Top Key West Travel & Transportation Services

Instead of waiting for a taxi or shuttle service from the Key West Airport, book a private transfer to Key West, Marathon Key, or Little Palm Island as well as a return trip. Choose from a luxury sedan for three people, an SUV that seats up to five, or a stretch limousine that comfortably fits six.

Forget the long lines and confusion associated with finding transportation from the many Key West International Airport arrivals. Skip the taxis and shuttles and travel with confidence by scheduling a private, luxury sedan that can carry up to three people. Then sit back and relax as the vehicle travels from the airport to any Key West accommodation. Please note: this service is available to Key West hotels only.

Why stress waiting for unreliable taxis or shuttle services to Key West Airport? Ensure peace of mind with a private transfer from your Key West, Marathon Key or Little Palm Island accommodation to Key West Airport (EYW). Reach the airport relaxed and with plenty of time to spare before your flight! Transfer services are available 24 hours a day, seven days a week. Choose from a luxury sedan transfer for three people, a sport utility vehicle transfer that carries up to five passengers or arrive in style in a stretch limousine that comfortably fits six. All vehicles feature stylish and spacious interiors and you will be met and escorted by a professional chauffeur.

If Your Flying Into or Out Of The City, Allow The Chiefton Group To Meet You There or Get You There… Get Curbside Pick Up / Drop Off Service. Enjoy The Scenic Ride From and/or The Scenic Ride Back to The Airport.

Take a tour of St. Thomas with a local guide, in your own private, air-conditioned vehicle with this tour, designed for groups of six to 14 travelers. You'll visit historic Fort Christian, take in the views from Mountain Top, Skyline Drive, and Drake's Seat, and have time to stop for some cocktails and souvenir shopping along the way.

Watch the sun set and the moon rise off the coast of Key West on this sunset cruise. Enjoy the scenery and peaceful calm of a late afternoon sail aboard a 70-foot catamaran with plenty of deck space to stretch out and enjoy the breathtaking view. Then watch a legendary Key West sunset as the sun glistens and gently settles into the water. Hearty appetizers plus champagne, wine, full liquor bar, ice-cold beer and soft drinks are included.

Try something new in Key West: parasailing. Adventure seekers who've booked this trip will love soaring over the Key West Seaport. The experience is available for singles, doubles, and even triples so it's a fantastic activity for a group of friends or a family. You'll board a state-of-the-art boat, get briefed by the crew, and then fly over the city—free as a bird.

Get ready to party in paradise on this guided, 2.5-hour Key West pub crawl. The beautiful island city of Key West is famous for its raucous bar scene. Visit some of its most popular and entertaining establishments, beginning downtown and then traveling to the historic seaport and back to busy Duval Street. Enjoy a domestic beer or mixed drink at each of the five locations and receive a free souvenir t-shirt to commemorate the event. Guests must be at least 21 years old to participate.

Explore the best that Key West has to offer on this narrated, Conch Train Tour. See Key West’s top attractions and learn about the Conch Republic’s history and residents, past and present. See where Ernest Hemingway used to hang out and find out why Harry Truman used to spend so much time here. Get to know Old Town Key West, from the Front Street Depot to Mallory Square and everything in between, including live onboard commentary from a professional tour conductor. It’s Key West’s original, and most iconic, sightseeing tour.

Enjoy an afternoon of swimming and snorkeling on this cruise off the coast of Key West. Spend a relaxing afternoon on a 69-foot catamaran headed to North America's only living coral barrier reef for the adventure of a lifetime. Pass some of Key West’s top attractions on the way, then dive right in to see more than 600 species of colorful fish, coral, and other sea life. This cruise includes professional snorkeling gear and instruction plus beer, wine, and soft drinks.

Get ready for fun in the sun on this dolphin watch and snorkeling adventure off the coast of Key West. Cruise away from the island city of Key West and see dolphins swimming alongside the boat, then jump in for a shallow-water snorkel at the Key West National Wildlife Refuge with many different species of marine life. Relax, feel the warm sea breeze and select from a variety of refreshing beverages on board the boat.

Discover some of Key West’s deepest, darkest secrets on a 60-minute ghost-themed trolley tour. The Trolley of the Doomed explores the darker side of one of the most haunted cities in the country. Experience Key West’s frightening past while traveling down the narrow, dark streets of Old Town, lined with 19th-century wooden houses that still bear the secrets of their former inhabitants. This tour is narrated by a 17th-century gravedigger guide who’s almost as scary as the stories being shared.

Explore the best that Key West has to offer on this narrated, hop-on hop-off trolley tour. Visit more than 100 points of interest among Key West’s top attractions, with an expert guide who takes you through the history of the city. Select from an unlimited 1- or 2-day pass to suit your schedule.

If you’re traveling to Key West for a special occasion, such as an engagement, anniversary, family reunion, or wedding, capture the moments with the help of a professional photographer. Plan to meet at your resort or the beach to have a personal photo shoot and receive the edited photos within two weeks.

Glamorous professional photo shoot in unique Key West locations. We will create amazing photo memories from your visit. You will be able to see undiscovered locations, and get the best photo story from your Key West visit. We can tailor each photo shoot to meet your requirements. Our Photoshoots are ideal for any Tourists - Solo Traveler - Couples - Groups - Hen/Bachelorette & Stag/Bachelor Parties - Families - Secret proposal/Engagement - Honeymoon - Experienced Influencers and Models - New Influencers and Models What's Included: A Private online viewing gallery - 1 hour = 20 professionally edited photos* - 2 hours = 30 professionally edited photos* - 3 hours = 40 professionally edited photos* - 4 hours = 50 professionally edited photos* * same set of images - A unique location professional shoot experience - DELIVERY - Up to 14 days after photoshoot. What's Excluded: - Transportation - Entry fees

Our biggest passion is to be behind the camera 24/7 and to capture the best moments of your trip while showing you the wonders of Key West. With more than 400 reviews on different platforms and several nominations for the best hosting photography experiences, we are super happy to offer our photography in Florida to travelers and locals! We will also help you find your way in the city and give you tons of tips to complete your perfect trip, as we know all the secrets of Key West and we love to connect! If it's your first time we will give you tips on how to pose and can bring more than one outfit. Whether for a vacation, professional or even wedding photography in Key West we are photography professionals and will provide you with unforgettable memories. You can also book our engagement photographers in Key West and use our concierge service to prepare an unforgettable engagement or proposal photo shoot. So whatever photography needs in Key West you might have, let's start!

Forget about fighting traffic and looking for a parking spot at the Key West International Airport. Skip all the headaches associated with getting to the airport and travel with confidence by scheduling a private, luxury sedan that holds up to three passengers. Then sit back and relax as a professional chauffeur drives from any Key West hotel to catch all the Key West airport departures 24/7. Please note: this service is available from Key West hotels only.