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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.

Articles, page 3

Selling online4 min read

Tour Operator Software With Inventory Management: What Actually Needs Tracking

A founder's view of the inventory details that matter when boats, crews, weather, and booking channels all share capacity.

Running the day5 min read

How to Start a Sunset Cruise Business: What I Would Set Up Before the First Guest

A practical founder-operator guide to building a sunset cruise product, route, weather plan, and booking handoff before the first guest.

Selling online8 min read

Google Ads for Tour Operators: Is Paid Search Worth It?

Real CPCs, minimum budgets, and Smart Bidding thresholds for tour operators weighing Google Ads — plus when SEO or direct booking wins instead.

Getting paid4 min read

Tour Booking Software vs a Spreadsheet: What Actually Breaks First

I compare the spreadsheet with the handoffs a tour booking system has to own, using the operator problem that started me building software.

Selling online7 min read

AI Chatbot for Tour Operators: What to Automate

A tour operator's guide to AI chatbots: what to automate (pricing, availability, cancellations) and what still needs a human.

Running the day4 min read

Tour Booking Handoffs: The Operator Story I Keep Coming Back To

Tour booking handoffs are where good trips get lost. I share the operator lesson that made me rethink every booking system.

Caribbean business5 min read

Things to Do in St. Lucia: What I Would Build Around as a Tour Operator

An operator's shortlist of St. Lucia products: the Pitons, Soufriere, Pigeon Island, and how to build tours the crew can actually deliver.

Running the day7 min read

Charter Boat Insurance Requirements for Six-Pack Operators

Six-pack charter insurance isn't one federal rule. See where marina, permit, and policy requirements come from, plus the coverage stack you need.

Selling online5 min read

SEO for Tour Operators: Why Your Booking Page Should Sound Like a Boat Schedule

A founder's practical take on writing tour pages guests can find, understand, and book - without turning your schedule into marketing jargon.

Running the day5 min read

Tour Operator Software With Reporting: What I Actually Check

The reports I would check before every trip: pending confirmations, deposits, balances, capacity, booking source, and the handoffs that still go wrong.

Selling online9 min read

Click-to-WhatsApp Ads for Tour Operators: A Cheaper Way to Get Direct Bookings in 2026

How click-to-WhatsApp ads work, what they really cost, and why they're a cheap direct-booking channel for tour and charter operators in 2026.

Getting paid5 min read

Jurassic Canyon Costa Rica: What I Would Compare Before Booking an Adventure Tour

A boat operator's take on what to compare before selling an adventure tour in Jurassic Canyon Costa Rica.

Getting paid8 min read

The 1099-K Threshold Rollback: What It Means for Your Tour Payouts in 2026

OBBBA raised the 1099-K threshold to $20K/200 transactions — but card payments have no minimum. Here is what tour operators actually need to know for 2026.

Running the day5 min read

Bus Charter Booking Software: The Handoff I Would Fix First

A founder's take on why the driver, office, and guest need one current bus charter trip record.

Caribbean business5 min read

Things to Do in San Diego for Couples: What Tour Operators Should Sell

A founder's guide to building romantic San Diego boat products that run well, from the route and weather plan to the booking handoff.

Getting paid11 min read

Credit Card Surcharge Laws by State: 2026 Guide

A plain-English, state-by-state look at where credit card surcharges are banned, capped, or disclosure-only in 2026 — and how tour operators add one compliantly.

Selling online5 min read

Attraction Booking Software: Where the Real Bottleneck Lives

The calendar is easy. A founder's take on the handoff between guests, agents, and the attraction crew.

Running the day5 min read

Kayak Rental Software: What I Would Set Up Before the First Launch

A dock-first guide to the kayak rental software checks I would run before the first guest arrives.

Running the day10 min read

OUPV License: What a Six-Pack Captain Actually Needs

The real OUPV/six-pack requirements: sea time, TWIC, drug testing, the exam, and what changes the day you take your first paid charter booking.

Getting paid5 min read

Adventure Tour Booking Software: What Has to Work When the Weather Turns

The ugly-day test I would use before choosing adventure tour booking software for a weather-sensitive operation.

Caribbean business10 min read

Things to Do in the Cayman Islands: An Operator's Shortlist

An operator's honest take on Grand Cayman: cruise-day picks vs. full-stay picks, Stingray City logistics, Bio Bay timing, and what to skip.

Running the day5 min read

Discounts Are Not a Booking Strategy: What I Learned Running Tour Boats

A founder-operator take on why blanket discounts miss the point - and how to use timing, capacity, and guest value to fill a specific departure.

Caribbean business4 min read

Montego Bay Hip Strip: How I Would Plan a Tour Around It

A practical operator guide to timing, pickups, and building a better Montego Bay Hip Strip tour.

Caribbean business10 min read

Things to Do in Antigua: An Operator's Shortlist

An operator's honest take on Antigua: cruise-day picks vs. full-stay picks, Shirley Heights timing, Stingray City, and the Barbuda day trip.

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