The Gloucester Schooner Festival is a North Shore tradition. Sept. 2nd-5th.
Located on historic Cape Ann, North of Boston, there are innumerable
cruising venues. Of course you can join in the racing too.
The Florida Keys are a great cruising ground - know the rules - get the local knowledge - meet the local sailors - eat the local cuisine - and have fun.
Small boats are challenging for weeking cruising - because of low speed it's not easy to cover miles. An alternative - a micro multihull to expand your range.
Thinking outside the box - some really exciting creations find their way into the Everglades Challenge. A hard thing for biased multihull sailors - to think there's an alternative is abhorrent! Be abhorred...