Super Sweet Proposals Onboard MedSailors

Why is a sailing holiday the best place to pop the question?

Imagine sitting on the bow of your sailing yacht watching a sunset cast flame-like reflections across a shimmering silver sea snuggled right up with that special someone — can it get any more romantic than that? Actually, we can name quite a few opportunities at sea that might make for the most romantic moments imaginable. To put it like Beyoncé, if you’re looking for that perfect moment to drop THE question, there isn’t a better time than a sailing holiday with your boo or bae to put a ring on it. We’ve put together the top reasons (and places) to pull off the proposal of all proposals while on a boat!

It’s As Unique As It Gets

We’ve had proposals atop fortresses, on clifftops, in waterfalls, underwater while snorkeling, aboard the yachts, and so many more. The opportunity to come up with a unique and unforgettable moment to drop the question won’t be hard. The hardest part will be choosing which of these amazing places to drop the knee at!

It’s Not Cliché

Some might wait to propose in a nice restaurant, or maybe in an iconic place on holiday like Paris or Rome like you see in the movies, but we think dropping the question during a sailing holiday that has been one of the best trips of both your lives is the absolute way to go. Most of the destinations MedSailors sails through are off the tourist path and as authentic as you can get. We bet any place you choose to propose, you won’t find another friend who’s dropped the question quite like that.

It’s Romantic AF

You want romantic? We’ve got it. From sunrise or sunset sails sipping champagne to historic fantasy towns and some of the most breathtaking natural landscapes in the world, take your pick! When friends and family find out that the proposal happened on a sailing adventure, awe and envy about how perfect it sounds are sure to follow.

Our Top Question Popping Tips

1. The Sunset Proposal

One proposal story we’ve had in the past that is simply gush-worthy. An unexpected sunset proposal with champagne and dinner aboard the boat, this is our top pick for question-dropping moments. Planning it with the skipper throughout the week, the fiancé to be had no clue as she thought her boyfriend was simply being a bit more romantic than normal and convinced the skipper to take them on a private sail. The rest of the group were in cahoots helping plan the evening, and under a golden sunset with the sea shining like a thousand diamonds, he pulled a diamond of his own! We know…awww.

2. The Fortress Proposal

Given many of the destinations have ancient castles or fortresses you can visit on your MedSailors holiday, this one is our choice for the fairy-tale like proposals. In Croatia at the fortified town of Korcula, we’ve had the question popped atop a defensive watchtower turned cocktail bar at sunset overlooking the sea. Another hotspot would be for the Game of Thrones and history lovers — what would be more magical than dropping the knee atop the giant stone walls of Dubrovnik In arguably one of Europe’s most fantastical city? Not many places can beat that. Another perfect spot is a sunrise hike to the Fethiye fortress in Turkey where you’ll find yourselves all alone in the ruins drenched in the golden light of the rising sun overlooking the sleepy town below.

3. The Secluded Proposal

Don’t be afraid to break away from the group and find your own secret escape for the big moment, the others in the group are bound to understand. Find yourself a secret hidden cove or secluded bay and take your partner for a nice wander or picnic. After you’ve found the perfect spot all to yourselves away from the world, make up a spread of food and drinks and surprise him or her with the question at the right moment. The skippers are experts on the islands and will be the best person to ask where a good escape is located.

4. The Break A Sweat Proposal

Nothing strengthens bonds more than going through a challenge together, and on many of our sailing routes have activities or destinations that take a bit of effort to overcome, but the reward at the top will be worth it and the perfect place to ask the question. On our Italy route, hike up the active volcano of Stromboli and with the backdrop of lava eruptions and an incredible sunset, hit the knee and bust out the ring! In Mljet in Croatia, you can cycle around turquoise salt water lakes and pick one of the hundreds of secluded coves to claim for your own and pop the question!


Make the perfect proposal happen and book your romantic MedSailors sailing holiday today! Or, you know, if someone needs encouragement about proposing, send this straight over to them!

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