From $370 per vehicle, a private one-way ride between Port of Miami and Winding Cypress by black SUV or van.
The rate below covers the entire 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. Want to be spotted by name in a busy crowd? A driver holding a name sign can be added for $20, 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 trip 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. A firm mileage for your exact pickup is not on file for this pairing, so no set number of minutes gets quoted; 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 can be added along the way — any extra stop runs $45 per thirty minutes — 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 calm 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 begin a Gulf-coast stay once the cruise ends. The broader Naples area 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.
Southwest Florida fills through the winter months, and the towns out toward Naples get busiest just as the cruise calendar peaks. If your sailing lands in that stretch, get the reservation locked early rather than in the final day or two, and drop your arrival details into that same note so the whole booking closes in a single pass.
A private ride starting at PortMiami is confirmed with a 50% deposit at booking; the remaining half goes straight to the driver on the day you travel. Fares are one-way and quoted per vehicle for the whole group, so a round trip back to the port is simply the one-way figure doubled, held under a single reservation. Once the deposit is in, the vehicle is locked and full driver details land the day before your pickup.
Meet-and-greet at the terminal is already part of the fare, and a name-sign pickup can be added for $20. A child seat runs $15 each, so tell the driver the ages over WhatsApp and the right seat is fitted before you arrive. Daytime hours run 7 AM to 9 PM with nothing added; a pickup outside that window carries a night fee on the SUV — $20 for a destination inside Miami-Dade or Broward and $50 for one past those counties, which a run out to Collier County falls under.
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.
The price is per vehicle, not per head — the whole group rides for the one rate shown above, whether that is the SUV or a van. Filling every seat adds nothing to the total, and a round trip is just the one-way doubled.
Plan on roughly one checked bag plus a carry-on per passenger, with room held back for cruise luggage. Traveling with extra or oversized bags? Send a note on WhatsApp first and the space is confirmed or the group is bumped up to a larger van. The driver handles loading and unloading at both ends.
Yes. Each child seat is $15 and installed before pickup — just pass along the children’s ages on WhatsApp when you book. That spares a family walking off a long sailing from wrestling seats at the curb.
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 trip stays private and reserved for your group alone — never a shared car. Ask on WhatsApp and a quote for your route comes straight back.
Reserve your private SUV or van and lock the cruise-day pickup for the run out to Winding Cypress. Message on WhatsApp at wa.me/17866828748 or call 786-682-8748 with your ship, terminal, travel date, group size, and drop-off address, and the vehicle and driver are confirmed. Booking a day or more ahead secures your time, and full driver details go out the day before you travel.
Reserving a few days ahead is ideal, and in peak season (holidays, spring break, big cruise weekends) a week or more keeps your first-choice vehicle available. Requests inside 24 hours are welcome but depend on availability, and those bookings are non-refundable once confirmed.
We run on reservations rather than on-demand pickups. A same-day request may still work if a driver is free: message us on WhatsApp with the pickup time and we will confirm quickly. Keep in mind that a ride booked within 24 hours of pickup cannot be refunded.
No. A 50% deposit holds the vehicle when you book online, and the other half goes to your driver on the day of the ride, in cash or by card. If you prefer to settle everything at once, choose Pay in full at checkout.
Yes. After the deposit, the remaining half is paid directly to your driver when the ride is done, cash or card, whichever you prefer. There is nothing else to pay unless you added an extra service.
Cancellations are free up to 24 hours before the pickup. Inside that 24-hour window the ride is non-refundable, and no-shows are treated the same way. Booking details such as an extra passenger or a child seat can still be updated until 12 hours before pickup.
The pickup time and other details can be adjusted until 12 hours before the ride, subject to driver availability; write to us as soon as your plans change. The travel date itself is fixed once booked, so double-check it before you confirm.
Payments run through Stripe over an encrypted checkout; we never see your card number. Card payments carry a 3% processing fee that is shown before you pay. Zelle is also accepted for the deposit with no fee: ask us on WhatsApp.
Not at all. Travelers reserve from all over the world, international cards are accepted at checkout, and we answer on WhatsApp and email in English, Spanish and Portuguese.
Yes. Give us the flight number when you book and your driver tracks it in real time, so the pickup follows the actual landing rather than the scheduled one, at no extra cost.
Message us the moment you know. We reschedule around the new arrival whenever a driver is available; because that counts as a change to the booking, the cancellation terms above still apply if the ride cannot be rebooked.
Your driver meets you at the MIA arrivals level at the curb, and that meet-and-greet is included in the fare. If you would rather be greeted inside the terminal with a name sign, add the name-sign welcome for $20 when you book.
You receive the meeting instructions in advance, and the driver contacts you the day before the ride to confirm every detail. On landing, head to the agreed curb; connect to the airport Wi-Fi and message us on WhatsApp if anything is unclear.
The day before the ride we send the driver’s name and phone number, and the vehicle details you need to spot the car. Vehicle photos on the site show the category booked; the exact model can vary.
Call or WhatsApp us at +1 (786) 682-8748 and we connect you right away. The pickup is always coordinated at the confirmed spot, and the courtesy waiting time keeps running from your landing or your scheduled pickup.
At the airport we wait up to 60 minutes after landing on domestic flights and up to 2 hours on international arrivals; at hotels, homes and the cruise port the courtesy wait is 15 minutes. Beyond that, waiting is billed like an extra stop, $45 per 30 minutes.
The distance and the usual driving time for this exact route are listed on this page. Real timing depends on traffic and the hour, which is why the driver plans the pickup around your actual landing or ship arrival rather than a fixed clock time.
Yes. Your driver loads and unloads every bag at the curb. Drivers do not go inside the hotel or terminal to collect luggage, so have it with you at the meeting point.
Each passenger can bring one large suitcase plus one carry-on. The black SUV carries up to 5 passengers as long as passengers plus large suitcases total 10 or fewer; larger groups or extra bags move to a van. Surfboards, bikes or many extra cases need a custom setup, so tell us before booking.
Yes. Add them when you book: a child seat for babies and toddlers up to about 3 years, or a booster for ages 3 to 5. Each seat is $20 and is fitted before the driver leaves for the pickup.
Planned stops are fine when you add them at booking, priced at $45 per 30 minutes with a 30-minute minimum, then $1.50 per extra minute. Unplanned detours on the day are not part of the fare.
Never. Every transfer is private: the vehicle carries only your group, door to door, with no other pickups and no waiting for strangers.
A black SUV for up to 5 passengers, a van for 6 to 9 and a larger van for 10 to 14. The fare table on this page shows the price for each. For groups above 14 we arrange several vehicles or a minibus on a custom quote.
No. We pick up and drop off at Miami International Airport, PortMiami and the other cruise terminals, hotels, private homes, offices and event venues across South Florida and beyond.
Yes. Wedding parties, corporate groups and private events get a tailored quote with the right mix of vehicles; message us with the date, head count and schedule.
Between 9 PM and 7 AM the black SUV adds a night fee of $20 inside Miami-Dade and Broward and $50 farther out. The fee is shown in the quote before you book, and daytime rides carry no surcharge.
The fare shown is for the exact route named on this page. For a different pickup or drop-off address, use the ride search on this site: it prices the real road distance instantly and lets you book on the spot.
The fare includes the driver, fuel and tolls, with no hidden fees. Only optional items add to it: the 3% card fee, a name-sign welcome, child seats, extra stops or the night fee, each shown in the quote before you pay. Tipping is at your discretion.
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.