Tailbox Raises $1.5 Million for AI-Based Tour Guide: Startup Funding Roundup

Four travel tech startups have announced nearly $12 million in funding over the past week.

>>Tailbox, a startup developing a platform for personalized tours powered by generative AI, has raised $1.5 million in seed funding from Link Ventures.

The startup was founded at the Massachusetts Institute of Technology by Bayazid Malikov and Eduardo Schuch as they were working on master’s degrees. The funding comes after a summer participating in the institute’s Delta V accelerator program, according to a blog post by Malikov published on Medium.

Malikov stated that Tailbox is developing an AI-powered platform meant to act as a digital tour guide that accommodates individual interests, such as history, food, architecture, or folklore. 

The startup is working with local agencies to build out data for specific areas, with the goal of helping travelers find “lesser-known treasures.”

“Imagine walking through Rome and receiving a real-time, AI-generated narrative about the Colosseum tailored specifically to your interest in ancient history, while someone else might get a story focusing on the architectural marvels of the same monument. AI, especially advanced large language models, holds the key to unlocking them,” Malikov said in the statment. “By processing and understanding vast amounts of information, AI can bring forth the hidden stories, nuances, and cultural insights in a personal level on every corner of the globe.

>>Vipio, an online booking platform for specialty vacation rentals, has raised $4.3 million (€4 million) from NOM.  

Netherlands-based Vipio said it focuses on specialty properties throughout Europe, such as tree houses, castles, beach houses, cottages, and windmills. The company said it recently added Freddie Mercury’s former vacation home to the mix. The startup said it accepts about 5% of properties that apply to be listed on the platform. 

“I happened to be looking with my son for a really special accommodation for a weekend away together. Finally, with a lot of effort, I found something on a camping website and figured that a specialized platform could have helped me here. Thus, Vipio was born,” said René Schoenmakers, CEO and co-founder of Vipio, in a statement. 

Prices range from €50 to €10,000 per night. 

The startup said it has made bookings for more than 100,000 people since it was founded in 2020.

The funding will go toward improving the platform, accelerating international growth, and hiring for the software, marketing, and sales departments.

>>Caravelo, which builds traveler subscription services for airlines, has raised $3.7 million (€3.5 million) in series A funding. Samaipata led it with participation from Adara Ventures and other existing investors.

The Barcelona-based company said it has worked with more than 20 airlines. Alaska Airlines last year began selling flight passes in partnership with Caravelo, and Volaris started a similar program this year. Wizz Air started a subscription program earlier this year, as well as Avancia.

The company said its revenue has grown more than 100% each year for the past three years, and its valuation increased 50% in the past year. In the typical subscription service, a customer pays a monthly fee to receive an allowance of flights. 

>>HotelYaari, a platform for investing in hotels, has raised $2.2 million (180 million Indian rupees) from Alios Ventures.

The India-based startup said it allows individuals to purchase a stake in luxury hotels for at least $6,000 (500,000 Indian rupees). Users would then get monthly payouts from room reservations and could expect their investments to appreciate over time, the company said. They also receive a certain number of free stays each year. 

“At the moment, we offer exclusive properties in some of the most sought-after destinations in India, including Goa, Jim Corbett, Mukteshwar, Rishikesh, Lonavala, Mussorie, and Shimla,” said Janardan Tiwari, founder and CEO of HotelYaari, in a statement. 

Company	Stage	Lead	Raise
Tailbox	Seed	Link Ventures	$1.5 million
Vipio	Unspecified	NOM	$4.3 million
Caravelo	Series A	Samaipata	$3.7 million
HotelYaari	Seed	Alios Ventures	$2.2 million

Skift Cheat Sheet

Seed capital is money used to start a business, often led by angel investors and friends or family.

Series A financing is typically drawn from venture capitalists. The round aims to help a startup’s founders make sure that their product is something that customers truly want to buy.

Series B financing is mainly about venture capitalist firms helping a company grow faster. These fundraising rounds can assist in recruiting skilled workers and developing cost-effective marketing.

Series C financing is ordinarily about helping a company expand, such as through acquisitions. In addition to VCs, hedge funds, investment banks, and private equity firms often participate.

Series D, E, and, beyond These mainly mature businesses and the funding round may help a company prepare to go public or be acquired. A variety of types of private investors might participate.