Both the Pro-Line 26 XP 2011 and the Pro-Line 29 Grand Sport 2008 are modified-V designs, both built in fibreglass, so the buying decision usually comes down to a handful of practical questions: how many people are you putting on the water, how far do you trailer, and what does your tow vehicle weigh?
On paper these two are close siblings in the size department - Pro-Line 26 XP 2011 at 26,3 ft versus Pro-Line 29 Grand Sport 2008 at 29,0 ft. Weight tells a clearer story for trailering families: the Pro-Line 29 Grand Sport 2008 tips the scales at 6 310 lbs - 930 lbs less than the Pro-Line 26 XP 2011 at 5 380 lbs. That difference is meaningful if you're working within a half-ton or three-quarter-ton truck's tow rating, especially once you factor in a motor, gear, and fuel.
The power gap is worth calling out. Rated to 600 hp, the Pro-Line 29 Grand Sport 2008 has a 150-hp advantage over the Pro-Line 26 XP 2011's 450-hp ceiling - enough to notice on acceleration and at cruising speed, particularly with a full passenger load. Fuel capacity breaks the other way: the Pro-Line 29 Grand Sport 2008 carries 240 gallons versus 200 gallons in the Pro-Line 26 XP 2011. On a lake day that's negligible, but for coastal cruising or long reservoir runs the extra range matters.
Both boats are rated for 8 passengers - a good fit for a family of four or five plus guests. Comfort at capacity is another matter; the longer hull typically means more seat options and better weight distribution.
Bottom line: The Pro-Line 29 Grand Sport 2008 at 29,0 ft is the right call if deck space, comfort, and entertaining are top of your list. The Pro-Line 26 XP 2011 at 26,3 ft wins on trailering ease, likely lower purchase price, and simpler docking - a solid choice for a buyer who wants more boat for less money.