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Funding & Investment in Travel

The New World of Travel Startup Funding

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This month, an 11-year-old startup called Flyr raised the largest single round of venture capital for a travel tech company in years: A total package of nearly $300 million. 

It’s a tough time for startup funding, and the Flyr deal is a shining example of what investors are willing to bet on: Tech that promises to modernize outdated industries and has a real business model with recurring revenue. 

Flyr’s basic pitch is to help airlines transform the retail experience into something more like online shopping with an AI-powered platform for dynamic pricing and personalized offers.

“We do deals that are tens of millions of dollars a year, and we do contracts that are five to 15 years in length,” Flyr CEO Alex Mans told Skift. “So that makes it a very, very strong business model with very high recurring revenue. And that, in turn, attracts great investors — especially long-term focused investors.”

Whether early or late stage, investors are more focused than ever on finding worthy startups. 

“The number of companies that were raising in 2020 and 2021, it was just enormous compared to what we’re seeing today,” said Gaurav Tuli, partner of F-Prime Capital, the fund affiliated with Fidelity Investments. “It’s far, far fewer companies raising, and also of much higher quality today.”

F-Prime Capital has invested in travel tech companies including Lighthouse, Canary Technologies, ConnexPay, and AvantStay.

Skift has been tracking startup funding in weekly columns for years and the change is all too clear. We’ve spoken with founders who’ve run out of money and those who’ve made it through several funding rounds. And we’ve spoken with investors about what they’re looking for now. From after the go-go period post-pandemic to the depths of 2022 and 2023, they all tell a similar story: There’s money to be had, but the bar is much higher. 

The Flyr platform is meant to make the airfare retail experience more like online shopping. Source: Flyr

No More Money: ‘The Trough Is Closed’  

For startups, the early 2020s felt a lot like the late 1990s. 

During that first Internet stock boom, investors flooded the market with billions of dollars, betting on unproven tech startups that promised to become gold mines with the genesis of the world wide web. Many of those startups did not have much more of a business plan than adding “.com” at the end of their names. Stock prices soared.

But reality set in by the year 2000 as many of these companies failed to generate profits. Share prices tanked and numerous tech startups went bankrupt.

Companies like Apple and Amazon managed to weather the storm, however, emerging stronger and more dominant as many others faded into obscurity. 

In the travel sector, the recent funding cycle is no different. As capital dries up, only the most resilient travel tech startups will survive. 

John Tertan founded the streaming platform Heygo in 2020 as a way to help people “travel” virtually during the pandemic, generating millions of dollars in income for tour guides.

The startup raised $20 million in February 2022 — a high amount for a series A round compared to today’s standards — but the company shut down permanently just over a year later. 

“The metrics changed post-Covid. There just wasn’t a big enough market for the amount of money that we raised,” Tertan told Skift at the time.

There was a record low in travel tech funding in 2023 as investors pulled back, wary of getting burned again.

Cabana, a camper van rental startup that also raised money during the pandemic, closed this year because it couldn’t secure another round of funding. 

“You’re seeing situations like this, where companies that raised a lot a couple years ago are now having to come back to the trough,” travel investor Cara Whitehill said at the time. “And the trough is closed.” 

But history shows that those who endure come out stronger for it.

cabana rv mobile hotel startup source cabana
Pictured: A camper van from the shuttered startup Cabana.

“Better companies with better entrepreneurs are getting funded, and they’re getting funded into an environment where there’s less noise,” Chris Hemmeter, managing director for travel tech venture capital firm Thayer Ventures, told Skift earlier this year. “In the old days when money was free and capital was flowing too easy, too many weak companies were raising money, and then they were just making noise, so they were making it harder for the good companies to advance.”

A Rebound in Funding for Late-Stage Startups

So far in 2024, there have been 15 travel startup fundraises exceeding $100 million. During the same period in 2023, that number was four.

That activity has already contributed to a significant upward shift in the total amount of funding this year versus last — a prediction by Skift Research that seems to be coming true. 

Startups involved in the travel industry, including next-generation aircraft companies, have raised $4.6 billion through mid-August 2024. That number was $1.8 billion in 2023. 

Source: Skift

But it’s older, later-stage companies that are primed to see cash coming their way. Skift Research found that series F rounds, meant for more mature startups, was the only funding stage that increased from 2022 to 2023, while all others saw a drop.

Laurence Tosi, managing partner and founder of WestCap, was Airbnb’s CFO starting in 2015 and helped Brian Chesky secure billions of dollars in late-stage startup funding. More recently, WestCap led Flyr’s last two funding rounds. 

Flyr, Mews, and TravelPerk are all attempting to cash-in on the long overdue need of upgrading the travel industry’s decades-old tech systems. 

Flyr has raised over $500 million since it was founded. Its annualized recurring revenue grew by 290% over the past 12 months, the company said, with clients including Avianca, JetBlue, Air New Zealand, and Virgin Atlantic. “I’ve never seen demand, maybe anywhere, for an infrastructure business like I’ve seen for Flyr,” Tosi said. 

Mews and Travelperk each secured over $100 million this year in later stage funding. 

Mews has raised over $340 million since 2012 to replace the outdated property management system at hotels. Travelperk has raised $513 million since 2015 for a modern business travel management platform.  

TravelPerk said it grew revenue 70% in 2023, and gross profit increased by more than 90%. Avi Meir, TravelPerk CEO and co-founder, told Skift that he decided to raise more capital to advance AI integrations. 

“We didn’t need the money. We were well advanced in our path to becoming profitable and breakeven from a cash flow perspective,” Meir said in January. “And that’s why we could raise with really good terms.”

The startup Canary Technologies raised $50 million this year for a platform focused on hotel guest management, with guest-facing products like mobile check-in and checkout, upselling, guest messaging, and digital tipping. 

Hotels are behind technologically, and like Mews, Canary’s pitch is helping them catch up. 

“Hoteliers see the criticality around that,” said Canary co-founder and CEO Harman Narula. 

Higher Stakes For Early Stage Startups

Earlier stage startups are still getting money, but it’s harder. 

Fed Pereira spent two years working with angel investors on his startup before even approaching venture capital firms.

“You can’t just go to a VC with a great idea. If it’s not proven in some way, then the VCs aren’t going to back it nowadays. They’re not handing money out willy-nilly anymore,” said Pereira, CEO of Lovetovisit, a UK booking platform for ticketed events and attractions.

That’s why he’s glad that Lovetovisit has three founders. 

While he was busy raising money, his co-founders — twin sisters Georgia Aubery and Alice Aubery — worked on building and growing the business. The startup said it has generated $9.5 million in revenue from more than 3.2 million users since it was founded in late 2020.

“When people say fundraising is a full-time job, it’s more than a full-time job,” Pereira said. “It was my life for about two years. I take my hat off to any sole founders out there. I do not know how they do it.”

From left, Lovetovisit co-founders Fed Pereira, Alice Aubrey, and Georgia Aubrey. Source: Lovetovisit

Investors like to see what they call “market fit” – a proven demand from paying customers. When they see it, they sometimes jump in right away. That was the case for the young apartment subleasing startup Ohana.

The founders had previously approached Wave Capital — a fund founded by two former Airbnb execs — but were turned down. Then, sales for the startup jumped from nothing to $1.2 million this spring in response to new short-term rental regulations in New York City. The Ohana founders showed those new numbers to the Wave investors and closed a deal in two weeks

“Before we found product market fit, it was very hard to raise. Once we had clear traction, it was really easy,” Ohana co-founder Ezra Gershanok told Skift in June. 

Tara Spielhagen, co-founder and CEO of Swiipr, raised a series A round of $7.7 million in June, but investors wanted to give her company closer to $38 million. And Series B investors with deeper pockets have already started approaching her about the next round.

Swiipr enables airlines to digitize payments to passengers as compensation for delayed flights or other disruptions, reducing the need for paper vouchers, bank transfers, or issuing cash at airports. The company has 26 airline clients, including British Airways, Play, Air India, Latam, and Norse. 

“It was terrible times for raising money. Very, very difficult times. We had a huge amount of traction nonetheless. We were oversubscribed five times on the investment,” Spielhagen said.  

“They saw the need for it. They saw that we’re really plugging a gap and that there’s an absolute need to transform these legacy systems.”

Little Hope for the Rest

While early stage startups struggle to raise money even while generating revenue, there’s little hope for those looking to fund unproven ideas. 

Most of the early AI trip planning startups released over the past couple of years were doomed from the start. They are attempting to build “revolutionary” apps on top of underwhelming generative AI tech, making next to no revenue. 

While a handful of AI trip planners have managed to raise seed money, many have closed without raising anything at all. 

Take Roam Around and Tripnotes. Each of them gained a lot of attention in early 2023 for websites that were basically ChatGPT wraparounds focused on trip planning. 

Roam Around and Tripnotes both closed earlier this year and sold their assets to other startups, each of the founders joining the respective teams. 

“The product that I was pitching was derogatorily referred to as a GPT-wrapper. That type of company was not getting funded,” Shie Gabbai, founder of Roam Around, told Skift earlier this year.

The AI agent from celebrity-backed trip planner app AskLayla, which acquired Roam Around.

Gilad Berenstein, a travel investor and advisor who has surveyed dozens of AI trip planners this year, believes those types of apps do have a chance. 

But the key, he told Skift earlier this year, is pushing forward to find the right niche market fit, probably not by directly competing with giants like Booking.com. 

And finding the right fit goes for any travel startup, not just AI trip planners. 

“The winners of the mobile revolution were not the first companies to have a mobile app,” Berenstein said. “It was the companies that made a commitment over multiple years to testing, to learning and iterating in the new medium.” 



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Inside Playa Grande Beach Club, A Boutique Hotel Reimagining Travel to the Dominican Republic

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Few destinations do an over-the-top beach vacation like the Dominican Republic. As all-inclusive travel grows in popularity even with the youngest generation of travelers, this Caribbean nation is drawing record-breaking numbers of travelers year-round, many of whom head straight to the island’s oversized resorts.

Beachfront development has long since pushed past the sugar-fine sands of Punta Cana and into new regions, with big-name hotels and resorts sprouting up in spots that were once known mostly to locals. Notably, the country’s first luxury wellness resort, Cayo Levantado Resort, debuted two years ago on a private island in the less-visited region of Samaná.

Meanwhile, the once tiny beach town of Miches is buzzing; Viva Miches by Wyndham, A Trademark All-Inclusive debuted in January, while Zemi Miches Punta Cana All-Inclusive Resort, Curio Collection by Hilton opening its doors less than a month ago.

Now On the North Shore

A mere blip on the map of the Dominican Republic, the area surrounding the small town of Rio San Juan is nearly untouched, even when compared to still growing destinations like Samaná or Miches. But zoom in on Google Maps and you’ll start to see the appeal of this less-visited region: brilliantly white stretches of sand stretch right up to the lush foliage of the tropical jungle. This couldn’t feel further from Punta Cana, but with beaches that are just as nice.

Amidst the larger-than-life developments of other coastlines, the properties here are tiny in comparison. Small, serene, and supremely exclusive, properties like the Aman-branded Amanera and ÀNI Dominican Republic, are quietly rewriting the narrative of the travel to the Dominican Republic as being limited to the oversized and overwhelming.

Even more special still is nearby Playa Grande Beach Club, a boutique property the likes of which there are few in the country, let alone the Caribbean. Home to just nine standalone bungalows spread across a spacious swath of beachfront property carved out of the jungle, its one-of-a-kind design and down-to-earth luxury make it a world all its own.

Inside Playa Grande Beach Club

Stepping off the golden sands of one of the country’s most beautiful beaches and onto the manicured grounds of Playa Grande Beach Club, it’s immediately clear that this is a destination all its own. Even from the beachfront, it’s visible: the property’s meticulously maintained grounds are packed with details to delight visitors. Fringed umbrellas shade beach chairs; vintage furniture fills spaces coated with colorful, handmade tiles; candy-colored drinking glasses for afternoon piña coladas by the pool look like they’re straight out of a doll house.

Playa Grande Beach Club’s praiseworthy design comes as no surprise to those who know its founding story. Among the property’s owners is Celerie Kemble, a renowned designer who had a hand in every detail of its creation and design.

Her distinctly island-inspired, Palm Beach-informed design touches every corner of the property. Each bungalow evokes its own unique spirit, with colorful pastel palettes paired with one-of-a-kind textiles and art collected from remote corners of the world, including from Kemble’s personal travels. The Dominican inspiration of the property is undeniable, calling on classic, colonial-era design in architectural details throughout.

To step inside your private bungalow, available in one-bedroom, two-bedroom, and three-bedroom layouts, feels like stepping inside a gingerbread house with a tropical twist. Mine mixed a rose and lime green color scheme, that started with the handpicked textiles on pillows and continue to the tiles spread across the bathroom floor. My bungalow had its own kitchen, with a vintage-inspired refrigerator stocked with goodies like Dominican beer, local mangoes and freshly-ground coffee should I want to wake for sunrise on the sand.

The bathroom was its own separate sanctuary, complete with a massive copper soaking tub as the centerpiece of its design. I marveled at its size: how could the floor hold its weight? Did the house have to be built around its oversized port? It was one of a number of supremely special touches that wove together the visceral visual journey at this one-of-a-kind property.

Home Away From Home

The intentionality of every design detail is Kemble’s love for the property made manifest, giving it lived-in, well-loved quality that makes it comfortable rather than imposing. Perhaps it’s the small size of the property, apt for less than thirty guests at a time, that enhances its homey feel. However, the family-and-friends-first founding of the property is even more likely the source of its welcoming vibe.

While Kemble was the creative mind behind the property’s design, she was just one of a close-knit group of owners who initially intentioned Playa Grande Beach Club to be a private destination reserved just for friends and family. Now, guests can book bungalows for their own home-away-from-home feel.

In addition to just nine bungalows, Playa Grande Beach Club has a main house with a restaurant and bar, a two-story library and lounge, a beachfront pool with a covered lounge area for lazing, and a small gym.

Rio San Juan and Beyond

For such a set-apart property far from the tourist crowds, there’s surprisingly plenty to do just outside the bounds of the resort. One morning I ventured out with a guide who led me up a mountainside that stands between the coastline and the expanses of the island, cracking open fresh coconuts, pointing out tropical fruit laden trees, and explaining the rich vegetation along our trek.

At the end of the path was an incredible viewpoint overlooking the island’s north coast, from which he pointed out the area’s best beaches and departures for the area’s other popular excursions: horseback riding, tours through the forest to swim in millennia-old sinkholes and boat rides through the mangroves.

“Why would anyone want to leave such a precious property?” I had thought, until I realized that I would need to plan a return trip to experience everything there is to do in this still largely untouched region of the country.

The Playa Grande Secret

There is plenty to do during a stay at Playa Grande Beach Club, but noticeable absent is the laundry list of amenities that often feel like a to-do list to modern travelers. Here, the luxury is in the space, the solitude, the stretch of sand that feels almost all your own. It is the serenity of dining in the grand, romantic main house, chatting with friends and family over farm-fresh food highlighting island-inspired flavors.

“The biggest benefit of staying at Playa Grande Beach Club is that you feel like you are in a family,” says Alexandra Jeronimo, General Manager of Playa Grande Beach Club.

“The hotel is a timeless place from yesteryear where generational stories are made,” she says, referencing both the intimate feel of the property and high return rate of guests. At this boutique property, bungalows sometimes book up to a year in advance by guests who don’t want to skip a season at Playa Grande.

It’s a destination to be shared with friends and family, but carefully. “A lot of visitors tend to say things like ‘I don’t know if I should tell anyone about this place, so I’ve decided to tell no one so I can keep it for myself,'” says Jeronimo. After all, what started as a hideaway for a group of close friends and family never lost its essence. Now, it that same sublime peace and welcoming spirit that makes Playa Grande Beach Club such a singular slice of paradise.





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Jim Thorpe bank to close downtown location to make space for tourists at train station

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Mauch Chunk Trust Company’s bank in downtown Jim Thorpe will close at the end of the year to make space for tourists.

The branch is located inside the borough’s historic train station, which houses the Jim Thorpe Visitors Center.

Out-of-towners who come for a train ride, take a jaunt on the adjacent trail or to visit the shops in town stop at the station to use the restroom and seek tourism information from the Pocono Mountain Visitors Bureau.

Closing the branch will make more space for the estimated 400,000 guests who stop by in a year, according to a press release.

The decision to close the branch was made in partnership with the Carbon County Commissioners to better accommodate the crowds.

Mauch Chunk is the borough of Jim Thorpe’s former name. The train station downtown currently houses a branch of Mauch Chunk Trust Company and the Jim Thorpe Visitors Center.
Entertainers and vendors often set up at Josiah White Park beside the train station in Jim Thorpe.

Haley O’Brien

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WVIA News

Entertainers and vendors often set up at Josiah White Park beside the train station in Jim Thorpe.

In the announcement, Patrick H. Reilly, President and CEO of Mauch Chunk Trust said, “As tourism in Jim Thorpe has grown over the years, we’ve seen many of our railroad station customers increasingly using our North Street and other offices because they are easier to access and have better parking.”

Reilly also said more customers have been using their mobile app for banking.

The Lehigh Gorge Scenic Railway has trains departing the station several times daily during the busy seasons.

The county currently pays for portable restrooms to accommodate the hundreds of thousands of people that visit each year.

“No concrete plans have been made yet,” Commissioner Wayne Nothstein said Friday, but added that renovating the station to add more restrooms has been part of the conversation.

Mauch Chunk Trust has seven locations in Carbon County and Tamaqua. The bank’s main office on North Street is on Jim Thorpe’s East Side.

The train station branch downtown will close on Dec. 1, 2025. An ATM will remain outside the building.

Visitors line up for train tickets for Lehigh Gorge Scenic Railway on a summer day.

Haley O’Brien

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WVIA News

Visitors line up for train tickets for Lehigh Gorge Scenic Railway on a summer day.





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EU Simplifies Schengen Visa Access for Frequent Turkish Travelers

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The European Commission has introduced a new set of regulations that make it easier for frequent Turkish travelers to obtain Schengen visas.

The changes apply to multi-entry short-stay visas, offering greater flexibility and longer durations for applicants with a consistent and compliant travel history.

With Turkish citizens having faced difficulties in securing Schengen visas in recent years, this development is seen as a major relief for those who frequently travel to Europe. The streamlined process is aimed at rewarding those who demonstrate responsible travel behavior and regular use of previous Schengen visas.

What the New Visa Rules Offer

The policy simplifies the visa acquisition process for Turkish nationals who have previously held and properly used Schengen visas. Travelers with a proven track record of regular travel and compliance will now be eligible for longer and multiple-entry visas, reducing both the paperwork and stress associated with repeat applications.

The graduated structure of the visa durations encourages continued lawful travel. Depending on their travel history and timing of application, Turkish citizens may now receive visas ranging from six months to five years in duration.

Visa Validity Timeline Based on Travel History

  • 6-month visa: For those who apply within one year of their last valid visa’s expiration.
  • 1-year multiple-entry visa: For applicants whose previous 6-month visa expired within the past two years.
  • 3-year multiple-entry visa: For those whose 1-year visa expired within the past two years.
  • 5-year multiple-entry visa: For travelers whose 3-year visa expired within the past two years.

The policy ensures that visa validity will never exceed passport expiration dates. Specifically, the visa’s end date must be at least three months before the passport’s expiry, ensuring alignment with EU border security regulations.

Countries Where the New Policy Applies

The revised visa rules will be recognized across all 25 Schengen member states, making travel significantly more convenient for eligible Turkish citizens. The countries are:

Belgium Bulgaria Czechia Germany Estonia
Greece Spain France Croatia Italy
Cyprus Latvia Lithuania Luxembourg Hungary
Malta Netherlands Austria Poland Portugal
Romania Slovakia Slovenia Finland Sweden

Who Is Excluded?

The new visa facilitation rules have clear boundaries. Turkish nationals applying for visas for professional reasons, such as truck drivers and other occupational categories, will not be eligible for the updated system. Similarly, third-country nationals residing in Türkiye who are not Turkish citizens will continue to be subject to the standard Schengen visa application procedures.

This limitation is designed to prioritize personal and tourism-related travel for Turkish citizens with proven histories of compliance and repeated visits to Schengen areas.

Official Statement from the Trade Ministry

Minister of Trade Ömer Bolat commented on the new measures by stating: “For those who have received a visa for the first time, in their second applications, it will be possible to obtain long-term and multiple-entry visas, starting from up to 6 months and extending to 1 year, 2 years, 3 years, and eventually 5 years.”

His statement reinforces the European Commission’s objective to reward trusted travelers by minimizing administrative burdens and maximizing convenience for repeat applicants.

What This Means for Turkish Travelers

The move reflects a broader shift in the EU’s approach to visa policy, balancing border control with traveler convenience. By easing access for compliant travelers, the Schengen zone could see increased tourism and business exchanges from Türkiye, a country with deepening ties to Europe.

Frequent Turkish travelers—especially those working in academia, business, and tourism—are likely to benefit the most. This policy could also reduce waiting times at consulates and streamline embassy workloads by lowering the frequency of repeated short-term applications.

While the new rules may not change the experience for all applicants, they mark a significant improvement for thousands of Turkish citizens who travel frequently and seek easier mobility across European borders.



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