Stay Another Day: How Your Content Can Inspire Guests to Book Early and Stick Around Longer

A woman in a bikini relaxes on the edge of a pool with a beautiful ocean view

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t’s been more than four years since COVID-19 kept us all at home, but we’re still feeling the urge to catch up on all that travel and exploration we missed. That sense of carpe diem has led to an increase in impulse getaways, with hotels and resorts seeing more last-minute bookings and shorter stays. Plus, it’s easier than ever to book and plan a vacation on your phone in an hour, rather than spending weeks mapping out an itinerary.

Late-arriving, here-and-gone visitors can be great to fill in holes left by cancellations and slow times, but they’re not the bread and butter of the hospitality industry. To inspire guests to book early and check in for longer stays, properties need to get creative and highlight the array of experiences they offer — making it clear that a couple of days isn’t nearly enough when there are so many enticing things to do, see, and eat onsite and in the area.

Here are some ideas for simple yet impactful content that invites travelers to stick around — plus ways to get the message out to your audience effectively.

Lean Into Seasonality

Think about timing and seasonality when crafting and sharing content: As fall begins, or even during the last dregs of winter, tap into your Northeast contacts and remind them that they can make their California dreamin’ (or Hawaii or Arizona or Florida dreamin’) a reality next year (at a lower price), if they book now.

You can also tap into the sentiments connected with holidays or other milestones. Send an email to your list around Thanksgiving encouraging them to plan their midwinter vacation: “Here’s something you’ll be grateful for in February — a week at the beach.” Or, around Mother’s Day, encourage them to bring Mom along on a once-in-a-lifetime family trip.

How to share the message: Email personalized with a first name is the best way to share offers with past customers — you want them to feel singled out and seen. (Studies show emails with personalized subject lines are 26% more likely to be opened, and personalized emails garner six times more revenue.) But a flash sale on social media is another approach, maybe with a 24-hour limit or for a pre-defined number of guests. Share seasonally focused content on social media as well, with images that show off your property.

Incentivize Them with Teasers

What do you want to think about when you’re not on vacation? Your upcoming vacation, of course. On the special offers page of your site (if you don’t have one, build it — they will come!), let visitors know that when they book early, say six months out, you’ll keep in touch and remind them of all the excitement in store for them.

Then, once someone books, add them to an email drip campaign for regular updates designed to entice them to plan their trip, get excited about the destination, and potentially add more nights to their stay. Emails might include details about local events happening when they’re with you, a quick video showing off your latest amenities, and other reminders of what makes your property unforgettable. It can be simple — if you’re by the sea, one of your emails could be a rundown of the average temperature and sunrise/sunset times on the week they’ll be with you, plus a gorgeous image and a message like “Wish You Were Here — Just XX Days!”

Once you’ve gotten soon-to-be guests pumped up and shown them how much there is to do on your property and in your area, throw in a few CTAs to book an extra day or two. If this seems like a lot of work, remember it won’t go to waste: All this cool content can be repurposed for multiple years and for other campaigns.

How to share the message: Ideally, your email platform will allow you to create an automated drip campaign. If not, you can schedule a series of emails weekly to each new group of guests. Plus, use the tidbits included in each email, like videos and property updates, for emails targeting new guests and social media posts.

Let Them Choose Their Own Adventure

According to a recent survey by the travel company Amadeus, 70% of global guests want hotels to provide information on unique activities in the area before they arrive, yet only 20% of them were able to get those recommendations. This is low-hanging fruit and — to mix metaphors — most of it is evergreen as well.

Create a seasonal tailored itinerary that’s tempting for both guests who’ve already booked and those who haven’t yet. You can change them up four times a year, or more often, but you don’t have to constantly reinvent the wheel. Focus on what makes your property and your area unique — cultural attractions nearby, your farm-to-table restaurant, weekly live music in your onsite wine bar, ways to connect with nature, and more.

How to share it: Make it a blog post, like this one highlighting Key Largo on the Opal Collection’s blog. And/or let guests download the PDF on your website and plan their itinerary; consider making it a day-by-day checklist (with lots of days!). Make sure to include an easy way to book — or to add days if they’ve already booked — once they see how much they want to fit in. Try a call-to-action like “Need extra days to do it all? We’ve got you covered” with an embedded link to a landing page that lets them make or add onto a booking at a discounted price.

Tap Into Their Taste Buds

Nothing slows the scroll like a luscious food photo. Tempt your list and followers to open your email or click on your post by teasing a recipe that’s unique to your onsite restaurant or bar. Highlight a seasonal ingredient, your mixologist’s latest craft cocktail, or a regional dessert that your chef has perfected.

Once you’ve whetted your reader’s appetites, take advantage when they’re onsite by leaving a card in their room that reminds them of the special regional dessert or signature fish dish they’ll find in your restaurant (feature dishes you offer year-round, so you don’t have to reprint often). You can also add treats that can be ordered between meals — like a late-night TV tray with crunchy, salty snacks, or, if your property has an outdoor fire pit, a house-made s’mores kit like this one crafted by the Ojai Valley Inn team.

How to share the message: Email and social both work well, with a link to the recipe on your website (maybe in a blog post). Include links on the landing page to your full menu and to your booking and/or special offers pages.

Invite Them to Something Special

Is there a beloved annual or one-time event in your area — and if not, are you up for creating one? Either way, you can entice guests to plan ahead and book longer stays by crafting an invitation to a weeklong, themed experience that leads up to the special occasion. It might be a big art show, a Pride parade, or a musical festival or concert — tour tourism, driven by stars like Taylor Swift and Olivia Rodrigo, is huge this year, with 44% of people saying they would use a concert as an excuse to visit a new destination.

Choose an event that makes sense for the ambiance of your property, the guests you typically host, and the audience you hope to build. If your property is a grand old hotel, partner with an antique book fair that comes to your city each year, and schedule of week of high teas, readings, and book discussion groups. (Share the books to be discussed only after visitors book their stays!) A great example is the annual Winter Wine Fest at Wentworth by the Sea, near Portsmouth, New Hampshire, which runs for a full month with events all along the way, from multi-course Grand Vintner’s Dinners to Bubbles & Jazz Brunches.

How to share it: Create an invitation tailored to the vibe of your event. If you have the budget for snail mail, an invitation postcard to your list could get their attention; otherwise, start with email invitations and post on social media if you don’t sell out fast enough.

Need help putting these ideas into action and sharing your messages far and wide? Contact our team of innovative content developers, writers, designers, and social media pros.

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