StayStrategy Releases Summer Booking Recovery Guide for Independent Operators

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Your Summer Bookings Are Behind. Here’s Why It’s Not What You Think.

Miami Beach, United States – June 26, 2026 / StayStrategy /

Independent hospitality operators are entering peak summer season in a weaker position than most anticipated. Demand for independent hotels softened through 2025, OTA dependence has reached record levels with commissions consuming 15% to 30% of revenue on the majority of bookings, and a structural shift in how guests discover travel options is creating a new visibility problem that most operators have not yet recognized.

That shift is AI search. ChatGPT, Perplexity, and Google AI Overviews have become active surfaces in the travel planning and booking process. A significant and growing share of guests now begin their search for hotels, short-term rentals, tour operators, and attractions in an AI tool rather than a search engine or an OTA. The operators appearing in those AI-generated answers are capturing demand that used to spread across the market. The operators who are not in those answers are losing bookings to competitors they cannot see and do not know they are losing to.

Chris LaColla has been tracking this shift from inside it. A commercial executive and AI strategist with senior leadership experience in revenue management, digital, ecommerce, and distribution at global travel brands, LaColla has spent years studying how AI systems discover, evaluate, and recommend travel and hospitality businesses to consumers. His research across hotel, short-term rental, tour, and attraction categories has produced a consistent finding: independent operators are systematically underrepresented in AI-generated recommendations, and the factors that determine inclusion are within their control.

LaColla is the founder of StayStrategy, a search visibility and performance marketing firm for independent hospitality operators. He founded the firm after a career running commercial marketing programs at major travel brands, where the research infrastructure, analytics capabilities, and distribution relationships that independent operators lack are simply part of how business gets done. StayStrategy was built to close that gap and to give independent operators the commercial marketing discipline the major brands apply, at a scale and price point that works for a business without brand infrastructure.

In response to the conditions independent operators are navigating this summer, LaColla today released Save the Summer, a tactical guide for boutique hotels, short-term rentals, tour operators, and attractions facing below-target bookings heading into peak season. The guide is built around a diagnostic framework that helps operators identify whether they are dealing with a visibility problem, a conversion problem, or a demand problem, three conditions that look similar on the surface but require completely different responses. Operators who misdiagnose the problem waste the limited time and budget available before peak season closes.

“Most operators who are behind right now are misreading the situation,” LaColla said. “They don’t realize shopping behavior is changing very quickly and they need to think about AI strategy today. There are important steps to take now to ensure that you are positioned for visibility in this new channel. This guide is designed to help operators who are struggling with bookings this summer and want a plan to recover before the season is wasted.”

LaColla’s work at the intersection of AI and travel and hospitality has given him a ground-level view of how the guest acquisition landscape is shifting across the sector. The same AI fluency that major technology and travel brands are building into their commercial operations is now reshaping how independent operators compete for visibility, and the operators who understand that shift now have a window to establish position before the gap between them and their competitors widens further.

StayStrategy has developed diagnostic methodology to assess AI search visibility for independent hospitality businesses across ChatGPT, Perplexity, and Google, and integrates that work with traditional search visibility and performance marketing to build unified guest acquisition programs for the independent operators it works with.

LaColla writes and publishes on AI in travel and hospitality marketing, AI-driven guest acquisition, search visibility for independent operators, and the commercial dynamics shaping hospitality performance in 2026. His perspective draws on enterprise commercial experience at major global travel brands and direct engagement with the independent hotels, short-term rental operators, tour companies, and attractions navigating the current environment.

StayStrategy works with boutique hotels, short-term rental portfolios, tour operators, and for-profit attractions across the United States. The firm works exclusively with independent operators, where the commercial discipline gap is largest and the opportunity to move the needle on direct bookings and AI-driven visibility is most significant.

Save the Summer is available at https://go.staystrategy.co/save-the-summer