There are 8 ways to get from Kissimmee to Massachusetts by plane, train (Amtrak), bus (Flixbus, Greyhound), car, bus, or train
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Fly to Boston Logan Airport
best- Fly from Orlando (MCO) to Boston Logan Airport (BOS)plane MCO - BOS
5h 18m$157–708Fly to Worcester Regional Airport
cheapest- Fly from Orlando (MCO) to Worcester Regional Airport (ORH)plane MCO - ORH
5h 59m$96–457Train (Amtrak)
- Take the train from Kissimmee Amtrak Station to Ny Moynihan Train Hall At Penn Stationtrain Silver Meteor
- Take the train from Ny Moynihan Train Hall At Penn Station to Bostontrain Acela
27h 21m$373–963Bus
- Take the bus from Orlando Bus Station to Washington Union Stationbus FlixBus N2472 / ...
- Take the bus from Washington Union Station to Bostonbus FlixBus N2605
30h 6m$203–334Drive 1,292.2 mi
- Drive from Kissimmee to Bostoncar 1,292.2 mi
22h 32m$236–341Fly to Bradley International Airport
- Fly from Orlando (MCO) to Bradley International Airport (BDL)plane MCO - BDL
6h 23m$139–429Fly to Manchester Airport, bus
- Fly from Orlando (MCO) to Manchester Airport (MHT)plane MCO - MHT
- Take the bus from Boston Manchester Airport to Bostonbus
7h 10m$272–618Fly to Theodore Francis Green State Airport, train
- Fly from Orlando (MCO) to Theodore Francis Green State Airport (PVD)plane MCO - PVD
- Take the train from TF Green Airport to South Stationtrain
7h 7m$153–571
Kissimmee to Massachusetts by train (Amtrak)
Comparing Your Travel Options
The cheapest way to get from Kissimmee to Massachusetts is to fly which costs $130 - $430 and takes 6h 23m.
The fastest way to get from Kissimmee to Massachusetts is to fly which takes 5h 18m and costs $150 - $750.
No, there is no direct bus from Kissimmee to Massachusetts. However, there are services departing from N Main St & E Cypress St and arriving at Boston via Orlando, Orlando Bus Station and Washington Union Station. The journey, including transfers, takes approximately 30h 6m.
No, there is no direct train from Kissimmee station to Massachusetts. However, there are services departing from Kissimmee Amtrak Station and arriving at Boston via Ny Moynihan Train Hall At Penn Station. The journey, including transfers, takes approximately 27h 21m.
The distance between Kissimmee and Massachusetts is 1160 miles. The road distance is 1299.7 miles.
The best way to get from Kissimmee to Massachusetts without a car is to train which takes 27h 21m and costs $370 - $1,000.
It takes approximately 5h 18m to get from Kissimmee to Massachusetts, including transfers.
Kissimmee to Massachusetts bus services, operated by Flixbus USA, depart from Orlando Bus Station.
Kissimmee to Massachusetts train services, operated by Amtrak, depart from Kissimmee Amtrak Station.
The best way to get from Kissimmee to Massachusetts is to fly which takes 5h 18m and costs $150 - $750. Alternatively, you can train, which costs $370 - $1,000 and takes 27h 21m, you could also bus, which costs $200 - $340 and takes 30h 6m.
What companies run services between Kissimmee, FL, USA and Massachusetts, USA?
Frontier Airlines, American Airlines, and four other airlines fly from Orlando (MCO) to Boston Logan Airport (BOS) hourly. Alternatively, you can take a train from Kissimmee Amtrak Station to Boston via Ny Moynihan Train Hall At Penn Station in around 27h 21m.
- Website
- southwest.com
Flights from Orlando to Boston Logan Airport
- Ave. Duration
- 3h
- When
- Saturday
- Estimated price
- $95–480
Flights from Orlando to Boston Logan Airport via Baltimore
- Ave. Duration
- 4h 52m
- When
- Every day
- Estimated price
- $100–490
Flights from Orlando to Bradley International Airport
- Ave. Duration
- 2h 42m
- When
- Every day
- Estimated price
- $110–600
Flights from Orlando to Bradley International Airport via Baltimore
- Ave. Duration
- 4h 52m
- When
- Tuesday, Wednesday, Saturday, and Sunday
- Estimated price
- $120–600
Flights from Orlando to Manchester Airport
- Ave. Duration
- 2h 58m
- When
- Every day
- Estimated price
- $95–470
Flights from Orlando to Manchester Airport via Baltimore
- Ave. Duration
- 4h 52m
- When
- Every day
- Estimated price
- $95–470
Flights from Orlando to Theodore Francis Green State Airport
- Ave. Duration
- 2h 46m
- When
- Every day
- Estimated price
- $70–370
- Website
- jetblue.com
Flights from Orlando to Boston Logan Airport
- Ave. Duration
- 3h 19m
- When
- Every day
- Estimated price
- $95–480
Flights from Orlando to Worcester Regional Airport
- Ave. Duration
- 2h 49m
- When
- Every day
- Estimated price
- $90–450
Flights from Orlando to Worcester Regional Airport via Fort Lauderdale
- Ave. Duration
- 5h 44m
- When
- Monday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $110–550
Flights from Orlando to Bradley International Airport
- Ave. Duration
- 2h 50m
- When
- Every day
- Estimated price
- $110–600
Flights from Orlando to Theodore Francis Green State Airport
- Ave. Duration
- 2h 50m
- When
- Every day
- Estimated price
- $70–370
- Website
- flybreeze.com
Flights from Orlando to Bradley International Airport
- Ave. Duration
- 2h 50m
- When
- Wednesday and Saturday
- Estimated price
- $130–410
Flights from Orlando to Bradley International Airport via New Bern
- Ave. Duration
- 4h 14m
- When
- Monday and Friday
- Estimated price
- $130–410
Flights from Orlando to Bradley International Airport via Myrtle Beach
- Ave. Duration
- 5h 9m
- When
- Monday and Friday
- Estimated price
- $130–410
Flights from Orlando to Theodore Francis Green State Airport
- Ave. Duration
- 2h 53m
- When
- Every day
- Estimated price
- $140–550
- Website
- aa.com
Flights from Orlando to Boston Logan Airport
- Ave. Duration
- 3h 5m
- When
- Every day
- Estimated price
- $95–480
Flights from Orlando to Worcester Regional Airport via Philadelphia
- Ave. Duration
- 6h 9m
- When
- Every day
- Estimated price
- $90–450
Flights from Orlando to Manchester Airport via Philadelphia
- Ave. Duration
- 5h 9m
- When
- Every day
- Estimated price
- $95–470
Flights from Orlando to Manchester Airport via Reagan Washington
- Ave. Duration
- 5h 4m
- When
- Saturday
- Estimated price
- $95–470
- Website
- delta.com
Flights from Orlando to Boston Logan Airport
- Ave. Duration
- 3h 8m
- When
- Every day
- Estimated price
- $95–480
Flights from Orlando to Boston Logan Airport via Raleigh/Durham
- Ave. Duration
- 4h 51m
- When
- Saturday
- Estimated price
- $100–490
- Website
- flyfrontier.com
Flights from Orlando to Boston Logan Airport
- Ave. Duration
- 3h 17m
- When
- Monday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $140–440
Flights from Orlando to Bradley International Airport
- Ave. Duration
- 2h 51m
- When
- Monday, Thursday, Friday, and Sunday
- Estimated price
- $150–550
- Website
- united.com
Flights from Orlando to Boston Logan Airport via Washington Dulles
- Ave. Duration
- 4h 48m
- When
- Monday
- Estimated price
- $100–490
Flights from Orlando to Manchester Airport via Washington Dulles
- Ave. Duration
- 5h 15m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $95–470
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Kissimmee Amtrak Station to Ny Moynihan Train Hall At Penn Station
- Ave. Duration
- 22h 53m
- Frequency
- Once daily
- Estimated price
- $310–800
- Website
- Amtrak
Train from Ny Moynihan Train Hall At Penn Station to Boston
- Ave. Duration
- 4h 21m
- Frequency
- Every 3 hours
- Estimated price
- $60–170
- Website
- Amtrak
Rome2Rio's guide to Amtrak Acela
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Ny Moynihan Train Hall At Penn Station to Boston
- Ave. Duration
- 3h 47m
- Frequency
- Every 4 hours
- Estimated price
- $50–750
- Schedules at
- Amtrak Acela
- Website
- Amtrak
- Business Class
- $50–490
- First Class
- $200–750
Train from TF Green Airport to South Station
- Ave. Duration
- 1h 29m
- Frequency
- Every 4 hours
- Estimated price
- $9–16
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $9–16
- Phone
- +1 (855) 626-8585
- Website
- Flixbus USA
Bus from Orlando Bus Station to Washington Union Station
- Ave. Duration
- 16h 35m
- Frequency
- Once daily
- Estimated price
- $130–200
- Schedules at
- Flixbus USA
Bus from Washington Union Station to Boston
- Ave. Duration
- 9h 25m
- Frequency
- Twice daily
- Estimated price
- $70–110
- Schedules at
- Flixbus USA
Rome2Rio's guide to Greyhound USA
Contact DetailsContact Details
- Phone
- +1 214-849-8100
- [email protected]
- Website
- Greyhound
Bus from Washington Union Station to Boston
- Ave. Duration
- 9h 45m
- Frequency
- Once daily
- Estimated price
- $75–130
- Website
- Greyhound
Bus from Boston Manchester Airport to Boston
- Ave. Duration
- 1h 30m
- Frequency
- Twice daily
- Estimated price
- $8–13
- Website
- Greyhound
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Booking & Getting There
Kissimmee to Massachusetts bus services, operated by Flixbus USA, arrive at Washington Union Station.
Kissimmee to Massachusetts train services, operated by Amtrak, arrive at Ny Moynihan Train Hall At Penn Station.
Yes, the driving distance between Kissimmee to Massachusetts is 1300 miles. It takes approximately 22h 32m to drive from Kissimmee to Massachusetts.
Book your Kissimmee to Massachusetts train tickets online with Omio.
There are 1765+ hotels available in Massachusetts.







