A Love Story on the island of Milos

David and Sydney, a warm and adventurous couple from Canada, share a deep passion for traveling to new destinations. This year, they chose Greece for their summer getaway - their very first visit to this beautiful country. What Sydney didn’t know, however, was that David had been secretly planning something even more special: a surprise proposal.

From the start, David was certain of what he wanted. He envisioned a private, intimate, and deeply personal experience, something that reflected their relationship. After a few conversations and suggestions, David decided to combine two of our most loved experiences: a private sunset cruise followed by a romantic dinner setting at one of the island’s finest restaurants.

We carefully curated every detail to make the day perfect. We arranged a professional photographer to discreetly capture each precious moment and included beautiful floral arrangements in Sydney’s favorite pastel tones. The plan was to cruise around Milos, enjoying its crystal-clear waters and stunning landscapes, proposing at sunset, before heading back for a candlelit dinner.

However, as often happens with Greek island adventures, nature had her own plans. A last-minute change in weather meant the cruise had to be adjusted. Instead of Milos, the couple set sail towards Kimolos island, where they discovered the enchanting Elephant Bay - a hidden gem known for its dramatic rock formations and serene beauty.

The change turned out to be serendipitous. Under soft island light, surrounded by turquoise waters, the couple enjoyed a blissful few hours of privacy, laughter, champagne, and pure joy. The photographer captured every natural moment and a heartfelt proposal on board.

After returning from the cruise, the evening continued with an intimate dinner setting near Sarakiniko, one of Milos’ most iconic locations. The restaurant had been beautifully decorated with fresh flowers, rose petals, and candles, creating an atmosphere of quiet romance.

It was an absolute pleasure working with David - his thoughtfulness and desire to create a meaningful experience made this proposal truly unforgettable. We’re so happy that everything came together beautifully despite the last-minute weather change. The result was even more magical than imagined - a story of love, spontaneity, and the timeless charm of the Greek islands.

We wish David and Sydney all the love and happiness in the world as they embark on this new adventure together!

Are you leaning towards a private cruise proposal too? Learn more in our guide and reach out to our team!