11
“Family Is Family”: Dylan Dreyer Gets Real on In-Laws Turks & Caicos Trip
Dylan Dreyer’s Special Family Vacation: How One Tradition Stayed Strong Through Big Changes
The Special Birthday Trip
Dylan Dreyer, the weather expert from the TODAY show, just turned 45! She celebrated in a place that feels like a second home to her family: Turks and Caicos — a beautiful group of islands with sandy beaches and blue water.
She was visiting the TODAY show’s 4th hour to chat with co-host Sheinelle Jones about this special trip. But this year, things looked a little different than usual.
A Tradition That Kept Going
Important Point
This vacation has been happening for 13 or 14 years! It started when Dylan was married to Brian Fichera. Even though they are no longer together, the tradition didn’t stop.
Here’s what makes this trip so special:
- Family time: Dylan’s three boys — Calvin (9), Oliver (6), and Rusty (4) — get to spend a whole week with their cousins
- Fun activities: Beach days, pool time, water park adventures, and family dinners
- Planned ahead: The trip was booked way in advance, like it always is
This Year’s Changes
| Who Usually Comes | This Year |
|---|---|
| Brian Fichera (Dylan’s former husband) | Couldn’t make it (scheduling conflict) |
| Two nephews | Couldn’t make it |
| Dylan + 3 sons | Went as planned |
| Former in-laws & cousins | Were there! |
Dylan never thought about canceling. She said: "To me, yes, it was a family I married into, but it’s a family I’m very close with."
Why Family Stays Family
Dylan talked about how much she loves her former in-laws:
- Sister-in-law — still close
- Mother-in-law — still close
- Father-in-law — still close (and very helpful — more on that below!)
Sheinelle Jones pointed out something really smart: Kids do better when adults keep extended family relationships strong, even after big life changes like divorce.
Dylan agrees. She wants her boys to keep their special bond with their cousins, no matter what.
The Best Part: Extra Helping Hands
A Surprise Luxury
Dylan got something rare on this vacation: time to relax!
With so many family members around, there were lots of "extra hands" to help watch the kids. Her father-in-law even declared himself "primary" — which means he took charge of supervising the kids at the pool and ocean.
Dylan’s Perfect Moment
"I would just sit back and I’m like, ‘All right, I’m just gonna soak this in,’" Dylan said. "I had a great time."
Numbered steps to Dylan’s relaxation:
- Arrive at the beach house with family
- Hand off the kids to eager grandparents, aunts, and uncles
- Sit back with a drink or book
- Enjoy rare peace and quiet
- Recharge while knowing the kids are safe and happy
What We Can Learn From Dylan’s Story
Key Takeaways
- Traditions can survive big changes — Divorce doesn’t have to mean losing the people you love
- Kids come first — Keeping cousin relationships strong matters more than adult complications
- It takes a village — Accepting help from family makes parenting easier (and more fun!)
- Choose kindness — Staying close with former in-laws creates a bigger support system for everyone
Summary
Dylan Dreyer showed us that family isn’t just about marriage certificates — it’s about the bonds you build and choose to keep. Her annual Turks and Caicos trip proves that with love, flexibility, and a focus on the kids, traditions can not only survive but thrive through life’s changes. And sometimes, if you’re lucky, your father-in-law becomes the best lifeguard ever, giving you a moment to just breathe and enjoy the view.
FAQ
Why did Dylan go on vacation with her ex-husband’s family if they’re divorced?
Because she considers them her family too! They’ve vacationed together for over a decade, and she wants her sons to stay close with their cousins and grandparents. Divorce ended her marriage, not those relationships.
Did Brian Fichera go on the trip this year?
No, he couldn’t make it due to a scheduling conflict. Two of the nephews also couldn’t come. But Dylan and her three boys still went.
How old are Dylan’s sons?
- Calvin is 9 years old
- Oliver is 6 years old
- Rusty is 4 years old
What did Dylan do while the other adults watched the kids?
She relaxed! She sat back, "soaked it in," and enjoyed some rare downtime while her father-in-law and other relatives supervised the kids at the pool and beach.
What did Sheinelle Jones say about Dylan’s choice?
Sheinelle praised Dylan, saying children benefit when adults preserve extended family relationships after major life changes like divorce. She thinks Dylan is setting a great example.
