Miami to Key West Day Trip with Trolley Tour
Overview
Experience 125 miles of amazing scenery on a tour down the Overseas Highway then spend an exciting afternoon riding a fun open-air trolley car around Key West.
Highlights
- Arrange free pickup from most Miami Beach & Downtown Miami hotels
- Enjoy sightseeing on the incredible Overseas Highway
- Listen to a narrated tour of the Florida Keys
- Spend the afternoon in exciting tropical Key West
- Explore Key West aboard a fun open-air touring trolley
Description
Don’t miss the Miami to Key West Day Trip with Trolley Tour – one of the best Cool Key West Key West day trips. This great Key West tour includes a scenic drive down the full length of the Florida Keys on the Overseas Highway and an afternoon in Key West with a trolley tour that makes exploring the island fun and easy. You can ride the open-air trolley around the island to over 100 points of interest in one non-stop tour or take advantage of hop-on, hop-off privileges at 13 designated trolley stops – perfect for enjoying the shopping, dining, history, and highlights of tropical Key West.
Get an early start from Miami aboard a luxury touring coach, with free shuttle service to the departure point from most hotels in Miami Beach and Downtown Miami. Ride down the world-famous Overseas Highway to see the sights of the Florida Keys in air-conditioned comfort with a professional driver at the wheel. Then tour the island in style from a breezy tropical trolley car and play the afternoon away in America’s Caribbean Paradise with no worries at all about driving, parking, or the evening return trip to Miami.
Check in for your tour around 7:15am then board the modern touring coach and settle in to a comfortable reclining seat. The coach departs Miami at 7:45am and runs down U.S. Highway 1 from the south Miami suburbs, across the Southern Everglades, and all the way down the Overseas Highway. This tour is an immersion in spectacular scenery for the entire 125 miles from Florida City on the tip of the Florida Peninsula to Key West, the last inhabited island in the Florida Keys.
Elevated seats and large panoramic windows on the coach are designed to help you enjoy the emerald ocean vistas, sandy coves, island resort towns, busy marinas, beautiful waterfront homes, and many other interesting sights the Keys have to offer. The Overseas Highway traverses 31 islands, and while you travel, a narrated guide presented in high-fidelity audio brings the natural and human history of the Florida Keys to life.
The coach crosses more than 40 bridges that span stretches of blue water between islands large and small. From Knights Key, on the southern tip of Marathon Key about 120 miles into the journey from Miami, the world-famous Seven Mile Bridge lifts the roadway above blue water. The Gulf of Mexico on one side and the Florida Straits on the other stretch to the horizon. This miracle of bridge engineering skill was one of the longest bridges in the world when it was finished in 1982. Speeding along the Seven Mile Bridge offers ocean vistas so dramatic that the bridge has been the setting for chase scenes in action movies like True Lies and two of the "Fast & Furious" films.
After a 6.79-mile-long crossing that will give you the thrilling sensation of flying low over the sparkling waves, the southwest end of the Seven Mile Bridge reconnects with land on tiny Little Duck Key. The beautiful State Park at Bahia Honda Key comes up in minutes. It’s the gateway to the Lower Keys and an entirely different world. Small villages, sportfishing marinas, winding channels, shallow, white sand-bottomed bays, and miles of undeveloped tropical bushland takes you into the exotic Caribbean even though Miami lies only a few hours north by road. It’s truly a marine wonderland, and from here, it is a short ride to Key West, America’s only Caribbean island paradise.
The coach arrives in historic Old Town Key West almost exactly at noon. You can explore the shops and restaurants in the waterfront district, walk a few blocks and grab lunch and a beverage on Duval Street, or go to the nearby trolley stop and take off on an island trolly tour. Antique-style trolley cars are lots of fun for photos, modern amenities make for comfortable touring, and open-air sides bring on the tropical feel while giving you unobstructed views all around. Hop on and off privileges mean you are free to linger at attractions like Duval Street, the Southernmost Point, Mallory Square, the Ernest Hemingway House and much more, then simply catch the next trolley coming by.
The Miami to Key West Day Trip with Trolley Tour is an easy way to arrange a side trip out of Miami and an excellent way to explore Key West. Booking is fast and easy with the Cool Key West secure online reservation system, and you get vouchers and all the necessary details delivered right to your smart phone or tablet. Plan ahead and book your Key West tour now because these popular Miami to Key West day trips fill up very quickly.
What's Included
- Round trip transportation from Miami
- 6 hours in Key West
- A narrated tour of the Florida Keys
- An exciting 90+ minute fully narrated tour of Key West covering over 100 points of interest.
- Gratuities
Meeting and Pickup
This activity ends back at the meeting point.
What To Expect
Begin your full-day trip to Key West with convenient pickup from your Miami hotel aboard a comfortable, air-conditioned coach equipped with a restroom. You'll have 6 hours to explore this charming island at your own pace, and this package includes a hop-on, hop-off trolley tour of all the sights in Key West.
Miami to Key West
Relax and enjoy your journey to the Florida Keys aboard our well-maintained luxury coach. Our knowledgeable tour guide will share fascinating stories about Key West's rich history and vibrant culture as you travel back in time across the iconic Overseas Highway.
6 hours in Key West • Hotel shuttle included
US Highway 1 (pass by)
Marvel at the stunning views along the scenic Overseas Highway. This iconic route, often called "the coolest road in the USA,” connects 31 islands with 43 bridges, making it a dream for photographs. Don't forget your camera!
Breakfast stop
Stop for breakfast and stretch your legs en route to Key West.
20 minutes • Food & drinks not included
Seven Mile Bridge (pass by)
This engineering marvel has been featured in numerous films and TV series, including Road House, Licence to Kill, True Lies, 2 Fast 2 Furious, and Burn Notice. It also appears in the video game Grand Theft Auto VI.
US 1 Mile Marker 0
Welcome to the southernmost point in the continental United States! Fun fact: Key West is closer to Cuba than it is to Miami.
Key West
You’ll arrive in Key West at approx. 11:55 AM. We provide a detailed map of the city to help you navigate and make the most of your time.
918 Caroline St, Key West
Have fun exploring!
Key West is extremely walkable, and you’ll have no problem finding amazing photo opportunities with attractions like The Southernmost Point in the USA, Ernest Hemingway’s Home & Museum, Fort Zachary Historic State Park, and The Key West Lighthouse, to name a few.
6 hours (approx.) • Attraction Tickets Not Included
Key West Trolley Tour
Tours depart from boarding locations approx. every 30 minutes. Stop #2 is one block from where you are dropped off in Key West.
90 minutes (approx) • Tickets included
Mallory Square
Stop #1: Mallory Square - Stop #1 is in front of the Sponge Market, next to the Key West Aquarium. Trolleys will pull up to the American flag, near the shark. Across the street is the Island Juice Bar.
401 Wall St • Near the corner of David Wolkowsky and Wall St
Historic Waterfront (one block from bus)
Stop #2: Historic Waterfront/Mac’s Sea Garden - Stop #2 is on a service road between Margaret and William, running parallel with Caroline. Guests can wait inside Mac's Sea Garden Gift Shop and see the trolleys pull up.
801 Caroline Street • Between Margaret & William St
Simonton Row
Stop #3: Simonton & Greene Streets - Stop #3 is on the corner of Simonton Row, in front of Diver's Direct, on the northwestern side of the street. There is a bench available for waiting guests. Across the street is Key West Aloe.
150 Simonton St • Corner of Simonton & Greene St
World Famous Duval Street
Stop #4: Duval Street/Crowne Plaza La Concha—On the west side of Duval Street, Stop #4 is directly in front of the Crowne Plaza La Concha Hotel. The trolley will stop in front of the hotel’s entrance doors.
430 Duval St • Near Duval & Fleming St
Bahama Village
Stop #5: Bahama Village Market - Stop #5 is in front of the Bahama Village complex directly on the corner, on the western side of the street.
804 Whitehead St • Corner of Whitehead & Petronia St
Midtown
Stop #6: Fairfield Inn - Stop #6 is located at the Fairfield Inn Hotel. The trolleys will stop in the central area of the parking lot.
2400 N Roosevelt Blvd
Roosevelt Station at Gates Hotel
Stop #7: Stop #7 is located near the Gates Hotel. Trolleys will stop at the covered benches located in front of the “Welcome to Key West” box-car mural.
3840 N Roosevelt Blvd • Across the street is the Atlantic Ocean.
Hampton Inn
Stop #8: Best Western Key Ambassador—Stop #8 is located at the Best Western Key Ambassador Hotel. The trolley will stop in front of the office area. Guests can wait inside the lobby to see the trolleys arrive.
3755 S Roosevelt Blvd • Across the street is the Atlantic Ocean.
East Martello Fort/ Robert The Doll
Stop #9: East Martello Civil War Fort - Stop #9 is at the East Martello Fort and Museum. The fort is located in front of the Key West International Airport. Trolleys will pull in front of the Museum in the parking lot.
3501 S Roosevelt Blvd • Fort tickets not included
Casa Marina Resort & Beach House
Stop #10: Casa Marina Resort & Beach House—Stop #10 is at the front doors of the Waldorf Astoria Casa Marina Hotel, railroad magnate Henry Flagler's showpiece. The trolley will pull into the parking lot and stop in front of the doors.
1500 Reynolds St
Southernmost Point Trolley Stop
Stop #11: Southernmost Point Trolley Stop—Stop #11 is located at the Southernmost Point Gift Shop. Trolleys stop directly in front of the store. Guests can shop inside while waiting, or benches are available outside. 511 South St • Free admission
Truval Village
Stop #12: Truval Village - Stop #12 is located on the southeastern side of Duval Street. Trolleys will stop on Duval Street near the corner.
500 Truman Ave • Corner of Duval St & Truman Ave
Angela Street Depot
Stop #13: Angela Street Depot - Stop #13 is immediately on the northwestern corner where Angela meets Duval. Trolleys will stop on Angela Street in front of the benches.
451 Angela St • Corner of Angela & Duval
Key West to Miami
At approximately 6:00 PM you will depart Key West with unforgettable memories of your day in paradise. You will be dropped off back at your original pick-up point.
4 hours (approx.) • Hotel shuttle included
Additional Info
- Confirmation is instant and will be received at time of booking
- Not wheelchair accessible
- Infants must sit on laps
- Stroller accessible
- Transportation has a toilet
- Suitable for travelers of all fitness levels
- What to bring: camera, comfortable shoes, sunglasses, sunscreen, swimwear, towel, travel pillow, and a smile!
- This tour will have a maximum of 59 passengers
Frequently Asked Questions
The answers provided below are based on answers previously given to travelers by the Cool Key West customer support team.
Are there beaches in Key West?
There are several beaches in Key West, with the most popular being located at Fort Zachary Taylor State Park. Key West is a great watersports destination, so bring a bathing suit and sunscreen, if you plan to get wet.
Can I bring luggage on the bus?
Yes, you may bring one piece of luggage and one carry on bag, per person.
Do we stop on the way to Key West?
It depends. If passengers wish to take a break, we will stop at the McDonalds in Tavernier at approximately 9:00 AM. There is also a convenience store and a grocery store in the same vicinity.
How do people dress in Key West?
Key West is super casual. A sundress for ladies and khaki shorts for the gets is as dressed up as anyone usually gets.
How long does it take to drive to Key West?
The road trip takes about 4 hours. Driving the Overseas Highway is a one-of-a-kind experience. You will see some of the most spectacular scenery in the State. You will literally be driving right over the ocean and across a thin chain of islands and bridges, including the famous 7-Mile Bridge. These bridges connect 34 islands that make up the Florida Keys.
How much free time do we have in Key West?
You’ll have approximately 6 hours to explore Key West at your leisure.
What are some good items to bring on the drive to Key West?
Here are some good things to bring to keep you comfortable on the trip: a smartphone, tablet computer, MP3 player, books, magazines, camera, snacks, sleeping shades, and a travel pillow.
What happens if only my activity in Key West is cancelled?
On occasion, activities in Key West will be canceled because of bad weather. In those cases, you will be refunded for the canceled part of your trip. Those refunds are as follows:
- If the Glass Bottom Boat Cruise is canceled due to weather, you will be issued a $60 refund.
- If the Snorkeling Trip is canceled due to weather, you will be issued a $60 refund.
- If Parasailing is canceled due to weather, you will be issued a $70 refund.
- If Trolley is canceled due to weather, you will be issued a $55 refund.
What is the weather cancellation policy?
If the Miami to Key West Day Trip with Trolley Tour must be canceled due to bad weather, and you cannot go on another day or time, you will be issued a refund by Cool Key West.
What is there to see in Key West?

You’ll have approximately 6 hours to explore Key West. Famous for its history, this tropical island is home to famous landmarks such as the Southernmost Point in the United States, Mel Fisher’s Treasure Hunting Museum, Ernest Hemingway’s House with the 6-toed cats, Fort Zachary Taylor, and a spooky above ground cemetery just to name a few. There’s also fun water activities, like snorkeling, a glass bottom boat ride, jet ski tours, and parasailing.
Where can I park my car?
If required, parking instructions for the Miami to Key West Day Trip with Trolley Tour will be included in your confirmation email.
Where is the meeting point for this activity?
Detailed check-in instructions – including meeting point address, Google map, and parking information – for Miami to Key West Day Trip with Trolley Tour will be included in your confirmation email from Cool Key West. Please be sure to double and triple check your email address is correct at checkout so this important email makes its way to you!
Will you pick me up from my hotel?
Yes. Free pick-up is available from all hotels in South Beach, Miami Beach, and Downtown Miami.
Will you take me back to my hotel after the tour?
Yes, after the tour, we will return you back to the hotel that we picked you up from. Cool Key West offers complimentary drop-off service to all hotels in Miami Beach and Downtown Miami.
Reviews
Average 4.60 out of 5 stars based on 2,763 traveler reviews collected by Cool Key West and partner sites such as Cool Destinations and TripAdvisor
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