There are 4 ways to get from Winter Park to Kiawah Island by train, plane, or unknown
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Train to Orlando, fly to Charleston International Airport, travel
best- Take the train from Winter Park to Sand Lake Roadtrain
- Fly from Orlando (MCO) to Charleston International Airport (CHS)plane MCO - CHS
- Walk from Charleston-Airport-CHS to Kiawah Islandunknown
4hTrain, travel (Amtrak)
- Take the train from Winter Park Amtrak Station to Charleston Amtrak Stationtrain Silver Meteor
- Walk from Charleston Amtrak Station to Kiawah Islandunknown
8h 8mTrain to Tampa, fly to Charleston International Airport, travel
- Take the train from Winter Park Amtrak Station to Tampatrain
- Fly from Tampa (TPA) to Charleston International Airport (CHS)plane TPA - CHS
- Walk from Charleston-Airport-CHS to Kiawah Islandunknown
7h 9mFly Orlando to Hilton Head Airport, travel
- Fly from Orlando (MCO) to Hilton Head Airport (HHH)plane MCO - HHH
- Walk from Hilton Head Airport (HHH) to Kiawah Islandunknown
7h 36m
Orlando (MCO) to Charleston International Airport (CHS) flights
Questions & Answers
The distance between Winter Park and Kiawah Island is 366 miles.
The best way to get from Winter Park to Kiawah Island without a car is to train and travel which takes 8h 8m and costs .
It takes approximately 4h to get from Winter Park to Kiawah Island, including transfers.
There are 1246+ hotels available in Kiawah Island.
What companies run services between Winter Park, FL, USA and Kiawah Island, SC, USA?
There is no direct connection from Winter Park to Kiawah Island. However, you can take the train to Sand Lake Road, walk to Office Ct & Sand Lake Sunrail, take the line 42 bus to Orlando International Airport, walk to Orlando (MCO) airport, fly to Charleston International Airport (CHS), then travel to Kiawah Island. Alternatively, you can take a train from Winter Park Amtrak Station to Kiawah Island via Charleston Amtrak Station in around 8h 8m.
- Website
- delta.com
Flights from Tampa to Charleston International Airport via Atlanta
- Ave. Duration
- 3h 57m
- When
- Every day
- Estimated price
- $80–420
Flights from Orlando to Hilton Head Airport via Atlanta
- Ave. Duration
- 5h 14m
- When
- Every day
- Estimated price
- $65–340
- Website
- aa.com
Flights from Tampa to Charleston International Airport via Miami
- Ave. Duration
- 3h 57m
- When
- Tuesday
- Estimated price
- $80–420
Flights from Orlando to Hilton Head Airport via Charlotte
- Ave. Duration
- 4h 47m
- When
- Every day
- Estimated price
- $65–350
Flights from Orlando to Hilton Head Airport via Philadelphia
- Ave. Duration
- 6h 29m
- When
- Saturday
- Estimated price
- $110–500
- Website
- flybreeze.com
Flights from Orlando to Charleston International Airport
- Ave. Duration
- 1h 28m
- When
- Every day
- Estimated price
- $65–250
Flights from Tampa to Charleston International Airport
- Ave. Duration
- 1h 32m
- When
- Every day
- Estimated price
- $140–340
- Website
- united.com
Flights from Orlando to Hilton Head Airport via Newark
- Ave. Duration
- 6h 59m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $120–550
- Phone
- +1 855-724-5411
- [email protected]
- Website
- SunRail
Train from Winter Park to Sand Lake Road
- Ave. Duration
- 27 min
- Frequency
- Hourly
- Estimated price
- $2–3
- Website
- SunRail
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Winter Park Amtrak Station to Charleston Amtrak Station
- Ave. Duration
- 7h 32m
- Frequency
- Once daily
- Estimated price
- $120–260
- Website
- Amtrak
Train from Winter Park Amtrak Station to Tampa
- Ave. Duration
- 2h 43m
- Frequency
- Once daily
- Estimated price
- $30–65
- Website
- Amtrak
Want to know more about travelling around United States
Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.
Related travel guides
Travelling to the US: What do I need to know?
Read the travel guide
Why you should take the train in the US
Read the travel guide



