Dr. Paul Borosky, DBA, MBA
A Business Consultant’s Perspective
Do Key West Customers Come Back?
In the second half of 2025, 55 percent of Key West visitors surveyed for the Monroe County Tourist Development Council had not been to the Keys in the previous three years.
Source: Monroe County TDC visitor profile survey, Key West, July to December 2025 (first-time or lapsed visitors).
So many Key West customers do not come back, at least not on their own. You can be the best charter captain, bartender, or guesthouse host on the island and still be new to the business side of keeping customers, and that side is where Dr. Paul, Key West business consultant, helps you get organized. The answer is a repeat-customer system: capture the name, give a reason to return, and stay in touch, with visitors and locals alike.
Questions first? Call or text Dr. Paul at (321) 948-9588.
Last Updated: 10/29/2026 · Written by Dr. Paul Borosky, DBA, MBA
The Key West Reality
An Island Where Many Customers Are Just Passing Through
Key West runs on visitors. That brings a steady stream of new faces, and a built-in problem: a big share of them may not be back for years, if ever. Here is what the Monroe County Tourist Development Council’s own visitor surveys show.
Sources: Monroe County TDC visitor profile surveys by Rockport Analytics, Key West, second half of 2025 and Keys-wide, annual 2025 (survey samples, not total visitor counts); airport figure via Key West Citizen.
Read that first number again. More than half of the Key West visitors in that survey were new to the Keys or had not been in years. A shop on Duval Street, a charter, or a guesthouse could be serving a mostly new crowd every season. Meanwhile, the locals who live here year round see every business on the island, and they remember who treated them well. Repeat customers Key West owners can count on come from both groups.
So the job is twofold: turn visitors into return trips and referrals, and turn locals into regulars.
Key West Resources Worth a Call
- City of Key West Business Tax Receipt
Needed to do business within city limits, which cover the Island of Key West and part of Stock Island north of U.S. 1. The City says receipt holders should also get a Monroe County Business Tax Receipt. City licensing FAQ.
- Greater Key West Chamber of Commerce
The island’s chamber, active on local issues like the future of Mallory Square. Key West Chamber.
- Florida SBDC at FIU
Hosted by Florida International University and serving Miami-Dade and Monroe counties. Find the center.
- Upselling vs. Cross-Selling: Examples for Small Business
Ready for Help?
Four Ways to Work With Dr. Paul
01 · Start Here
Business Consulting
Build your customer list, return offer, and seasonal follow-up with Dr. Paul, sized for an island business.
Business consulting →02
Business Plan Writing
Planning to expand on the strength of repeat customers? Dr. Paul writes the plan and the financials a lender wants.
Business plan writing →03
Fractional CFO/COO
Want someone tracking repeat sales and cash through the season with you? Dr. Paul works with you part time.
Fractional CFO and COO →04
Small Business Education
Learn customer retention, referrals, and marketing basics at your own pace with free guides written for owners.
Small business education →Two Kinds of Customer
Visitors and Locals Come Back for Different Reasons
Do Key West customers come back? The ones you plan for do. But a visitor and a local need different reasons, and one system does not fit both.
| Question | Visitor customer | Local customer |
|---|---|---|
| How often can they buy? | Once a trip, maybe once a year | Every week or every month |
| What brings them back? | A reason to book again next trip | Habit, convenience, and being known by name |
| Their biggest value to you | Referrals and reviews back home | Repeat visits all year, including slow months |
| What to capture | Email, home city, trip month | Name, phone, what they usually buy |
| Best follow-up | A note before next season and a share-with-a-friend offer | A regulars perk and a personal thank you |
Most owners collect nothing from either group. The fix is a habit: capture the name, give a reason to return, and stay in touch. The small business marketing guide covers each piece.
Score Yourself
The Repeat-Customer Scorecard
Give yourself 0 for no, 1 for sometimes, and 2 for yes, every time. Be honest. Nobody sees this but you.
| Statement | No | Sometimes | Always |
|---|---|---|---|
| You can pull up a list of last year’s customers today | 0 | 1 | 2 |
| You capture a name and contact on most sales | 0 | 1 | 2 |
| Customers get a clear reason to come back (a perk, a booking, a next service) | 0 | 1 | 2 |
| You contact past customers at least once a season | 0 | 1 | 2 |
| You ask happy customers for referrals and reviews | 0 | 1 | 2 |
| You know roughly what share of this month’s sales came from repeat buyers | 0 | 1 | 2 |
0 to 4: every customer is a one-time sale, and you pay full price to replace them. 5 to 8: the pieces exist but nothing connects them. 9 to 12: you have a system. Now track the repeat share every month and push it up.
Scored low? That is the Organize step of Dr. Paul’s Organize-Plan-Grow™ Strategy: get the customer list in one place before you try to grow it.
The Key West Calendar
Fantasy Fest, the Navy, and Repeat Customers Key West Owners Miss
Two local groups come back on a schedule of their own. Plan your follow-up around them.
Sources: Keys Weekly, Fantasy Fest 2026; Military OneSource, Naval Air Station Key West.
Fantasy Fest was started by local owners to bring visitors in during a slow October, and Keys Weekly says it draws tens of thousands each year. That makes it a ready-made return date. Capture names during the festival, then send a short note in late summer with next year’s dates and a reason to book with you again.
The Navy has been in Key West since 1823, and Naval Air Station Key West sits on Boca Chica Key. Military families could be your most loyal locals while they are stationed here, and the most useful referrals when they leave. Ask a family that is moving on to pass your name to the family taking their place.
From the Book
Dr. Paul’s Insight: Word of Mouth Needs a Push
“I’ve never spent a coin on marketing. Word of mouth works! Doesn’t it?”
Dr. Paul’s take: Word of mouth works, but on its own it circles the same crowd. The room stays full of the same faces until those faces move away or stop coming. In Key West, where so many customers are visitors, waiting for word of mouth alone could mean waiting a long time. A simple ask, a referral card, or a note before next season gives the word a way to travel. Read more on making word of mouth work on purpose in the small business marketing guide.
Show the Math
How One Sale Turns Into Five
Winning a new customer costs far more than keeping one. Here is why, with made-up numbers you can swap for your own.
Illustration · made-up Key West charter, rounded numbers| Where the sale comes from | Sales | Revenue at $150 |
|---|---|---|
| The first booking, found through $60 of advertising | 1 | $150 |
| The same customer books again on next year’s trip | 1 | $150 |
| Two friends they referred book their own trips | 2 | $300 |
| A reader of their review books | 1 | $150 |
| Total from one paid customer | 5 | $750 |
Same $60 of advertising. One way, it buys $150 in sales. The other way, it buys $750, and the ad cost per sale drops from $60 to $12. What changed is that the owner captured the name, asked for the review, gave a referral card, and sent a note before next season.
The same math works for a local coffee counter or salon, just faster: one new regular who comes back four more times this year is five sales from one win. For the rest of the sales questions in this series, see the South Florida business consultant page.
Keep the Customers You Win
The Book on Word of Mouth That Works
Dr. Paul’s Fabled Forest Business School Series · Book 4
Marketing for Small Businesses
Word of mouth, referrals, reputation, and follow-up, taught through one Fabled Forest owner per chapter. Chapter 19 is about the owner whose room is always full of the same faces. Part of Dr. Paul’s Fabled Forest Business School Series, with a worksheet at the end of each chapter you can use the same day.
Get Book 4 on Amazon →FAQ
Repeat Customer Questions Key West Owners Ask
How do I get customers to come back?
Can a tourist business really get repeat customers?
Do I need a City of Key West Business Tax Receipt and a Monroe County one?
Can Dr. Paul help me build a repeat customer system?
The cheapest customer in Key West is the one who already knows you.
Keep Going
More for Key West and South Florida Owners
Dr. Paul Borosky, DBA, MBA
Business Consultant, Author & Educator | 14+ Years | 1,000+ Clients Served
Dr. Paul Borosky, DBA, MBA is a business consultant, author, and educator, and the founder of Quality Business Plan. He works with Key West and South Florida owners on customer retention, referrals, and marketing, business planning, financial modeling, fractional CFO services, and the everyday problems of businesses that depend too much on their owners. He is the creator of Dr. Paul’s Organize-Plan-Grow™ Strategy, author of numerous published books on Amazon including Dr. Paul’s Fabled Forest Business School Series, and publisher of over 1,000 business-focused videos on YouTube. He has taught as an adjunct college instructor and teaches in Florida public schools.
This page is for general educational purposes only. It is not legal, financial, tax, accounting, or other professional advice. Any worked example uses an illustrative business with rounded figures; local data is cited to its sources and changes over time. For decisions about your own business, consult a qualified professional.