Skip to content

How To Start A Profitable Multi-Day Tour Company [Ep. 87]

This post contains affiliate links to trusted partners. If you purchase through these links, I earn a commission at no extra cost to you. Thank you!

By Jessie Festa. This episode on how to start a tour and travel business contains affiliate links to trusted partners I think you’ll love!

Want to learn how to start a multi-day tour company that takes people to exciting destinations around the world?

Well, you’re in luck, as in this episode of The Profitable Travel Blogger Podcast, we’ll be going over how to start a travel and tour business.

Our guest for the episode is Kelly Lewis, the founder of the boutique women’s tour company Damesly. By the end of this episode, you’ll understand:

  • How to choose your tour destinations
  • What goes into planning a tour itinerary
  • Tips for pricing your tours
  • How to market your tours so that they are profitable
  • And more!

In short, if you’re confused about how to start a tour and travel business the right way, this episode can help.

Table of Contents

How To Start A Multi-Day Tour Company [Podcast Episode Audio]

Click here to listen on Apple Podcasts/iTunes

Click here to listen on Spotify

Click here to listen on Amazon Music

Click here to listen on TuneIn

Invite: How To Make Money As A Travel Blogger [Free Workshop]

While we’re on the topic of blog monetization, I’d love to invite you to my free workshop: 10 Powerful Ways To Make Money Travel Blogging.

During the 60-minute on-demand workshop, you’ll learn:

  • Myths related to monetizing a blog (that may be holding you back!)
  • Strategies for creating profitable content (so those blog posts, emails & social shares lead to income!)
  • Tips for earning recurring passive revenue as a blogger (so your income grows even when you’re away from your laptop!)
  • How to create products that you know your audience will buy (so you don’t waste your time!)
  • Advice for growing your affiliate income (with a strategy that truly works!)
  • And more!

Plus, your free ticket to this actionable workshop also includes a Q&A, limited-time replay, and special bonuses.

Click here to grab your seat in the free travel blog monetization workshop.

how to start a multi-day tour company

How To Run A Tour Company [Episode Transcript]

The following is a summary of the podcast episode sharing how to monetize your blog through tours. It is transcribed as best as possible, with paraphrasing included. For the full strategy on how to launch a tour company, make sure to listen to the audio version of the podcast above.

One of the biggest struggles for many travel bloggers is trying to figure out how to monetize. And one way to really take control of your income is to create your own products, services, and experiences.

A very natural product to create is a multi-day tour—which is exactly what we’ll be discussing how to do in this episode.

Our guest is Kelly Lewis, the CEO of Damesly, a boutique women’s tour company that travels to Jordan, the Philippines, Greece, Morocco, and more.

In this episode, Kelly will be sharing how to choose your destination, plan your tour itinerary, pin down your pricing, and other tips to help you create and launch your own profitable tours.

If you’re curious about how to start a travel and tour business, keep reading to learn important steps for getting set up for success!

1) Thank you so much for taking the time to share your tips! To start, can you tell us more about yourself and your business, and what inspired you to start a tour company?

My name is Kelly Lewis, and I’m the founder of Damesly, a boutique tour company exclusively for women.

Damesly was born out of a realization in 2016. As I looked at the tour industry landscape and conversed with friends in the travel sector, it became evident that there was a gap in the market.

While there were tours tailored to the younger demographic and those catering to seniors, there seemed to be a lack of options for women in their thirties and forties—professionals with disposable income yearning for travel experiences tailored to their needs.

Thus, Damesly emerged from the idea of creating a community for women like us who desired to explore the world in a comfortable and enriching environment.

Damesly multi-day tour company homepage
Damesly is a boutique multi-day tour company for women

2) For a travel blogger who might be thinking about launching tours, what are some of the pros and cons they should be aware of?

I’ve been in the travel industry for quite some time. Before starting Damesly, I was a travel blogger. My first travel blog, Travel Bug Juice, began in 2009.

Then, I ran GoGirl Guides, providing guidebooks for women starting in 2010, followed by the Women’s Travel Fest.

I mention this to highlight that I didn’t start from zero; I already had a community of female travelers.

For me, starting a tour company seemed like a natural progression. We were discussing travel, providing travel tools, suggesting destinations—why not actually take people traveling?

The biggest challenge in starting a company is identifying the target market.

Initially, it may feel like you’re only talking to friends and family, constantly sharing on Facebook. This self-promotion can be draining, but it’s important to be persistent.

In terms of starting a tour, the pros include getting paid to see the world, forming lifelong friendships, and being part of a transformative journey for your clients.

I’ve witnessed clients evolve over eight days—from being reserved and going through tough times like divorce to coming alive and tapping back into their energy. This is powerful and overrides all the cons.

Speaking of cons, there are many. It’s not an easy job; there’s always a risk of something going wrong, medically or with client relationships. There are times when you’ll need to steer the ship back on course during a tour.

It’s a learning process, but for me, the pros far outweigh the cons.

tour group hiking to Tiger's Nest in Bhutan
Traveling the world and helping people have transformative journeys are two of the biggest pros to starting a tour company. Photo of the Tiger’s Nest in Bhutan, one of Damesly’s many destinations, is via suketdedhia / Pexels.

3) Let’s say this travel blogger has decided, yes, I want to move ahead with launching my first tour. What should their first step be?

Start with destinations you’re familiar with, which will make creating a tour much easier.

For instance, when I began, I organized tours to Hawaii and Arizona, places I knew well.

Craft your offer based on your knowledge of the destination. Build partnerships with destination marketing companies or organizations.

As you grow, focus on where you want to go and what experiences you want to offer. And, always prioritize enjoyment in your business.

4) I also own a local tour company called NYC Photo Journeys, where the tours are all local to New York. So I find this idea of selecting destinations for your tours fascinating. How do you go about choosing where you’ll go on your international tours?

For our multi-day adventures, we prioritize bucket list experiences that are difficult to plan independently.

Take our Kenya tour, for example, where guests stay at the Giraffe Manor. It’s exclusive and requires connections to secure a reservation, making it a coveted experience.

Giraffe Manor is a favorite of Damesly’s guests, as they get to interact with Rothschild’s giraffes. Photo: Frans van Heerden via Pexels.

Another example is the Albuquerque Balloon Fiesta, which demands some planning but offers a unique travel adventure.

We ensure these experiences are seamlessly packaged for our clients. Our enthusiasm for these destinations is genuine and contagious, translating into genuine excitement for our clients.

This passion is key to driving sales and creating memorable experiences. Remember that as you make your own tour.

5) Once you’ve chosen the destination you have to create the itinerary. How do you go about putting this together and also handling the logistics from abroad?

When organizing international tours, we rely on local partners known as Destination Management Companies (DMCs).

If you’re curious about how to start a travel tour company or how to put together a tour itinerary, DMCs will be a really important component.

These are our on-ground operators who handle logistics such as transportation, accommodations, and local guides. They possess invaluable local knowledge and expertise, making them essential for crafting seamless itineraries.

Finding reliable DMC partners. Finding dependable DMC partners is crucial. We conduct thorough research online, seek recommendations from travel communities, and leverage personal connections forged through extensive travel experiences. This collaborative approach ensures that our international multi-day tours are meticulously planned and executed.

Tailoring itineraries to client preferences. Collaboration with our DMC partners is key to crafting exceptional itineraries. For instance, when planning a luxury tour to India, we prioritize comfort while visiting iconic sites like the Taj Mahal. We work closely with our partners to arrange transportation and other logistics, ensuring every detail meets our high standards.

Aligning pricing with quality service. Understanding our clients’ preferences is paramount. Initially, I struggled with pricing, but over time, I realized the importance of aligning pricing with the level of service we aim to provide.

Recognizing industry diversity. As you dive into how to start your own tour business, realize that the tour industry offers a range of experiences, from budget to luxury. To succeed, it’s crucial to define your target audience and tailor your messaging, itinerary, and pricing accordingly.

This journey of self-discovery involves refining offerings to resonate with your ideal clientele. Start by understanding who you want to serve and build from there.

tour company owner creating an itinerary budget
Align your tour pricing with quality service to offer an amazing guest experience. Photo: Karolina Grabowska via Pexels.

6) How do you go about pricing a tour, and are there other financial considerations they should be thinking about?

When it comes to how to run a tour company, one of the most important considerations is pricing. Here are some tips:

Determining tour price beyond per-trip profit. When pricing a tour or creating a business plan for a tour operator, it’s essential to look beyond per-trip profitability. Consider the annual financial needs of your business—including operating expenses, employee salaries, and benefits—and ensure that your pricing aligns with the long-term sustainability of your business.

Acknowledge the mental aspect of pricing. Sometimes, you can justify higher prices by offering flexible payment options. For example, if a Kenya Safari is priced at $9000, offering a payment plan or setting up a customer portal for flexible payments can make it more manageable for clients.

Consider your personal salary & business sustainability. Factor in your personal salary requirements and what the business needs to thrive, and also think about the inclusions you offer in your tours and their perceived value to your clients. Pricing should reflect the level of service you provide and cover the expenses necessary to maintain your business operations.

Adjusting pricing for sustainability. In my early days as a tour operator, I priced tours under $3000 for an eleven-day trip, which proved unsustainable. A colleague’s feedback prompted me to reassess. I increased prices by $1000, delivering a higher level of service. Surprisingly, clients appreciated the enhanced experience and were willing to pay a higher price.

Don’t be afraid to adjust prices. Clients often recognize and are willing to pay for quality. Don’t hesitate to adjust your pricing to reflect the value you provide. Over time, I’ve learned that quality service justifies higher prices. Don’t be afraid to adapt your pricing strategy to better align with your business goals and the expectations of your clientele.

group of women on a Damesly international tour
Damesly tour group

7) How do you build and maintain relationships with local businesses and attractions in the destinations you operate?

Building and maintaining relationships with local businesses and attractions is straightforward—it’s about being a good person and conducting business with integrity:

  • Paying invoices on time,
  • taking care of your partners,
  • and showing genuine interest in their well-being fosters trust and loyalty.

In Morocco, for instance, our operators have become close friends whom we communicate with regularly, not just about business but also on a personal level.

Similarly, our partnerships in Cuba are built on mutual respect and camaraderie.

It boils down to honesty, frequent communication, asking questions, and treating them with the same respect and care as you would a friend.

Maintaining these relationships is essential as they are integral to the success and enjoyment of our tours.

8) How do you go about successfully marketing your tours and getting people to book?

While I wish I could give an exact methodology for how to market a new tour, effective marketing will vary for everyone; however, I can tell you what has worked for us:

1. Growing and nurturing an email list. Every time we send out a newsletter, we make a sale. Weekly newsletters and trip drops via email are instrumental in driving bookings. We also have a dedicated Facebook group, the “Dames List,” where we offer first dibs to our travelers.

2. Lead generation advertising. While paid advertising hasn’t been highly successful for us, lead-generation ads have shown promise. For instance, our ad for an upcoming Philippines tour directs interested individuals to a form, allowing us to capture their emails for future marketing efforts.

3. Building a community. Community building and regular social media posting are essential. SEO has also played a significant role in our visibility.

Media outreach has helped boost our SEO, as we were featured in prominent publications like the New York Times, Elle, Shape, and Cosmopolitan, enhancing our credibility and visibility.

A note on budget considerations. When researching how to open a tour company, you may be tempted to hire a company to help you market.

In my experience, while media outreach is helpful, hiring a PR company may not be the best use of limited startup funds. It’s essential to prioritize spending and focus on strategies that bring the best results.

magazines on a table
While media outreach can help market your tour, think twice about spending too much on an expensive PR company when you’re first launching your tour company. Photo: EVG Kowalievska via Pexels.

9) How do you handle unforeseen challenges or disruptions during a tour?

Dealing with unexpected challenges is inherent to the nature of travel, but we’ve found ways to handle these issues and prepare, like:

Empowering tour leaders. Damesly employs 11 tour leaders who undergo extensive training to handle various scenarios. Recently, we launched a “Certified Tour Leader” course to share our expertise and equip others in the industry.

Financial empowerment is crucial, so each leader receives a petty cash allowance to address unforeseen expenses and enhance the tour experience, even in challenging situations.

Embracing adaptability. Travel disruptions can range from bus breakdowns to group conflicts, but we view them as opportunities to pivot and enhance the experience. For instance, during a bus breakdown, our leaders might use petty cash to treat everyone to ice cream, improving spirits despite the setback.

Each challenge is a chance to find creative solutions and elevate the tour experience.

Setting clear boundaries and decisions. Early on, I learned the importance of decisiveness in tour itinerary planning.

Instead of offering multiple options for activities, clarity is key. By setting a definitive plan, we avoid potential disappointment and confusion among travelers.

Additionally, maintaining high energy and positivity as a tour leader is crucial, as our demeanor sets the tone for the entire group’s experience.

Continuous learning and growth. Every challenge provides valuable lessons in boundaries, trip structuring, and self-awareness. I’ve honed my approach over the years, recognizing the importance of clear communication, adaptability, and maintaining positive energy throughout the journey.

Keep these tips in mind as you dive into how to start a tourism company.

Be decisive when creating the itinerary for your tours. Whether you visit the waterfall or go snorkeling, your guests will love it! Photo: Francesco Ungaro via Pexels.

10) Thank you so much for sharing your wisdom about how to start a tour operator business! Before we sign off, can you let everyone know where they can find you?

Thank you!

Alright, now I hope you enjoyed this episode. I hope you feel inspired and empowered to monetize your blog by starting a tour company.

Before you go, don’t forget to grab access to the 10 Ways To Make Money Travel Blogging Workshop, which will help you monetize your blog faster and easier.

And of course, make sure to subscribe so you don’t miss future episodes sharing these bite-sized strategies for bloggers who want to turn their blogs into profitable full-time businesses.

Happy blogging!

Monetize Your Blog With These Helpful Past Episodes:

How To Host Profitable Retreats

How To Create Content That Sells & Converts On Social Media

How One Woman Quit Her Job To Blog Full-Time

How Niching Down Can Help You Grow & Monetize Your Blog

15 Creative Ways To Promote Affiliate Links

How To Grow & Monetize On Instagram As A Blogger

How To Make A Resources Page That Grows Your Blogging Income

6 Ways To Validate An Online Course Idea

How To Increase Your Amazon Affiliate Income As A Travel Blogger

How To Create A Free Email Course That Grows Your List & Income

Click here for all profitable blogging podcast episodes.


Connect With The Profitable Travel Blogger Podcast

Stay In The Loop

Do you want to get notified when new episodes publish?

Then make sure to opt-in for podcast email notifications sent to your inbox!

You can do that by clicking here.

Subscribe + Review (To Win A Prize!)

Love learning new blogging strategies to help grow your website traffic, community, and income?

Click here to subscribe on iTunes to be notified when new episodes publish.

I’d also be extremely grateful if you’d leave a review right here and let me know your favorite part of the episode or a takeaway you walked away with. By leaving a review, you help the show be seen by more people, helping the episodes to have a greater impact.


Each month, I’ll be choosing one reviewer at random to win a FREE seat inside one of my masterclasses.

Winners can choose from:

  • How To Grow Your Blogging Income Through Facebook Ads
  • How To Land Paid Press Trips As A Travel Blogger
  • How To Make Money (Fast) With Affiliate Marketing
  • How To Start A Tour Company In Your Own Backyard
  • How To Start A Blog, Grow An Audience & Make Money
  • Build Your Blogging Profit Plan Masterclass

Winners will be chosen at random from the reviews and will be notified via email, so make sure to send me — jessie (at) jessieonajourney dot) com — your email address so I have it. 


What are your top tips for how to start your own tour company?

Enjoyed this episode on how to start a travel tour business? Pin it for later!