Miami to Key West Day Trip with Trolley Tour
Overview
Our best Key West day trip features a scenic Overseas Highway tour and 6 hours in unique Key West plus fun hop-on hop-off trolley rides all around Key West.
Highlights
- FREE pickup & drop-off at most Miami hotels
- Explore Key West aboard a hop-on, hop-off touring trolley
- Enjoy sightseeing on the incredible Overseas Highway
- Listen to a narrated tour of the Florida Keys
- Spend the afternoon on the tropical island of Key West
Why Travelers Choose This Tour
Leaving the planning and driving to the professionals lets you enjoy Key West to the fullest!
Description
The Cool Destinations Miami to Key West Day Trip with Trolley Tour is one of the best Key West day trips because it includes a scenic drive down the full length of the Florida Keys on the Overseas Highway, an afternoon in Key West, and a trolley tour that adds to the fun of exploring the island. The open-air island trolley offers hop-on, hop-off convenience to make it easy to enjoy the shopping, dining, history, and highlights of tropical Key West.
Board a luxury touring coach with free transfer to the departure point right from your hotel door, then see the sights of the Florida Keys in air-conditioned comfort with a professional driver at the wheel. You can tour Key West in style aboard the Key West Trolley and play the afternoon away in America’s Caribbean Paradise with no worries about driving, parking, or the evening return trip to Miami.
From the south Miami suburbs across the Southern Everglades on U.S. Highway 1 all the way down the Overseas Highway through the tropical settings of the Lower Keys, you will be surrounded by spectacular scenery. Settle in to your soft, comfortable seat on the modern touring coach and enjoy panoramas that include emerald ocean vistas, sandy coves, and beautiful waterfront homes. Full-length viewing windows are perfect for grabbing a few photos, and a narrated guide program presented in high-fidelity audio brings the natural and human history of the Florida Keys to life.
The coach crosses more than 40 bridges as the road spans stretches of blue water between inhabited and uninhabited islands large and small. From Knights Key, just off the southern tip of Marathon Key, the world-famous Seven Mile Bridge soars over the crystal water with the Florida Straits on one side and the Gulf of Mexico on the other. The views from this engineering miracle are so dramatic that the bridge has been used for chase scenes in action movies like True Lies and several of the Fast & Furious films. It feels like the coach is flying low over the waves until the road touches land 6.79 miles later on uninhabited Little Duck Key.
Continuing into the Lower Keys, mangrove forests, tropical scrub, small island villages, and sportfishing marinas recall the days when the watery wonderland of the Florida Keys was mainly wilderness inhabited by hardy mariners and pioneering sport fisherman. A short time later, the tour arrives in Old Town Key West. It's right around noon, perfect for lunch in one of the city’s unique restaurants and a full afternoon of riding the fun and funky Key West Trolley around the island.
The trolley cars combine classic styling with modern amenities to deliver a smooth, comfortable ride, lots of fresh air, and wide-open views from every seat. Hop off at any stop to explore the city's highlights and hideaways. Hop back on to continue touring on your own timeline. The trolley offers easy access to Duval Street, Mallory Square, the Southernmost Point, the Ernest Hemingway House and other top Key West attractions plus museums, galleries, shopping, and dining. With 13 conveniently-located stops, riding the Key West Trolley lets you make the most of your Key West visit.
Experience the Overseas Highway, one of America’s classic road trips, and enjoy the unique attractions of tropical Key West on a Cool Destinations Miami to Key West Day Trip with Trolley Tour. These popular Key West day trips fill up quickly, so use our secure online booking system to reserve your seats now!
What's Included
- Round trip transportation from Miami Pickup & drop-off at most Miami hotels.
- Hop-on Hop-off Trolley Tour Exciting 90+ minute fully narrated tour of Key West covering over 100 points of interest.
- 6 hours in Key West (approx.)
- A narrated tour of the Florida Keys by expert tour guides
- Meals
- 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.
Book Online
Our secure website provides real-time availability, instant confirmation, and free, no-questions-asked cancellations up to 24 hours before your rental begins.
Safe & secure • Easy breezy • Hassle-free
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 Route 1: The Overseas Highway (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.
Yes, it's really seven miles long!
US Route 1: Mile Marker Zero
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 accessibleThe motorcoach has no wheelchair lift, and wheelchairs can't be accommodated in the cabin. However, as long as the individual can navigate the steps and use a regular seat and their wheelchair is foldable for storage in the luggage compartment, it is possible. Assistance must be provided by a caregiver in the individual's group.
- Infants must sit on lapsThere is no charge for lap infants. If you are bringing a car seat for your baby, you must purchase a regular-priced seat ticket.
- Stroller accessibleMust be foldable and will be stored in the luggage compartment.
- Transportation has a toilet
- Suitable for travelers of all fitness levels
- What to bringCamera, comfortable shoes, sunglasses, sunscreen, swimwear, towel, travel pillow, and a smile!
- The minimum age for this tour is at your discretion
- This tour will have a maximum of 59 passengers
Frequently Asked Questions
(28)Q: What type of transportation is used for the Miami to Key West Day Trip with Trolley Tour?
A: You will travel on a comfortable motorcoach with up to 59 seats, depending on whether it’s a double-decker or not (motorcoach is assigned based on group size and availability). Read more Apr 2025
Traveler Photos
Reviews
Average 4.60 out of 5 stars based on 2,830 traveler reviews collected by Cool Destinations and partner sites such as Trustpilot, Viator, and TripAdvisor
Additional Info
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Frequently Asked Questions (28)
The answers provided below were previously given in response to questions from Cool Destinations customers.
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You will travel on a comfortable motorcoach with up to 59 seats, depending on whether it’s a double-decker or not (motorcoach is assigned based on group size and availability).
Apr 2025We make a quick stop on the way to Key West for breakfast.
Feb 2022There is only one drop-off point for all passengers. It’s not a huge distance from there to the different activities (usually 3-5 blocks away).
May 2024Both upper and lower deck has wide-view windows.
Aug 2021We can pick them up at Regency Miami Airport at 1000 NW 42nd Ave. Just across Fairfield Inn.
Dec 2021You should select Bayside Marketplace, 401 Biscayne Blvd, Miami, FL 33132 when booking. This is the main terminal and direct departure point for the Miami to Key West Day Trip with Trolley Tour.
Feb 2023Yes, our air-conditioned coach bus has a restroom (and WiFi!)
May 2023You will be dropped off at 908 Caroline Street, Key West, FL 33040.
Mar 2022The closest pick-up to the airport is the Airport Regency Hotel at 1000 NW 42nd Ave, Miami, FL 33126.
Sep 2022There 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.
Sep 2021Yes, you may hop on from any of the stops.
Nov 2024Yes, you may bring one piece of luggage and one carry-on bag per person
Please note that if you leave it on the bus during your free time, the bus is not 100% locked, and we will not be responsible for any loss or damage.
Mar 2024It 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.
May 2023Key West is super casual. A sundress for ladies and khaki shorts for the gets is as dressed up as anyone usually gets.
Jan 2022The 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.
Feb 2021You’ll have approximately 6 hours to explore Key West at your leisure.
Aug 2024Here 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.
Jan 2022On 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.
May 2023You’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.
Sep 2022Yes. Free pick-up is available from all hotels in South Beach, Miami Beach, and Downtown Miami.
Sep 2024Yes, after the tour, we will return you back to the hotel that we picked you up from. Cool Destinations offers complimentary drop-off service to all hotels in Miami Beach and Downtown Miami.
Jun 2023- For a full refund, you must cancel at least 24 hours before the tour start time.
- If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.
- Any changes made less than 24 hours before the tour start time will not be accepted.
- Cut-off times are based on the tour local time (EDT).
- Round trip transportation from Miami. Pickup & drop-off at most Miami hotels.
- Hop-on Hop-off Trolley Tour. Exciting 90+ minute fully narrated tour of Key West covering over 100 points of interest.
- 6 hours in Key West (approx.).
- A narrated tour of the Florida Keys by expert tour guides.
- Meals.
- Gratuities.
This tour requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
Apr 2025The minimum age for this tour is at your discretion.
Apr 2025If a date or time is not listed on the calendar, it’s sold out or unavailable for another reason. Support cannot assist further if a date or time is not on the calendar.
If you find a date and time that works for you, book it NOW because things always sell out at this time of year.
Apr 2025Accessibility information for the Miami to Key West Day Trip with Trolley Tour is as follows:
- Not wheelchair accessible
- Suitable for travelers of all fitness levels
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 Destinations. Please be sure to double and triple check your email address is correct at checkout so this important email makes its way to you!
Mar 2024What's Included
- Round trip transportation from MiamiPickup & drop-off at most Miami hotels.
- Hop-on Hop-off Trolley TourExciting 90+ minute fully narrated tour of Key West covering over 100 points of interest.
- 6 hours in Key West (approx.)
- A narrated tour of the Florida Keys by expert tour guides
- Meals
- Gratuities
Additional Info
- Confirmation is instant and will be received at time of booking
- Not wheelchair accessibleThe motorcoach has no wheelchair lift, and wheelchairs can't be accommodated in the cabin. However, as long as the individual can navigate the steps and use a regular seat and their wheelchair is foldable for storage in the luggage compartment, it is possible. Assistance must be provided by a caregiver in the individual's group.
- Infants must sit on lapsThere is no charge for lap infants. If you are bringing a car seat for your baby, you must purchase a regular-priced seat ticket.
- Stroller accessibleMust be foldable and will be stored in the luggage compartment.
- Transportation has a toilet
- Suitable for travelers of all fitness levels
- What to bringCamera, comfortable shoes, sunglasses, sunscreen, swimwear, towel, travel pillow, and a smile!
- The minimum age for this tour is at your discretion
- This tour will have a maximum of 59 passengers
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