The weddings stand as testimony to the government's determination to make Robben Island — a symbol of fear and hatred during the apartheid era — into a monument to love and reconciliation in the new democratic South Africa.
"We chose Robben Island because you only get married once in your life and we wanted it to be a very special occasion," said Mario Pare, a native of Quebec, Canada, who was tying the knot with his South African fiance Jacqui Middlewick.
Pare, who was also celebrating his 36th birthday, said his family in Canada was not surprised at the choice of venue.
"We like to be a bit different," he said. "It's like paradise to be married on an island."
A homeless couple and a pair infected with the AIDS virus were among those exchanging vows and fumbling for rings in the ceremony in the small chapel that was used to pray for the sick in the days when the island was a leper colony.
Balloons inscribed "I love you" and red cardboard cupids hung on the chapel walls. Busloads of tourists looked on as the couples posed for photographs after the ceremony.
And, just for a day, Verona Kawie and Samuel Williams were able to forget the squalor of their tiny shack and their grinding poverty and celebrate in style.
The pair, who have been together for 12 years, discovered six years ago they were HIV positive. It was their AIDS counselor who encouraged them to get married and made contact with the Home Affairs department responsible for the ceremony.
"It feels wonderful," said Williams, 57, as he emerged from the chapel into the bright sunlight. "Wonderful," echoed his 39 year-old wife as she gazed into his eyes and gave him a toothless smile.
They had to scramble to borrow clothes for their special day and couldn't afford a ring, but said they didn't care. A charity covered the cost of the $24 boat journey, and the ceremony was free.
Patrick Chauke, chairman of parliament's Home Affairs portfolio committee, said that next year, homosexual couples would be invited following a constitutional court ruling that same-sex marriages should be legalized.
"If I were to get married again to my wife, I would definitely do it here because it is such a special place for South Africans," Chauke told the congregation crowded into the chapel.
More than 100 couples have been married in the Valentine's Day ceremonies on the island since they first started in 2000.
"Valentine's Day is a day of love, peace and happiness and represents Robben Island of today," said Home Affairs spokesman Mantshele wa ga Tau. "In the past it was a place of hatred, fear and incarceration."
The wedding party was taken on the seven-mile trip from Cape Town in one of the boats used to transport warders to the prison island were African National Congress leader and Nobel Peace Prize laureate Mandela was incarcerated for 14 of the 27 years he spent behind bars.
The island was declared a national museum in 1997 and each year attracts more than 300,000 visitors, who are shown around by former prisoners.
For Valencia Daniels, dressed in a traditional white wedding dress, it was her first trip.
"It's great, fantastic," she enthused. "And very, very romantic."