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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 · 23 Oct 20265 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, and What to Book First

Things to do in St. Croix, from Buck Island and the Salt River bio bay to forts, rum and Cane Bay, plus what to ask before you book a boat.

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, from a Caribbean boat guy

How I'd spend a St. Thomas day as a Caribbean boat guy: beaches, boat trips, St. John, and when I'd book through the ship.

Getting paid7 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.

Selling online5 min read

Tour guide jobs: what operators look for when hiring

What operators look for when they hire tour guides and boat crew, from job types to work permits, and why the trial day beats your CV.

Running the day5 min read

How to start a boat rental business: what I'd check first

I walk through starting a self-drive boat rental: bareboat rules, renter cards, insurance, fleet, and why the checkout briefing matters most.

Getting paid10 min read

Why Tour and Charter Operators Keep Getting Flagged as 'High-Risk' Merchants (and What Actually Fixes It)

Tour and charter bookings get coded MCC 4722 — here's why that reads as high-risk, what Visa/Mastercard chargeback rules mean, and what actually fixes it.

Getting paid5 min read

GetYourGuide vs Viator: which to list on first

GetYourGuide vs Viator for Caribbean operators: audience, commission, cancellations, payouts and calendars, and why I'd list on one first.

Selling online7 min read

TripAdvisor Instant Booking: It's Really Viator

TripAdvisor Instant Booking for tours runs entirely on Viator. Here's the real commission, fees, eligibility rules, and a yes/no framework for operators.

Running the day5 min read

How to get a captain's license: what I'd tell a new deckhand

Getting a US six-pack or Master license, plus why deck time as a mate matters more than the paper before you run guests.

Caribbean business5 min read

Things to do in Anguilla

Should you day-trip Anguilla or stay? An operator's take on beaches, the cays, the ferry crossing, local food and boat racing.

Selling online9 min read

Axe Throwing Booking Software: What It Actually Needs

Axe-throwing and escape-room venues need waivers that block check-in, per-lane/room capacity, and reset buffers — not generic tour booking software.

Selling online5 min read

How much to tip a tour guide, from the operator side

How much to tip a tour guide, what I see guests give on Caribbean boats, and how operators should handle crew pools, card tips, and gratuity.

Running the day4 min read

Tour Operator Itinerary Software: What the Crew Actually Needs

A guide to itinerary software: test whether the guest plan and crew's working view stay in sync from booking through departure.

Selling online8 min read

Bike Tour Booking Software: Fleet Tracking & Routes

Generic tour platforms cap bikes by category, not by frame. Here's what bike tour booking software needs for fleet tracking and multi-day routes.

Getting paid5 min read

Food Tour Booking Software: What I Would Compare Before I Pick One

A practical way to compare food tour booking software: test the guest booking, host handoff and guide's day-of list before you choose.

Getting paid9 min read

Checkfront Pricing: What You Actually Pay (2026)

Checkfront costs $99/month plus a 3% booking fee — and that's before payment processing. Here's what you actually pay at real booking volumes.

Running the day5 min read

How to Start a Tour Guide Business: What I Would Get Right First

My operator's take on what to get right before launching a tour guide business: the trip, real costs and booking handoff.

Caribbean business5 min read

Things to Do in Bonaire: What I Would Build Around as a Tour Operator

My operator's take on Bonaire day trips worth building around: reef, wind, mangroves, land outings and what to tell guests before they book.

Getting paid11 min read

Charter Boat Crew: 1099 Contractor or W-2 Employee? A Plain-English Guide

Captain, mate, or dockhand — 1099 or W2? A plain-English test for charter crew, plus the seaman exemption and what misclassification actually costs.

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