The Vacation Guest Journey: A Comprehensive Guide
by azulomo | 12 min read
Master the Art of Hosting with a Journey-Led Approach
Why the Guest Journey Matters
If you think the guest journey starts with the click of a "Book Now" button, think again. The real magic begins much earlier—somewhere between the first craving for an escape and a late-night scroll through dreamy Portugal stays on Instagram. Understanding the full guest journey is like having a secret roadmap to your guests' hearts (and future bookings).
For vacation home owners, especially in scenic regions like coastal Portugal, knowing the complete guest journey isn't just a marketing trick—it's the bedrock of excellent hosting. Each stage of this journey presents a golden opportunity to connect with guests, make them feel seen, and turn their holiday from just "nice" to "absolutely unforgettable."
This guide breaks down the eight essential stages of the guest journey: from the dreamy beginnings to that warm, fuzzy "we're coming back next year!" moment. Along the way, we’ll explore the psychology behind each decision, the touchpoints that matter most, and the role you play in making the journey seamless and special.
If you can understand how guests think, feel, and choose at each step, you’ll naturally create more meaningful, memorable stays. Whether you're just starting out or refining an established rental, this journey-focused approach will help turn one-time visitors into loyal, returning guests.
1. The Dreaming Stage: Where Wanderlust Begins
The dreaming stage is where the holiday begins—long before any bookings are made. It’s that wistful moment when someone, stuck in traffic or doing the washing up, thinks, “I need a holiday.” It’s vague, romantic, and driven entirely by emotion.
At this point, guests aren’t browsing listings—they’re imagining. A photo of a sun-drenched terrace, a friend’s glowing story about Portugal, or a dreamy Instagram reel might be all it takes to spark curiosity. And just like that, your property becomes part of their fantasy. This stage is all about inspiration. As a host, your job isn’t to provide check-in details or rates—it’s to create a feeling. Think stunning photography, mood-setting captions, and an authentic, inviting online presence.
Guests don’t dream of booking forms—they dream of slow mornings, golden light, and sea breezes. If your vacation home embodies the emotion they’re chasing, you’ve already made a lasting first impression.
Psychology & Influences:
This stage is emotionally driven. The guest might not know where they want to go yet, but they do know how they want to feel: relaxed, inspired, adventurous, cared for. Social media is powerful here—those shots of a whitewashed villa in the Algarve or a candlelit terrace in Comporta? They linger.
Key Touchpoints:
Instagram and Pinterest
Travel blogs and editorial features
Word-of-mouth from friends who rave about their last trip to Portugal
Host Tips:
Curate your Instagram to be more than just photos. Tell visual stories.
Share experiences: sunrise coffee spots, hidden coves, lazy afternoon nooks.
Engage with local tourism boards or travel content creators.
You may not be selling yet, but you're already being considered. This is your chance to enter your future guest’s subconscious. Be present, be beautiful, and above all, be memorable.
2. The Research and Planning Stage: When Ideas Take Shape
Now the daydream turns practical. Your guest is deep in research mode—browsing properties, comparing regions, reading reviews, and planning the perfect escape. Tabs are multiplying as they weigh up Portugal’s coastlines, countryside, or hidden gems.
This stage blends emotion with logic. Guests are still inspired, but now they’re seeking reassurance. They want to know: Is the property as lovely as it looks? Are the reviews solid? Is the location right for their needs? Touchpoints like your listing details, high-quality photos, and past guest feedback become critical. External content—travel blogs, local guides, and destination inspiration—can nudge their decision too.
As a host, be clear, informative, and welcoming. Highlight what makes your home unique, what’s nearby, and why guests love staying. The goal? Turn curiosity into confidence.
Psychology & Influences:
The guest wants to feel informed and in control. They are validating their dream with logic, turning emotion into action. They'll weigh up value, convenience, amenities, and vibe. A charming photo isn’t enough—now they want the details to match.
Key Touchpoints:
Your website or booking page
Listings on Airbnb, Booking.com, or Plum Guide
Google reviews and testimonials
Regional content ("Top 10 things to do in Tavira")
Host Tips:
Ensure your listings are informative, honest, and benefit-led.
Include location context: what’s nearby? Why this place?
Add travel guides and highlight experiences.
At this stage, you’re auditioning. Make it count. Offer clarity, warmth, and proof that you’re worth their holiday.
3. The Selection Stage: Narrowing the Options
The shortlists are forming—and hooray, you’re on one! But so are a few others. Now comes the moment of comparison, where guests move from browsing to deciding. It’s less about general appeal and more about what feels right and fits the plan.
Guests are weighing up both practicality and personality. Is there parking? What’s nearby? Does the place feel welcoming, unique, or memorable? Their head wants convenience, but their heart wants a vibe that matches their holiday dreams. First impressions really count here—your top five photos, key amenities, and reviews are all under the spotlight. The tone of your listing, how you describe the space, and the atmosphere you convey can all be deciding factors.
As a host, focus on what makes your property stand out to the right kind of guest. Be specific and authentic. If they can picture themselves in your home, relaxing into their ideal getaway, you’re on your way to winning the booking.
Psychology & Influences:
Guests weigh practicality against charm. Are you within walking distance of that cute cafe? Does your terrace have a view? Is the bed king-sized? Little touches can tip the scale.
Key Touchpoints:
Your headline photo and first 5 images
Guest reviews and testimonials
Competitive pricing and calendar availability
Host Tips:
Lead with your strongest image.
Showcase unique features (firepit, outdoor shower, hammock by the vines).
Highlight your personality and responsiveness.
Think of this as your first date with the guest. You want to come across confident, consistent, and appealing. It's not just about what you offer—it's how you make them feel.
4. The Booking Stage: Sealing the Deal
Now it’s getting real—your guest is ready to commit. They've weighed their options, imagined themselves sipping wine on your terrace, and decided this is the one. But before you pop the bubbly, know this: even at the finish line, a clunky or confusing booking process can still cost you the win.
This stage is all about trust, ease, and confirmation. The emotional energy is still there (they’re excited!), but it’s now tempered by the desire for a smooth, risk-free experience. Guests want to feel reassured that their choice is secure, that their payment is safe, and that all the practical bits—check-in, keys, cancellation policy—are clear and fair.
Psychologically, this moment is about certainty. There should be no lingering doubts or open questions. If your booking flow is overly complicated, missing information, or includes hidden fees, it can introduce just enough friction to prompt hesitation—or worse, a last-minute change of heart. Your touchpoints here matter more than ever: booking platforms like Airbnb or Booking.com, your direct booking site if you have one, your messaging, your automated emails. Everything needs to be seamless, secure, and friendly.
As a host, your role is to smooth the path. Make your booking process feel like a warm handshake—clear, professional, and welcoming. Be quick to respond with a personal note confirming the reservation and expressing your excitement. Bonus points if you offer something helpful straight away, like a local tip or a packing suggestion.
The booking stage is your guest’s moment of commitment—and your chance to reward their trust. Make it feel like the beginning of something special, not a transaction. Because from this point forward, you’re no longer just a listing. You’re their holiday home.
Psychology & Influences:
At this point, guests seek security and ease. They want reassurance that they’re making the right choice and that their holiday is locked in.
Key Touchpoints:
Booking interface (on Airbnb, your site, etc.)
Confirmation email and payment security
Booking terms and refund policies
Host Tips:
Make your booking process idiot-proof.
Provide a clear breakdown of costs and what’s included.
Follow up quickly with a warm thank-you message.
Congratulations—they’ve picked you. Now's the time to reinforce that they made the right decision and that the holiday magic has officially begun.
5. The Preparation Stage: The Countdown Begins
The booking’s confirmed, the flights are sorted, and the holiday playlist is already playing. Now begins the final countdown—a mix of growing excitement and those 2 a.m. questions like, “Wait… do they provide towels?”
This is when emotion shifts from choosing to anticipating. Guests are picturing what they’ll wear, where they’ll eat, and how they’ll spend lazy afternoons. But alongside the excitement, the need for reassurance creeps in. Are the beds as comfy as the reviews said? Is the parking straightforward? Will the Wi-Fi cope with a sneaky work call?
Psychologically, this stage is about control. Guests want to feel prepared. Even small uncertainties can create doubt, which is why timely, clear communication is so important. Key touchpoints include pre-arrival emails, welcome messages, and digital guidebooks. Guests appreciate clarity—check-in details, directions, what to pack, and what to expect. A friendly message a few days before arrival can calm nerves and build trust.
As a host, this is your chance to set a positive tone before they arrive. Share a guide with personal recommendations—where to get the best coffee, which beach is quietest, and what’s worth booking in advance. You’re not just offering accommodation—you’re offering peace of mind.
Done well, this stage builds both confidence and excitement. Your guests won’t just arrive ready for holiday mode—they’ll arrive already feeling welcomed, expected, and at ease.
Psychology & Influences:
This is where expectation meets anticipation. Guests crave reassurance, tips, and answers to questions they may not even know they have yet.
Key Touchpoints:
Pre-arrival emails or welcome packs
Local recommendations and packing tips
Communication platforms (WhatsApp, email, Airbnb messaging)
Host Tips:
Send a pre-arrival email with check-in details, parking, and contact info.
Share a digital guidebook with personal recommendations.
Offer a warm message a few days before arrival.
Your guest is nearly there, suitcase half-packed and dreaming of pasteis. Your job is to calm nerves and build excitement—so they arrive smiling.
6. The Experience Stage: Showtime
Lights, camera, check-in—it’s showtime. This is when anticipation meets reality. Your guest steps through the door, suitcase in one hand, expectations in the other, and immediately starts noticing everything. Does it look like the photos? Is it clean? Where’s the wine glass cupboard?
This stage is the heart of the guest journey. It’s not just about meeting expectations—it’s about creating comfort, surprise, and delight. Within the first 10 minutes, guests form a strong impression. If the space feels clean, calm, and welcoming, you’ve already won half the battle. Psychologically, guests are seeking reassurance. They want to feel they’ve made the right choice and can truly relax. Early hiccups—like confusing check-in or forgotten essentials—can sour the mood quickly, even if everything else is great.
Touchpoints here are sensory and practical: how the space looks, smells, and functions. Thoughtful touches—a welcome note, some local wine, or neatly folded beach towels—go a long way.
As a host, think beyond just “providing a space.” You’re curating an atmosphere. Light, scent, small comforts, and a sense of ease all help your guest settle in and start their holiday on the right foot. Nail this stage, and you’re not just offering a stay—you’re delivering a memory.
Psychology & Influences:
First impressions set the tone. The welcome, the smell, the temperature, the view—all feed into how your guest judges their choice.
Key Touchpoints:
Check-in process (self-service or hosted)
First 10 minutes in the property
Cleanliness, design, comfort, amenities
Host Tips:
Ensure everything is spotless and styled just like the photos.
Leave a personal note or welcome gift.
Be available but not intrusive.
This is your guest’s "main event." Make it not just pleasant but exceptional. The memories they create here will determine what they say next.
7. The Sharing Stage: Telling the World
Happy guests don’t just slip away with a quiet thank you—they go home with stories to tell, selfies to post, and recommendations to give. This is the moment when your hosting efforts ripple outward. Whether it’s a glowing online review, a tagged Instagram reel, or a dinner party anecdote, the sharing stage is where memories become marketing.
Psychologically, this stage is rooted in validation and connection. Guests love to share experiences that made them feel good—it’s a way to relive the joy and offer value to their social circle. A great stay becomes part of their identity: “We found this charming little place in the Algarve—you’d love it.” Sharing is also a form of reward for you, the host, even if guests don’t realise it. They’re repaying the experience with their voice.
The key touchpoints here are digital: Airbnb and Google reviews, social media tags, direct feedback, and guestbooks (yes, the physical kind still work wonders). A property that photographs well or has distinctive features—a vine-draped courtyard, a retro record player, a locally sourced breakfast basket—is more likely to be snapped, shared, and remembered. As a host, you can gently encourage sharing without being pushy. Leave a thank-you card inviting them to leave a review. Create Instagram-friendly corners with beautiful lighting or props. Say thank you personally, and ask if they’d be happy to share feedback. Some guests just need a small nudge to spread the word.
This stage is your referral engine. A single five-star review or tagged photo can inspire dozens of future bookings. Make it easy and enjoyable for guests to share—and make sure they leave with stories worth telling. Because in the world of vacation homes, the best marketing isn’t paid. It’s personal.
Psychology & Influences:
Sharing is both a way for guests to relive joy and to build their personal brand. If your stay offers shareable moments, they’ll do the marketing for you.
Key Touchpoints:
Guestbook, emails, or follow-ups
Social media tags and check-ins
Review requests
Host Tips:
Encourage guests to share with a personalised thank-you message.
Provide a designated Instagram spot (a hammock with a view, anyone?).
Respond to reviews kindly and professionally.
Reviews are currency. The more you gather, the more you attract. Every delighted guest is a future guest magnet—treat them accordingly.
8. The Returning Stage: The Encore
The bags are unpacked, the holiday snaps have been posted, but the glow of a great trip lingers. For guests who had a memorable stay, the thought often comes quickly: “We should come back next year.”
This stage is all about retention. Happy guests who felt relaxed, welcomed, and looked after are far more likely to return—because why gamble on somewhere new when they already know your place feels like a holiday home from home? There’s also a strong emotional pull here. Guests remember the morning coffee on your terrace, the quiet beach you recommended, the warm welcome. If you’ve created a positive, memorable atmosphere, it becomes part of their personal travel story—and one they’ll want to repeat.
Touchpoints include post-stay thank-you emails, gentle follow-ups, and seasonal updates. A small gesture—like a returning guest discount or priority booking notice—can make them feel appreciated and nudge them toward rebooking.
As a host, your goal is to keep the connection alive. Stay friendly, stay relevant, and keep your past guests in the loop. The returning stage is your chance to become more than a one-time stay—you become part of their holiday tradition.
Psychology & Influences:
Loyalty is built on emotional connection and trust. If you made the stay easy, warm, and special, you’ve already planted the seed of return.
Key Touchpoints:
Follow-up emails or seasonal updates
Repeat guest discounts or exclusive offers
Occasional social media engagement
Host Tips:
Create a mailing list for past guests.
Offer returning guest incentives.
Remember birthdays or anniversaries, if appropriate.
A returning guest isn’t just a repeat customer—they’re your biggest fan. Treat them like old friends and they’ll keep coming back, season after season.
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Final Thoughts: It’s a Journey, Not Just a Stay
Mastering the guest journey isn’t about being perfect at every touchpoint; it’s about being thoughtful, responsive, and human. In Portugal or beyond, vacation home hosting is no longer just about the space—it’s about how you make guests feel from start to finish.
Walk beside them, anticipate their needs, and sprinkle a little magic throughout. Because when you design a guest journey that feels effortless and unforgettable, you’re not just hosting a stay. You’re creating a story worth retelling.
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Beyond Touchpoints: Mapping the Guest’s Emotional Journey
Now that we’ve explored the practical stages of the guest journey—from the dreamy beginnings to the return visit—it’s time to go one layer deeper. Because behind every click, check-in, and cup of coffee on the terrace, there’s something quietly powerful unfolding: emotion.
An emotional journey map gives you a window into your guest’s internal experience—their highs, lows, doubts, and delight—across every phase of their stay. It reveals how they feel, not just what they do, and that insight is gold when it comes to designing memorable stays. This approach adds emotional data and storytelling to your existing customer journey map, helping you connect on a more human level.
Curious to see how your guest’s heart responds as much as their head? Let’s explore how emotional journey mapping can transform not just the guest experience, but your entire hosting mindset.
And if you're ready to host with more heart, sign up below to our Slow Hosting Series—an insightful guide to your hosting journey.
With warmth,
azulomo
Hosting the slow living coastal way—wherever you are.
“Each stage of the guest journey offers an opportunity to build trust and delight.
From the first Instagram scroll to the final farewell message, it’s all connected.
Hosts who understand this flow stand out in a crowded market.”
