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Explore Worldwide + Second City Partnership

Explore Worldwide and The Second City are teaming up to give you the chance to win an unforgettable trip to Costa Rica!

The Second City is one of the world’s most iconic comedy institutions, known for launching the careers of legendary comedians like Tina Fey, Steve Carell, and Keegan-Michael Key. With its roots in Chicago, The Second City is famous for its sharp improv, smart satire, and unforgettable live performances that have been making audiences laugh for over 60 years.

This partnership celebrates the spirit that both improv and adventure travel share — stepping outside your comfort zone, embracing the unexpected, and connecting with others along the way. Together, we’re bringing that adventure to life through travel and laughter.

What do you win?

Explore Worldwide will provide a free Highlights of Costa Rica tour for one person, including roundtrip flights. The winner can redeem the trip on any available 2026 departure.
 

 The winner will enjoy an 8-day adventure through Costa Rica, exploring volcanoes, rivers, rainforests, and beaches alive with wildlife, creating a perfect adventure for anyone who loves nature and discovery.

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Additional Prize!!!

The second winner will receive an online Improv 1 class through The Second City. 

Improv 1 introduces students to the fundamental concept of “Yes, And” in improvisation. Through group exercises and games, students will explore impulse & spontaneity, listening, being present in the moment, taking risks, finding agreement (making & accepting offers) and other basic building blocks of improvisation, all in a supportive environment that embraces the idea of trusting yourself and failing joyfully.

A chance to learn something new. 

Contest Terms and Conditions


1. The price is a tour for two, travelling together with Explore Worldwide on Highlights of Costa Rica Tour (Tour Code: BCC) to include a flights credit voucher worth up to total of CAD$1000 or USD$750.

2. The prize draw is open to residents of the USA or Canada aged 18 years or over, except employees of Explore Worldwide Ltd (Explore) and their families, or anyone else professionally associated with the promoter. 

3. The promotional period commences on November 05, 2025 at 00:01am (EDT) and closes at 11:59pm (EDT) on November 19, 2025.   

4. No purchase is necessary. To enter the prize draw individuals must simply fill out the Costa Rica web entry form with customer full name, email address and country to qualify your entry.

5. Lost, late, incomplete or incomprehensible entries will be deemed invalid. The promoter is not responsible for any technical issues (or other), which impede an entry being submitted correctly and/or in full. No robot or automated entries will be accepted. Only one entry per unique valid email address is eligible and duplicate entries will be deleted. Explore’s decision to disqualify an entry is final and no correspondence will be entered into. 

6. One prize winner will be drawn at random from all eligible entrants by an Explore representative by  November 19, 2025. The prize winner will be notified by email within 2 working days of the draw.

7. In the event that the prize notification email is returned as undeliverable or should the winner be unable to accept their prize within 20 working days of being notified, it will be deemed that the winner has forfeited their prize and Explore reserves the right to award the prize to an alternative winner drawn from all remaining eligible entries. 

8. Explore reserves the right to request proof of residency at the stated address and identification for verification before issuing the prize.

9. The one prize winner will receive an Explore small group tour for one adult (aged 18 or over) travelling on the ‘Highlights of Costa Rica’ tour. Total prize value worth up to $2,200 USD/ $3,000 CAD.

10. The prize trip includes accommodation (on a twin-share or double basis), ground transport, some activities and some meals as shown on the itinerary, an Explore Tour Leader, local guides as per the tour trip notes and airport transfers both ways in the tour country to/from the hotel (if flights are booked to/from the recommended airport). It does not include optional activities on tour, additional meals on tour or any daily expenses. 

11. The flight credit voucher only can be used to cover economy class return flights from an international airport convenient for the winner, to/from the designated arrival and departure airport of the chosen tour. Hold luggage is included. Flights must be booked through Explore and will be economy return, whether direct or indirect (but will exclude any expenses due to a scheduled stop-over/transfer).

12. The prize does not include flight optional extra such as seat selection, additional luggage, upgrades, extra flight meals and any other chargeable services.

13. The prize trip can be booked for any available departure date in 2026. The prize trip must be booked at least six weeks prior to the departure date.

14. Additional passengers may be added to the booking but will be subject to availability and will be charged the full adult price applicable at the time of booking.

15.The booking must be made directly with Explore (see www.exploreworldwide.com) and is subject to Explore’s normal Booking Conditions (see www.exploreworldwide.com/essential-information/terms-and-conditions).  

16. The prize is an Explore small group tour. It is not a voucher for the prize value. The prize is not transferable and cannot be redeemed in full or part for cash or any other alternative prize or vacation. 

17. In the event of unforeseen circumstances, Explore reserves the right to withdraw or amend the prize at any time and without notice. 

18. Explore Worldwide is committed to protecting and respecting your privacy and will only use your personal information in accordance with these Terms and Conditions and Explore Worldwide Privacy Policy which is available here. 

19. By entering, you agree that any personal information provided by you with your entry may be held and used by the Explore Worldwide or its agents and suppliers to administer the competition. 

20. The Promoter is Explore Worldwide Ltd, Nelson House, 55 Victoria Road, Farnborough, Hampshire, GU14 7PA.  

 

 

 

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