What I Learned Running a Tour Business for Over 30 Years

Business Summary

Lauren Heffernan built Ciclismo Classico around a combination of cycling, travel, education, and personal connection. Her account emphasizes hands-on sales, distinctive tour design, strong guide relationships, and marketing that builds trust—not just reach.

Strategy, Product, and Growth

• Start with a focused offer and grow from experience. Lauren began with two Tuscany tours, based on her familiarity with the roads and region. She did little formal market research; she believed cycling and Italy would attract customers and started small.
• Differentiate through themes and interests. Rather than presenting only routes or destinations, Ciclismo Classico organizes tours around passions such as food and wine, culture, history, islands, and family travel. Its slogan, “Pedal your passion,” reflects this approach.
• Use “matchmaking” to fit customers to trips. Lauren asks about a prospective guest’s cycling experience, fitness, interests, and preferred settings, then recommends an appropriate tour. The website also labels tours by difficulty, such as beginner or intermediate.
• Sell the experience, not just the itinerary. Lauren cautions against letting customers compare tours only by price, hotels, or services. She sees guides, routes, and the overall experience as key parts of the product, and describes active travel as potentially transformative.
• Keep innovating. Tour concepts may emerge from a theme, a local discovery, or an event. Lauren’s approach is to develop an idea, test it, and see what resonates, while recognizing that each idea needs an execution plan.

Sales and Customer Qualification

• Prioritize direct conversation. The website accepts booking inquiries, but customers cannot simply enter a credit card and complete a booking. The team prefers to speak with prospects to understand their needs and confirm the trip is a good fit.
• Qualify through questions and listening. Lauren asks whether someone has taken a bike tour before and invites them to describe themselves and what they enjoy. She says she can often assess fit within a few minutes of conversation.
• Treat the customer list as a long-term asset. In the early days, Lauren personally called leads, sent holiday cards and paintings, and built relationships over time. She still checks in with past customers individually.
• Use automation without losing the personal touch. The company has a website chatbot, but Lauren often handles the chat herself. She values technology while continuing to favor direct contact.

Marketing and Public Relations Playbook

• Make excellent delivery the foundation of marketing. Lauren identifies referrals and repeat business from satisfied guests as among the most effective forms of growth.
• Build relationships through events. Ciclismo Classico has run a jingle ride and a film festival. During the pandemic, the company used Zoom to host cooking lessons and wine events led by tour guides. The events served existing customers, introduced new people to the company, and gave guides a way to stay engaged.
• Combine digital reach with human connection. The company works with a social media marketing agency and uses Facebook and Instagram campaigns. Lauren says digital leads can be costly and short-lived, while event contacts and personal relationships may stay in the database for years.
• Use PR around a specific angle. Lauren recommends identifying what is distinctive or newsworthy—for example, the Eroica vintage-bike ride in Tuscany—rather than pitching only a general destination or tour. She has pursued coverage through tourism-industry conferences, local publications, and community partnerships.
• Vet outside partners. Before working with influencers, agencies, or other providers, ask for references, contact past clients, and check whether the partner has delivered similar results. Lauren applies the same principle to hiring.
• Maintain a steady email relationship. The company sends a weekly email blast, usually on Sunday mornings, featuring carefully selected photos and useful or inspiring content as well as trip promotions. Lauren also writes blogs and uses social posts to test which topics and angles resonate.
• Use low-cost, relationship-led marketing. Lauren describes guerrilla marketing as investing time and energy when a startup has little budget. Her example is building the business one customer relationship at a time.

Hiring, Guide Development, and Retention

• Recruit for service orientation, energy, and humility. Lauren values people who enjoy sharing knowledge and serving guests. Teachers and people with hospitality experience can be strong candidates.
• Look beyond enthusiasm for the activity itself. A guide who mainly wants to ride may not be right for a guest-facing role. Lauren looks for curiosity, initiative, responsiveness, and a willingness to help.
• Screen through multiple signals. Her process includes phone conversations, resumes, guide meetings, and training. She also considers practical requirements such as first-aid knowledge and mechanical skills.
• Build tours collaboratively. Some guides have proposed and developed itineraries in regions they know; Lauren gives the example of a guide who helped create the company’s first Piedmont trip.
• Retain guides through autonomy and appreciation. Lauren credits long tenure to meaningful freedom on tours, trust in guides’ personalities and judgment, empathy for the demands of the job, good communication, and pay she says is above industry standards.
• Invite staff input. Guides help scout and shape itineraries, giving the product contributions from across the team.

Website, Systems, and Distribution

• Curate the website around customer interests. Its thematic categories grew out of the company’s printed brochures and Lauren’s view that the offering is broader than cycling alone.
• Vet website providers carefully. After earlier problems with websites, Lauren chose a provider based on due diligence and a commitment to a robust site with a long shelf life.
• Use third-party booking channels selectively. The company uses Peak 15 and works with TourRadar to some extent, but Lauren notes that these channels require significant setup and ongoing administration. They have not become the company’s primary growth engine.
• Value sales partners who curate. Lauren recalls All Adventure Travel as effective when it represented a small group of operators and knew their offerings well. She believes that depth of knowledge can be more useful than a large, undifferentiated marketplace.

Metrics and Timelines Mentioned

• 30+ years running the business; Lauren described having 31 years’ experience during the interview.
• Two tours in Tuscany in the company’s first year.
• An initial database of about 100 leads; Lauren estimated converting roughly 80% through personal follow-up.
• Approximately 50 tours in the company’s broader inventory, with around 50 offered in a given year and offerings rotated. Custom and private tours were in particularly high demand at the time of the interview.
• Tour guides and staff had an average tenure of about 10 years, according to Lauren.
• The company sends a weekly email newsletter, generally on Sunday mornings.
• Lauren described a historical magazine article as filling two or three trips in one instance.
• The interview included an example of a customer exploring a 60-day Italy trip for a 60th birthday with 60 friends; it illustrates custom-trip interest, not a typical booking.
• Lauren described paid digital leads as having become substantially more expensive, but gave no specific CAC, revenue, margin, or conversion benchmarks.

Presenters and Sources Mentioned

• Presenters: Lauren Heffernan (Ciclismo Classico) and Shane Whaley (Tourpreneur host).
• Organizations, platforms, and sources discussed: Ciclismo Classico; Tourpreneur; ATTA conferences; Outside magazine; Bicycling magazine; California Bicyclist; All Adventure Travel; A29 (website provider); Peak 15; TourRadar; Facebook; Instagram; Zoom; Strava; and the Wanderer app.
• People and collaborators named: Chris Torres (social media marketing); guides Claudio Bisio, Marcello, Sandro, and Elisa.