42-foot boat
    5.0 • 376 reviews
    $1,279& up
    6-Hour Private Sailing Charter in Kennebunkport
    Sailing

    6-Hour Private Sailing Charter in Kennebunkport

    Sail for 6 hours with your private group of up to 6

    Sail for 6 hours with your private group of up to 6
    5.0 • 376 reviews
    $1,921& up
    Private 4-Hour Sailing Charter in Kennebunkport
    Sailing

    Private 4-Hour Sailing Charter in Kennebunkport

    Sail Saco Bay for 4 hours with your private group of up to 6

    Sail Saco Bay for 4 hours with your private group of up to 6
    5.0 • 376 reviews
    $1,172& up
    Sail a 4-Hour Private Sunset Cruise in Kennebunkport
    Sailing

    Sail a 4-Hour Private Sunset Cruise in Kennebunkport

    Extend your private sunset sail to 4 hours, with space for up to 6 guests

    Extend your private sunset sail to 4 hours, with space for up to 6 guests
    5.0 • 376 reviews
    $1,493& up
    Wednesday Night Sunset Cruise With Live Music
    Portland

    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 • 132 reviews
    $53/ person
    Sail to Wood Island Lighthouse Tour From Kennebunkport
    Sailing

    Sail to Wood Island Lighthouse Tour From Kennebunkport

    Sail to Wood Island and tour inside the lighthouse and keeper’s house

    Sail to Wood Island and tour inside the lighthouse and keeper’s house
    5.0 • 376 reviews
    $395/ person
    Sail to Wood Island Lighthouse Private Tour in Maine
    Sailing

    Sail to Wood Island Lighthouse Private Tour in Maine

    Sail to Wood Island and tour inside the lighthouse and keeper’s house

    Sail to Wood Island and tour inside the lighthouse and keeper’s house
    5.0 • 376 reviews
    $1,707& up