Michael Doyle will today link up with Pompey’s squad as they jet off for their Portugal training camp.
The central midfielder will spend the next six days with the Blues as they continue in their attempts to sign him.
Tom Craddock has also been invited on the trip to the Algarve, where they will be based in Vale de Lobo.
The 28-year-old has spent the past two days training with Pompey after being invited back to the club by manager Paul Cook.
Flying out this afternoon, it will be an opportunity for the new-look squad to bond, especially following the arrival of seven fresh recruits over the summer.
Cook is highly familiar with the region in the south of Portugal, having taken Chesterfield there in the past.
Now he will follow suit with the Blues, accompanied by his new backroom staff – assistant manager Leam Richardson and first-team coach Ian Foster.
Cook has already stressed the need for hard work and has had his squad in for training since Wednesday.
That was an alteration to the original pre-season return date of Monday, June 29.
Among those players booked in to jet off to Portugal are his seven summer recruits – Kal Naismith, Gary Roberts, Adam McGurk, Adam Barton, Christian Burgess, Kyle Bennett and Enda Stevens.
Meanwhile, Paul Robinson is available to play again following the fractured cheekbone which kept him out of the final 10 matches of last season.
The squad are scheduled to return to England on Thursday, July 2.
Their friendly schedule kicks off at the Hawks on Saturday, July 11, followed by the trip to Bognor on Friday, July 17 (7.30pm).