Plan a Family Trip
That Everyone Will
Talk About for Years
Stress-free, joy-filled travel for all ages —
curated by a professional who handles it all.
Plan a Family Trip That Everyone Will Talk About for Years
Stress-free, joy-filled travel for all ages — curated by a professional who handles it all.
What Types of
Trips Do We Plan?
Whether it’s grandparents, toddlers, teens, or all of the above — I’ll make sure everyone has something to love.
- Multigenerational Vacations
- Milestone Birthdays & Celebrations
- All-Inclusive Beach Trips (with kids’ clubs!)
- Educational + Cultural Itineraries
- Family Cruises & Excursions
From multigenerational getaways to milestone celebrations, I help families create personalized trips with smooth logistics, built-in fun, and zero overwhelm.
Why Travel With TWC?
✔️ Trips tailored to your family — not pre-packaged itineraries
✔️ One planner for it all — flights, resorts, excursions, and more
✔️ Stress-free travel logistics — even for large or multi-gen groups
✔️ Insider perks like room upgrades, free nights, and group rates
✔️ A real human on your team — before, during, and after the trip
Best Family Trip Ever
“On behalf of all 20 of us — kids, grandkids, family, and friends — thank you, Stephanie, for putting together such a wonderful trip to Punta Cana. Your patience, organization, and attention to detail made everything run smoothly. We were able to truly relax, laugh, and make lifelong memories.
You made this experience unforgettable. We’re already dreaming of the next one — and we know exactly who to call.”
— Doug Gehrke, proud Dad & Opa
What Clients Say About Us:
THE MASTERMIND BEHIND TWC
Meet Stephanie
With a background in wedding planning, floral design, and luxury travel, I bring a unique blend of creativity and coordination to every journey. I started my first business in Wisconsin, Cover it With Class, and in 2020, expanded my passion into planning full destination celebrations and romantic getaways worldwide.
Whether you’re saying “I do” on a beach, honeymooning in Italy, or escaping for a once-in-a-lifetime trip, I handle both the event and the travel with care, elegance, and personal attention.
From logistics to luxury, I make your dream experience feel effortless.
Let’s bring it to life—schedule your free consultation today.
Steph
OUR AWESOME TWC SIDE KICK
Meet Beth
Introducing Beth, our new travel partner at TravelWithClass! With her expertise in family travel, Beth ensures every detail is seamlessly coordinated, from kid-friendly accommodations to smooth logistics. She’s here to make your family adventures stress-free and unforgettable.
Let’s Make Your Next
Family Trip Effortless.
Whether you’re traveling with 4 or 14, I’ll help you plan a trip filled with ease, connection, and unforgettable memories.
Not Ready to Book Yet?
Grab our free family travel guide here.
Not Ready to Book Yet? Grab our free family travel guide here.
free!
The Smart Guide to Family & Group Trips
From Budgeting to Booking —
Without the Chaos
