$1000/mo Helping People Plan Trips: Inside the Travel Advising Side Hustle

What if you could turn your love of travel into an extra income stream and build a travel advising side hustle that fits your life?

Bailey Richert is back on the show to pull back the curtain on how you can do it too.

You might remember Bailey from one of our early episodes, where we talked about building an online course business. Today, we’re switching gears to talk about her newest side hustle: helping people plan epic trips as a travel advisor.

Bailey runs UnlistedTravel.com and MakeTravelYourJob.com, and she’s managed to create a flexible, low-overhead business doing something she’s genuinely passionate about.

Listen to Episode 670 of the Side Hustle Show to learn:

• how travel advisors actually get paid
• what it takes to set yourself up for success in this field
• creative ways to find clients

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How Travel Advisors Make Money with a Side Hustle

To show what’s possible as a travel advisor, Bailey shared a recent trip she planned for a couple heading to London.

This was a 6-day, 5-night romantic getaway, and she charged a $100 upfront planning fee — non-refundable, and common among travel advisors today. Planning fees usually range from $20 to $50 per day of travel, so $100 was a fair starting point.

After that, Bailey got to work crafting their itinerary: booking hotels, tours, and transfers.

The real earning potential comes from commissions. Bailey booked her clients at the Fleming’s Mayfair Hotel in central London and earned a 15% commission — higher than the usual 8-12% because of her host agency partnership.

The hotel booking totaled $2,442, and 15% of that came out to $366. With her 70/30 split with the host agency, Bailey kept $256 from the hotel booking alone.

Add that to her $100 planning fee, and she earned $356 on a single trip — without factoring in extras like transfers or tours, which could have added even more.

As she put it, “Your job as the travel advisor is to be thinking about all of the different elements that someone is going to need on their trip… and also to make it enjoyable… You can be earning commissions on all these different things.”

How to Get Started with Your Travel Advising Side Hustle

Your job as a travel advisor isn’t just about planning a trip; it’s about making the whole experience easy for your clients.

You’re taking the overwhelm off their plate. You’re giving them peace of mind. And you’re helping them actually enjoy the process.

But to make things easy for your clients, first, you have to make it easy on yourself to get set up the right way.

You don’t need to go through months of expensive certification or licensing to become a travel advisor. Thanks to “host agencies,” you can get started a lot faster than you might think.

Here’s the basic setup Bailey recommended to build your travel advising side hustle:

Get an Accreditation Number

To book trips and earn commissions, you need an accreditation number, like an IATA number (International Air Transport Association).

You could apply for your own, but that route takes months and thousands of dollars.

Bailey’s recommendation is to join a host agency instead. They already have the accreditation, and you can use theirs to start booking right away.

Find a Host Agency

Bailey pointed to HostAgencyReviews.com as a great place to start your research. You’ll find reviews, comparisons, and insights into what each host agency offers.

Bailey herself works with Fora Travel, which she recommends for beginners. Fora charges $300 a year once you’re accepted — a small price to get access to their network, training, and tech tools.

Understand the Relationship

When you work with a host agency, you’re an independent contractor, not an employee.

You run your own business, set your own focus, and keep the bulk of your commissions.

In exchange, the host agency handles the vendor relationships and tracks down your commissions, so you can stay focused on serving your clients and building your brand.

Creative Ways to Market Your Travel Advising Business

Almost every travel advisor starts the same way through word of mouth.

Your first clients are often friends, family, and people already in your network. Maybe you’re already the “go-to travel person” for your circle.

(You can also learn more from Bailey directly through maketravelyourjob.com)

But Bailey shared a ton of smart ways to go beyond that and start building a real client pipeline.

1. Offer a Referral Incentive

Bailey uses a strategy where she tells her clients, “If you refer another person to me who ends up successfully booking a trip, I’ll waive your planning fee for your next trip.”

You lose a little on the next planning fee, but you gain a whole new paying client. Plus, it taps into your network’s network.

2. Specialize in a Niche

You could focus on:

• Luxury travel (bigger commissions)
• Business travel and retreats (small companies often need help)
• Location-specific expertise (like being the go-to person for Japan trips)
• Theme-specific trips (like honeymoons or adventure travel)
• Cruises (which Bailey mentioned is an entire specialty on its own)

Having a specialty makes it way easier for people to refer you — “Oh, you want to plan a honeymoon? You have to talk to Bailey!”

3. Host Location-Themed Events

For example, Bailey suggested hosting a Japan-themed dinner night where they:

• Serve traditional food
• Give a short, fun presentation about the country
• Highlight a few resorts or experiences you can book (plus perks they get through you)
• Pass out your business card at the end

4. Attend Trade Shows Where Your Clients Hang Out

Instead of just sitting behind a computer, get out there!

Bailey knows a travel advisor who specializes in romantic trips and honeymoons, and she simply attends bridal shows, mingling with brides and handing out her card. She doesn’t even rent a booth!

You could also team up with local bridal shops, photographers, or event planners… anywhere your ideal clients are already gathering.

5. Offer Free “How to Travel” Info Sessions

You can do it in places like libraries or community centers. You can discuss how to apply for a passport, when you need a visa, or even common travel mistakes to avoid.

These events naturally attract people who are interested in traveling but might feel overwhelmed.

6. Start a Location-Specific Facebook Group

For example: “Travel Tips for London Visitors.”

Share tips, answer questions, build trust. And when people are ready to book a trip, you’ll be the obvious person to help them.

It’s the same strategy Rob Pitingolo used for his DC walking tour business — sharing free, helpful content upfront that led people to book his services later.

7. Organize Trips for Local Groups

Sometimes opportunity is right in front of you.

Bailey mentioned how local groups (like a book club that just read a novel set in Ireland) might want to organize a group trip.
You could be the one to step in and plan it for them.

8. Connect with Local Businesses

Finally, don’t underestimate small businesses in your area.

While “corporate travel advisor” might sound imposing (you’re probably picturing a huge Fortune 500 company), tons of local businesses need help planning retreats, incentive trips, or executive travel.

Reach out to your local chamber of commerce or networking groups and let them know you offer travel services.

Tools/Tech

CRMs:

• Travelify
• Traveljoy
• Tern

Itinerary Builders (If your CRM doesn’t come with a built-in one):

• Safari Portal
• Canva (if you’re still starting)

Will AI Replace Travel Advisors?

Bailey had a really clear and refreshing take on this.

Yes, AI can be a helpful tool. It can spit out a sample itinerary or suggest popular places to visit.

But AI can’t customize based on your style and needs. Can it call a trusted private driver in Colombia? And when a flight gets canceled or plans change mid-trip, you’re not calling ChatGPT for help.

As Bailey put it, the people who use AI to plan their trips “aren’t really my ideal clients anyway.”

Her clients want a personal touch, insider access, and the peace of mind that everything’s handled.

Mistakes or Surprises?

One of Bailey’s biggest mistakes is thinking your host agency will send you clients. In reality, you have to market yourself — through referrals, events, networking, and content. Clients don’t just show up.

Another is not taking the business seriously. If you’re not investing in systems, marketing, and client service, it’s easy to burn out.
Even if you’re starting small, treat it like a real business from day one.

And for her biggest surprise, she realized she was already planning trips for free and didn’t know she could turn it into a paid side hustle. If people already trust you for travel advice, you might have a business ready to go.

Travel Perks, FamTrips, and Smart Tax Tips

Being a travel advisor can come with some great perks, but you’ve got to be smart about it.

Some travel expenses might be tax-deductible if you’re running a real business. Bailey recommends checking with a pro like TaxesForTravelAgents.com to stay on the safe side.

Fam trips are discounted or free trips for travel advisors to learn about destinations and hotels. They are great when running your travel advising side hustle.

You can find opportunities through vendors, DMOs (Destination Marketing Organizations), or sites like Mexico FamTrips.

Tip: You usually need to be actively booking clients to qualify.

Even on personal trips, Bailey suggests reaching out to business development managers at hotels. Introduce yourself, ask for a quick tour, and start building the connections that can set you apart.

What’s Next for Bailey?

Bailey’s aspiring to expand her travel advising business beyond friends and family and becoming a go-to travel expert for a wider audience.

She’s also passionate about showing others how flexible and rewarding the travel advising world can be, especially for millennials and Gen Z travelers who want more freedom without going full digital nomad.

Bailey’s #1 Tip for Side Hustle Nation

2025: “Don’t buy that premium domain.”

2016: “If you want people to buy your courses, provide value. Make it a no-brainer.”

Episode Links

• Episode 184 with Bailey Richert
• 11 Exciting Ways to Get Paid To Travel The World
• UnlistedTravel.com
• MakeTravelYourJob.com
• HostAgencyReviews.com
• Fora Travel
• Is ClickASnap Legit? How Photographers Can Make Money From Photo Views
• Travelify
• Traveljoy
• Tern
• Safari Portal
• Canva
• $100k with AI-Coded Apps
• TaxesForTravelAgents.com
• Mexico FamTrips

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