Matching a modified vee Eastern 27 Islander 2013 against a deep vee Eastern Eastern 248 Explorer 2009 means you're likely deciding between two genuinely different on-water experiences. Hull type shapes everything from ride quality and fuel burn to dock handling and resale trajectory.
Size is the most obvious dividing line here. The Eastern 27 Islander 2013 measures 27,3 feet overall (2013), giving it roughly 3,3 additional feet of deck space compared to the Eastern Eastern 248 Explorer 2009 at 24,0 feet (2009). At 8 lbs and 35 lbs respectively, both sit in a similar weight class — either should pair comfortably with most mid-size SUVs and half-ton trucks, though always confirm your specific tow rating with the motor added.
For family outings this is probably the sharpest distinction between the two. The Eastern 27 Islander 2013 is rated for 8 passengers, while the Eastern Eastern 248 Explorer 2009 caps at 7. If you're regularly pulling extended family or a group of friends onto the water, the extra seats on the Eastern 27 Islander 2013 could be the deciding factor.
Bottom line: Choose the Eastern 27 Islander 2013 if your priority is putting more people on the water — it handles 8 passengers and at 27,3 ft it has the deck room to back that rating up comfortably. The Eastern Eastern 248 Explorer 2009 is the smarter pick if you want a lighter, easier-to-trailer boat rated for 7 that costs less to run day-to-day.