Booking Software Buyer's Guide: 5 Questions Before You Choose

Choosing booking software is one of the most impactful decisions a charter operator makes. The wrong choice costs you money every month. The right choice saves you time, books more trips, and grows with your business.

Before you compare features or pricing, answer these five questions about your operation. They'll narrow your options dramatically.

Question 1: What's Your Monthly Booking Volume?

This is the single most important factor for choosing a pricing model.

The Math That Matters

Take your average monthly revenue and multiply by the percentage fee you'd pay. If that number is higher than a flat monthly fee, you're overpaying.

Example: 40 trips × $500 = $20,000/mo. At 7%: $1,400/mo in platform fees. A flat $39-89/mo saves you $1,300+ every month.

Question 2: How Important Is OTA Distribution?

Be honest: where do your customers come from?

If Most Customers Find You Through OTAs (Viator, GetYourGuide):

• You need a platform with strong OTA integrations
• Channel management (syncing availability) is essential
• FareHarbor, Rezdy, and Bokun excel here
• The distribution justifies higher fees

If Most Customers Find You Directly (Google, referrals, social):

• OTA integration is a "nice to have," not essential
• You're paying percentage fees for distribution you don't use
• Flat-fee platforms or simple booking tools work fine
• Invest the savings in Google Ads or social media instead

The 80/20 Question

Where do 80% of your bookings come from? If it's direct, you don't need to pay for distribution infrastructure you barely use.

Question 3: What Features Do You Actually Need?

Every platform advertises 100+ features. Most operators use 5-10 regularly. Identify yours:

Charter-Specific Features to Look For

These features matter specifically for fishing charters but aren't standard on tour platforms:

• Weather cancellation policies: Automatic handling based on conditions
• Multi-boat scheduling: Managing several boats with different capacities
• Captain/crew management: Assigning crew to trips
• Fishing-specific waivers: Maritime risk disclosures
• Equipment tracking: Rod counts, safety gear, bait inventory
• Tide/conditions awareness: Trip timing based on water conditions

Question 4: What's Your Growth Plan?

Where will you be in 2-3 years?

Staying Solo (1 boat, 1 captain)

• Simple is better. Don't overpay for multi-boat features you won't use.
• Flat pricing protects you as you maximize your single boat's bookings.
• Focus on reliability and ease of use.

Growing Fleet (2-5 boats in 2-3 years)

• Multi-boat scheduling becomes essential
• Staff management features matter
• Make sure the platform scales without dramatic price jumps
• Can it handle different trip types on different boats?

Building a Brand (Multiple locations, employees)

• Enterprise features (API, white-label, custom workflows) become relevant
• OTA distribution might matter more at scale
• Consider platforms with dedicated account management
• Data portability matters — you don't want to be locked in

Question 5: What's Your Actual Budget?

Be realistic about what booking software is worth to your operation.

The Value Calculation

A good booking system pays for itself through:

• Reduced no-shows: Even preventing 2 no-shows/month at $500/trip = $1,000 saved
• Time savings: 5 hours/week of admin work × your hourly rate
• More bookings: 24/7 online booking captures customers you'd otherwise miss
• Fewer mistakes: Double-bookings, missed confirmations, lost waivers

If your software costs $100-200/month and prevents even a single no-show, it's paid for itself.

What You Should Pay

Notice: as your revenue grows, booking software should cost a smaller percentage. If it doesn't (because you're on percentage pricing), you're subsidizing the platform's growth with your success.

Making the Decision

Step 1: Answer the Five Questions

Write down your answers. Be honest, not aspirational.

Step 2: Eliminate Mismatches

Any platform that doesn't fit your volume model, feature needs, or budget is out. Don't force a fit.

Step 3: Try Before You Buy

Any platform worth considering offers a free trial or demo. Use it. Book a fake trip. See how the customer experience feels.

Step 4: Check the Exit

Before committing, understand:

• Can you export your customer data?
• What happens to upcoming bookings if you switch?
• Is there a contract term? Cancellation fees?
• Who owns your customer email list?

Step 5: Start Simple

You can always upgrade later. Start with the platform that solves your immediate problems (online booking, deposits, reminders) and grow into advanced features as you need them.

Common Mistakes to Avoid

1. Choosing based on the biggest feature list — you'll use 10% of features. Choose based on the 10% that matters to you.
2. Ignoring the pricing model — the cheapest-looking platform at low volume becomes the most expensive at high volume.
3. Not considering switching costs — if you'll outgrow the platform in a year, factor in migration hassle.
4. Overlooking mobile experience — your customers book on phones. Test the mobile booking flow yourself.
5. Forgetting about support — when something breaks at 6am before a charter, can you get help?

The best booking software is the one that fits your operation today and can grow with you tomorrow — at a price that makes sense at every stage. Answer the five questions, do the math, and choose with confidence.