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Running a tour business, written by people who do.

Guides on selling, getting paid and running the day, from operators in the Caribbean and beyond.

Running the dayMichael · 13 Nov 20265 min read

How to Deal With Difficult Customers on a Tour

How to deal with difficult customers on a tour or charter: close the information gap before they board, then listen, hold safety calls and refund wisely.

Caribbean business5 min read

Things to Do in Puerto Rico: An Operator's View of Demand

What visitors to Puerto Rico book, who sells it, and what that means for tour and charter operators, from cruise piers to bio bays and the Ceiba ferry.

Caribbean business5 min read

Sargassum Season: What It Means for Caribbean Tour Operators

Sargassum season runs spring to early fall. What 2025 and 2026 records mean for Caribbean tour operators, and why guest messaging matters most.

Running the day5 min read

Snorkeling Gear Guide for Snorkel Tour Operators

A former snorkel captain on stocking a loaner fleet: mask sizes, full-face policy, cleaning between guests, vests vs life jackets and sunscreen laws.

Getting paid5 min read

Stripe vs PayPal for Tour Operators: A Caribbean Take

Stripe vs PayPal for tour operators: fees, payouts, disputes and guest checkout, plus Caribbean account and withdrawal limits.

Running the day5 min read

What Is a Deckhand? The Job From the Deck to the Wheel

What is a deckhand on a Caribbean tour boat? The daily work, what operators hire for, deckhand salary data, and how the job leads to captain.

Caribbean business5 min read

Things to Do in Nassau: What Tour Operators Sell

Nassau saw 6.1 million cruise guests in 2025, but a crowded wharf is not a full boat. What sells, where bookings come from and the rules operators face.

Caribbean business5 min read

What Is Shoulder Season? A Caribbean Operator's Take

What is shoulder season? The stretch between peak and low season. Here's when it hits the Caribbean and how operators should price and staff it.

Running the day5 min read

How to Start a Kayak Rental Business: Wind Comes First

How to start a kayak rental business: gear costs, permits, insurance, pricing, wind rules and a lost-paddler plan, from a St. Maarten boat guy.

Selling online5 min read

Wix vs WordPress for Tour and Charter Operators

Wix vs WordPress for a small tour or charter business: real monthly costs, who maintains it, mobile speed, booking widgets and what breaks in season.

Getting paid12 min read

Caribbean Tour Operators Using Stripe With a US or European Bank Account: Is It Legal, and What Does It Cost You in Tax?

Running your island tour company's cards through a US or European Stripe account? What it can break, what tax you still owe locally, and how to fix it.

Selling online5 min read

Boat Names for Charter Operators: What Sells, What Sinks

Boat names that sell: how charter and tour operators can pick a name guests can say, search, find on booking pages and pass on to friends.

Caribbean business5 min read

Things to Do in Cozumel: Where the Bookings Come From

What Cozumel visitors book, who sells it, and the park rules, port closures and sargassum that shape the week for tour and charter operators.

Caribbean business4 min read

Regenerative Tourism: What It Means for Tour Operators

Regenerative tourism for Caribbean tour and charter operators: what it means, why guests ask, and what to do that's real rather than greenwashing.

Running the day5 min read

How to Start a Jet Ski Rental Business

How to start a jet ski rental business: permits, insurance, buying skis, safety briefings, pricing, deposits, weather rules and online booking.

Selling online5 min read

Wix vs Squarespace for Tour and Charter Operators

Wix vs Squarespace for tour and charter operators: 2026 prices, booking tools, widgets, languages, and why your booking engine matters more.

Running the day5 min read

Family Business Succession for Tour and Charter Operators

Family business succession for tour and charter operators: what to move out of the founder's head and phone long before anyone takes over.

Caribbean business5 min read

Things to Do in St. Croix: Running a Small-Island Product

What St. Croix visitors book, and what it means for operators: few cruise calls, hotel desks, Buck Island concessions and moon-timed bio bay trips.

Caribbean business5 min read

Caribbean Tourism Statistics: What They Mean for Operators

Caribbean tourism statistics: what the CTO 2025 and 2026 numbers mean for operators, from cruise vs stayover guests to seasonality and your own bookings.

Selling online5 min read

Fishing Charter Marketing: Sell the Captain and the Date

Fishing charter marketing: sell the captain, show your open dates, price half and full days clearly, and turn fish reports and past anglers into bookings.

Getting paid5 min read

Stripe vs Square for Tour and Charter Operators

Stripe or Square for a tour business? Compare US rates, payouts, refunds, disputes and holds, and check your island is supported before anything else.

Running the day9 min read

Pre-Purchase Marine Survey for a Charter Boat: What It Actually Costs (and What It Catches Before You're Stuck With It)

What a pre-purchase marine survey costs per foot, what surveyors check, and how findings affect your USCG inspection and insurance underwriting.

Running the day5 min read

Charter boat captain salary: what the job really pays

Charter captain pay isn't the day rate, it's the year. An operator's take on day rates, tips, slow season and keeping good captains.

Caribbean business5 min read

Things to Do in St. Thomas: An Operator's Cruise-Day Map

What St. Thomas visitors book, where the bookings come from, and the park, Coast Guard and BVI rules that shape a tour business there.

Getting paid8 min read

Interchange Fees, Explained for Tour and Charter Operators

What is an interchange fee? A plain-English breakdown of the three-layer card fee stack, with a worked tour deposit vs. balance payment example.

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