We used to have a Pearson 26 back in the mid 70's and sailed it from Western CT up to Martha's Vinyard, Block Island, Shelter Island etc... It is a very responsive sailor and can handle rough whether but also can be a rough ride in the LI Sounds steepish chop. The Sea Dog II Held family of 5 comfortably enough for weekend and week long cruising and did OK round the buoys as well.
I would consider a boat of that size but would prefer to have an inboard...it's just easier, quieter and more powerful. There will be many wind challenged July days when you want to get from A to B...just sayin'.