By Kristin K. Sullivan, General Manager, The Alice Destin
There’s something undeniably enchanting about holiday proposals. The glow of candlelight, the sparkle of ornaments, and the warmth of family all come together to create a storybook moment. For many couples, the holidays symbolize more than celebration — they represent love, connection, and the promise of new beginnings.
Between Thanksgiving and New Year’s, thousands of couples choose this magical season to get engaged. Whether under a glittering tree, beside a cozy fire, or during a festive family gathering, holiday proposals blend excitement, nostalgia, and the joy of involving loved ones in one of life’s most meaningful surprises.
I’ve been behind the scenes of many proposals, and it’s always an honor to help create the perfect setting. I’ve hidden in wild places to keep candles lit and curious strangers away. My favorite was organizing a family scavenger hunt where the bride’s family competed against the groom’s — only to discover in the end that the bride had already found her ring, duct-taped inside a conch shell at a bar in Key West. Moments like these embody the magic of the engagement experience.
We look forward to creating many unforgettable proposal settings at The Alice.
The Meaning Behind A Holiday Proposal
A proposal during the holidays is more than just a shiny new ring; it is a memory tied to a season already rich with emotion. The holidays naturally draw us closer to what matters most—love, gratitude and togetherness.
Choosing to propose during this season weaves your engagement story into the fabric of family traditions. Each year when the decorations go up or the first fire is lit, you’ll relive that magical moment again. It becomes a part of your shared history; a story that begins with “Remember when…?”
Setting The Stage: Finding The Right Moment
Not all proposals need to be grand gestures. Sometimes, the most meaningful settings are the simplest. Think of a quiet Christmas morning when the house is still, or at the family’s annual beach bonfire under the stars. The key is authenticity and choosing a moment that reflects your love story.
For the sentimental couple: Propose while trimming the tree or hanging the final ornament.
For the family-focused pair: Pop the question right before the family holiday toast or after dinner when everyone gathers for dessert.
For the adventurers: Plan a destination moment; on the dock at The Alice during sunset or a quaint cottage getaway by the firepit, a Christmas Eve sailing, or a surprise gourmet dinner for two under the stars.
The best proposals blend personal meaning with genuine emotion.
Bringing Family into The Magic
This season is about connection; and sharing that joy with loved ones creates memories that last a lifetime. The blending of two families creates a bond for the remainder of your lives together.
Here are some creative ways to include family in your proposal:
1. The “Gift Within a Gift” Reveal: Wrap the ring box inside several layers of boxes and pass it around during the gift exchange. When your partner opens the final box, you will be down on one knee.
- A Family Toast to Forever: Ask both families to gather for what they think is a holiday toast; then turn it into your proposal moment.
- Hidden Helpers: Enlist siblings or parents to help set the stage; string twinkle lights, decorate the space or cue the music just before the big reveal.
- Holiday Photos with a Twist: Schedule a “family photoshoot” and surprise your partner mid-photo with the proposal. The photographer will capture every priceless reaction. Your family not only shares in the surprise, but becomes part of your love story.
5. Capture on Video: Hire a Videographer to film the big moment.
Keeping It A Surprise: Subtle Planning Tips
Balancing secrecy and family involvement takes a bit of finesse.
– Limit the circle of trust. Only tell those who truly need to know, and who can keep a secret!
– Coordinate logistics early. You may wish to hire a professional planner to assist. The holidays are busy, so plan times, travel and props well in advance.
– Have a backup plan. Weather, travel delays or unexpected guests can shift the timeline.
Remember, surprises are not about perfection; they are about sincerity.
Capturing The Moment
Whether you hire a professional photographer or ask a trusted family member to record discreetly, capturing the moment ensures that joy is preserved forever.
Candid reactions, laughter, and happy tears become part of your engagement story—something to share for generations.
Afterward, consider creating a keepsake to commemorate the day:
– A custom ornament engraved with your engagement date
– A framed family photo from the proposal
– A short video compilation shared at your engagement party or wedding reception
Final Reflections: Love, Family and Forever
A holiday proposal blends love and tradition, reminding us that the greatest gifts are the people we share life with. Including family means you’re not just proposing to one person — you’re bringing two families together.
The laughter, the tears, the glow of the season — it’s a kind of magic that lasts far beyond the moment.
Whether it’s Christmas Eve under a shining tree, a New Year’s toast beneath fireworks, or a quiet winter morning with just the two of you, remember this: love, wrapped in intention and family, is the most timeless tradition of all.
1. Plan ahead: The holidays book up fast, reserve photographers, florists, and venues early; The Alice still has dates available for the 2025 season.
2. Think logistics: Hide the ring carefully (and keep it away from curious relatives).
3. Choose the right words: Speak from your heart; perfection is not the goal; authenticity is.
4. Include loved ones mindfully: Only invite those who enhance the moment.
5. Celebrate softly: Do not rush to post online; cherish and relish your private joy first.
ABOUT THE AUTHOR
Kristin Sullivan is the General Manager of The Alice, a new luxury Destin wedding and event venue. Through her decades of experience as a Luxury Destination Wedding Planner and Creator of The Bridal Retreat, she is dedicated to creating meaningful experiences and giving back with heart. Her passion is serving couples and families while they celebrate life’s most cherished moments with beauty, purpose and joy.
