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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 2

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: The Charter Operator's Map

Anguilla from the helm: who books charters, the marine park rules, Road Bay clearance and cruising permits, and how to quote and stand out.

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.

Selling online5 min read

What Makes a Good Tour Guide? What I Learned on the Boat

What I learned from Eagle Tours: a strong tour guide pays attention to guests and crew, knows their limits, and gives new guides room to grow.

Running the day5 min read

How to become a Viator supplier: what I would prepare

What I would have ready before opening the Viator supplier portal: one trip, a clear meeting point, net vs retail, cut-offs, held seats, a weather plan.

Running the day9 min read

Charter Boat Maintenance Checklist: What Keeps You Legal, Insured, and Running

USCG inspection items, safety-gear service intervals, and the records insurers want — the charter-specific maintenance checklist generic boat guides skip.

Getting paid5 min read

Boat Rental App vs Booking Software: What I Would Actually Compare

A boat operator's practical comparison of guest apps, booking software, shared availability, payments, crew handoffs, and a two-week test.

Selling online13 min read

Mailchimp vs Klaviyo for Tour Operators: Picking an Email Platform for a Seasonal Booking Business

Both are built for online stores. Here's how Mailchimp and Klaviyo actually compare for a seasonal tour or charter business's pricing, lists, and reminders.

Running the day5 min read

SEO for Tour Operators: The First Page I Would Fix Before Buying Ads

A founder's practical take on SEO for tour operators: fix the trip page and booking path before buying ads or chasing more traffic.

Caribbean business5 min read

Aruba Snorkeling Tours: What I Would Build Around as an Operator

An operator's guide to building an Aruba snorkeling tour around clear promises, clean handoffs, weather plans, and a day the crew can deliver.

Getting paid7 min read

Tap to Pay on iPhone for Tour and Charter Operators: Is It Worth Ditching the Card Reader?

Tap to Pay on iPhone costs the same as a reader but needs signal for every sale. Here's when it works dockside and when charter operators still need a reader.

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