10 Day Trips from in Key West That You Shouldn't Miss

June 25, 2021 Elouise Mccaul

Does time ever pass in the Florida Keys? Everyone and everything in Key West seems to go at its own pace, right down to the ice melting slooooowly in your margarita glass. Of course, it’s not all limes and leisure – Key West is known as the “Winter White House” because of its appeal to visiting U.S. presidents, and the island has been home to literary greats like Ernest Hemingway and Tennessee Williams. The diving here is phenomenal, as is the kid-friendly Florida Keys Eco-Discovery Center.
Restaurants in Key West

1. Private Tour of Florida Keys from Marathon to Key West

Up The Keys
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5.0 based on 2 reviews

Visit the one-and-only island city of KEY WEST! Enjoy a narrated tour on the way down, and island music on the way back. HIGHLIGHTS • See the sights in Key West • Stay for the Key West sunset • Plenty of Free Time • Designated Driver • Narrated Tour Do what you want in Key West! We're doing the driving! Choose to sightsee, enjoy a happy hour, eat a nice dinner, check out Mallory Square at sunset, take a sunset sail, and more! Sit back & enjoy the scenery as we drive down to Key West. We're licensed like a limousine, so you can enjoy your favorite beverages en route. Learn the history, culture, and ecology of the Florida Keys & Key West from your friendly local guide. See the Southernmost Point, Hemingway's House, Mile Marker Zero, Sloppy Joe's, and Mallory Square It's more like a road trip than a tour - ask questions, point out wildlife, make new friends.

Inclusions: Local Driver/Professional Tour Guide, Live commentary on board, Hotel pickup and drop-off

Exclusions: Gratuities

Reviewed By N7806XTaaronj

The Tour Guide (Rick) was personally, knowable and very informative about Key West. He asked us what were some of our interests and incorporated in the tour. He advised us that we could stop at any point on the tour if we had a need.

2. Private Tour of Florida Keys from Key West: 7-Mile Bridge, Beach, and Key Deer

Up The Keys
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5.0 based on 8 reviews

Private, exclusive tour of the islands near Key West. The only land-based tour in the Florida Keys, operating from Key West. Small groups of up to 12 travel in a comfortable customized air-conditioned vehicle along the Overseas Highway. Drivers are professional tour guides who share fun and interesting information about the Florida Keys and the islands we traverse. Experience the iconic 7-Mile Bridge, relax on the world-famous Bahia Honda Beach, and photograph endangered Key Deer on Big Pine Key. Children are welcome. This tour is customizable. You'll love this tour so much, you'll book it again next year!

Inclusions: Variety of sandwiches & chips, water & sodas, Entry Fees, Air-conditioned vehicle, Hotel Pick-Up

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Reviewed By N7806XTaaronj

The Tour Guide (Rick) was personally, knowable and very informative about Key West. He asked us what were some of our interests and incorporated in the tour. He advised us that we could stop at any point on the tour if we had a need.

3. Small-group private Key West tour with expert guide

Banana Joe Tours
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5.0 based on 1 reviews

Our Key West tour is carried out by a real tour guide with over 10 years of Florida experience, who will explain everything on the way to Key West and answer all your questions. Of course, we have built in some points on the route where you can leave the van and go on an exploration tour on foot and take pictures. We look forward to seeing you. Your Banana Joe team

Inclusions: Private transportation, Florida expert tour guide, small groups, Insider knowledge

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Reviewed By 540saschag

We loved our Miami City Tour with Hagen! He showed us Miami from a local point of view!! The tour was very informative and engaging. Highly recommended!!

4. Key West Shore Excursion: Conch Tour Train

Conch Tour Train
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4.3 based on 6 reviews

When you arrive in port in Key West, take a Conch Tour Train shore excursion on your own; you’ll see the best of Key West on the tour that's been entertaining visitors to the Island City since 1958. You’ll hear legends and lore of this charming tropical paradise like stories about Henry Flagler's railroad, which arrived in Key West September 22, 1912, and forever changed the Island City.

Inclusions: Narrated train ride tour, Local taxes

Exclusions: Gratuities, Food and drinks, Port pickup and drop off

Reviewed By Brian B

Provides a look at Keywest without walking around. Do the tour first thing in the morning. There are several stops that you can jump off to see sites. Apparently the city requires masks on public transportation. I've been on better type tours.

5. Key West Day Trip from Miami with South Beach Bike Rental

South Florida Trikke
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4.3 based on 3 reviews

This full-day trip to Key West from Miami includes a 4-hour ride across of one of America's most unique motor journeys, the scenic 110-mile Overseas Highway combines ocean views, 42 bridges, natural wonders and history like no other place. Each region of the Keys has its own unique character, worlds away from big cities and theme parks. After you enjoy a full day in the Keys, please visit our shop where you can pick up your free bike rental for a full day ( 9am to 6pm ), to explore South Beach during your stay in Miami.

Inclusions: Hotel pickup and drop-off, Air-conditioned vehicle

Exclusions: Gratuities

Reviewed By Stephen B

It was fun and informational! Equipment easy to use and worked great. Big on safety. Would do it again.

6. Key West Conch Tour Train

303 Front St, Key West, FL 33040, USA Conch Tour Train
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4.2 based on 159 reviews

Experience the best of Key West on the famous Conch Tour Train! One of Florida’s most popular attractions, the Conch Tour Train has been entertaining visitors to the ‘Island City’ for decades. Learn about the history of the train, a tribute to Henry Flagler's engineering miracle when he brought the railroad to Key West in 1912, and explore this charming tropical paradise on a leisurely train ride around the island!

Inclusions: Narrated train ride tour, Local taxes

Exclusions: Gratuities, Food and drinks

Reviewed By where2nextbabe

I would suggest if you are going to do this tour, do it as one of the first things you do. We did this the 2nd day we were here. The thing is, we rented a golf cart the first day and so we had already seen most of the things on this tour. The tour guide did have some good info and we did get some interesting info on things we did see prior. So, take the train tour and then decide what you want to go back and spend some time at. It also gives you and idea of where everything is. You do have to wear a mask, you get a 10 minute stop about half way through the tour to use the restroom, buy snacks, drinks or souvenirs. Just know that where you buy your tickets is not where you board. You board about a block down from the main ticket office. Which is really not a big deal.

7. Miami to Key West Day Trip with Optional Activities

Travel to Key West
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4.2 based on 292 reviews

- Ride across 34 islands and 42 bridges known as the Florida Keys. You will travel through the 7 Mile Bridge - one of the longest in the world! The road is bordered by the emerald water of the Gulf of Mexico to the west and the Atlantic Ocean to the east. Make sure you take pictures! You will have approximately 6hrs in Key West to explore the island at your leisure. Key West lies at the end of the chain of islands known as the Florida Keys and is the southernmost city in the continental United States. - Key West is known for its clear blue waters, sun-filled skies, and laid-back attitude. In addition to being a great vacation spot, the city has also served as an artistic refuge, a presidential retreat, and a military post. - Water activities are very popular in Key West too! We offer Snorkeling, Parasailing, and Glass Bottom Boat tours. Note: If the activities get canceled for any reason, we will refund them, however, we will NOT refund the tour to Key West ($39 value).

Inclusions: Transport by air-conditioned coach bus, Narrated tour, Hotel pickup and drop-off, select hotels only in Sunny Isles, Miami Beach, and Downtown Miami., Activities, if option selected, Map of Key West and Guide knowledge on what to do/see and how to get around!, Day Trips (Round Trip), One Way Trips (MIA-KW) & Overnight Trips Available.

Exclusions: Food and drinks

Reviewed By Denise T

This trip was a bit of a disappointment. We were picked up at the Embassy Suites at 530am in Ft. Lauderdale and expected to be on the bus, but were picked up by a shuttle driver that took us to the bus, and then for the next 2.5 hours, we picked up alot of other folks...finally made it on the way to Key West around 830am, and we were told we would stop for bathroom at 9am. However, there were 2 accidents that kept us locked in traffic for almost 2 hours..so no stop u til we finally got to Key West at 1230pm..that was 7 hours one way! They told us to meet the bus at 6pm. Now, Key West is a lovely, tourist town, and we are not museum goers or shoppers or tour takers or bar hoppers so we really didn't need 6 hours, but we made the best of it and rented a scooter..that was fun! VERY HOT DOWN THERE so bring water and sunscreen!!! Nice town! Then we got on the bus at 6 and made it back to Miami around 915pm, then proceeded to drop allllll those people off and then at 1030 we met up with our shuttle driver and made it back to our car at 1115pm! It would be nice if the company told you that there are multiple stops before you get on the road to Key West...much better if you just drive yourself. Air conditioning on the bus could be a bit better too. Not gonna do that again ????

8. From Miami: Key West with options like Snorkel with Drinks

Miami Beach, FL, USA US2U Tours
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3.8 based on 6 reviews

Enjoy the scenic and breathtaking drive on the Overseas Highway One passing Key Largo and the famous Seven Mile bridge to America’s southernmost city Key West. If you selected the snorkel option in Key West we will board a boat and go out to the reef where we will snorkel and experience Florida's underwater world. After the snorkel tour you will have some time to experience the highlights of Key West on your own. If you selected the transportation only tour option you can enjoy 6 hours of leisure to exploring the islands turquoise waters and white sandy beaches or the small white Victorian conch villas and lush tropical gardens. Stroll along Duval Street with it’s cute shops, galleries and cafes to the famous southernmost point monument only 140 km or 90 miles north of Cuba. Key West’s Caribbean flair and charm will seduce you and is a favorite day tour from Miami. Round trip transportation is included  

Inclusions: round trip transportation, pickup & drop-off from any Miami Beach hotel along Collins Avenue between 1st and 65th Street or central meeting point located at Holiday Inn, 340 Biscayne Boulevard, Downtown Miami, guaranteed seat on the air-conditioned bus to and from Key West, 6 hours leisure in Key West, driver/guide in English/Spanish, Use of Snorkeling Equipment (If Option Selected), unlimited drinks on the boat if option is selected, 2-3 hour boat/snorkel tour in Key West if option is selected

Exclusions: Optional Key West activities are not included if option is not selected

Reviewed By ElleOli

The bus driver literally left us at the stop when he clearly asked where we were headed (Everglades). Bus driver seemed to have no idea what was happening. We never made the trip after waiting 1 hour for transportation...

9. Key West Day Trip from Miami with Optional Activities

Gray Line Miami Tours
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3.8 based on 603 reviews

No visit to South Florida is complete without a journey to Key West! There are plenty of ways to enjoy your time on this culturally and history-rich island. You can take it slow with a leisurely day soaking up Key West's laid-back atmosphere, quaint shops and outdoor cafés or if you are looking for more activity, there are upgrades available. Get out on the water on a glass-bottom boat ride, snorkeling cruise or parasailing adventure, or see the attractions on dry land on the Hop-on Hop-off Trolley Tour or with a ride on the Conch Train. The 12-hour day trip from Miami to Key West is a mesmerizing trip not to be missed.

Inclusions: Day trip to Key West by bus, Hotel pickup and drop-off from Miami Beach/Downtown hotels with English/Spanish Driver and Guide, If Upgrade is selected- Glass Bottom Boat, Trolley, Conch Train, Parasail, Snorkeling , All taxes, fees and handling charges, Hand Sanitizer

Exclusions: Gratuities, Food and drinks, Admissions unless stated

Reviewed By B4415UXcrystalh

Motor coach bus that was used was semi non functional such as seats were broken not able to sit them upright. The compact restroom on the bus was deployable. Very nasty not able to flush, there was a bucket to collect the urine. In the midst of a pandemic there was no hand sanitizer in the restroom. The smell was unbearable. This was a three hour trip to and from Miami going to the Key West. I asked them to clean it and the driver agreed. On the way back the smell was worse. The driver used the restroom and as I stated no hand sanitizer in there. So that means he urinated and did not wash his hands. As he walked back to the front he was touching some of the seats with his nasty hands. Asked for some spray and he got an attitude. He drove 11/2 hours before offering a rest stop, when he did stop the gas station was closed, so he drove another 45 minutes before stopping for restroom. I had to spray my own perfume to try and cover up the urine smell. Not to mention when we got to the snorkeling adventure the changed the site as to where we was going. The people there was answering question with an attitude. Stating that we didn’t have to go, so try to get your money back. Terrible customer service.

10. Key West Dolphin Spotting or Snorkel Boat or free time options

South Beach, Miami Beach, FL 33139, USA US2U Tours
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3.3 based on 30 reviews

Enjoy the scenic and breathtaking drive on the Overseas Highway One passing Key Largo and the famous Seven Mile bridge to America’s southernmost city Key West. Enjoy ca. 6 hours of leisure to enjoy the islands turquoise waters and white sandy beaches or the small white Victorian conch villas and lush tropical gardens. If you select the Dolphin Snorkel option a ca 3 hours Dolphin Spotting Snorkel Tour is included. Stroll along Duval Street with its cute shops, galleries and cafes to the famous southernmost point monument only 140 km or 90 miles north of Cuba. Key West’s Caribbean flair and charm will seduce you and is a favorite day tour from Miami. Round trip transportation is included  

Inclusions: round trip transportation if option selected, pick-up & drop-off from select hotels if option selected, ca. 6 hours leisure in Key West if option selected, 3 hours Dolphin-Spotting Snorkel Cruise if option selected, Use of Snorkelling equipment

Exclusions: Dolphin Spotting Snorkel Tour is only included if option is selected, Miami pickup & drop off if option is not selected

Reviewed By ElleOli

The bus driver literally left us at the stop when he clearly asked where we were headed (Everglades). Bus driver seemed to have no idea what was happening. We never made the trip after waiting 1 hour for transportation...

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