The beautiful city and historic seaport of Key West, Florida, has earned its reputation as one of the best places in the United States for vacations, recreation, corporate retreats, work outings, and much more.
It’s the perfect place to catch some sun, have some fun, and hold the occasional business meeting. This island paradise is perfect for corporate retreats or team-building exercises that can help employees get to know each other better, especially those who work remotely.
A tour we think you'll love
Let’s take a closer look at must-see locations and group activities to visit as part of your group’s upcoming Key West corporate events.
1) Illuminate Your Team Spirit With A Night Kayaking Tour
Key West Paddle offers an amazing and unique experience to its guests as the only night kayaking tour in the city. It’s an amazing opportunity to see wildlife and beautiful scenery in a whole new light.
Our night kayaking tours create camaraderie and allow team members to get to know each other better while enjoying a fun and unforgettable experience.
Team members can explore Key West’s historic mangrove tunnels in single or double-glass bottom boats affixed with LED lights that illuminate the area’s beautiful marine life and allow you to view sea creatures and scenery as you’ve never seen them before.
You’ll be accompanied by two local and knowledgeable guides who can explain the area’s rich history, as well as facts about the creatures you view. As a local, family-run business, we understand the importance of building and fostering connections.
We also offer a Key West sandbar excursion, the perfect incentive trip for smaller groups (up to six people at a time). It covers locations in the Jewish Basin sandbars and Mud Keys, as well as a picturesque sandbar at Snipe Point.
Ready to create unforgettable memories with your team? Book your unforgettable tour today and experience the magic of Key West like never before!
2) Step Into Literary History At The Hemingway House
The former home of famed novelist Ernest Hemingway is now a museum dedicated to his life and works. Fans of “The Sun Also Rises”, “The Old Man and the Sea”, “For Whom the Bell Tolls,” and the Humphrey Bogart/Lauren Bacall classic “To Have and Have Not” will love seeing an intimate look at the author’s life.
The Hemingway House is open 365 days a year from 9 AM to 5 PM, and no reservations or appointments are needed. This makes it easy to fit into the schedule no matter what the hours are for your corporate event.
Alternatively, as a team-building exercise, you can separate employees into pairs or small groups, have them take the tour, and then compare notes. Employees can showcase their attention to detail and reveal parts of their personalities or interests by revealing which parts stood out to them the most.
Fun fact: Hemingway wrote some of his most famous works, including “To Have and Have Not,” while living in this house.
Let’s explore some nearby treasures that the group members will surely appreciate:
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Key West Lighthouse – Located across the street, offering panoramic views of the island
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Fort Zachary Taylor Historic State Park – Offers beautiful beaches and historic fort tours
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Truman Little White House – A historic site where President Harry S. Truman spent his winters
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Southernmost Point – A must-see landmark that marks the southernmost location in the continental U.S., offering a perfect photo opportunity
3) Discover Serenity And Team Bonding In Tropical Gardens
The Key West Tropical Forest & Botanical Garden is another great location for team-building exercises. Team members can explore the unique and beautiful plant life (including the orchid filled trees), go birdwatching (or “birding,” as it’s more correctly known), and otherwise enjoy the amazing nature of Key West’s tropical paradise.
Good to know: The venue also hosts a yoga night once a month, if your schedule happens to align. It’s also a great location for a scavenger hunt if you want to add some Key West team building as part of your visit.
4) Experience The Vibrant Energy Of World Famous Duval Street
Duval Street is one of the most famous thoroughfares in the Florida Keys and is one of Key West’s biggest attractions. Cafés, shops, galleries, delicious food, and more line this mile-long street on the southern end of town.
The street is so famous that it has its own 24-hour webcam so that even people thousands of miles away can enjoy the amazing street in all its glory. It’s also home to some of Key West’s finest nightlife, allowing team members to enjoy a well-earned reward at the end of their day.
Don’t miss these must-visit spots when you explore Duval Street:
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Cowboy Bill’s Honky Tonk Saloon is the southernmost country bar in the United States. Owned by a former cowboy, Bill’s is another once-in-a-lifetime experience in a city full of them.
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La Te Da is a restaurant and a piano bar that also features a hotel and a cabaret for those who want a location with more than just drinks.
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Willie T’s is a great place for mojitos, frozen drinks, and much more. They also offer steak and seafood if you’re hungry for more than just the standard bar fare.
Depending on your team’s physical fitness, abilities, and desires, bike rentals are available, so you can cycle around the island and enjoy the beautiful sights.
Pro tip: For great Key West team building, you can all rent bikes and take photos at various points, then meet up in a designated location and share your pictures with the group. This will allow team members to showcase their personalities and help them better understand and be understood by their colleagues.
5) Boost Team Collaboration With An Exciting Scavenger Hunt
Speaking of which, Key West Hunt hosts The Southernmost Scavenger Hunt, an exciting way to reward your team and help further build their connection during your trip. Team members can explore the island while hunting for clues and building lasting connections with each other.
If you’d like something even more special, the scavenger hunt can also be customized for your company and its employees. No matter whether you go with the standard or a uniquely tailored adventure, your team’s bond will be strengthened by having fun together during your next corporate event.
6) Celebrate Team Success At Mallory Square’s Sunset Celebration
Although Mallory Square is located on the northern end of Duval Street, the waterfront plaza truly deserves its own entry. A popular location for many years of the island’s rich history, some of the best shops, bars, and delicious food in Key West can be found here.
Give these awesome restaurants around Mallory Square a try:
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Two Friends Patio Restaurant offers local seafood and much more but the main attraction is their delicious breakfast menu, which can’t be missed.
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Duetto is an Italian restaurant that features traditional pizza from Italy, panini, and other traditional Mediterranean cuisine with gelato for dessert.
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Bistro 245 offers indoor and outdoor seating that you can enjoy depending on your mood. Their fabulous brunch menu is one of the finest in Key West.
It is also home to the famous Sunset Celebration, a nightly festival that begins two hours before the sun sets. It features jugglers, psychics, magicians, musicians, and much more. It’s the perfect spot to make memories with your group that will last a lifetime.
Fun fact: The Sunset Celebration at Mallory Square has been a tradition for over 50 years, attracting visitors from all over the world.
7) Relax And Rejuvenate On A Secluded Private Beach
Several hotels and resorts in Key West offer private beach access, which can create the perfect team building experience. Employees who don’t otherwise enjoy meetings probably won’t mind one that takes place under the sun of this amazing tropical paradise.
With a few basic supplies, you can also play games and complete other group activities to promote togetherness and help your team truly bond. Since it’s included as part of your accommodations, it’s also some of the cheapest event space your company will ever book.
If it isn’t part of your accommodations, you can also easily book private charters in Key West to beaches that might not be private but are secluded.
Plan Your Unforgettable Team-Building Event In Key West
No matter how long you’re in town, you won’t want to miss the unique opportunity to enjoy one of Key West’s most amazing attractions. Our intimate night kayaking tours will give you and your team members a night to remember and a story to tell for years.
Your group will love the tour so much that we recommend booking it for your first night in Key West. It provides the perfect Key West team-building opportunity, as two employees can be placed in the same glass-bottom boat and will literally have to work as a team to paddle the kayak during the trip. Who says team-building activities can’t be fun?
The perfect accompaniment to your night kayaking adventure, a private sandbar charter can help enhance your meetings or corporate parties in Key West. Your group can enjoy an amazing open-air meeting space while enjoying some fun on the sandbars.
Whether you and your group are here for Key West corporate events, business meetings, an incentive trip, or any other special event, you won’t want to miss the sweeping views and amazing marine life. Book your next unforgettable adventures today!
