From $340 per vehicle, a private one-way ride between Port of Miami and Winding Cypress by black SUV or van.
The rate below covers the whole vehicle for a private, one-way run to any Winding Cypress address — set the moment you book and never nudged by traffic or cruise-day demand.
Once your ship ties up at PortMiami and you walk out of the terminal with your bags, the driver is already at the curb — meet-and-greet comes with every booking, so there is no app to open and no pickup lot to hunt down. Share your ship name and terminal when you reserve, and the driver follows the vessel’s real arrival, shifting the pickup time on their own if customs or the disembark line runs long. Desire to be spotted by name in a busy crowd? A driver holding a name sign can be added for $40, which helps on mornings when several ships empty out at the same hour. From the curb it is a straight load-in and off toward the Gulf coast.
The journey to Winding Cypress is among the longer ones on the board, running west out of Miami on I-75 — the leg known as Alligator Alley — toward the Naples side of Collier County. The true clock depends on your terminal, when the ship releases, and the traffic that morning. What stays fixed is the shape of the day: one unbroken door-to-door leg, with no side-trips beyond what you request. On a stretch this long a brief rest stop of up to thirty minutes is included along the way — something families with young children often welcome. Mornings when several ships release together crawl around the terminals; a mid-day departure clears the port faster.
Winding Cypress is a gated, master-planned neighborhood on the Naples edge of Collier County, the peaceful southwest corner of the state. People head here for a home or a family visit rather than a tourist strip — think detached houses, lakeside and preserve views, foot trails, and a residents’ amenity center instead of a nightlife scene. Most cruise passengers dropped here are coming to see family, look in on a winter home, or start a Gulf-coast stay once the cruise ends. The broader Naples region around it is known for quiet Gulf beaches, golf courses, and an unhurried pace. For gate rules and guest details, the Winding Cypress Homeowners Association site is the official source, and its resident contact page lists who to reach before you pull up to the gate.
Yes — disembarkation morning is exactly what this ride is built around, with the driver at the curb as you step out of the terminal. Book at least a day ahead so a vehicle can be set aside for your group. A shorter-notice request is still reviewed by hand, though same-day space is never promised.
Yes. Beyond cruise-port pickups, the same private SUV and van cover point-to-point rides to MIA and other drop-offs across the region. Every journey stays private and reserved for your group alone — never a shared car. Ask on WhatsApp and a quote for your route comes straight back.
Winding Cypress is 127.2 miles from the Port of Miami by road, about 2 hours 7 minutes without heavy traffic via I-75 (Alligator Alley). The fare is per vehicle: $340 for the Black SUV, $450 for the Van and $550 for the Van XL. Pickup is at your cruise terminal curb at PortMiami.
| Road distance | 127.2 miles |
|---|---|
| Black SUV, 1-5 | $340 |
| Drive time | 2 hours 7 minutes |
| Van, 6-9 | $450 |
| Main roads | I-75 (Alligator Alley) |
| Van XL, 10-14 | $550 |
| Back from Winding Cypress | $340 / $450 / $550 |
Going back works the same way. The driver meets you at your address in Winding Cypress and takes you to your cruise terminal at PortMiami, 127.2 miles away, in about 2 hours 7 minutes with light traffic. Fares for the return from Winding Cypress are $340 (Black SUV), $450 (Van) and $550 (Van XL). The booking box below opens with the two points swapped. Book the return
Winding Cypress is 127.2 miles by road from the Port of Miami. In light traffic the drive takes about 2 hours 7 minutes via I-75 (Alligator Alley); rush hour can add time, but it is a fixed fare, no traffic or surge charges: $340 for the Black SUV.
Set the pickup for when you expect to clear the cruise terminal, allowing for customs and the luggage hall. From the terminal, Winding Cypress is 127.2 miles away, about 2 hours 7 minutes in light traffic.
At the curb outside your own cruise terminal (the terminals are listed below). Before the pickup you get the driver’s name, car and plate; when you are outside with your bags, message us and the car pulls up for the ride to Winding Cypress.
Count people and big suitcases together: up to 10 fit the Black SUV at $340. Larger groups going to Winding Cypress take the Van at $450, for 9 passengers and 9 cases, or the Van XL at $550, for 14 and 14. One carry-on each is included.
Yes. The return from Winding Cypress to the Port of Miami costs $340 in the Black SUV, $450 in the Van and $550 in the Van XL. Allow about 2 hours 7 minutes for the drive, plus a margin, before your boarding time; the return section above has the booking link.
Every policy in full: FAQ
Getting a big group off the ship and out to Winding Cypress is usually a headache, but one pre-booked private van took the stress right out of it. No rideshare app to fight with — we just went straight from the curb to the car. The night before, we got a text with the driver’s name and license plate, so there was no wondering which car was ours when we walked out.
There were six of us stepping off at PortMiami, and one private transfer to Winding Cypress was far simpler than splitting into cars. There was a courtesy waiting window from the agreed time, so we never had to rush to gather the bags.
Primera vez de crucero por mi cuenta desde PortMiami, y tener un auto privado listo en la acera para el viaje a Winding Cypress lo hizo todo simple.
Just as easy as it sounded — a driver waiting, bags loaded, and a comfortable ride out to Winding Cypress. We’ve already earmarked them for our next cruise out of PortMiami.
Todos nosotros bajamos del barco juntos y fue un alivio tener una van privada esperando en la terminal para el viaje a Winding Cypress — todos en un solo vehículo. El viaje a Winding Cypress fue cómodo y sin apuros, con clima controlado, y pudimos relajarnos tras el crucero. Lo último que quieres tras un crucero es un viaje que falle, y este fue justo cuando lo necesitamos. Sin estrés alguno.