Family Travel, Honeymoons, Cruises & Destination Weddings—Thoughtfully Mapped
Whether you are planning a family vacation, dreaming about your honeymoon, searching for the right cruise, or organizing a destination wedding, I help you sort through the options and create a trip that fits your priorities, travel style, and budget.
Every journey thoughtfully mapped.
Hi! I’m Kelsey Welsman, a Fora-certified travel advisor, lifelong traveler, mom of two young children, and soon to be dog mom.
After traveling to more than 35 countries across five continents and spending over a decade managing complex international operations, logistics, contracts, and travel, I learned that the best experiences rarely happen by accident. They come from choosing the right place, anticipating the details, and having someone who can calmly keep everything moving.
Today, I use that experience to plan family vacations, honeymoons, cruises, and destination weddings with the same care and precision I once brought to international programs and executive travel.
I understand the practical details that can transform a trip: the right room or cabin location, a pace that works with children, smooth transfers, realistic travel days, organized guest communication, and a plan for the unexpected.
My goal is not simply to book your trip. It is to help you feel confident that the trip is right for you.
Family Travel
Cruises, European adventures, beach vacations, ski trips, all-inclusive resorts, and multigenerational travel planned around the realities of traveling with children
Honeymoons
Personalized honeymoon planning for couples seeking relaxation, adventure, culture, or a thoughtful combination of all three.
Cruises
Resort and destination research, room-block coordination, guest travel support, transfers, and organized communication for couples and their guests.
Destination Weddings
Guidance choosing the right cruise line, ship, itinerary, cabin category, onboard location, excursions, transfers, and pre- or post-cruise accommodations.
Ready to start planning? Visit the Services page to explore customized planning packages designed to curate your travel, itinerary, and experiences — all with the expert guidance of someone who’s been there.
Reviews!
“Kelsey is a dream to work with. Rarely have I collaborated with someone who is so incredibly efficient, responsive, and complete in their work. I came to her with just some loose ideas of an itinerary and she presented me with several attractive options for each step in our journey. Kelsey was also really amenable to any changes I wanted to make and really rolled with the whole process, despite me being a bit chaotic at times. Even while we were on our trip she was helping us book last minute ventures and accommodations. I could not recommend Kelsey more highly!
I could not recommend Kelsey more highly!”
-James E.
“Kelsey planned a 10-day adventure through Spain, and it was absolutely flawless from start to finish. As a senior couple, we wanted a trip that balanced comfort, culture, and a bit of adventure — and Kelsey delivered all of that and more. Every detail was thoughtfully arranged with smooth flight connections and charming lodging in each city. All tickets and transfers were confirmed in advance resulting in a pleasant international travel experience. We highly recommend Waypoint Travel by Kelsey. It was a perfect trip and we can’t wait for our next international adventure. Italy may be next!”
– Elaine N
“Kelsey helped to arrange airport transfer and secure a room upgrade, early check in and favourable rates. Extremely pleasant and communicative throughout – could not recommend more highly!”
-Lucy F
“Kelsey planned the most Amazing 14 day vacation to Copenhagen, Athens, and island of Naxos off the coast of Greece. It was the best travel experience and vacation we’ve ever taken. So relaxing as everything was so thoroughly planned ahead. It was seamless from start to finish with all out connections planned out in advance. Kelsey narrowed down some Airbnb’s and let us pick the ones that met our needs the best. She is so aware of travel apps, currency, and safety tips that made our trip so relaxed and enjoyable. Even our transport to and from our hotels and Airbnb‘s were covered. The extra added bonus was she hooked up with a friend who was a local that had majored in archaeology to give us private tours for 2 1/2 days in downtown Athens. We can’t say enough about her expertise in traveling.”
-Dawn & Tom W
