Aileen and Jan’s first meeting took place on Mallorca, one of Spain’s Balearic Islands in the Mediterranean – probably one of the most idyllic places for a romance to blossom. Though they’d only known each other a few days, a genuine interest had piqued, and they were smitten enough to start a long distance relationship. Eventually, life brought the two of them back to the Big Apple, where they were finally able to be together. They celebrated their wedding in Anguilla, an island surrounded by clear blue seas, closely resembling the place where their story first began.
Why did you decide on Anguilla for your wedding?
Aileen: I had always pictured getting married in the Caribbean. When Jan moved home from London, we took a long trip to Anguilla and stayed at the Four Seasons. We fell in love with the island and both thought it would be amazing to have a destination wedding there.
Jan: I had always pictured doing something outdoors, though I was never specifically set on having a beach wedding. Aileen had always wanted a Caribbean wedding, which made it easy to agree on where it should be done. Of all the islands and resorts we researched, many of them had lots of great reasons to choose them, though the Four Seasons in Anguilla was the one that checked the most boxes. We also knew the property well and felt an extra sense of comfort knowing that we wouldn’t be making choices blindly.
What is it like to plan a destination wedding?
Aileen: You need to be very organized given that the logistics are more complex than a typical stateside wedding. The good things are that the wedding is held somewhere exotic, the events take place over many days, guests use it as an excuse for a vacation, and people naturally relax in that setting. Challenges are that it’s impossible to meet with your teams in person as often as you would like, but if you’re proactive with communication, this doesn’t have to be an obstacle.
Jan: The main positive thing about a destination wedding is that you get to take trips there for planning purposes, but really it’s just an excuse to take another fun vacation. The biggest difficulty is that you can’t visit each space as often as you’d like to help with the planning. Lastly, you have fewer choices on an island, which can be both a pro and a con; it’s a pro in that it simplifies decision making, but it’s also a con because you’re restricted to some degree.
What was the best planning advice you received?
Aileen: Make sure you get along with the photo and video team because you’ll spend more time with them than anyone else on the wedding day. It’s completely true and everyone from The Day was a pleasure to have with us. On a related note, Ira suggested we do our first look before the ceremony because once it’s done, you just want to go be with your guests rather than rushing through photos. We listened to him and of course, he was right.
Jan: Let your future wife make the important decisions, but help enough that she knows you care.
We fell in love with the island and both thought it would be amazing to have a destination wedding there.
The main positive thing about a destination wedding is that you get to take trips there for planning purposes, but really it’s just an excuse to take another fun vacation.
We chose Stand By Me...That song feels timeless to me and I’ve always envisioned it as my first dance.
What song did you choose for your first dance?
Aileen: We chose Stand By Me by Ben King. That song feels timeless to me and I’ve always envisioned it as my first dance. Luckily Jan agreed!
Jan: Aileen loves oldies, and I thought it was very sweet, too.
If you had to pick your top three moments of the day, what would they be?
Aileen: Our first look, dancing with my husband throughout the night, and the fireworks show.
Jan: Our first look, seeing Aileen in her dress for the very first time. Walking into the reception, getting introduced as husband and wife for the first time and hearing everyone cheer. Being on the dance floor with all of our best friends pumping us up.
Is there anything you’d do differently?
Aileen: I would have had a second dress. I loved my gown and told myself I wanted to wear it through the whole reception, but I didn’t realize how warm I would get wearing that all night on the dance floor.
Jan: Have more fans on the dance floor, it was way hotter than we expected!
- Second Shooter Nathan Smith
- Planning Allana Connor of Four Seasons Anguilla
- Cake & Catering Four Seasons Anguilla
- Dress Oscar de la Renta from Mark Ingram Atelier
- Floral Design Couture Concepts
- Hair & Makeup Four Seasons Anguilla Spa
- Lighting Couture Concepts
- Music Omalie 360
- Music, DJ Isaac Hindin-Miller
- Stationery Atelier Isabey
- Venue Four Seasons Anguilla