Switching Booking Software: The Pre-Season Checklist

The coastal season runs full through the summer. The window to change booking systems is roughly October 1 to mid-January: late enough that the season has shown you what broke, early enough to be live and tested before spring.

Work through this in order. Steps 1 and 2 come before you talk to anyone, because they set your deadline.

Step 1. Find your contract date first

Do this before you shop. Half an hour.

• Locate your current agreement, not the marketing page
• Write down the renewal or end date
• Write down the notice period and count backward to your real deadline
• Note how notice must be given: email, a specific address, or a form
• Put all three dates in your calendar now, with a warning two weeks before the deadline

What the vendor terms say, as of September 2026: FareHarbor's terms provide for 15 days' notice. Peek Pro renews automatically and requires notice 30 days before the renewal date. Others vary.

Treat those as a starting point, not your answer. Read your own contract. Terms change, and yours may have been negotiated. If your platform charges a percentage or a fee to your renters, get the exact rate from your own statements rather than from any figure you read online, including ours.

Step 2. Export everything while you still have access

Two hours. Do it before you give notice, not after.

• Customer list with names, phone numbers, email addresses
• Full booking history: dates, carts, amounts, statuses
• Signed rental agreements and waivers, with the date each was signed
• Damage and condition records, plus the photo files themselves
• Payout and settlement history for your accountant
• Any custom pricing, coupon or discount setup, screenshotted if it will not export

• Open every file you exported. A CSV you have not looked at is not a backup.
• Store the exports somewhere permanent that is not the old platform

Chargebacks and insurance claims land months later, about bookings from a system you no longer have a login for. This step is why.

Step 3. Sort out card processing

One to five business days, mostly waiting.

• Find out whether your current processor is yours or the platform's
• If the platform runs its own merchant account, you are opening a new one and you should start now
• If you have your own Stripe or Square, check the new platform connects to it
• Confirm where in-flight refunds get issued from during the cutover
• Note your payout schedule on the new setup, because it may differ

Underwriting on a new merchant account can take days. Starting this late is the most common reason a switch slips past the window.

Step 4. Stand up the new booking page on a subdomain

An afternoon.

• Pick a subdomain: book.yourbusiness.com or reserve.yourbusiness.com
• Point the DNS record at the new platform and confirm the certificate is active
• Leave your existing website exactly as it is

You are changing where bookings are taken, not rebuilding your site. Your pages keep their rankings, your Google Business Profile keeps its link, and if the new system disappoints you, you change one link back.

Step 5. Rebuild the fleet by hand

An afternoon for twenty carts.

• Every cart entered with year, make, model, VIN, plate
• Photos uploaded, primary photo chosen
• Existing damage logged on each cart before the first rental of the season
• Rates, weekly discount and any minimum or maximum rental length
• Rest days between rentals, so a cart cannot be booked out before it is cleaned and charged
• Delivery zones and fees, or pickup location and hours
• Add-ons with their stock counts
• Tax rate and any state or local surcharge, as its own labeled line
• Minimum driver age
• Blackout dates

Doing this by hand rather than importing is how you find out what the new system actually models, before a customer does.

Step 6. Load your agreement and your terms

An hour.

• Rental agreement text entered and reviewed for this season
• Cancellation, weather and late-return terms match what the agreement says
• Confirm the platform records which version of the agreement each booking signed

Step 7. Test the whole path yourself

An hour. Do not skip this.

• Book a real cart on a real date with a real card
• Sign the agreement as a renter would
• Check the confirmation email arrives and reads correctly
• Cancel it and issue the refund
• Confirm the money moved in both directions
• Do it once on a phone, because most renters book on a phone
• Have someone who does not work for you try it and watch where they hesitate

You will find two things wrong. Everybody does.

Step 8. Handle bookings that span the cutover

Ongoing until the last one clears.

• List every reservation already taken for dates after your switch
• Decide: re-enter them in the new system, or run them out in the old one
• If re-entering, block those dates in both systems so nothing double-books
• If running them out, keep the old account live and read-only until the last one returns
• Tell affected renters only if something they see changes, such as a new confirmation email

Step 9. Give notice

Ten minutes, on the date you calculated in step 1.

• Send notice in the exact form the contract requires
• Keep a copy and note the date sent
• Ask for written confirmation that the account will not renew
• Confirm when your access ends, and pull a final export the day before

Step 10. Switch the links

An hour.

• Booking button on your website
• Google Business Profile appointment link
• Facebook and Instagram bio links
• Any listing, directory or property-manager page pointing at the old system
• Your own text shortcuts and email signatures

The realistic timeline

Two to four weeks from first demo to live, if merchant onboarding cooperates. Most of that is waiting, not working. The hands-on time is roughly a day and a half spread across a few weeks.

If you start in October, you have room for something to go wrong. If you start in February, you do not.

Vendor terms and notice periods were checked against published vendor documents in August and September 2026 and change without notice. Your own contract governs. Nothing here is legal advice. We rent carts at Welaka Golf Carts and built Greenlit to run it.