ShoreTrips logo Shore Excursions - City Tours - Day Activities


Per Person $114 USD
Child (Ages 6 through 12 years) $93 USD
Child (no food samples included) (Ages 5 and under) $0 USD
*Selections and optional choices will be made during checkout


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ShoreTrips says...

This tour does not include entry into the Hemingway House. As that tour can only be handled by Hemingway House docents, it can be your choice to do it before or after Authentic Hemingway. It is interesting to see his writing desk but remember, the property is home to 40 to 50 polydactyl cats as well.

One of Key West's most famous residents was the literary legend Ernest Hemingway. Upon visiting the island of Key West Florida in the early 20th century, Hemingway instantly fell in love with the ambiance of the island, drawn to the island's unique atmosphere that makes you feel like you are in a completely different country while still within the United States. Some of the things that brought Hemingway to Key West were the amazing offshore fishing, the laid-back drinking culture at the bars, the friendly but quirky residents of the island, and the year-round balmy tropical weather and warm breezes that gently caress the island on any given day. It didn't hurt that his wife's uncle gave the couple a massive estate (though in great need of renovation) as a gift, which became a great anchor to a city much like his adored Havana.

You will be meeting your special guide at the Hemingway home. Rather than begin the tour inside the home, we will start our adventure by moving through town, listening to stories and infamous tales of Ernest's life here. Learn about how Hemingway arrived to Key West and what kept him there. As you pass by some of the favorite haunts of his daily life, stories abound around town. This tour will bring you to the real places that Hemingway supported, where he worked and played, including where he watched and refereed boxing matches. You will see where he moored his boat, Pilar, and the bookstore where his books were sold. His first apartment in town where he finished “A Farewell To Arms” is still standing as well.

During the tour you will partake in some food samplings as Key West is also known for some tasty local street food. Rambling through the areas where he caught the train, chartered boats and fished, your mind will paint a picture of all he saw in this relaxed town, and so similar to his haunts in Cuba.

Finally, you will see where he did most of his drinking, both the spot of the original Sloppy Joes and the current one. This authentic tour is so special in a city where the water activities often take over. Often the incredible culture is overlooked and since Hemingway is still one of our most illustrious and prolific writers, seeing his lifestyle will help understand those novels.

Today, the Hemingway legacy is very much present in Key West. The home he lived in is still there for a visit. As the tour of the Hemingway home must be delivered by a Hemingway House docent guide, we suggest that you do this part either before or after our tour of the Hemingway lifestyle and highlights. It will be our portion of the Hemingway immersion that will deliver the daily highlights, insight and infamous tales of Ernest's life in Key West.

  • This Tour Includes:
  • A passionate and knowledgeable guide
  • An easy walking tour to see Hemingway's haunts
  • Samples of 3 local foods and a beverage
  • Tremendous insight and stories of Hemingway's time in Key West

Days of Operation

Mon - yes
Tue - no
Wed - no
Thu - no
Fri - yes
Sat - yes
Sun - yes

Departures (local time)

  • 10:45 AM (2 hrs)

Transfer / Meeting Instructions

See Special Instructions Specific pick up or taxi instructions will appear on your voucher after you purchase your trip.

Special Instructions

• Gratuity is not included.
• Entry into the Hemingway home is not included. If you wish to see the inside, including the gardens, pool, and writing studio, please allow time before or after our tour. Tickets need not be pre-reserved for the 30-minute home tour but are not included in this experience.
• This is a WALKING TOUR. It is moderately paced and suitable for most fitness levels.
• You will be covering about 1.7 miles during the tour.
• Food samples included are grilled chicken street tacos, conch fritters and key lime pie and a rum punch. There are no substitutions.
• Wear comfortable clothing and shoes for walking.
• We suggest bringing a small bottle of water, sunscreen, and a hat.
• Tour runs rain or shine. Ponchos are provided if necessary.


• You should be able to walk just under 2 miles, mostly flat surfaces.
• The food tasting has no substitutions.
• This tour can be arranged as a Private tour. Please contact ShoreTrips for pricing.