About Us
We’re Paul and Simon — and we’ve clocked up a lot of kilometres.
Roam Wisely is a family-owned travel agency based in the Hawkesbury region of NSW, specialising in multi-generational family travel for families all over Australia. We help families plan trips that genuinely work across different ages, energy levels and expectations — not just the logistics, but the structure that makes the whole thing feel manageable.
Between us, we’ve been travelling since 1999, USA road trips, Japan, South Korea, Singapore, UK, cruises, theme parks, and everything in between. Almost every trip on our list, we’ve done together. So when we talk about what works and what doesn’t, it’s not theory, it’s from actually being there.
Meet Paul & Simon
Roam Wisely is proudly family-owned and operated.
👨 Paul — started this with a simple love of travel and a long list of road trips through the USA. These days, some of Paul’s favourite travel moments come from experiencing destinations through his children and grandchildren. Travelling with young grandchildren changes how you plan everything — the bases, the pacing, the transitions — and that experience is now at the core of how Roam Wisely approaches every multi-generational itinerary.
👨💼Simon is a qualified travel agent and the detail person behind every itinerary. He makes sure the logistics hold up, the flights make sense, the bases are in the right spots, and nothing gets missed. He has been on almost every trip on the list too, which means the advice he gives comes from personal experience, not just a booking system.
Personal experience and professional service come together to create trips designed around what actually matters: the right structure for your whole group, across every generation travelling with you.
What we actually know (because we’ve done it)
We’ve travelled through Japan, South Korea and Singapore with grandchildren in a stroller. Train travel in all three countries is genuinely family-friendly, but there are things worth knowing before you go. Not every station exit has a lift, and finding the right one makes a real difference when you’re navigating a busy platform with a pram. That’s the kind of detail we’ll tell you upfront, because we’ve worked it out ourselves.
We’ve also done long-haul USA trips covering multiple states: Atlanta, Tennessee, Baltimore, Pittsburgh, Chicago and Anaheim on the 2024 trip alone. We know how to pace an itinerary across different ages so it doesn’t exhaust anyone halfway through.
Why families come to us
Most families we talk to aren’t stuck on where to go. They’re stuck on how to make it work for everyone. Kids, parents and grandparents all travelling together means different energy levels, different mobility needs, and different ideas of what makes a good day. They’ve got ideas and research, but no structure they feel confident booking from.
That’s exactly what the complimentary planning call is for. We help you work out the order of decisions: routes, bases, pacing across generations, what’s realistic, and what to leave out. Once that’s clear, the rest falls into place quickly.
We work with families travelling with young children, families with teens, and grandparents travelling with grandchildren. The planning looks different for each group, and we adjust accordingly.
Why the planning-led approach works
Most travel agencies start with a booking. We start with a structure. That means by the time anything gets committed to, the plan already makes sense for your whole group. The accommodation layout works, the pacing is realistic, and nobody arrives exhausted on day one.
Why Book With Us?
✅ Personalised service from real people who love travel
✅ Access to the best deals on flights, hotels, tours, and attractions
✅ Expert planning and insider tips
✅ Support every step of the way
Based in Hawkesbury, working with families everywhere
We’re locals in the Richmond/Hawkesbury area but work with families all over Australia. Everything is handled remotely: a phone or video call, followed by a detailed plan you can actually book from.
If you’d like to talk through your next trip, the first planning call is complimentary, and there’s no obligation.
Planning deposit: $150, credited to your booking when you proceed.