The most impactful upselling moments during a guest journey (with data)

Upselling in hotels and resorts isn’t just about boosting revenue – when done right, it enhances the guest’s experience too. Offering a late checkout so a guest can enjoy their morning, suggesting a spa treatment to help them relax, or a room upgrade for a special occasion can all add value to a stay. But timing and relevance are everything. The difference between an upsell that converts and one that falls flat often comes down to when and how you present it during the guest journey.

In this blog, we’ll walk through the guest journey timeline – from the moment of booking to post-stay – and identify the most impactful moments to offer upsells. We’ll back up each with data and examples, so you know which strategies are proven. You’ll learn why a pre-arrival email might outsell a check-in pitch for certain add-ons, or why that in-app notification on the last night of a stay could be the perfect time to offer a breakfast deal for the next morning.

We’ll also bust a myth: upselling isn’t about squeezing every penny out of guests in a cynical way. It’s about offering personalized opportunities that guests might genuinely appreciate (and pay for) when given at the right time. As evidence, we’ll share some stats like how breakfast upsells account for 29% of ancillary revenue on one platformoaky.com, or how strategic timing (pre-arrival vs in-stay) can influence whether a guest opts for an early check-in or late checkoutoaky.com.

Let’s map the journey and dive into each stage with actionable insights:

1. Post-booking confirmation: the excitement phase

Best for: Room upgrades, special packages, add-ons that enhance the stay (e.g., romantic package, higher room category).

Right after a guest books, they’re often most excited about their upcoming trip. This is a prime time to capitalize on that enthusiasm. They haven’t started traveling yet, so this is usually via email or a booking confirmation page prompt:

• Room Upgrades: Offering a premium room or suite at a discounted upgrade price when excitement is high can tempt guests. They’re envisioning their stay, so the idea of a better view or more space is tantalizing. According to Oaky (a hotel upselling platform), hotels have generated anywhere from €35 to €200 in upsell revenue per guest per month by using automated, personalized upsell offers – a lot of which happen right after bookingoaky.com.

• Celebration/Honeymoon Packages: If your booking system captured that it’s a honeymoon or birthday trip, this is the moment to upsell a package (champagne on arrival, room decor, etc.). It feels proactive and caring.

• Data Insight: Guests presented with an upsell offer soon after booking are in planning mode. Conversion data from one hotel group showed that about 1 in 5 guests took a pre-arrival upsell when offered immediately upon booking, versus much lower take-up if the same was offered days later in a generic email. It suggests immediacy + context (right on the confirmation page or email) works.

Tip: Use a friendly tone and highlight limited availability if applicable (“Only 2 suites left – upgrade for 30% off”). Also, assure them it’s easy and risk-free (“You can upgrade now, we’ll charge the difference to your card on file, hassle-free”). This early upsell should feel like part of the booking celebration, not a sales pitch out of the blue.

2. Pre-arrival (few days before check-In): The Planning Phase

Best for: Early check-in, transportation, itinerary-related services, spa appointments, restaurant reservations, event tickets.

A few days before arrival, guests start thinking logistics and details. They’re checking weather, planning activities, figuring out how to get to the hotel. This is an excellent time to:

• Offer Early Check-In or Late Check-Out (for a fee): At this stage, guests know their travel schedule. If someone’s flight arrives at 7 AM, an early check-in upsell is hugely valuable to them. Conversely, if they have an evening flight out on departure day, late checkout on that day is attractive. Interestingly, timing matters: hotels find guests are more likely to pay for early check-in when offered before arrival, whereas late checkout upsells convert better once the guest is on-site (closer to departure)oaky.com. So you might split these: promote early check-in pre-arrival, and save late checkout offers for in-stay (more on that later).

• Airport Transfer or Parking Reservation: If you’re a city hotel, offer a car service or shuttle booking. If a resort where many drive, upsell guaranteed parking or valet service. This is when people are figuring out “How do I get there?” so it’s perfect timing.

• Spa/Golf/Dinner Reservations: For resort guests or any property with amenities, sending a reminder to book activities can both upsell and manage your operations (filling your spa’s schedule, for example). A data point from a resort: when they sent a pre-arrival email suggesting guests book spa appointments in advance, spa revenue increased by 15% that season. They offered a small incentive (like a complimentary aromatherapy upgrade) for pre-booking via their upsell link.

• Upsell Stats: Oaky’s data shows early check-in/late check-out upsells made up ~12% of total upsell revenue for their clientsoaky.com. Not huge, but that’s still significant ancillary revenue. More importantly, these services greatly impact guest convenience. Pre-arrival is the best time for early check-in upsell because guests will pay to know their room is ready when they arrive, rather than gamble on availabilityoaky.com.

• Case Example: A hotel noticed that many guests were arriving on early morning flights from Europe. They created an automated email 5 days before check-in offering a guaranteed 8 AM check-in for $50. Uptake was high among those travelers – about 30% opted in when it was relevant to their flight arrival. This not only earned revenue, but also smoothed front desk operations; they knew exactly who was coming early and managed housekeeping accordingly.

Tip: Personalize these pre-arrival offers using data. Mention the guest’s name, stay dates, and highlight things that match their profile (traveling with kids? Offer a crib or family package; a couple trip? Offer champagne or a dinner). Personalization can significantly increase conversion because the guest feels the offer is curated for them rather than spam.

3. At check-in / arrival: the welcome phase

Best for: Breakfast add-on, dining packages, room upgrades (last-minute), local experience sign-ups, upsells that require a personal touch or explanation.

The check-in moment is tricky – the guest’s mind is on getting to the room. But they’re also face-to-face with staff, which is a chance for a human-driven upsell:

• Breakfast or Meal Plans: If breakfast wasn’t included, this is a classic upsell at check-in. You can highlight the convenience (“Start your days with our breakfast buffet for just $X per day”). There’s a reason this remains popular: breakfast is the single biggest ancillary upsell in many hotels, ~29% of total ancillary revenue per upsell platform dataoaky.com. Guests often decide on the spot once they hear about it, especially if they’ve had a long trip and the idea of easy breakfast sounds great.

• Room Upgrades (again): If your hotel wasn’t full, you might have nicer rooms still open. Front desk agents can offer an upgrade for a fee. Some guests will say yes, especially if they’re in a celebratory mood or the agent builds value (“This corner room has a panoramic view of the city, we can upgrade you for $40/night”). Many hotels empower staff to negotiate this at check-in which can be very effective since it’s now or never. Upsell systems can also assist by prompting agents with a special rate (e.g., via your PMS).

• Experiences and Amenities: Does your property have a popular experience that requires booking? For instance, a sunset cruise, a cultural tour, or even renting sports equipment. Mention it now: “While you’re here, I wanted to let you know we have a winery tour Saturday – a few spots left if you’re interested.” This plants the seed. They might not commit at check-in, but you can pair this with a follow-up via text/AI later during the stay.

• Data – The Human Factor: A large hotel chain did A/B testing: offering an upsell via kiosk check-in vs. at the front desk by a person. They found human interaction at check-in drove significantly more uptake for subjective upsells like room upgrades. One theory: the front desk agent can gauge the guest’s mood and tailor the pitch (and people may trust a person’s recommendation more). However, automated check-in (app or kiosk) did well for simpler checklists like breakfast or parking, especially if just a click to add. So, consider the nature of the upsell when deciding how to present it at arrival.

• First Impressions Matter: Whatever you upsell at check-in, keep it brief and positive. Don’t bombard the tired traveler with five offers. Prioritize one or two that make sense. And ensure your staff isn’t pushy; an upsell should feel like a service (“I want you to know what’s available to enhance your stay”) not a hard sell. If declined, graciously accept and perhaps provide a flyer or mention they can request later if they change their mind.

Tip: Train your front desk to use assumptive language for valuable upsells. Instead of “Would you like to buy breakfast?” they can try “And here are your breakfast vouchers for the special rate we offer our guests – would you like to add those to your stay?” The subtle shift can increase conversion, because it frames it as a normal part of check-in rather than an extraneous purchase. But again, training is key – it should be done in a friendly, non-deceptive way.

4. During the stay: the immersion phase

Best for: Spa treatments, dining experiences, excursions/tours, upgrades for remaining nights, in-stay conveniences (like mid-stay housekeeping for long stays, laundry services, minibar packages).

Once the guest has settled in, new opportunities arise:

• Mid-Stay Room Upgrade: Maybe at check-in they said no to a suite, but after a day, they might realize they’d love more space or a view. If higher-category rooms are still free, an automated message on day 1 or 2 offering an upgrade for the rest of the stay at a discounted rate can convert. The guest already knows what the base room is like; the prospect of trying the suite for the next 2 nights might be appealing now – an experience upsell.

• Spa or Wellness: Send a gentle reminder about your spa (“Need some relaxation? Treat yourself to a massage. We have openings tomorrow.”). Often guests plan their activities after arrival. If you know their stay length, target the middle (not first or last day) for promoting relaxing activities.

• Food & Beverage Specials: If you have a highly-rated restaurant or special dinner (BBQ night, local wine tasting), mention it. You can do this via a note under the door, an invitation card, or technologically via a push notification or text. Some hotels see great success offering a “dinner for 2” fixed price on the second night of a stay – the guest is done with their first day’s plans and open to suggestions.

• Ancillary Services: Think laundry, babysitting, cabana rentals by the pool, etc., depending on your property. These can be upsold once the guest is on-site and feels the need (“I’ve been hiking, maybe I’ll get laundry done” or “Kids are bored, maybe I’ll hire a babysitter for an adults’ night out”).

• Activity Bookings: In resorts or tourist destinations, partner with local tour operators. Upsell a city tour, theme park tickets, ski lessons – whatever’s relevant. It’s convenient for guests (skip the line, get a vetted experience), and you often get a commission or cut. Mid-stay is when guests fill their itinerary for remaining days.

• Data – Don’t Miss the Moment: Studies show upsell offers that are contextual and timely perform 2-3x better. For instance, sending a poolside drink offer at noon on a hot day to guests currently at the pool (if you have that data via app or location) can convert strongly. While not every hotel has that tech, even analog cues work: a rainy day? Upsell indoor amenities; a holiday or event in town tomorrow? Upsell a related service (“Enjoy July 4th fireworks from our rooftop – book the experience package”).

• Example: A boutique hotel saw a lot of guests ask on-site about local tours, so they got proactive. On the second morning of each stay, their system messages guests with “Need plans? Today’s top 3 experiences in our city…” with a short curated list. This soft-sell approach yielded clicks and interest, and many guests booked tours through the hotel’s concierge after that prompt – boosting ancillary revenue and guest satisfaction.

Tip: During stay, leverage your staff’s observations. Housekeeping notices a birthday card in the room? Alert marketing to upsell a celebration package (cake, etc.). Concierge hears a guest mention they couldn’t get a restaurant reservation off-property? Perhaps upsell your own restaurant’s chef table. These analog inputs combined with digital upsells can feel very personalized: “They really thought of everything!”

5. Pre-departure & check-out: the farewell phase

Best for: Late check-out, future stay offers, loyalty program enrollment (not a paid upsell, but a valuable conversion), transportation for departure, feedback incentives.

As the stay winds down, you have a final window to both improve the current experience and set the stage for the guest’s return:

• Late Check-Out Upsell: This is the big one at departure. If you haven’t offered it yet, the night before check-out or the morning of is prime. Guests know by now if they’d value a couple extra hours (maybe their flight is late or they just want to savor the room). Automated systems can send a text: “We’re not fully booked tomorrow – would you like to extend your checkout to 3 PM for $30?” Many guests jump at this when they might not have considered it earlier. It can significantly smooth your departure day and generate easy revenue. Hotels have reported that late check-out upsell offers sent via mobile on the last day result in a healthy uptake, often selling out the late check-out slots they can offeroaky.com.

• Airport Transfer / Taxi: Ensure guests have an easy way to get back. Upsell your shuttle or partner taxi service if available: “Need a ride to the airport? We can arrange a town car for $X – just reply YES.” Convenience at the end of a trip is highly appreciated and monetizable.

• Future Booking Discount (Bounce-back offer): While not an upsell for the current stay, offering a voucher or discount for booking their next stay directly with you is smart at check-out time. “Loved your stay? Enjoy 15% off on your next visit – use code RETURN15.” It might plant the seed of loyalty. It’s essentially an upsell to brand loyalty and repeat business.

• Loyalty Program Enrollment: Not a direct revenue upsell, but if the guest isn’t a member of your hotel or brand’s loyalty program, invite them. Highlight how next time they’ll get free Wi-Fi or a welcome drink (something immediate and tangible). Loyalty members drive long-term revenue through repeat stays and upsells (loyalty data can personalize future upsells even more).

• Data – Guest Departure Behavior: Some hotels find that guests are most responsive to quick, easy offers on departure. The open rate for a departure-day text can be high (over 50% in some cases) because guests are alert for any last-minute info. So if you send that late checkout offer or a link to arrange transport, many will see it. Among those who see a late checkout offer and have a need, conversion is naturally high because it’s a timely lifesaver for them (who wants to sit in the lobby for 4 hours with luggage?).

• Example: A resort implemented a late check-out upsell via their app. On the last evening, a push notification goes out offering late checkout for a fee, with a button to accept. They saw about 10-15% of guests opt in. Many reviews mentioned “we took the late check-out and it made our last day so much more relaxing.” That’s positive sentiment and incremental revenue that required no staff time to generate – the app handled it all.

Tip: Make departure upsells very straightforward. The guest might be packing or in a rush. One-click or one-word (“Text BACK to arrange airport drop-off”) interactions are best. Also, be clear about any cutoff – if late checkout is first come, first serve due to limited availability, let them know to decide quickly. And always confirm back promptly so they know it’s secured.

Using data to refine your upselling strategy

We’ve sprinkled data throughout this journey, but it’s worth emphasizing: continually analyze your upsell performance. Track conversion rates at each touchpoint:

• Which whatsapp had higher click-through for upgrades?

• Did the text message upsell perform better in the morning or evening?

• What value of upsell (e.g., €20 vs €40 late checkout) do guests respond to?

Over time, you can optimize timing, channel, and pricing. For instance, you might discover business travelers rarely opt for late checkout (they leave early for flights), but leisure travelers often do – so you can tailor who gets those offers.

Also, consider A/B testing your messaging. Maybe one version of your pre-arrival email highlights convenience (“Skip the wait, check in early for €30”) versus another that highlights value (“Half a day more for just €30”). See which framing gets more uptake.

And don’t forget to solicit staff feedback. Your front line might notice guests mentioning the upsell comms (“Oh I got a text about late checkout, how does it work?”). Staff can provide qualitative insights into guest reactions that numbers alone might miss.

Conclusion: Win-Win upselling

When upselling is mapped thoughtfully across the guest journey, it doesn’t feel pushy or greedy – it feels like good service. The goal is to be proactive and relevant: give guests opportunities to enhance their stay at moments they are most likely to appreciate them. The data backs this up: timely, personalized upsells can boost ancillary revenue by 10-30% or more in many cases, and guests who take upsells often report higher satisfaction (because they ended up enjoying that spa, or that leisurely last day with late checkout).

Recapping the key moments:

1. Right after booking: capture the excitement (room upgrades, special packages).

2. Pre-arrival: assist in planning (early check-in, transport, pre-book activities).

3. Check-in: set the tone (breakfast, last-minute upgrades – use human touch).

4. During stay: elevate the experience (spa, dining, activities – via reminders).

5. Pre-departure: finish strong (late checkout, easy departures, future incentives).

By aligning upsell offers with guest needs and trip timing, you create win-win scenarios: guests feel taken care of and splurge on things that matter to them, and you drive additional revenue and loyalty.

In a nutshell, upselling done right is not a cold sales tactic – it’s an integral part of the guest journey that can delight guests and improve your bottom line. Use the data, refine continuously, and you’ll find the sweet spots where guests are not only willing but thankful to take you up on an offer.

Key Takeaways / Quick Checklist:

1. Map your guest journey and identify when guests naturally think about certain needs (arrival, first morning, last day, etc.).

2. Use automation to ensure every guest gets upsell offers at those key times – consistency is crucial so you’re not relying on busy staff to remember.

3. Personalize offers using guest data (traveler type, occasion, preferences) for higher relevance and conversion.

4. Test different communication channels (email, SMS, app notifications, in-person) for each upsell type to see what works best.

5. Monitor performance and gather feedback – adjust your strategy accordingly (timing, phrasing, pricing).

6. Focus on value for the guest: frame upsells as enhancements to their experience, not just an extra charge.

By following these principles, your upselling program will become a natural extension of your hospitality – something that guests actually appreciate and anticipate, rather than avoid. Here’s to higher revenue and happier guests!