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    • Home
    • About Us
    • Upcoming Trips
    • Custom Groups
    • CONTACT
  • Home
  • About Us
  • Upcoming Trips
  • Custom Groups
  • CONTACT

Who We Are

OUR MISSION

At Pickleball in Paradise by Dream Destinations, we take pride in our expertise and passion for creating unforgettable travel experiences. As an award-winning, all-women travel agency based in Ontario, with agents across the GTA and beyond, we specialize in group travel of all sizes. Our team handles every detail - from flights and accommodations to excursions and on-site logistics - so you can relax and enjoy the journey. With your love for pickleball and our proven travel expertise, we’ll match you with the perfect resort and destination to create a tailored pickleball getaway that’s as fun as it is stress-free.

Our Group Specialists

Kirsty Roberts, Agency Owner

Annalise Roberts, Luxury Travel Advisor

Annalise Roberts, Luxury Travel Advisor

Countries Visited: 40

Best Pickleball Resort: Beaches Turks & Caicos


Certified Caribbean Expert

Sandals & Beaches Elite Advisor


I have a strong focus on group travel, specializing in pickleball groups, destination weddings, corporate meetings and incentive travel.  I have the expertise to handle every detail with care and precision. I work cl

Countries Visited: 40

Best Pickleball Resort: Beaches Turks & Caicos


Certified Caribbean Expert

Sandals & Beaches Elite Advisor


I have a strong focus on group travel, specializing in pickleball groups, destination weddings, corporate meetings and incentive travel.  I have the expertise to handle every detail with care and precision. I work closely with clients to ensure that group travel experiences are seamless, memorable, and tailored to meet specific needs - making every event or trip extraordinary.


Air Canada Vacations Rising Star 2023 & 2024

Outstanding Business Ownership Award 2025

Annalise Roberts, Luxury Travel Advisor

Annalise Roberts, Luxury Travel Advisor

Annalise Roberts, Luxury Travel Advisor

Countries Visited: 27

Best Pickleball Resort: Sandals South Coast


Certified Caribbean Expert

Sandals & Beaches Elite Advisor


I create unforgettable getaways that let you enjoy pickleball in paradise. Caribbean all-inclusive resorts are my specialty. I handle every detail for groups of all sizes so you can simply focus on playing, relaxing, an

Countries Visited: 27

Best Pickleball Resort: Sandals South Coast


Certified Caribbean Expert

Sandals & Beaches Elite Advisor


I create unforgettable getaways that let you enjoy pickleball in paradise. Caribbean all-inclusive resorts are my specialty. I handle every detail for groups of all sizes so you can simply focus on playing, relaxing, and making lasting memories. My passion is matching you with the perfect destination - where premium travel meets your love for the game.



Air Canada Vacations Social Media Star 2025

Featured in the Toronto Star - Travel Section


Pickleball In Paradise by Dream Destinations

Envoyage Canada 35 McCaul Street, 7th Floor Toronto, ON M5T 1V7 CANADA TICO Registration Number: 50016384

905-965-2325

Copyright © 2026 Pickleball In Paradise by Dream Destinations - All Rights Reserved.

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