The 5-5-5 Guest Experience System

Get 10 more reviews in 30 days. Small moments that move ratings and repeat stays.

You get judged in 15 minutes

Ever wonder why your best hospitality gets “just okay” reviews? Guests remember peaks and endings. You can design those moments. Here’s your playbook to turn the next five bookings into raving fans and better reviews.

The 5-5-5 method: engineer memorable guest moments

You’re judged in three windows:

• First five minutes: arrival and first impression set the tone.

• Best five minutes: personalized surprise, micro-itinerary, proactive fix.

• Last five minutes: checkout, warm farewell, easy review.

Nail those and you’ll see higher reviews, more repeat bookings, and fewer “how do I get in?” texts.

5-5-5 sprint targets

• Reviews in next 30 days: +10 vs last 30

• Average rating lift: +0.1 to +0.2

• First reply time: under 15 minutes

• Night-one check-in sent: 5 of 5 bookings

• Reviews posted: at least 3 of 5 bookings

Scoreboard (copy/paste)

Track your next five bookings with this:

Here is an example:

Paste this table somewhere visible. At Day 30, reply with a screenshot, and I’ll share anonymized highlights in a future issue!

Plug-and-play message templates

First reply after inquiry
Hi {First Name}, welcome to {Property}. I saw {trip reason}. One thing that would make this stay perfect? Reply with codes like 1B 2A 3C 4D and your must-do. I’ll prep it.

Night-one check-in
Quick check on {Property}. How’s everything so far? Anything I can improve by tomorrow? I noted your {preference} and can handle fast fixes.

Review request (24–48 hours after check-out)
Would you share one tip future guests should know about {Property}? It helps others choose well and means a lot for small places like ours. {Review Link}

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“Stay Fit” guest quiz

Email this quiz to your guests. (Reply with codes like 1B 2A 3C 4D.)

1. Travel style: A) Relax and recharge B) Explore everything C) Work and focus D) Family-friendly

2. Morning drink: A) Coffee B) Tea C) Neither

3. Pillow firmness: A) Soft B) Medium C) Firm

4. Arrival time: A) Before 3 pm B) 3–6 pm C) 6–9 pm D) After 9 pm (late)

5. Must-do for this trip: {short answer}
   Anything else we should know? {optional note}

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Arrival brief blueprint (5 bullets)

Parking photo
Wi-Fi password
Door code
Where the coffee lives
Late-night food options

Low-cost surprise ideas

Vacation rental: one local snack that fits most diets + two nearby grocery suggestions.
Boutique hotel: offer a choice of three welcome scents or playlists at check-in.

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5-5-5 checklist

First 5: lights on, Wi-Fi visible, clear door code, personal welcome line, local tip.
Best 5: surprise matched to quiz, a micro-itinerary, a fix offered before they ask.
Last 5: easy check-out, thank-you message, review link, forgotten-item plan, warm goodbye.

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Fail-safe plan

If a guest flags an issue, reply within 10 minutes, thank them, state the fix, confirm when done, and add a $5–$10 make-good matched to their quiz preference.

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14-day rollout

Days 1–2: paste the three core messages into your PMS or CRM.
Days 3–4: add the quiz macro and a “preference” field to guest profiles.
Days 5–6: write the arrival brief and include one photo.
Days 7–8: stock 30 tiny surprises under $3 each.
Days 9–10: create short review links and set a 48-hour follow-up.
Days 11–12: test messages with a friend and remove any jargon.
Days 13–14: run 5-5-5 on two bookings, then standardize.

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Copy this into your AI tool

Act as a hospitality copywriter. I operate a {vacation rental, boutique hotel, or other property} in {location}. Create three guest message templates that feel warm and human: first reply after an inquiry, night-one check-in on night one, review request 24 to 48 hours after check-out. Keep each under 60 words, include one field for a saved preference, avoid buzzwords, and write in my voice: friendly, clear, welcoming. Provide placeholders in braces.

From the blog

If bookings feel harder than they should, map the guest journey and fix the hidden friction. Small, aligned actions build trust and loyalty fast. Read more.

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Run the 5-5-5 pilot

Paste the scoreboard, send the three messages, and reply with a screenshot on Day 30. I’ll share anonymized highlights in a future issue.

Always time for you

Stuck or just want to say hi? I always have five minutes for you. Reply to this email with a question or a quick hello. I read every note personally.

Cheers,
Kay @ Smart Pineapple 🍍

PS: 🎙️ New podcast, short and practical. If you like this newsletter, you’ll love the show. Follow on Apple | Spotify

Try 5-5-5 now. Share your scoreboard and join the movement of hosts who make moments—and get the reviews they deserve.