One of the costliest mistakes in outdoor hospitality isn’t underspending on acquisition; it’s ignoring past guests. While operators are rightfully investing to capture new, first-time guests, the highest-ROI bookings come directly from guests who already know, trust and love your property.
There are two reasons this is a significant source of future bookings:
- Repeat Cycles: Transient, seasonal, and long-term guests alike have built-in repeat booking habits.
- Referral Power: Outdoor hospitality is deeply fraternal. Future bookings frequently stem from direct word-of-mouth recommendations.
The Typical Math Behind Lifetime Guest Value
| Segment | Stay Value | Frequency Per Year | Years Active | Lifetime Value Estimate |
| Weekender | ~$250 | 3x | 8 | $6,000 |
| Annual Vacationer | ~$600 | 1x | 6 | $3,600 |
| Seasonal | ~$3,000 | 1 Season | 5 | $15,000 |
| Full-Time | ~$750/mo. | 12x | 1.5 | $13,500 |
Passive Guest Retention Costs You Revenue
Assuming repeat bookings are ‘built-in’ or happen organically is a high-risk assumption. While exceptional service and overall positive experience lay the foundation, passive reliance leaves your repeat pipeline vulnerable to proactive competitors, both in the local market and from afar.
You can minimize this erosion risk and give yourself the best possible shot at retaining the repeat booking (and in many cases, accelerate the velocity even more). How? With strategic outbound touches:
- One-to-All: Full database communications conveying upcoming on-site and local area events, property updates, special pricing and a ton more.
- One-to-Many: Segmented outreach campaigns targeted by stay history, i.e., timely messaging to last year’s Memorial Day weekend guests during next season’s peak booking windows with advance re-booking incentives.
- One-to-One: Highly personalized outreach that speaks precisely to who they are, when and how they stay, and what matters to them based on the data, preferences and tags via an integrated PMS (property management system) or CRM (customer relationship management) platform.
When it comes to driving and accelerating retention, the math adds up fast. Retain just one guest from each segment above for a single year, and you’re looking at over $13,000 in stay value. Multiply that across a real, active guest base, and the numbers get serious quickly.
It’s not unreasonable to assume no one reads emails anymore or responds to texts, but that’s simply not what the facts say. You might ignore retail emails for months until you need a new jacket. The moment you’re in the market, that email becomes a launching point. Your guests operate the exact same way. Outbound outreach works because it meets buyers at the exact moments of intent.
The Email Funnel: What the Data Shows
Here’s what we commonly see across outdoor hospitality email campaigns, which is drawn from both client and published industry benchmarks from many of the sources you’re likely familiar with.
| Email Conversion Per 500 Emails Sent | Amalgamated Outdoor Hospitality Data |
| Open Rate | 25% – 35% |
| Click Through Rate | 3% – 5% |
| Booking Conversion Rate (% of Clicks) | 10% – 18% |
| Bookings | 2 – 4 |
That data’s for “one-to-all.” Segmented “one-to-many” lists spike conversions considerably and one-to-one outreach drives bookings into the double digits.
Turning Word-of-Mouth into a Systematized Channel
Referrals represent another massive revenue engine and, in many ways, are even more compelling. We regularly conduct proprietary guest insight surveys and the data below, gathered from over 2,000 completed responses across a cross-section of property types and regions, reveals a clear pattern in how outdoor hospitality guests discover properties:
All Properties

Long-Term/Seasonal Properties

For all property types, the total Referral from Friend spread is 12% to 57%.
So, what are you doing to drive and ensure active and enthusiastic referrals from your guests to family, friends and associates?
While this is happening organically, the smart properties are taking it beyond “tell a friend.” How? Via the same methods described above in guest retention and expansion, i.e., timely and tasteful outbound communications.
How Do You Communicate With Your Acres of Diamonds?
Here are the primary ways that work best when used complementarily.
- Email & Text are typically handled by your Property Management System (PMS), a CRM or commonly on a manual basis through platforms like Mailchimp or Constant Contact, which both offer crucial compliance, templates and ease of use for either channel (email or text).
- Phone is the most straightforward with the fewest dependencies. You have the data and relationship context; it’s about picking strategic times in your calendar to make personal outreach.
Everything’s Better When It’s Wired Together: Automating the Engine.
The basics above are doable by any property, almost immediately. But wiring your website, PMS, (and CRM where applicable) together to automate outreach, thank-you messages after checkout, a follow-up call task two weeks later, and seasonal offers before peak booking windows creates an automated retention and referral engine instead of a hope.
This doesn’t require a from-scratch build; it starts with mapping what to say, to who, and when. From there, the right technical integrations do the heavy lifting and repetitive tasks. And candidly, you already know how all this works…you’re on the receiving end of this from the greater hospitality industry all the time.
The key message is: thanks to evolutions in technology, it’s all within your grasp to do and do in a very specific-to-outdoor hospitality and highly personal way.
Summary
Driving retention and referrals is a proven driver of new reservations, and the cost in time, effort, and money is fractional compared to most acquisition strategies. By treating your guest list as an active asset rather than a static database, you protect and mine your acres of diamonds and secure higher-margin revenue for years to come.
Gregg Kuperstein is the CGO of Indio by Big Rig Media, a marketing technology platform. To have a conversation or explore the value of your acres of diamonds reach out here: https://www.getindio.com/acres-of-diamonds/.











