Category: Private Transportation

A Ride from uber: Know What You’re Getting Into

There’s no doubt that a ride from Uber remains one of the most widely used options for getting around, with the company reporting over 20 million rides per day globally in 2025. But as the platform continues to grow, Uber and similar app-based services like Lyft have remained under ongoing scrutiny—especially when it comes to safety, accountability, rider experience, and not to mention the surge pricing.

On a recent Thursday evening – one of the busiest times for rides home from LGA – UberX cost $73 more than Teddy’s Private Car, and UberBlack was $151 more. Why? Because rideshare companies rely on surge pricing to lure enough part-time drivers onto the road. Teddy’s, by contrast, provides steady availability with company-owned vehicles and full-time, well-compensated professional chauffeurs. This model ensures greater consistency, safety, and reliability every time you ride.

In many cases, a professional private car service may be a smarter, more reliable alternative. Here’s why:

A Professional, Safer Transportation Experience

Uber drivers undergo a multi-step background check, but these checks are still conducted by third-party vendors—not law enforcement—and often do not include fingerprinting, unlike the strict vetting processes required for licensed livery and taxicab drivers. According to safety studies, third-party checks can be up to 43 times more likely to miss disqualifying criminal history.

Even with improvements to Uber’s technology and safety reporting tools, loopholes remain. For instance, someone with a criminal background could register using someone else’s identity, and enforcement mechanisms remain reactive rather than preventive. In some cases, an otherwise “approved” driver may hand off their Uber account or vehicle to another person without Uber or the passenger knowing.

And even when the driver is legitimate, the nature of gig work means many rideshare drivers work excessive hours just to earn a livable wage, which can raise concerns about fatigue, focus, and long-term safety behind the wheel.

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At Teddy’s Transportation System, we’re proud to share some exciting news: MotorTrend has named the 2025 Lincoln Nautilus its SUV of the Year!

This award is a major endorsement of the very vehicles that make up the heart of our luxury private car service. In fact, 80% of Teddy’s primary car service fleet is the Lincoln Nautilus — and now it’s officially recognized as the best in its class. Read More

According to a recent report by TravelPerk, 61% of U.S. companies plan to increase their travel budgets this year, recognizing the dual benefits of revenue generation and bolstering employee morale. 

The report underscores that the C-suite executives are increasingly acknowledging the pivotal role of business travel in delivering a solid return on investment. On average, these leaders attribute about a third of their companies’ 2023 sales growth to the direct impact of in-person meetings. This trend highlights the indispensable nature of face-to-face interactions in building and maintaining client relationships, with a compelling 95 percent of leaders indicating that their company would likely lose customers without such in-person engagements. Read More

Opposed to the crowds, long lines, lengthy walks and traffic congestion encountered at other airports frequented by Connecticut and New York-based travelers, Tweed New Haven Airport (HVN) offers a smooth and simple alternative hometown airport experience. Yet while HVN’s adjacency to multiple major highways and commuter railways make it Connecticut’s most convenient and easily accessible airport, Tweed New Haven parking presents challenges that can throw a wrench into your travel plans. Read More

New York City was named the most congested city in the U.S. in 2022 by the Annual TomTom Traffic Index, as reported by News 4 New York last week. Woo hoo.

The News4 report said it takes an average of 23 minutes and 39 seconds to drive 6 miles in Manhattan and that the worst hour is Thursdays, 4 to 5PM. Luckily for Teddy’s many very busy business travelers, Teddy’s has flat fares for travel between Manhattan, or the airports, and towns like Darien, New Canaan and Greenwich thus avoiding a penalty when having to travel during rush hour.

And please don’t just think of Manhattan when you think of New York City. “NYC” is comprised of five Borough. In addition to Manhattan, New York City includes the Bronx, Brooklyn, Staten Island and Queens. Queens is where two major NYC airports, LaGuardia (LGA) and John F Kennedy (JFK) are located; a major draw for the millions of residents of southern Connecticut’s Fairfield County and of Westchester County, NY.

Greater New York has two other busy, centrally located airports including Newark Liberty (code EWR for some reason). Westchester County Airport (HPN), in White Plains, is busy too.

In 1938, a bill was passed to cap the number of taxi medallions at that year’s current amount of 13,595

• A 2019 report in CityLimits.org has the current number of medallions at roughly the same!
• Uber and Lyft, however, added “80,000” more according to The Verge in 2018. John McCarthy, a spokesman for the Metropolitan Transit Authority, told AM NY that “proliferation of Uber and Lyft over the past years has worsened Manhattan’s traffic.”

Counterintuitive to most, but ‘several studies including a 1993 Pricewaterhouse study, found that overall, in many cities deregulated, (as) the supply of taxicabs increased, fares increased, service quality declined and there were more trip refusals, lower vehicle quality …with only minor improvements in availability” as quoted from a Connecticut Legislative Fellow, Kristina Sadlak in a 2004 report to the Connecticut General Assembly.

Stories abound about taxi drivers, both traditional and of Uber, etc., of drivers now having to sleep in their cars most nights to make ends meet.

“Airports were planned for taxi lines, not this other large vehicle transportation mode,” said Tanvi Gandham, a management consultant in a New York Times article.

Congestion fees are already paid, on private car service, for trips to or from Midtown Manhattan, for people traveling from Greater White Plains or anywhere within New York State. Interstate private car service continues to be exempt, so far, saving $2.35 for passengers from Stamford, Greenwich and on through Westport, Wilton, Ridgefield, etc..

The other U.S. cities on top of the Tomtom report are Washington, San Francisco, Boston, Chicago and Baltimore.

In New York, like in many cities, Uber and Lyft used armies of people with bags of cell phones to go straight to the people to buy a nice car (or rent, often by the week or shift) and become a taxi driver for them. THEN, when called upon by the City of New York and lawmakers in Hartford, Boston, New Haven and more, plead for mercy on behalf of all those people that invested in cars in regard exempting them from having to apply for taxi permits or get the physical fitness card or fingerprinted background checks required of most more traditional taxi drivers.