There are 11 ways to get from Massachusetts to Kissimmee by plane, train (Amtrak), bus (Greyhound, Flixbus), 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 Boston Logan Airport to Orlando
best- Fly from Boston Logan Airport (BOS) to Orlando (MCO)plane BOS - MCO
6h 16m$136–708Fly Worcester Regional Airport to Orlando
cheapest- Fly from Worcester Regional Airport (ORH) to Orlando (MCO)plane ORH - MCO
6h 19m$106–558Train (Amtrak)
- Take the train from Boston to Ny Moynihan Train Hall At Penn Stationtrain Northeast Regional
- Take the train from Ny Moynihan Train Hall At Penn Station to Kissimmee Amtrak Stationtrain Silver Meteor
28h 10m$654–1,714Bus
- Take the bus from Boston to Newark Penn Stationbus Greyhound US0235 / ...
- Take the bus from Newark Penn Station to Orlando Bus Stationbus FlixBus N2473
29h 7m$215–335Drive 1,295.2 mi
- Drive from Boston to Kissimmeecar 1,295.2 mi
22h 30m$229–331Bus to Manchester Airport, fly to Orlando
- Take the bus from Boston to Boston Manchester Airportbus
- Fly from Manchester Airport (MHT) to Orlando (MCO)plane MHT - MCO
6h 45m$123–570Train to Theodore Francis Green State Airport, fly to Orlando
- Take the train from South Station to TF Green Airporttrain
- Fly from Theodore Francis Green State Airport (PVD) to Orlando (MCO)plane PVD - MCO
7h 8m$194–722Train to Bradley International Airport, fly to Orlando
- Take the train from Springfield to Hartford Amtrak Stationtrain
- Fly from Bradley International Airport (BDL) to Orlando (MCO)plane BDL - MCO
7h 1m$140–630Train to Tweed-New Haven Airport, fly to Orlando
- Take the train from Springfield to New Haventrain
- Fly from Tweed-New Haven Airport (HVN) to Orlando (MCO)plane HVN - MCO
7h 32m$230–710Fly Boston Logan Airport to Tampa, train
- Fly from Boston Logan Airport (BOS) to Tampa (TPA)plane BOS - TPA
- Take the train from Tampa to Kissimmee Amtrak Stationtrain
8h 28m$178–1,173Train to Bradley International Airport, fly to Tampa, train
- Take the train from Springfield to Hartford Amtrak Stationtrain
- Fly from Bradley International Airport (BDL) to Tampa (TPA)plane BDL - TPA
- Take the train from Tampa to Kissimmee Amtrak Stationtrain
9h 16m$182–695
Massachusetts to Kissimmee by train (Amtrak)
Comparing Your Travel Options
The cheapest way to get from Massachusetts to Kissimmee is to fly which costs $130 - $750 and takes 6h 16m.
The fastest way to get from Massachusetts to Kissimmee is to fly which takes 6h 16m and costs $130 - $750.
No, there is no direct bus from Massachusetts to Kissimmee. However, there are services departing from Boston and arriving at N Main St & W Cypress St via Newark Penn Station, Orlando Bus Station and Florida Mall. The journey, including transfers, takes approximately 29h 7m.
No, there is no direct train from Massachusetts to Kissimmee station. However, there are services departing from Boston and arriving at Kissimmee Amtrak Station via Ny Moynihan Train Hall At Penn Station. The journey, including transfers, takes approximately 28h 10m.
The distance between Massachusetts and Kissimmee is 1150 miles. The road distance is 1302.7 miles.
The best way to get from Massachusetts to Kissimmee without a car is to train which takes 28h 10m and costs $650 - $1,800.
It takes approximately 6h 16m to get from Massachusetts to Kissimmee, including transfers.
Massachusetts to Kissimmee bus services, operated by Greyhound USA, depart from Boston station.
Massachusetts to Kissimmee train services, operated by Amtrak, depart from Boston station.
The best way to get from Massachusetts to Kissimmee is to fly which takes 6h 16m and costs $130 - $750. Alternatively, you can train, which costs $650 - $1,800 and takes 28h 10m, you could also bus, which costs $210 - $340 and takes 29h 7m.
What companies run services between Massachusetts, USA and Kissimmee, FL, USA?
Frontier Airlines, American Airlines, and four other airlines fly from Boston Logan Airport (BOS) to Orlando (MCO) hourly. Alternatively, you can take a train from Boston to Kissimmee Amtrak Station via Ny Moynihan Train Hall At Penn Station in around 28h 10m.
- Website
- southwest.com
Flights from Boston Logan Airport to Orlando
- Ave. Duration
- 3h 20m
- When
- Saturday
- Estimated price
- $120–650
Flights from Boston Logan Airport to Orlando via Baltimore
- Ave. Duration
- 5h 5m
- When
- Tuesday, Wednesday, and Saturday
- Estimated price
- $130–650
Flights from Manchester Airport to Orlando
- Ave. Duration
- 3h 15m
- When
- Every day
- Estimated price
- $110–550
Flights from Manchester Airport to Orlando via Baltimore
- Ave. Duration
- 5h 22m
- When
- Every day
- Estimated price
- $110–550
Flights from Theodore Francis Green State Airport to Orlando
- Ave. Duration
- 3h 2m
- When
- Every day
- Estimated price
- $110–600
Flights from Theodore Francis Green State Airport to Orlando via Baltimore
- Ave. Duration
- 4h 55m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $120–600
Flights from Bradley International Airport to Orlando
- Ave. Duration
- 3h 5m
- When
- Every day
- Estimated price
- $110–600
Flights from Bradley International Airport to Orlando via Baltimore
- Ave. Duration
- 5h 3m
- When
- Every day
- Estimated price
- $110–600
Flights from Bradley International Airport to Tampa
- Ave. Duration
- 3h 7m
- When
- Every day
- Estimated price
- $120–600
- Website
- jetblue.com
Flights from Boston Logan Airport to Orlando
- Ave. Duration
- 3h 24m
- When
- Every day
- Estimated price
- $120–650
Flights from Worcester Regional Airport to Orlando
- Ave. Duration
- 3h 16m
- When
- Monday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $100–550
Flights from Worcester Regional Airport to Orlando via Fort Lauderdale
- Ave. Duration
- 5h 39m
- When
- Monday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $120–600
Flights from Theodore Francis Green State Airport to Orlando
- Ave. Duration
- 3h 14m
- When
- Every day
- Estimated price
- $110–600
Flights from Bradley International Airport to Orlando
- Ave. Duration
- 3h 14m
- When
- Every day
- Estimated price
- $110–600
Flights from Boston Logan Airport to Tampa
- Ave. Duration
- 3h 28m
- When
- Every day
- Estimated price
- $130–650
- Website
- flybreeze.com
Flights from Boston Logan Airport to Orlando via Myrtle Beach
- Ave. Duration
- 5h 14m
- When
- Tuesday
- Estimated price
- $210–1,200
Flights from Theodore Francis Green State Airport to Orlando
- Ave. Duration
- 3h 22m
- When
- Every day
- Estimated price
- $180–700
Flights from Bradley International Airport to Orlando
- Ave. Duration
- 3h 24m
- When
- Wednesday and Saturday
- Estimated price
- $120–600
Flights from Bradley International Airport to Orlando via New Bern
- Ave. Duration
- 4h 28m
- When
- Monday and Friday
- Estimated price
- $120–600
Flights from Bradley International Airport to Orlando via Raleigh/Durham
- Ave. Duration
- 5h 8m
- When
- Thursday and Sunday
- Estimated price
- $120–600
Flights from Tweed-New Haven Airport to Orlando
- Ave. Duration
- 3h 9m
- When
- Thursday and Sunday
- Estimated price
- $180–1,100
Flights from Bradley International Airport to Tampa
- Ave. Duration
- 3h 24m
- When
- Every day
- Estimated price
- $210–1,200
Flights from Bradley International Airport to Tampa via Raleigh/Durham
- Ave. Duration
- 5h 25m
- When
- Thursday and Sunday
- Estimated price
- $210–1,200
Flights from Bradley International Airport to Tampa via Myrtle Beach
- Ave. Duration
- 6h 59m
- When
- Wednesday and Saturday
- Estimated price
- $210–1,200
- Website
- delta.com
Flights from Boston Logan Airport to Orlando
- Ave. Duration
- 3h 19m
- When
- Every day
- Estimated price
- $120–650
Flights from Worcester Regional Airport to Orlando via New York La Guardia
- Ave. Duration
- 6h 37m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $100–550
Flights from Boston Logan Airport to Tampa
- Ave. Duration
- 3h 23m
- When
- Every day
- Estimated price
- $130–650
Flights from Boston Logan Airport to Tampa via Raleigh/Durham
- Ave. Duration
- 7h 9m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $130–650
- Website
- aa.com
Flights from Boston Logan Airport to Orlando
- Ave. Duration
- 3h 30m
- When
- Every day
- Estimated price
- $120–650
Flights from Worcester Regional Airport to Orlando via Philadelphia
- Ave. Duration
- 5h 32m
- When
- Monday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $100–550
Flights from Manchester Airport to Orlando via Philadelphia
- Ave. Duration
- 5h 40m
- When
- Every day
- Estimated price
- $110–550
Flights from Manchester Airport to Orlando via Charlotte
- Ave. Duration
- 5h 52m
- When
- Monday, Thursday, Friday, and Sunday
- Estimated price
- $110–550
- Website
- aveloair.com
Flights from Tweed-New Haven Airport to Orlando
- Ave. Duration
- 2h 50m
- When
- Every day
- Estimated price
- $190–650
- Website
- flyfrontier.com
Flights from Boston Logan Airport to Orlando
- Ave. Duration
- 3h 29m
- When
- Monday, Tuesday, Thursday, Friday, and Sunday
- Estimated price
- $120–440
Flights from Bradley International Airport to Orlando
- Ave. Duration
- 3h 8m
- When
- Monday, Thursday, Friday, and Sunday
- Estimated price
- $150–490
- Website
- united.com
Flights from Manchester Airport to Orlando via Washington Dulles
- Ave. Duration
- 5h 44m
- When
- Every day
- Estimated price
- $110–550
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Boston to Ny Moynihan Train Hall At Penn Station
- Ave. Duration
- 4h 2m
- Frequency
- Every 3 hours
- Estimated price
- $120–200
- Website
- Amtrak
Train from Ny Moynihan Train Hall At Penn Station to Kissimmee Amtrak Station
- Ave. Duration
- 23h 8m
- Frequency
- Once daily
- Estimated price
- $600–1,000
- Website
- Amtrak
Train from Springfield to Hartford Amtrak Station
- Ave. Duration
- 32 min
- Frequency
- Every 3 hours
- Estimated price
- $14–22
- Website
- Amtrak
Train from Springfield to New Haven
- Ave. Duration
- 1h 15m
- Frequency
- Every 4 hours
- Estimated price
- $30–55
- Website
- Amtrak
Train from Tampa to Kissimmee Amtrak Station
- Ave. Duration
- 1h 18m
- Frequency
- Once daily
- Estimated price
- $40–65
- Website
- Amtrak
Train from Springfield to Hartford Amtrak Station
- Ave. Duration
- 32 min
- Frequency
- Every 3 hours
- Estimated price
- $14–22
- Website
- Amtrak
Train from Tampa to Kissimmee Amtrak Station
- Ave. Duration
- 1h 18m
- Frequency
- Once daily
- Estimated price
- $40–65
- Website
- Amtrak
Rome2Rio's guide to Amtrak Acela
Contact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Boston to Ny Moynihan Train Hall At Penn Station
- Ave. Duration
- 3h 49m
- Frequency
- Every 4 hours
- Estimated price
- $50–750
- Schedules at
- Amtrak Acela
- Website
- Amtrak
- Business Class
- $50–490
- First Class
- $200–750
Train from South Station to TF Green Airport
- Ave. Duration
- 1h 30m
- Frequency
- Every 4 hours
- Estimated price
- $9–16
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $9–16
Rome2Rio's guide to Greyhound USA
Contact Details
- Phone
- +1 214-849-8100
- [email protected]
- Website
- Greyhound
Bus from Boston to Newark Penn Station
- Ave. Duration
- 5h 20m
- Frequency
- 4 times a day
- Estimated price
- $45–75
- Website
- Greyhound
Bus from Boston to Boston Manchester Airport
- Ave. Duration
- 1h 5m
- Frequency
- Twice daily
- Estimated price
- $9–14
- Website
- Greyhound
- Phone
- +1 (855) 626-8585
- Website
- Flixbus USA
Bus from Boston to Newark Penn Station
- Ave. Duration
- 4h 50m
- Frequency
- 3 times a day
- Estimated price
- $40–65
- Schedules at
- Flixbus USA
Bus from Newark Penn Station to Orlando Bus Station
- Ave. Duration
- 20h 35m
- Frequency
- 4 times a week
- Estimated price
- $170–260
- Schedules at
- Flixbus USA
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Booking & Getting There
Massachusetts to Kissimmee bus services, operated by Greyhound USA, arrive at Newark Penn Station.
Massachusetts to Kissimmee train services, operated by Amtrak, arrive at Ny Moynihan Train Hall At Penn Station.
Yes, the driving distance between Massachusetts to Kissimmee is 1303 miles. It takes approximately 22h 30m to drive from Massachusetts to Kissimmee.
Book your Massachusetts to Kissimmee train tickets online with Omio.
There are 34+ hotels available in Kissimmee.







