Your Connecticut Family Vacation Planner
Mom of three. Disney expert. Cruise enthusiast. I plan family vacations that work for kids and parents — all for free, from Glastonbury, CT.
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Disney World with Kids
Walt Disney World is the most popular family vacation destination in the world, and it is also one of the most complex to plan. As a mom of three who visits Disney regularly, I know firsthand what works with kids — and what does not.
I build Disney itineraries that balance ride time with rest, match park plans to your children's ages and energy levels, and include the character experiences, dining, and special moments that make Disney truly magical for families. From choosing the right resort to securing hard-to-get dining reservations, I handle it all.
Whether your kids are toddlers experiencing their first character breakfast or teenagers ready for the thrill of TRON Lightcycle Run, I create a plan that keeps everyone happy. Visit my dedicated Disney planning page for more details.
Family Cruise Vacations
Cruises are one of the best vacation options for families because they offer something for every age group, all in one place. Kids have dedicated clubs and activities, parents can enjoy adult-only spaces and dining, and the whole family comes together for port days and shared experiences.
Disney Cruise Line is my top recommendation for families with younger children — the kids clubs are supervised and themed, the dining rotation is fun for everyone, and private islands like Castaway Cay are designed with families in mind. For families with older kids and teens, Royal Caribbean offers incredible onboard activities including rock climbing, surf simulators, and waterslides.
Connecticut families have the added advantage of cruises departing from New York and New Jersey, meaning no flights needed. Learn more on my cruise planning page.
All-Inclusive Family Resorts
All-inclusive resorts take the stress out of family vacations by bundling meals, drinks, activities, and entertainment into one upfront price. No tallying up restaurant bills, no surprise charges, no "can I have another juice?" guilt — everything is included.
For families, I recommend resorts like Beaches (by Sandals), which features waterparks, Sesame Street character experiences, and supervised kids programs. Club Med is another excellent choice with their all-inclusive approach that includes kids clubs, sports instruction, and family-friendly entertainment.
I help families find the right resort based on their children's ages, travel dates, and budget. Explore more options on my all-inclusive resort planning page.
Planning Tips for Traveling with Kids
Advice from a mom of three who has learned these lessons firsthand.
Build in Rest Days
The biggest mistake families make is overscheduling. I always build pool days, late mornings, and downtime into every itinerary. A rested family is a happy family, and the vacation should feel like a vacation.
Plan Around Nap Schedules
For families with toddlers and preschoolers, I structure park days around nap times. Early morning rope-drop sessions, midday pool breaks, and evening returns to the park — this rhythm keeps everyone in good spirits.
Book Kid-Friendly Dining
Not every upscale restaurant is right for a family dinner. I recommend dining options that are fun for kids and enjoyable for adults. Character meals, themed restaurants, and buffets with variety make mealtimes part of the adventure.
Pack Smart
I provide detailed packing lists tailored to your destination, including items most families forget. From stroller rain covers for Disney to reef-safe sunscreen for beach resorts, small details make a big difference.
Involve the Kids
Kids who help choose activities and restaurants are more invested in the trip. I help families create a balanced itinerary that includes something each family member picked, so everyone feels like the vacation is theirs.
Have a Backup Plan
Weather happens. Meltdowns happen. I always have alternative activities and rainy-day plans ready so a change in plans does not derail your trip. Flexibility is key when traveling with children.
Spring Break and Summer Vacation Ideas
Connecticut school calendars drive when most families can travel, and I specialize in making the most of those windows. Spring break and summer are the most popular times for family vacations, and early planning is essential to securing the best availability and pricing.
For spring break, popular options include Disney World, all-inclusive resorts in the Caribbean, and short cruises from New York. Summer opens up even more possibilities — longer cruise itineraries, Universal Orlando trips, and multi-destination family adventures.
I also help families take advantage of shoulder seasons and school breaks like February vacation and holiday weeks. Sometimes the best value and shortest lines happen outside the peak summer months. I will help you find the sweet spot between your schedule, budget, and dream destination.
Why Families Trust Kelly
Real experience, real credentials, and a genuine passion for helping families travel better.
Do you have kids yourself?
Yes. I am a mom of three, and I travel with my family regularly. I know what it is like to manage different age groups, navigate theme parks with a stroller, and find restaurants where everyone is happy. My advice comes from real, personal experience — not just a brochure.
Is your service really free?
Yes, completely. I am compensated by the resorts, cruise lines, and travel providers I book through. You pay the same price (or often less, thanks to agent-exclusive deals) as booking on your own, but with full personalized planning included. There are no hidden fees or catches.
What age kids do you plan trips for?
All ages. I plan vacations for families with infants, toddlers, school-age kids, and teenagers. I also plan multi-generational trips that include grandparents. Each trip is customized based on who is going and what everyone enjoys. Learn more about my background.
What if I am not sure where to go?
That is one of my favorite questions. If you know the dates, the budget, and who is traveling, I can present several options tailored to your family. Disney, a cruise, an all-inclusive resort — or something completely different. I love helping families discover their perfect vacation style.
Are you a certified travel agent?
Yes. I am CLIA and IATA certified and affiliated with Main Street Magic, an established travel agency. I have over a decade of experience planning vacations for families across Connecticut and beyond. Based in Glastonbury, CT, I bring professional expertise and personal passion to every trip.
Plan Your Family's Next Adventure
From Disney to cruises to beach resorts, I take the stress out of family vacation planning. Fill out a quick form and I will create a personalized plan for your family — for free.