From $630 per vehicle: a private, one-way ride from Port of Miami to Hillside Inn in a chauffeured SUV or van.
These are fixed one-way fares for the whole car or van, tolls and fuel included, so the total is known before anyone gets in.
Disembarkation at Port of Miami is easier with a driver already outside the terminal. The greeting at the curb is part of the price, the Meet & Greet at the terminal adds $40, and the vehicle is yours alone from the port to the destination, luggage included.
Hillside Inn sits inland in the Winter Garden and West Orange area of central Florida, reached from the cruise terminals by a straight run up Florida’s Turnpike. It is a real change of scenery from the port — a corner of the state shaped by quiet main streets, weekend markets, and a chain of lakes rather than coastline and cruise traffic. Arriving here means leaving the busy edge of Miami behind and settling into a slower, more inland pocket of Florida for the days ahead.
Winter Garden gives the surrounding area much of its character, and a good deal of it gathers along historic Plant Street. The shops and storefronts there set an unhurried tone, and on Saturdays the Winter Garden Farmers Market fills the same stretch with local stalls and easy foot traffic. For travelers reaching Hillside Inn after a long drive up from the port, it makes a simple first outing — somewhere to stretch your legs, find a coffee or a bite, and get your bearings without planning much at all.
Beyond the town itself, the landscape opens up. Windermere and the Butler Chain of Lakes lie close by, threading the West Orange countryside with water and open green space that stands in clear contrast to the port you started from. Between the slow pace of Plant Street and the lakes at the edge of town, guests at Hillside Inn tend to find their footing quickly. The area rewards an easy schedule, and arriving by private transfer means you reach the door ready to enjoy it rather than worn out from the journey.
After you disembark, the chauffeur meets you curbside at your terminal rather than somewhere out in a parking lot. Your bags go straight into the vehicle with full luggage assist at the curb, and from there it is one direct leg — no stops, no transfers along the way. The route follows Florida’s Turnpike for the roughly 249.3 miles from the port to Hillside Inn, a single run that keeps the trip simple from the moment you clear the terminal.
Plan on roughly 250 to 258 minutes door to terminal, depending on traffic and the hour. The vehicle is yours alone for the whole drive, so you set the pace and the timing around your own group. Pickup is scheduled to your actual disembarkation, and free wait time is built in, so a slow morning coming off the ship does not throw off the ride.
Hillside Inn in Clermont is 249.5 miles from the Port of Miami by road, about 4 hours 7 minutes without heavy traffic via Florida’s Turnpike. The fare is per vehicle: $630 for the Black SUV, $900 for the Van and $1110 for the Van XL. Pickup is at your cruise terminal curb at PortMiami.
| Road distance | 249.5 miles |
|---|---|
| Black SUV, 1-5 | $630 |
| Drive time | 4 hours 7 minutes |
| Van, 6-9 | $900 |
| Main roads | Florida’s Turnpike |
| Van XL, 10-14 | $1110 |
| Back from Hillside Inn | $630 / $900 / $1110 |
For the trip back, your driver picks you up at the main entrance of the inn and drives the 249.5 miles to your cruise terminal at PortMiami in about 4 hours 7 minutes. The return fare is $630 for the Black SUV, $900 for the Van and $1110 for the Van XL. The booking box opens with Hillside Inn as the pickup; just add the date and time. Book the return
Hillside Inn is 249.5 miles by road from the Port of Miami. In light traffic the drive takes about 4 hours 7 minutes via Florida’s Turnpike; rush hour can add time, but it is a fixed fare, no traffic or surge charges: $630 for the Black SUV.
Book the time you expect to walk out of the terminal with your bags, not the docking time. The waiting rules for slow disembarkation days are on the FAQ page linked below. The drive to Hillside Inn then takes about 4 hours 7 minutes.
Outside the cruise terminal, at the curb. Driver, car and plate arrive by message ahead of the pickup, so you know who to look for; the drive to Hillside Inn starts as soon as the bags are loaded and takes about 4 hours 7 minutes.
In the Black SUV ($630 to Hillside Inn) passengers plus big suitcases can add up to 10, so five people with five cases fit. The Van ($900) carries 9 passengers and 9 big cases, the Van XL ($1110) 14 and 14, and everyone keeps a carry-on.
We do. The driver picks you up at Hillside Inn and takes you to your cruise terminal for $630 (Black SUV), $900 (Van) or $1110 (Van XL). Plan on about 4 hours 7 minutes for the 249.5 miles, more at rush hour.
Every policy in full: FAQ
Viajando con los chicos, todo el interior estaba ordenado. no hubo que buscar a nadie, el auto estaba doonde dijeron. El viaje tomó unos 25 minutos.
I didn’t feel like chasing a ride the morning I disembarked, so I arranged a private car from the terminal to Hillside Inn. The last thing you want after a week at sea is a ride that falls through, and this was rock solid. Booking was quick, I got a solid confirmation, and everything matched what I was told.
Nuestra familia de seis bajó del barco en PortMiami y el conductor ayudó con toda la pila de equipaje para el viaje a Hillside Inn. Teníamos todo el plan antes de que el barco atracara, así que no quedaba de qué preocuparse en la terminal.
Our family of six came off the ship at PortMiami and the driver loaded every cruise bag for the ride to Hillside Inn. The fare was set up front, the same number we were quoted. Booking was simple, we got clear pickup details, and everything matched what we were told. Highly recommend.
Cruising with the family, we didn’t want any disembarkation-day chaos, so a private van straight over to Hillside Inn was perfect. Getting to Hillside Inn first thing meant we could settle in without waiting around.