Winston Transportation Group

What Winston Transportation Group does

Winston Transportation Group (legal entity Winston American Transportation, Inc.) is a third-generation, family-owned ground transportation company headquartered in Medford, New York, operating under the current brand since 1973 (predecessor Tootsie Taxi was founded in 1967 by Martin Laschever). The company operates door-to-door private car, van, taxi, and motorcoach services across the New York metropolitan area and Florida, serving airport travelers, cruise passengers, wedding parties, corporate clients, leisure tourists, and seasonal 'snowbird' travelers between New York and Florida. Core service offerings include airport transfers to JFK, LaGuardia, Newark, and MacArthur airports, cruise terminal transportation, wedding shuttles, winery and brewery tours, sporting event packages (including the 2026 US Open at Shinnecock Hills), hourly charters, and corporate accounts.

The technology stack centers on a mobile-optimized website (winstontrans.com) with 256-bit encryption and an online reservation system accepting bookings 12 hours to 12 months in advance. The platform integrates Flightview flight tracking software that automatically adjusts reservations based on flight number or schedule changes. A multi-source driver rating system collects post-trip customer feedback via Google, Facebook, and Yelp. Operations are supported by a 24/7 call center staffed 365 days per year. The company holds an executive board seat at The GO Group and partners with GO Airport Shuttle to extend national and international coverage beyond its direct operating footprint.

Winston's revenue model is primarily transactional (per-trip fees), with a subscription/recurring component for corporate accounts that offer volume discounts and weekly or monthly billing programs. Pricing tiers span economy sedans (starting at $75 to ISP/LGA), luxury sedans, private SUVs ($130–$138), executive vans (10–13 passengers), minibuses (21–37 passengers), and 55-passenger motorcoaches, plus specialty packages for weddings, winery tours ($55–$280 per person), brewery tours (from $23), and baseball outings (from $150). Distribution is direct-to-consumer via website and call center, supplemented by email marketing (Constant Contact), social media, and industry association partnerships including AGTA, LILA, and Discover Long Island. The company is privately held with no disclosed investors, no parent company, and no public ticker.

Name

Winston Transportation Group

Legal name

Winston American Transportation, Inc.

Website

https://winstontrans.com

Company type

Private

Founded year

1967

Operating status

Operating

Headcount range

11–50 employees

Short description

Winston Transportation Group is a third-generation, family-owned ground transportation company based in Medford, NY, offering door-to-door airport, cruise, wedding, corporate, and event transportation across the NY metro area and Florida via online booking and Flightview integration.

Ownership category

akta.pro rank

Product category

Ground Transportation Services

NAICS

Limousine Service (485320), Limousine Service (48532), Scenic and Sightseeing Transportation (487)

SIC

Transportation Services (4700)

akta.pro primary industry

Private Airport Transfer & Chauffeured Services (THAIAFAB)

akta.pro secondary industries

Chauffeured / Black Car & Executive Car Services (THACAIAC), Private Transportation & Chauffeur-Hosted Experiences (THAJALAD)

Keywords

• Airport car service
• Private chauffeur transportation
• Wedding event transportation
• Wine tour transportation
• Group charter services

Headquarters

HQ city

Medford

HQ country

United States

HQ region

North America

Offices1 record

Markets served

GTM type

B2C

Offering type

Services

Cost components

Personnel, Operations, Marketing or Sales, Technology or R&D, Infrastructure

Revenue model

1. Airport Transfers: Private car and van service to/from major airports including JFK, LaGuardia, Newark, and MacArthur (ISP). Pricing varies by distance and vehicle type. Prepayment required at time of booking.
2. Cruise Terminal Transportation: Private sedan and van service to Manhattan, Brooklyn, and Bayonne cruise terminals. Round-trip transfers commonly booked. Reservations required.
3. Wedding Transportation: Hourly charter and point-to-point service for wedding parties. Sedans and SUVs available with no hourly minimums. 10% discount offered for wedding guests' airport transportation.
4. Winery and Brewery Tours: Package tours to Long Island wineries and breweries. Economy, Value, and Classic tour packages include transportation plus optional tastings. Pricing per person based on group size.
5. Baseball Game Transportation: Package transportation to Mets and Yankees games including tickets and food/drink vouchers. Group rates for 10+ passengers.
6. Hourly Charters: Hourly charter service for groups and events using minibuses and motorcoaches. Corporate accounts eligible for discounts with weekly or monthly billing programs.
7. Corporate Accounts: Corporate accounts qualify for discounts with larger accounts receiving larger discounts. Weekly or monthly billing programs available for corporate clients.

Pricing tiers

Go-to-market motion2 records

Distribution channels3 records

Marketing channels7 records

Core offering

Winston Transportation Group is a family-owned ground transportation company that sells private chauffeured car, van, taxi, and charter bus services to travelers and event customers. Its primary offerings are door-to-door airport transfers (JFK, LaGuardia, Newark, MacArthur ISP), cruise terminal transportation (Manhattan, Brooklyn, Bayonne), wedding and event transportation, winery and brewery tours, baseball game packages, US Open golf event transportation, and the Florida Snowbird Connection between New York and Florida. The service is delivered by professional background-checked chauffeurs and supported by a 24/7 call center, a 256-bit encrypted online booking system, and Flightview-based real-time flight monitoring.

Product overview

Winston Transportation Group is a ground transportation company operating a diversified portfolio of private car and shuttle services across Long Island, New York City, and Florida. The offering is structured as a multi-tiered service platform spanning five main categories: (1) Airport Transportation including Airport Car Service, Economy Service, and Private Van Service for groups; (2) Private Car Services including Black Car Service for executive travel and Winston Taxi for traditional taxi service; (3) Event & Charter Services encompassing Group & Event Hourly Charters with minibuses and motorcoaches; (4) Specialty Experiences including Winery Tours, Brewery Tours, Wedding Transportation, Baseball Game Transportation, and US Open Golf Transportation; and (5) Cruise Terminal Transportation to Manhattan, Brooklyn, and Bayonne ports. The company also operates a regional presence through Manhattan, Brooklyn, and Queens Car Services, and connects Florida to New York through the Florida Snowbird Connection. All services share a unified operational infrastructure including a 24/7 call center, online reservation system, flight monitoring capabilities, and professional chauffeur network.

Differentiator

Problem solved

Functional benefit

Quantifiable outcome

• 4.6 Google Rating based on 550 reviews
• +3 more outcomes

Named customers1 record

Segments8 records

Ideal customer profiles5 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Feature3 records

Partnerships

14 partnerships are on record, tiered core and minor.

• GO Airport ShuttlecoreChannel Partner/ Reseller/ DistributorThrough partnership with GO Airport Shuttle, Winston Transportation Group serves destinations across the United States and worldwide. GO is a national online reservation system that connects passengers with affiliated transportation providers.
• GO GroupcoreStrategic or Co-development PartnerWinston Transportation Group is an executive board member of The GO Group, enabling nationwide and international service coverage through affiliated transportation companies.
• American Ground Transportation Association (AGTA)minorOthersIndustry association for ground transportation companies providing networking, standards, and advocacy.
• Limousine Industry Association (LILA)minorOthersTrade association representing limousine and transportation industry companies.
• Medford Chamber of CommerceminorOthersLocal chamber of commerce representing Medford area businesses.
• Discover Long IslandminorGTM or Marketing PartnerRegional tourism marketing organization promoting Long Island destinations and businesses.
• GO Boston TransportationminorChannel Partner/ Reseller/ DistributorFeatured affiliate partner for Boston and New England transportation services.
• Flight Line, Inc.minorChannel Partner/ Reseller/ DistributorFeatured affiliate partner for Boston area transportation services.
• Colonial LiveryminorChannel Partner/ Reseller/ DistributorFeatured affiliate partner for New England ground transportation.
• Hubert LimousineminorChannel Partner/ Reseller/ DistributorFeatured affiliate partner for Charlotte, NC transportation services.
• Airport Express (Chicago)minorChannel Partner/ Reseller/ DistributorFeatured affiliate partner for Chicago area airport transportation services.
• GO Airport Shuttle & Executive Car Service (Florida)minorChannel Partner/ Reseller/ DistributorFeatured affiliate partner for Fort Lauderdale, Miami, and South Florida transportation.
• CocotoursminorChannel Partner/ Reseller/ DistributorFeatured affiliate partner for Dominican Republic transportation services.
• GO Puerto Rico ShuttleminorChannel Partner/ Reseller/ DistributorFeatured affiliate partner for Puerto Rico transportation services.

Scale indicators6 records

Recent moves6 records

Expansion highlights5 records

Direct peers

• Dial 7 Car & Limo Service: NYC-based car service operating a large sedan and SUV fleet for airport transfers, point-to-point, and corporate travel across the metropolitan area. Closely aligned operating model, customer segments, and technology (online booking, app) to Winston's airport and black-car services.
• Blacklane: Global pre-booked chauffeur service operating in 50+ countries with airport transfers, intercity rides, and event service. Directly comparable in the pre-booked airport and city-transfer model, with a more global footprint than Winston.
• Groundlink (formerly XOOM): NYC-based online car service platform offering airport transfers, hourly charters, and point-to-point service with vetted drivers. Same airport-transfer-first product positioning and digital booking experience as Winston, with overlapping NYC metro customer base.
• Boston Coach: Northeast-focused executive car service operating premium sedans and SUVs for airport transfers and corporate accounts. Same target customer (corporate travelers, executives) and same premium-vehicle, with-chauffeur model as Winston's black car service.
• Carmel Car & Limousine Service: Long Island-headquartered car and limousine service with the largest TLC-licensed fleet in the NYC metro area, offering airport transfers, corporate accounts, and event transportation. Directly comparable geography, customer base, and service mix to Winston, and the closest same-region competitor.
• EmpireCLS Worldwide Chauffeured Services: Luxury chauffeured transportation company serving airports, corporate accounts, weddings, and special events in the NYC metro and nationally. Strong product overlap with Winston across airport transfers, corporate, and event-driven services.
• Carey International: Global chauffeured ground transportation provider serving airports, corporate travel, and events. Operates in the NYC market and offers a premium executive product directly comparable to Winston's black car and corporate account offerings.

Broad incumbents

• Uber: Global mobility platform with UberX, Uber Comfort, and Uber Black directly competing with Winston's airport sedan and SUV services at lower price points. Incumbent in the same airport-transfer category with vastly greater scale and capital access.
• Lyft: Mass-market rideshare platform with growing airport and premium (Lyft Lux, Black) offerings across NYC. Indirect but powerful competitive force on Winston's airport sedan and SUV service via price and convenience, though business model differs materially.

Regional players

• Allstar Limousine: Long Island-based limousine and car service specializing in weddings, proms, and corporate transportation. Regional peer with overlap in the Long Island wedding and event transportation segment where Winston competes.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat4 records

Key risks7 records

Key highlights7 records

Customer concentration

• Xx.com/WinstonShuttle
• YouTubeyoutube.com/user/winstontrans
• Facebookfacebook.com/Winstontrans
• LinkedInlinkedin.com/company/winston-airport-shuttle

Revenue estimate

Valuation estimate

Number of profiles

Profiles1 record

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about Winston Transportation Group