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under 20 ft

Cornish Shrimper

No matter what you do with this boat—coastal cruising, gunkholing, or racing—you’ll definitely turn heads while sailing though the harbor.

Beneteau First 20

Just shy of 21 feet, the Beneteau First 20 is the smallest boat in this builder’s lineup. But don’t let the size fool you. The

Marblehead 22 Daysailer

20 Best Small Sailboats for the Weekender

Whether you want to cruise to your next destination at a fast pace or are striving for a simple, easy to sail vessel, this fleet of trailerable sailboats and pocket cruisers will fit your needs and budget.

4-Pack of Vintage Pocket Cruisers

Four capable small boats remind us of the glory days when size didn’t matter and a fine sail didn’t require setting a record or crossing an ocean.

Cornish Shrimper

No matter what you do with this boat—coastal cruising, gunkholing, or racing—you’ll definitely turn heads while sailing though the harbor.

Beneteau First 20

Just shy of 21 feet, the Beneteau First 20 is the smallest boat in this builder’s lineup. But don’t let the size fool you. The

Marblehead 22 Daysailer

20 Best Small Sailboats for the Weekender

Whether you want to cruise to your next destination at a fast pace or are striving for a simple, easy to sail vessel, this fleet of trailerable sailboats and pocket cruisers will fit your needs and budget.

4-Pack of Vintage Pocket Cruisers

Four capable small boats remind us of the glory days when size didn’t matter and a fine sail didn’t require setting a record or crossing an ocean.

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