The Caribbean Series returned to Havana in 1953, but the trophy did not stay in Cuba. The Cangrejeros de Santurce, representing Puerto Rico, claimed the championship in the Cuban capital — a result that demonstrated the competitive equilibrium the tournament was beginning to develop despite Cuban clubs' early advantages. Santurce was carrying one of the most talent-rich rosters in Puerto Rican winter baseball history during this period, and a championship in Havana carried particular resonance given the city's stature in the baseball world of that era. No Most Valuable Player is formally recorded for this edition, and some details remain unverified. The Cangrejeros' title was nonetheless a landmark for Puerto Rican baseball in the regional context, arriving at a time when the island's winter circuit was maturing rapidly. Winning on Cuban soil, in a city that was effectively the spiritual headquarters of Caribbean baseball, gave this championship a significance that extended beyond the round-robin standings.
Champion: Cangrejeros de Santurce · Country: Puerto Rico · Host: Havana, Cuba · Manager: James Clarkson
It was the 2nd Caribbean Series title for Cangrejeros de Santurce and the 2nd for Puerto Rico, which has won 16 in all. Havana hosted the tournament for the 2nd time.
The 1952 edition was won by Leones del Habana in Panama City. Criollos de Caguas took the 1954 title in San Juan.