How to Get Engaged on a Sailboat

catamaran_sunset_guadeloupeLet me paint you a picture. You’re in the French Caribbean, which turns out to be one of the most magical mixes of French culture and laid back island life. Delicious French wines and decadent cheeses are as plentiful as insanely strong rum punches and tropical fruits. You’ve spent the last week island hopping on a Lagoon 450 and you made it to your last anchorage of this way too short of a trip. It’s a bittersweet moment.

But, lets back up.

The morning was a mix of highs and lows. An early morning departure afforded another beautiful sunrise – one of my absolute favorite times to be sailing. After six choppy – yet seasickness free! – hours you finally make it to Base Terre. You’ve been watching the outline of the volcano slowly appear from behind the veil of morning fog. The hike up Base Terre to see the waterfalls is said to be one of the best in the Caribbean, the waterfalls definitely taking your breath away. I had been looking forward to that excursion the entire trip.

When we finally reached our desired anchorage it was giving everyone a weird gut feeling. The moorings looked unkempt and anchoring was tough because of the drastic drop off. The only good anchoring spots were taken by boats in varying states of derelict. After multiple failed attempts to pick up the one usable mooring (they didn’t have any lines to grab coming out of the ball) we headed to the next closest anchorage a little bit defeated and hoped for better luck. But, luck was not on our side (or was it?!). The next anchorage was just as bad. After a few more laps around both anchorages (just in case!) we gave up and raised sail. We were heading to the Pointe-a-Pitre, where we would eventually catch our flight back to NYC.

Besides the fact that everyone was a little sad that this was going to be our last sail of the trip, it was quite an enjoyable sail. The sun was shining, the wind was blowing and Jon and I saw a giant sea turtle while we were up on the fly bridge. It was so big we were worried it was something half sunk that could potentially hurt the boat! As we were approaching the anchorage and cruise ships began to come into clear view, I took another look at the guidebook and noticed another anchorage just 3 miles away. This one was sandwiched between a tiny island covered in palm trees and the main island. One last night anchored next to a cute island sounded much better to me. “Turn to starboard!” I wasn’t about to have my last real day in paradise anchored next to factories and floating cities.

This abandoned lighthouse marks Ilet du Gosier
This abandoned lighthouse marks Ilet du Gosier

Despite my insane shouts, no one opposed and thirty minutes later we were anchored in arguably the most amazing anchorage of the entire trip. Not only were we anchored in front of a super cute island with an abandoned lighthouse and an open beach bar, there was also a reef just a short swim from our boat. After the anchor was set, we all dove in for a snorkel. There were a few coral heads full of fish and a conch graveyard. We all got excited when we thought we stumbled upon a bunch of conch (hello conch salad!), but sadly all of them were empty. When I couldn’t take battling the current any longer I indulged in a cockpit shower. I had to do something about the rat’s nest that had taken residence on the top of my head. The Lagoon 450 was so luxurious. I had hot and cold water to choose from and it didn’t come from me mixing cold water into the boiling solar shower! We got so fancy on this trip. Up next was hitting the beach bar.

The fact that Jason had pulled out 2 different dresses for me to wear to the island should have tipped me off that something was up, but it didn’t. He said he just wanted to get a few pictures of me on the bow before we headed to the beach bar and I shrugged it off. Whatever, we were having a great vacation; he just wanted to remember it. I just had no idea how much! What really should have tipped me off was that both Tory and Jon were also taking pictures but, again, I didn’t think too much of it.

Magical proposal on a catamaran in Guadeloupe
I still can’t believe that heart shaped cloud appeared just as Jason dropped to one knee. Photo via Sail Me Om.

After Jason snapped a few pictures he came up to me, wrapped his arms around me and whispered sweet nothings in my ear. You’re amazing… blah blah blah… I love you… blah blah blah…. Will you give me an early birthday present? He grabbed my left hand, spun me around with such control So You Think You Could Dance choreographers would be impressed and dropped to one knee. With tears streaming down my face (happy tears!) the man I am so madly in love with asked me to marry him. Given it was April Fools Day I immediately blurted out, “Is this for real?,” partially thinking this may be some elaborate joke. After Jason assured me it was in fact a real proposal I looked into the eyes of this beautiful man and said, “YES!” With the realization settling in as to why both Jon and Tory were also taking pictures, I mumbled, “I’m really glad I washed my hair.” Priorities people, priorities!

This is what happens when you fake propose on April Fools Day on a sailboat
What would have happened if Jason really fake proposed on April Fools Day. Photo via Sail Me Om.

Even after six years together I have no idea where we’ll end up or what we’ll be doing, but with Jason by my side I know our life together will be one hell of an adventure.

Morals of the story are to always have a back up anchorage (or two!) and what may initially seem like bad luck, may end up being an extremely fortunate diversion to something magical. Oh, and getting engaged on a sailboat in the Caribbean to a sexy man is a pretty excellent day.

How to get engaged on a sailboat in Guadeloupe
Self-timer success! Our first sunrise the morning after our engagement. Sunrise truly is one of my favorite times of the day.


  1. Congrats to you both – and love the photos!! There is truly no better place to get engaged than on a boat (I speak from experience)! Enjoy this magical time in your life!! Jessie