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Top Portland Sailing Trips

Portland Tall Ship Cruise on Casco Bay

What better way to see the delights of Portland than from the sea in one of the famous schooner tall ships. Join us for this …More

What better way to see the delights of Portland than from the sea in one of the famous schooner tall ships. Join us for this...

2 hours Free Cancellation
4.6 (242)
from
$101
Portland ME: Casco Bay Boat Tour w/ Island Yoga + Mimosas or Wine

This experience combines three things you rarely get in one outing: a small-group boat tour, yoga on a Casco Bay island, and a celebratory drink …More

This experience combines three things you rarely get in one outing: a small-group boat tour, yoga on a Casco Bay island, and a celebratory drink...

3 hours Free Cancellation
5.0 (2)
from
$185
Private Half Day Sailing Charter in Portland Maine

A half-day sailing charter offers a unique and personalized way to explore the stunning Maine coast. Departing from downtown Portland, this private experience aboard Sasa, …More

A half-day sailing charter offers a unique and personalized way to explore the stunning Maine coast. Departing from downtown Portland, this private experience aboard Sasa,...

4 hours Free Cancellation
5.0 (1)
from
$158
Portland Tall Ship Private Charter on Casco Bay

What better way to see the delights than in the style of a private charter for you and five friends or family members? Experience the …More

What better way to see the delights than in the style of a private charter for you and five friends or family members? Experience the...

2 hours Free Cancellation
from
$1,069

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