Often when we think of the most beautiful and exciting places to sail, we imagine the Caribbean or the Mediterranean. And it’s true, both of these destinations offer so many islands and beautiful coastlines you’d be hard-pressed to say anything negative about them. But, there are many beautiful sailing grounds that can easily go overlooked; one of these is North America.

LateSail’s got you covered for some of the best sailing in the region, with charters for the Northwest, East Coast and of course sunny Florida.

Sail Chesapeake Bay for wonderfully protected waters and other advantages including good anchorages and a forgiving bottom. The towns and villages in this region are truly a joy to discover. Annapolis is the largest metropolis, but you can also experience the charm of the smaller places that have made the New England region so famous.



The bay is over 200 miles along, and is known for its fishing industry. This benefits boaters in one of the most important ways of all: great food! Sample the freshest lobster, crab, oysters and other fresh seafood prepared New England-style. There’s also great sailing culture along the bay, meaning it’s easy to meet locals and get help if you need it.

If you’ve dreamed of sailing in Florida, you can cruise through the keys on the southwest side of the state. It’s an easy journey and you’ll be able to enjoy the gorgeous tropical climate of the Caribbean. There are also coral reefs and great marina facilities.



Heading back up north, we have excellent options for sailing near Vancouver, Canada. This area’s vast majestic beauty is sure to make a deep impression, and opportunities for hiking, swimming and many other activities. Discover dramatic waterfalls and bring your binoculars to spot an abundance of wildlife including whales, eagles and deer.



Airports for these destinations are easy to access, and you’ll find friendly helpful tour operators to help you get going. Call us to find out more about sailing in North America.

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