The Best of Key West

Women having a blast walking the beaches of Key West
January 28 – February 1, 2025
LOCATION: Key West, Florida, USA
PRICE: $3,495

Active Adventure for Women in Key West, Florida

In Key West, the southernmost point in the US, you can enjoy beautiful beaches and sunsets, discover local wildlife and immerse yourself in maritime, literary and political history. A casual getaway with much to offer the adventurous. We’ll swim and snorkel with dolphins, see Hemingway’s House, Mallory Square and Duval Street of course, kayak in the mangroves, enjoy bicycling through Old Town, and discover the excellent cuisine of this notorious city. If you’ve never been to Key West before, you are in for a real treat. We’ll have time for multiple activities, food and culture, museums, relaxing in the sand and more. There is something for everyone in Key West, and the winter brings warm temperatures, water activities galore, beaches for miles, and so much fun! This is an unpack once and chill trip!

Key West Activities at a Glance

  • Dolphin Watch & Snorkel

  • Hemingway’s House

  • Kayak in Mangroves

  • Unpack once and chill

  • Bicycle in Old Town

  • Miles of Beaches

  • Photographer’s Dream

  • Foodies Trip

Best of Key West Itinerary

Day 1

Arrive in Key West, Florida by 3pm, and transfer to our meet up point at the hotel. Your Canyon Calling Trip Leader will greet you and get you checked in. We will meet as a group in the hotel lobby and head out to enjoy fabulous Key West. The walking food tour celebrates the Cuban and Caribbean influences of both food and culture. We’ll stop at five locations, complete with a sweet treat, a beverage of choice, and designed to introduce you to authentic island flavors like cuban roast pork, fresh fish, vegetarian options, a signature rum drink, and of course, key lime pie! We’ll walk off the beaten path and into historic neighborhoods and hidden gems. Our five plus tastings will serve as our Welcome Dinner as we get to know one another. We’ll head back to our hotel and maybe enjoy the pool before ending our first day with delicious memories in our heads. Stay at Fairfield by Marriott Key West at the Keys Collection.

Day 2

After breakfast, we’ll stroll around Old Town Key West and enjoy the local flavor including lunch. This afternoon we’re off to experience the magic of Key West’s wild bottled-nosed dolphins! Our Captain will guide our private journey through the sparkling waters around Key West. On our adventure we will experience the natural wonders of Key West’s famous coral reefs, backcountry mangrove habitat, diverse bird populations, and local marine life, including of course the resident dolphins. We’ll learn about the dolphin’s social behavior, physiology, healing and spiritual aspects. We witness the behavior of these incredible mammals in their own habitat. Enjoy a snorkel and swim in the waters around Key West. Tonight we’ll enjoy another excellent dinner before heading back to the hotel or wander around town a bit more.

On each trip I’ve shared with you I’ve watched as the women you gather together become a community and learn to love, share and become more tolerant and accepting of the differences in the world.
— Lou, Vancouver

Day 3

After breakfast, we’ll hop on our bikes (optional activity) for an historical journey around the island of Key West. We’ll enjoy a fun and informative experience. Discover the history, architecture, and culture of what they call “The Conch Republic”. We’ll see Hemingway’s house, Mallory Square, the Customs House, the cemetery, and all the highlights of Old Town Key West. We’ll end it with (of course) a perfectly chilled slice of key lime pie. Yum! After this fun activity, we’ll have lunch (yes life is short so we’ll have dessert first), then the afternoon is free to enjoy the beach, find your favorite happy hour place, or just chill. We’ll go to Mallory Square to see the famous sunset, entertainers and the artists. Dinner tonight is at a special place – such wonderful food options on this tiny island!

Day 4

After breakfast, you have the morning free to wander and shop Key West. We’ll meet up around noon for a delicious lunch. This afternoon we’re off on a kayak adventure in the mangroves. We’ll explore the Key West mangroves on this guided kayaking tour as we learn about the geology of the Florida Keys and the region’s coastal environment. Tropical fish, crabs, jellyfish, sea birds, and other animals make their home in the mangroves, so be on the lookout for local wildlife on our eco-adventure. Along with our experienced guide, we’ll paddle at a relaxing pace and explore the shallow, calm, blue-green waters of the back country of Key West. Our adventure will give us a chance to view the mangrove environment up close, along with its marine life. After our activity we’ll head back to the hotel to relax and get cleaned up for our Farewell Dinner. As the gorgeous Key West sun sets, we’ll recount our lively and fun times, enjoying the company of our road sisters one last evening.

Day 5

Enjoy the hotel amenities until it’s time to transfer to the airport, or choose to extend on your own and play in Key West.

What’s Included:

  • 4 days/4 nights fully guided tour by a Canyon Calling Trip Leader
  • All land transportation as outlined in this itinerary
  • All accommodations, double occupancy
  • All meals from dinner on Day 1 through breakfast on Day 5
  • All guided activities and excursions
  • All local guide’s gratuities
  • All entrance fees and permits

What’s Not Included:

  • Transportation to/from Key West, Florida
  • Alcoholic beverages and items of a personal nature
  • Optional gratuity to your Trip Leader at the end of the tour


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