On a pilgrimage the practical sequence is simple. Go to confession once early in the trip, in English at St. Peter's or one of the churches on vatican-confession-times-and-english-speaking-confessors; one confession covers several indulgences within the 20-day window. Receive Communion at Mass on the day of each indulgenced visit, since a separate Communion and a separate prayer for the Pope are needed for each plenary indulgence. Make the visit itself with a real pause for prayer, not a walk-through, and say the Our Father and the Creed, then an Our Father and Hail Mary for the Pope's intentions.
The condition people miss is detachment: the Penitentiary says that if the disposition is less than complete, the indulgence is partial rather than plenary. That is not a reason to skip the attempt, only a reason not to treat the indulgence as a receipt. It may be applied to oneself or to a deceased person, never to another living person.
Standing indulgenced visits in Italy include the four papal basilicas in Rome, the Porziuncola at Assisi any day of the year, and any parish or Franciscan church from noon August 1 to midnight August 2. The sick and those who cannot travel can gain the indulgence by uniting themselves spiritually with the pilgrimage and fulfilling the conditions when able. The overview is on how-do-i-obtain-a-plenary-indulgence-on-pilgrimage.