The window between booking and arrival is 30–90 days of wasted potential for most hotels. Well-built pre-arrival email sequences lift upsells by +20%, cut cancellations by -15%, drive 5-star reviews +30%, and build loyalty for next year. Here are the 5 emails you should be sending, with the timing and content for each.
The typical hotel owner sees the booking come in, fires off an automatic confirmation, and then… silence until the guest shows up. That's 60–80% of revenue potential left on the table. In reality, the run-up to arrival is exactly when a guest is most receptive to upsells — they're excited about the trip ahead.
The 5-email pre-arrival sequence
Email 1: Booking confirmation + welcome (immediate)
Not the automated email from your booking engine. Build your own, branded properly. What it should include:
- A short welcome + an image of the hotel.
- Confirmation details (dates, room, total).
- A save-the-date calendar invite (.ics file).
- A link to the 360° tour so they can revisit their room.
- "Reply directly if you have any questions" — not a no-reply email.
Email 2: 21 days before arrival — pre-trip planning
The goal: become their concierge before they arrive. You send:
- "Top 5 restaurants we recommend" (3 of your own + 2 partners).
- "Best beaches based on your dates" (the winds shift week to week).
- Activity options: yacht charter, sunset photography, Delos tour — with a link to book.
- Mykonos packing tips (humidity, wind, dress code for high-end venues).
On this email, 15–25% book activities before they even land. That's ROI your ads simply don't deliver.
Email 3: 7 days before — upsell + logistics
By now the guest is mentally "locked in". Time for upsells:
- "Upgrade to a suite for €X more" — with a small discount so it reads as genuine value.
- An "Airport transfer" booking link.
- "Pre-stocked fridge" — wine, water, snacks delivered.
- "Welcome dinner at our restaurant" (with a reservation link).
- "Spa pre-booking" (high-demand slots are where the opportunity often slips away).
The target: 30–50% open rate, 8–12% upsell conversion. That's €200–€800 in extra revenue per guest.
Email 4: 24 hours before — what to expect tomorrow
Practicalities + reassurance:
- Check-in time + early arrival options.
- The weather forecast for the next day.
- Driver info / pickup details.
- A brief intro to the staff ("You'll meet Maria at reception").
- A WhatsApp number for instant contact.
The goal: a zero-stress arrival and a strong first impression from the moment they set foot on the island.
Email 5: Day of arrival (morning)
Short and genuinely excited:
- "We can't wait to welcome you today!"
- A final logistics check (e.g. "Your driver Yannis is on standby at 14:30").
- 1–2 photos of the staff waiting to greet them.
- A WhatsApp link in case anything changes.
Bonus emails (Day +1, +3, post-departure)
Not part of the pre-arrival sequence, but they complete the loop:
- Day +1: "How's your stay so far? Anything we can adjust?" — catches issues early, before they turn into bad reviews.
- Day +3 (mid-stay): "Try our private dinner experience" (last-minute upsells).
- Day +1 after departure: "Thank you + link to a Google Review" (a request that's critical for ranking).
- Day +30: "We miss you! Here's an exclusive next-year discount" (loyalty).
The tools you'll need
To automate all of this, you need:
- An email platform: Mailchimp (free up to 500 contacts), Brevo (free up to 9,000 emails/month), Klaviyo (paid, but brilliant for segmentation).
- Booking engine integration: your engine (Sabee, Cloudbeds, Mews) needs to fire a trigger to the email platform whenever a booking comes in.
- Segmentation: at least 3 groups — luxury guest (suite/villa), regular guest (standard room), repeat guest (a different sequence).
Setup time: 2–4 weeks the first time round (templates, integrations, copy). After that it runs on autopilot.
Frequently asked questions
Which language should I write in?+
How many emails is too many?+
Does this work for a small hotel?+
How much setup time the first time?+
Ready for automated pre-arrival?
With the Compass Series Lighthouse, the entire email automation is included. Set up once, then it runs on autopilot for every one of your guests.