Plan Your Family’s Next Holiday With a Travel Agent for Wollongong
Multi-generational family holidays planned by Paul and Simon — working with families right across the Illawarra, from Wollongong and Figtree to Corrimal, Dapto, Shellharbour and Kiama. Book a free 30-minute planning call. No quote pressure. No upselling. No spam.
- ✓ Free 30-minute planning call — we talk through your trip before we book a thing
- ✓ A plan that works for kids, parents and grandparents — not just the cheapest option
- ✓ A genuinely local travel agent for the Illawarra — we work with Wollongong families by phone and video, so distance is never the barrier
- ✓ IATA TIDS accredited · Aussie Specialist certified · backed by 5★ verified reviews
My first use of a travel agency, and Roam Wisely showed me it’s a great experience. Expectations were met, and good advice was on hand for every query.
Why Wollongong and Illawarra families still use a travel agent in 2026.
It’s a fair question. With every airline, hotel and theme park selling direct online, what does a travel agent actually do? Honestly — for one person taking a city break, often not very much. But for a family of six across three generations, planning a holiday that has to work for everyone, the maths changes completely.
The real cost of a DIY trip isn’t the price of the flights. It’s the twenty-plus hours families typically spend researching, the small decisions that quietly undermine the trip later, and the unanswered questions that send people in circles for weeks. A good travel agent saves you most of those hours — and prevents the three or four mistakes almost every family makes when they do it themselves.
That’s the gap we fill. As a travel agent working across the Illawarra, our job isn’t to sell you a brochure. It’s to sit down with you, understand who’s actually travelling, and build a trip that holds together — from the drive up Mount Ousley to the flight home.
Why we’re the travel agent Illawarra families trust.
Because we plan trips for families up and down the Illawarra, we work around the realities you actually deal with. We know the airport runs — the M1 and the Mount Ousley descent up to Sydney’s Kingsford Smith, when the Princes Motorway backs up, and how the South Coast Line connects through to the city and the airport. We know the NSW school-holiday weeks (and which ones clash with mid-semester breaks). We know how a Dragons home game at WIN Stadium or a summer weekend on Grand Pacific Drive changes your timing. And we plan inside a realistic Illawarra household budget — not an idealised brochure version.
Getting an Illawarra family to the airport is its own planning problem, and we build it into every trip. Most international and interstate journeys still run through Sydney’s Kingsford Smith — around ninety minutes up the M1, longer in holiday traffic — so we time departures to avoid the worst of the Mount Ousley and motorway crawl, and we’ll tell you when the South Coast Line is the saner option with kids and luggage. Shellharbour Airport at Albion Park handles a handful of domestic routes, and where one fits your trip we’ll use it. That’s the kind of local knowledge a national call centre simply doesn’t have.
What multi-generational planning actually means.
“Multi-generational” sounds like marketing language. In practice it means a trip where a four-year-old, a thirteen-year-old, two parents in their thirties or forties, and one or two grandparents in their sixties or seventies are all on the same itinerary, on the same days, eating the same meals, walking the same distances and sleeping in the same accommodation. Each generation has different energy, different mobility, different patience, and a different idea of what a “good day” looks like.
That’s the part DIY booking can’t really plan for. The accommodation that suits the parents is rarely the one that suits the grandparents. The flight that’s cheapest is rarely the one that gets a tired family through customs at a sensible hour. The “must-do” experience for the teenagers is often the one that leaves the four-year-old in tears by lunch.
Our job as your Illawarra travel agent is to listen to who’s actually travelling and structure the trip so all of that holds together. The first call is free. If you want us to build the full plan, there’s a $150 planning commitment — credited back in full when you book your trip through Roam Wisely.
The destinations we specialise in.
These are the trips we plan most often for Illawarra families — and the ones we’ve travelled ourselves, often with our own grandchildren in tow. That’s research no brochure can do.
USA Family Holidays
Hawaii, the mainland theme parks and the big cities. We break the long flight and plan the order so day one feels exciting, not exhausting.
Japan Family Holidays
Easier than people expect with grandparents — transit is excellent, no driving required. We map the pacing across cities and seasons.
South Korea Holidays
Seoul and beyond, with on-the-ground knowledge a brochure can’t give you. Great for families wanting something a little different — easy public transport and plenty to keep every generation interested.
Australian Family Escapes
From Queensland’s theme parks and beaches to the trips closer to home. Short flights, easy logistics, and rest days built in.
Family Cruises
Departing from Sydney, so no flights at the start. We match the right ship, cabin layout and itinerary to your specific family — ideal for three generations.
DIY holiday planning vs. using a local travel agent.
Not a sales pitch — just an honest comparison of what each looks like when you’re planning a multi-generational family trip.
Doing it yourself
- ✕20+ hours of research across ten or more browser tabs.
- ✕Guessing whether a hotel has stairs — or sits 40 minutes from where you actually need to be.
- ✕Flights chosen on price that land everyone at 11pm, exhausted, on day one.
- ✕No backup when a flight is cancelled mid-trip. You sort it out at 2am with airline support.
- ✕Discovering visa issues three weeks before departure — along with the school clash and the missing transfer.
Planning with us
- ✓One 30-minute call and a structured plan built for you — no more solo research spirals.
- ✓Verified accommodation that genuinely works for three generations, not whatever ranks first.
- ✓Flights routed around family energy and arrival windows, so day one feels exciting, not exhausting.
- ✓A phone call away to a local NSW agent if a flight is cancelled or plans change mid-trip.
- ✓Proactive handling of visas, school clashes and logistics — sorted before they become a problem.
Three steps to a trip that works for everyone.
You don’t need more browser tabs. You need a structure the whole family can travel inside.
Free Planning Call
A 30-minute conversation about who’s travelling, what matters and what you’ve already half-decided. No quote pressure — we just want to understand the trip first.
Your Family Plan
We build the pacing, bases, transport, room layouts and must-do priorities. $150 planning fee, credited back when you book your trip through us.
Book & Travel
We coordinate the flights, hotels, cruises, tours and insurance. If plans shift mid-trip, we’re here. You travel; we handle the changes.
Local to the Illawarra — by phone or video, wherever you are.
Most planning happens over the phone or by video, so you don’t need to travel at all to work with us — whether you’re in Wollongong, Figtree, Dapto, Shellharbour or down towards Kiama. Paul and Simon are based in Richmond; for Illawarra families, phone and video keep things simple, and you get the same hands-on planning either way. Mon–Fri, by appointment.
Real trips. Real reviews.
Amazing team, sorted everything for us so we didn’t have to worry about our holiday. Couldn’t recommend them more.
Very helpful when booking my trip to the Gold Coast — easy, quick and clear experience.
Very helpful in being able to book and help plan my trip to the USA. The detail and care was excellent.
The questions Wollongong and Illawarra families ask first.
Do I need to come into an office to work with you?
No. Most planning calls happen by phone or video — we work the same way whether you’re in Wollongong, Figtree, Dapto, Shellharbour or anywhere across the Illawarra. Paul and Simon are based in Richmond; for South Coast families, phone and video are almost always the easier path, and you get exactly the same planning. We’re appointment-only — book a call and we’ll set a time.
Are you really local, or is this a marketing thing?
We’re a genuine NSW family business — Paul and Simon, based in Richmond. We’re not a national chain with a local branch. We plan trips for families right across the Illawarra, and because we live and travel in NSW we know the airport runs, the school-holiday weeks and the road and rail realities that actually affect your trip from Wollongong.
I’m in Shellharbour / Kiama / Dapto — should I still call?
Yes. We work with families right across the Illawarra, from the northern suburbs and Wollongong through to Figtree, Dapto, Shellharbour and Kiama. Almost everything is done by phone and video, so wherever you are on the South Coast, working with us is simple.
What’s the easiest way to get to the airport from the Illawarra?
For most international and interstate trips it’s Sydney’s Kingsford Smith — roughly ninety minutes up the M1, more in holiday traffic — so we plan departure times around the Mount Ousley and motorway crawl, and we’ll flag when the South Coast Line is the easier option with kids and bags. Shellharbour Airport at Albion Park covers a few domestic routes, and where one suits your trip we’ll build it in.
Is the first call really free, with no obligation?
Yes. The initial 30-minute planning call is on us, with no obligation. If you decide to move ahead with detailed planning, a $150 planning commitment applies — and it’s credited back when you book your trip through Roam Wisely. If we’re not the right fit, we’ll tell you that on the first call.
What’s actually included in the $150 planning commitment?
The planning commitment covers the structured work after the free call — building a trip plan tailored to your family, including pacing, accommodation recommendations, transport, room configurations, must-do priorities and any specialist research (visa, insurance, medical considerations). It’s credited back in full when you book through us.
What if our trip is mostly domestic — is it worth using a travel agent?
For one or two travellers on a simple domestic trip: often no — you can book it yourself in under an hour. For three generations travelling together: almost always yes. The value comes from the hours we save you, the small decisions we make so the trip works for everyone, and the support if something goes wrong mid-trip.
Do you book everything, or just plan it?
We do both — but planning comes first. We build the plan, then if you’re happy with it, we book the flights, accommodation, cruises, rail, tours, theme park tickets and travel insurance. One team, one phone number to call if something needs adjusting.
What countries do you specialise in?
Australia, Japan, the USA, South Korea, Singapore, the UK and Ireland — plus regular trips to Fiji, Bali, New Zealand and the South Pacific. We’ve travelled to all of these with our own grandchildren in tow, which is the kind of research no brochure can do.
Do you do cruise bookings as well?
Yes — South Pacific, Disney Cruise Line, P&O, Royal Caribbean, Princess and most others. Cruises are particularly good for multi-generational trips because grandparents can rest while parents and kids do more energetic things. We help match the right ship, cabin layout and itinerary to your specific family.
What’s the best time to call?
Mon–Fri during business hours — the booking calendar above lets you pick any 30-minute slot that suits you, including some after-hours options. If you’d rather just call, the number is 02 45 099 240.
How far in advance should I be planning?
For multi-generational international trips, ideally 6–9 months out — particularly if school holidays are involved, or if Japan, the USA or Europe in summer. We can absolutely work with shorter timelines, but the earlier we start, the more options you have on flights and accommodation.
Are you IATA accredited?
Yes. Roam Wisely is IATA TIDS accredited, an Aussie Specialist (Tourism Australia) certified agent, and holds a series of destination certifications including Tokyo Tourism Expert, Nevada Trailblazer, California Star and Ireland Specialist. ABN 26 798 035 783.
Let’s plan a trip that works for everyone.
Free 30-minute planning call. No quote pressure. No upselling. We’ll tell you straight whether your trip idea will hold together — and what to do if it won’t.
Verified 5★ reviews · IATA accredited · Family-owned, serving Wollongong & the Illawarra
