A split stay is a good idea only issue will be transportation. You can hire a driver, take the Knutsford Express or rent a vehicle and drive yourself. Portland is lush, breath taking, truly is beautiful, really stands out. People are "real" meaning little to no hassle, easy going vibe. A lot to do and see in the area but you will need transportation or a driver to get around, it's not walk-able like Negril. Most of the guesthouses and hotels are outside of the town center and very few are 'on" the water. Nightlife doesn't compare to Negril, but does have some. Local parties, upscale live music at GeeJam and Trident, as well as a handful of dinner spots and Great Huts offers a cultural show and dinner, food is very good. There is also a club in Boston. I love that I don't have to be on guard like in Negril. I don't have to think most are out for the hustle, that's one aspect of Portland that I love and the beauty. I can sit for hours and just "be" yes it's that beautiful and special. But I do miss the nightlife and variety of Negril evening activities that's why I just do both when I can.