Planning a holiday with kids, parents and grandparents?
We are your local travel agent in Penrith, Richmond and Hawkesbury, helping families structure trips that work across every generation.
Stop second-guessing your family trip.
Multi-generation travel adds layers most families don’t expect: different energy levels, mobility needs, budgets and expectations all travelling together.
Most families don’t get stuck choosing a destination. They get stuck deciding what will realistically work for everyone — the pacing, the accommodation layout, the transport, the rest days.
That’s where a travel agent who understands multi-generational planning makes the difference.
We’re Paul and Simon from Roam Wisely Travel, your local Penrith and Richmond travel agents. Families usually come to us when they’ve got ten tabs open but no clear plan that works for kids, parents and grandparents together.
Why Families Choose Roam Wisely as Their Travel Agent
We’re Paul and Simon from Roam Wisely Travel.
We’re not just travel agents — we’re a family who travels. Between us, we’ve covered the USA, Japan, South Korea, Singapore and the UK, much of it with young grandchildren in tow.
✅ Based in Richmond, NSW, serving Penrith, Hawkesbury and Greater Sydney
✅ Real experience across multi-generational family travel
✅ Planning-led approach, not booking-led
Most families contact us after weeks of research and move forward faster once the structure is clear.
Why Families Trust Us to Coordinate Their Trip
Most families contact us after weeks of research — and move forward faster once the structure is clear.
Multi-Generational Travel Planning Services.
What we coordinate (so every generation travels well)
We plan flight timing around your family’s energy levels, connection times and arrival windows, so day one feels manageable, not exhausting.
We recommend locations and room setups that suit kids, parents and grandparents, considering space, walkability, comfort and accessibility.
We match ship size, cabin configuration and port pacing to your family’s travel style, especially when different generations want different experiences.
We suggest tours and activities that enhance the trip without overwhelming it, well-paced, age-appropriate and worth the time.
We structure park days around stamina, rest breaks and realistic expectations, so no one is burnt out halfway through.
We map drive times and stopovers that work for your whole family, factoring in luggage, comfort and different travel rhythms.
We build rail days into your itinerary so they’re efficient and enjoyable, with seat planning and simple transitions between bases.
We help you understand what matters for your trip, especially when travelling with multiple generations, so you’re protected appropriately.
Multi-generation trips aren’t about booking pieces.
They’re about structuring the whole plan properly.
Prefer to start in writing? Submit an enquiry instead.
Travel Agent Serving Penrith, Richmond, Hawkesbury & Western Sydney
Roam Wisely Travel is a family-owned travel agency based in Richmond, NSW. We work with families across Penrith, Hawkesbury, Western Sydney and throughout Australia.
Whether you’re in Penrith, Richmond, Windsor, Blacktown or anywhere in Greater Sydney, we can help you plan your next multi-generational family holiday. Everything is handled remotely — phone or video consultation, followed by a detailed plan you can book with confidence.
We specialise in trips that need to work for kids, parents and grandparents together: USA family holidays, Japan with young children, South Korea, Singapore, UK trips, Australian domestic travel, cruises and theme park packages.
How Multi-Generational Travel Planning Works
Multi-generation trips aren’t about booking pieces. They’re about structuring the whole plan properly.
What changes when a travel agent plans it properly:
✅ A route that matches your group’s time, energy and mobility needs
✅ Bases that reduce packing, unpacking and long transit days
✅ Clear “must-do vs nice-to-do” priorities so no one feels rushed
✅ Support if plans shift mid-trip
Your initial consultation is complimentary.
Planning deposit: $150 (credited to your booking when you proceed)
Let’s build the plan together properly.
Ready to Plan Your Multi-Generational Holiday?
You don’t need more tabs open.
You need a clear structure that works for everyone.