The 36-Month Guest Journey: Building Relationships That Last
From first stay to lifetime loyalty: The exact 36-month roadmap for turning one-time guests into repeat customers worth $3,000+. Includes timing, touchpoints, and real messaging examples.
Sarah's Journey: From Stranger to VIP
Month 0: Sarah books your cabin for a weekend getaway. She finds your property on Airbnb after 2 hours of searching. You're one of 47 listings she viewed. She books.
Month 1: She stays, loves it, leaves a 5-star review. You capture her email via your digital guidebook. She leaves feeling happy but has no plans to return.
Month 12: She receives your email: "Planning your next getaway? We have 3 weekends left this summer." She remembers how peaceful it was. She books again.
Month 24: She's now a repeat guest. You send a "VIP Winter Special - $200 off for you." She books her third stay and brings her sister.
Month 36: Sarah has stayed 4 times and referred 2 friends. Her lifetime value: $4,800. Her relationship with your property: priceless.
This didn't happen by accident. It happened because you had a plan.
Why Most Hosts Lose Touch After Checkout
Here's what typically happens after a great stay:
The Traditional (Broken) Approach:
The Solution: The 36-Month Guest Journey Framework
Instead of one-and-done transactions, think of each guest as a 3-year relationship. Here's the complete roadmap:
The Complete Guest Journey Timeline
📍Month 0: Foundation Phase (The Stay)
Goal: Deliver exceptional experience + capture contact info
Critical Actions:
✓ Success Metrics for Foundation Phase:
💌Days 2-7: Post-Stay (The Critical Window)
Goal: Cement positive memory + plant seed for return
Email Sequence:
Hi [Name],
We hope you made it home safely! It was wonderful having you at [Property Name] this past weekend.
[Personal touch: "We noticed you spent a lot of time on the deck - wasn't that sunset view amazing?"]
If you enjoyed your stay, we'd be grateful if you could leave us a quick review on [Airbnb/VRBO]. Your feedback helps future guests discover what makes [Property Name] special.
[Leave review button]
P.S. We'd love to host you again! Keep an eye out for special offers for returning guests. 😊
Warm regards,
[Your Name]
🌱Months 1-6: Active Nurture Phase
Goal: Stay top-of-mind through value-add content
Send 5-6 emails in the first 6 months. Not every email is about booking - most are about building familiarity and affinity.
Why This Sequence Works:
- 5 value emails : 1 ask email ratio builds trust before selling
- Each email reinforces positive memories of their stay
- You become the local expert they trust
- By Month 6, you're top-of-mind when they plan their next trip
🎯Months 8-12: First Re-Booking Window (Make or Break)
Goal: Convert to second booking - this determines if they become repeat customers
⚡ Why Months 8-12 Are Critical:
Industry data shows 75% of repeat guests book their second stay within 8-18 months of their first. If you don't secure a second booking by Month 18, the likelihood drops to under 20%. This is your highest-leverage window.
The Anniversary Email (Month 10-12):
Hi [Name],
Can you believe it's been a year since you stayed with us at [Property Name]?
[Include their actual stay dates and a photo from that time period - powerful nostalgia trigger]
We've been thinking about you and would love to welcome you back. To make it special:
→ 10% "Welcome Back" discount just for you
→ First pick of available dates
→ We remember how you loved [specific detail] - it's even better now!
Here are the dates still available for [upcoming season]:
[Show 4-6 specific available date ranges with pricing]
We'd be honored to host you again. What do you say?
[Book Your Return Stay button]
Warmly,
[Your Name]
P.S. This discount expires in 7 days - these dates are filling up fast!
Expected Results:
If They Book: You've Created a Repeat Customer! 🎉
Guests who book a second time have a 60-70% chance of booking a third time. You've now entered the "loyalty phase" of the relationship.
💎Months 13-24: Relationship Building Phase
Goal: Strengthen loyalty, encourage third booking, introduce referrals
Shift to quarterly touchpoints (4 emails/year). These guests have proven they like you - now it's about staying in their consideration set.
The VIP Psychology:
By explicitly calling guests "VIPs" and giving them special treatment, you:
- Make them feel valued and appreciated (emotional loyalty)
- Create perceived exclusive access (scarcity/status)
- Justify premium pricing vs. competitors
- Increase likelihood of referrals (people share good things)
🌟Months 25-36: Loyalty & Advocacy Phase
Goal: Cement lifetime relationship, maximize referrals, create advocates
By Year 3, your best guests have stayed 3-5 times. These are your true VIPs - treasure them.
Exclusive Benefits for 3+ Stay Guests:
Quarterly Emails (Year 3):
The Math: ROI of Building Relationships
Let's calculate the cost vs. value of implementing this 36-month journey:
Investment (Per Guest)
Return (Per Guest)
Your 30-Day Implementation Checklist
Ready to start? Here's how to launch your 36-month guest journey program in the next month:
Week 1
- Set up digital guidebook with email capture (target: 90%+ capture rate)
- Create email list in your platform (Mailchimp, GuestLoop, etc.)
- Write your "thank you + review request" template (Day 2-3 email)
Week 2
- Write your first 3 nurture emails (Months 1-3 from the framework above)
- Schedule them as templates/drafts in your email platform
- Set up automation rules if your platform supports it
Week 3
- Write Months 4-6 nurture emails
- Create your "anniversary email" template (Month 10-12)
- Define your VIP discount policy (10-15% for repeat guests)
Week 4
- Build your quarterly email calendar for Years 2-3
- Set up referral program (tools: ReferralCandy, GuestLoop, or manual tracking)
- Launch! Start capturing emails from your next guest arrival
🚀 Pro Tip: Start Small
You don't need all 20 emails written on Day 1. Start with the first 3-4 emails and build as you go. The key is to start capturing emails today - you can refine your nurture sequence later. Every day you wait is a guest you can't follow up with.
Real Results: My Properties' 3-Year Journey
When I implemented this framework for my Blue Mountains properties starting in 2022:
What Changed:
By Year 3, nearly 40% of my revenue came from guests I already knew - with zero OTA fees and minimal marketing cost. This is what the guest journey framework delivers.
The Bottom Line
Most vacation rental hosts think about bookings. Successful hosts think about relationships.
A booking is a one-time transaction worth $600.
A relationship is a 36-month journey worth $3,000+.
The difference? A plan.
You now have that plan. The only question is: Will you use it?
Start Building Your 36-Month Guest Journeys Today
GuestLoop automates the entire 36-month framework: email capture, nurture sequences, VIP tracking, and referral management. Your guests get the experience, you get the revenue.
Pre-built email templates included • No credit card required • 5-minute setup