- Must visit
The Charles Hosmer Morse Museum Of American Art
Important museum in Winter Park housing the world’s most comprehensive collection of works by Louis Comfort Tiffany.
Omio recommends booking the flight as it is the most popular option from Ossining, NY to Orlando, FL among Omio's users. If you are prioritising price take the flight with prices starting from $275. For those with little time consider booking a flight which can get you there in 2h 55m. The ticket price range depends on the travel mode: a flight costs an average of $275, and a train costs an average of $528.
Distance: 969 miles (1561 km)
| Train | Most popular Flight | Bus | Driving |
|---|---|---|---|
$528 Average price | $275 Average price Cheapest | $309 Average price | $221 Average price (fuel + tolls) |
24h 49m Average total duration 24h 19m Onboard + 30m Additional time* | 5h 55m Average total duration Fastest 2h 55m Onboard + 3h 0m Additional time* | 36h 19m Average total duration 35h 49m Onboard + 30m Additional time* | 17h 47m Average total duration (door-to-door) |
Direct Options | Direct Options | Direct Options | Direct Options |
This is compared to other travel options from Ossining, NY to Orlando, FL:
A flight is $34 (€28) less than a bus for this route with tickets for a bus from Ossining, NY to Orlando, FL costing on average $309 (€255).
A flight is $252 (€208) less than a train for this route with tickets for a train from Ossining, NY to Orlando, FL costing on average $528 (€435).
Other travel options to Orlando, FL take longer:
Train takes on average 24h 19m.
Bus takes on average 35h 49m.
Tickets start at around $528 (€435) compared to roughly $221 (€182) in fuel and tolls — a saving of about $-306.81 (€-252.79). The journey takes 24h 19m versus 17h 47m by car, so you'll arrive a bit later, but you can work, read, or sleep along the way rather than spending the time behind the wheel. You'll also save the hassle of parking at the other end.
Driving is worth it if you're on a tight schedule, travelling as a group, or want to stop somewhere en route.
Compare bus, train, and flight prices over the next three weeks. See the best deals at a glance, find the lowest fares, and choose the option that fits your budget.
Trains from Ossining, NY to Orlando, FL run on average 2 times per day, taking around 24h 19m. Cheap train tickets for this journey start at $528 (€435) but you can travel from only $275 (€227) by flight.
The earliest train runs at 15:50, the last at 15:50. The fastest train covers the 969 miles (1561 km) distance in 25h 14m.
Distance 969 miles (1561 km) |
Average train duration 24h 19m |
Cheapest ticket price $528 (€435) |
Trains per day 2 |
Fastest train 25h 14m |
First train 3:50 PM |
Last train 3:50 PM |
Cheapest Month Apr |
Cheapest Day Wed |
High Season Jan - Mar |
Low Season Jan - Mar |
Discover the best of Orlando — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Orlando trip today.
Important museum in Winter Park housing the world’s most comprehensive collection of works by Louis Comfort Tiffany.
Established fine art museum in Loch Haven Park with American art, African art, and rotating contemporary exhibitions.
History museum in a restored 1927 courthouse covering Central Florida history, tourism, and local culture.
Downtown’s signature lakefront park with a walking loop, skyline views, swan boats, and frequent public events.
Elegant shopping and strolling district lined with trees, boutiques, galleries, and some of the area’s prettiest blocks.
Popular area around the boat tour docks and chain of lakes, known for scenic views and upscale residential charm.
A pressed sandwich with roast pork, ham, Swiss cheese, pickles, and mustard on Cuban bread. It reflects Central Florida’s strong Cuban influence and is a local staple.
Fried alligator tail pieces, usually served with a dipping sauce. This is a classic Florida specialty that visitors often try for a taste of regional cuisine.
A famous Florida dessert made with tart key lime filling in a pie crust, often topped with whipped cream. It is one of the state’s most iconic sweets.
An established Orlando favorite for creative sushi and Japanese small plates, with a stylish upscale setting.
A well-known gastropub in nearby Winter Park, celebrated for refined American cooking, craft beer, and a lively but polished atmosphere.
A historic Florida Spanish-Cuban restaurant in Celebration, famous for Cuban sandwiches, paella, and traditional decor.
Moderate overall. Theme parks and hotels can be pricey, but casual dining and chain options are fairly affordable by major U.S. city standards.
Tip 18-20% in restaurants. Bartenders: USD 1-2 per drink. Taxis/rideshares: 10-15%. Hotel staff: USD 2-5. Small tips appreciated for valet, delivery, and housekeeping.
Find answers to the most common questions about traveling from Ossining, NY to Orlando, FL by train. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest train, the cheapest option, or tips for making the most of your visit at Orlando, FL, this guide helps you travel smarter and with confidence.

Most Ossining, NY to Orlando, FL trains use the Cronton-Harmon Station to Winter Park Station station pair. Use this guide to compare Ossining, NY and Orlando, FL train stations on this route, check city-centre transport, alongside checking practicalities like train station facilities and services.
Orlando Station is 1 km from Orlando city centre. Public transport options include:
Orlando Station has practical services for this route, including Lockers, Parking, Dining, Taxis, Accessibility, WC, Hotel, Lost and Found Office, Ticket Office, Bike Parking, Information Desk, and Luggage Carts.
Food options include: Mary Mary Bar, The Boheme
Ticket office support is available at Orlando Station. Information desks are located in the main hall.
Luggage storage is available at Orlando Station. Lost and found is available at the station.
Available at Orlando Station: Parking, Taxis, WC.
Available at Orlando Station: Bike Parking.
Accessibility facilities are available at Orlando Station: Elevators, ramps, restrooms.
Nearby hotels include Orlando World Center Marriott, Grand Bohemian Hotel Orlando, Aloft Orlando Downtown.
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