The Wauwinet Nantucket Surprise Proposal | Amy & Charles


Amy and Charles met in the summer of 2010 in Charleston, SC. Charles was at a block party of a mutual friend and Amy was wearing a Lilly Pulitzer dress per usual, and he was wearing a Greek life shirt from the college she went to. They instantly connected since they had many friends in common. She was a charismatic, confident, fun and a stunning young lady who he simply loved to see. Whenever they would bump into each other around town, she would always stop to say hi and catch up. Since she was in medical school at the time, her course load and work schedule was quite tough, but in her last year they started to hang out significantly more. As they began to see each other often, he noticed how much they shared in common and how great she really was. Charles fell for her over the course of a few months and they started dating in early 2013. Unfortunately, his timing was poor due to the fact that she had matched into a residency program in Boston and was moving in less than six months. They knew it would be tough, but everything was going perfect. Charles and Amy knew they had to give the relationship a go, even with the distance. They did and less than a year later, Charles landed a job and moved up to Boston to be closer to Amy. What a great decision that was for them. Charles loves everything about Amy and Boston and he honestly felt it was one of the best and smartest decisions of his life.

Fast forward to the proposal (3 ½ years later…) Charles knew he wanted to do something special. Something different that he knew would be special to them for the rest of our lives. Nantucket was the obvious choice since they had always planned to visit, but were never able to make it happen with crazy work, training and school schedules. To make it all a surprise, Charles planned an elaborate day that Amy would remember forever…

It was Saturday, June 30th, 2016 and the day started for Charles at 5:30am. He mentioned to Amy the night before that he had to work early, but what she didn’t know was this would be a special day. He left the house by 6:30am and on his way out, he gave her a card and told her not to open it till 8am. He immediately walked out the door, got in the car and drove to Hyannis port to catch the ferry to Nantucket. In the meantime, Amy was certainly suspicious but went back to sleep. At 8am she opened the first card; it was long and sappy, but in short it mentioned that it would be a special day and that she should get ready, call her mom to figure out what to wear, and be at her favorite nail salon by 9:30am. Charles knew at that point she knew what was going on. When she arrived at the nail salon she was met by her best friend in Boston. They had their nails done and hung out for a few hours until her friend (who played dumb the whole time) said it was time for them to go separate ways. She put her in a car with the destination pre-determined and with two more cards which he had pre-written. She opened the next card that included a boarding pass to go to Nantucket and yet another long and sappy message. When she arrived at Logan she later mentioned to Charles that she was a wreck. She ordered a shake from Johnny Rockets, but never picked it up because she was so flustered. Eventually she boarded a Cape Air flight and flew over to Nantucket. When she landed, she was instructed to open the next card. That card was short and sweet. It gave her an address and told her to enjoy the scenery of the beautiful island. Charles told her in the card that he would see her soon and couldn’t wait to see her. All during this time, he was at the Wauwinet hotel setting a few things up, meeting with me to plan the engagement, and having a drink or two to calm his nerves. Luckily everything was falling perfectly into place.

When Amy arrived, she was greeted by two young men that worked for the hotel. Charles showed them pictures of her ahead of time and told them what she would be wearing. They immediately took her purse and escorted her to the beach. As she walked up, she saw me taking pictures of her and knew the big moment was approaching. As she walked over the dune, I could see her face and how happy she was. She was of course surprised and they were both nearly in tears. He gave her a big hug and they walked down the beach just talking casually. After walking for a few moments, he stopped and looked at her. He got down on one knee and shared to her that he wanted to spend the rest of his life with her and asked her to marry him.  After all that SHE SAID YES!! They then toasted their engagement on the beach and shared their favorite food together oysters. The champagne that they shared together was extra special to them. They had bought it in Napa on their first real vacation together in 2014 that they specifically saved for a special occasion. Who knew they would be drinking it on the day and night of their engagement? Then we took some amazing pictures. Charles and Amy were so over the moon excited and they were glowing. These two couldn't stop smiling and laughing the whole time. The day was just absolutely perfect. It as their fairy tale come true!