Waterbury, CT Travel Agent

LaShaya Bennett
Lashaya Bennett
www.travelfunfly.com
860-357-8628

About Cruise Planners - Travel Fun Fly

About Travel Fun Fly


Travel Fun Fly was built on a simple belief — travel should feel exciting, not overwhelming.


Founded by LaShaya Bennett, Travel Fun Fly was created after making the decision to step away from a traditional career during one of the most uncertain times in the world, and fully pursue a passion for travel. What started as a leap of faith has grown into a trusted, full-service travel business helping individuals, families, and groups plan meaningful experiences around the world.


Travel Fun Fly is proudly family-owned and operated, built with the support of my husband Patrick and inspired by our daughters, Zola and Xena.


We specialize in land, air, and sea travel — from cruises and all-inclusive resorts to customized vacations — all designed with a personalized approach. No two travelers are the same, and your trip shouldn’t be either.


What truly sets Travel Fun Fly apart is the level of support and care behind every booking. In a world where most people book online and hope for the best, we provide real guidance, real-time support, and real solutions when plans change.


Through strong partnerships with top travel suppliers, we’re able to offer competitive pricing — often the same as what you’ll find online — with added value, perks, and a level of service you won’t get from a website.


We also believe in traveling smarter and safer. That’s why we’ve expanded our services to include TravelSafe — offering CPR training and travel preparedness education, so our clients feel confident and protected wherever they go.


At Travel Fun Fly, you’re not just booking a trip.


You’re gaining a travel advisor, an advocate, and a partner in your experience from start to finish.


Plan, book, travel well.

Hours of Operation

Monday 9:00am - 3:00pm
Tuesday 9:00am - 3:00pm
Wednesday 9:00am - 3:00pm
Thursday 9:00am - 3:00pm
Friday 9:00am - 3:00pm
Saturday -
Sunday -

Testimonials

For many years, a cruise vacation has been a personal aspiration, and I am grateful to Travelfunfly for curating an exceptional package that allowed me to fulfill this desire. My experience aboard the MSC Seaside was truly outstanding. - Maria B.
Extremely satisfied- No complaints AT ALL
LaShaya shared a half day city wide tour with me for my recent trip to Punta Cana,DR. I’m very into history, culture, people- staying on the resort could never be an option for me. The trip she recommended was perfect for me as a solo traveler. The tour guide was from the area, professional, and fun. We went shopping, horseback riding, cigar rolling, lunch in the mountains. I will use LaShaya’s services for excursions and more for all of my trips moving forward. - Ronaé M.
I can’t say enough good things about Lashaya and Pat From start to finish, they make planning a trip completely stress-free and enjoyable. Every detail is always handled with care ,from flights and accommodations to special excursions and local recommendations. What really stood out was how responsive and knowledgeable they are & tailored everything perfectly to preferences and budget. I’ve already recommended them to friends and family, and I’ll definitely be booking my next adventure with them!!! If you’re looking for someone who genuinely cares about creating unforgettable travel experiences, look no further! - Tashia O.
Nothing compares to the security of booking with a travel agent and knowing they will be there to assist, answer questions and guide you before during and after your vacation is done
This trip was awesome the food was delicious, the kitchen staff was Amaizing, when we Ask to meet the Cheff He was so Plesant M Normal D this experience with our families of 10 we all of agreed. keep up the good work. - Lorraine L.
LaShaya was absolutely amazing! Her accessibility, knowledge and professionalism with planning our family cruise for 22 attendees was bar none! We can’t wait to plan the next trip with you LaShaya! ???? ?? The Persaud Family ???? - Shanna P.
Lashaya was an absolute pleasure to work with. She was not only super attentive and responsive, but also accessible and patient. She was phenomenal with the planning of our 22 member family cruise! I plan on using her for all of our future cruises and family trips! The best in 5 Star Service!!! - Shanna & Bheesham P.
Excellent communicator. Very knowledgeable and courteous. - Shanta J.
Honestly, Pat hooked me and my family up with the best accommodations and transportation in Jamaica! We will definitely use again! - Susie L.
I had so much fun on this cruise vacation with one of the best travel advisor LaShaya! She was very good with making the trip planning so smooth, she was fun to work with. She ensure that she communicated step by step process for the trip from things to bring to selecting the best excursions and ensure that my partner and I had a good time. I will only book with her and her company for any travel needs. Thanks for an amazing time! - Jessi E.
LaShaya & Patrick are the best. They listen to what you are looking for and suggest and find the perfect vacation for you. They are very informative and are able to answer any questions I had. Thank you LaShaya & Patrick. - Pamela L.
Amazing experience - Krystal L.
Lashaya was an absolute pleasure to work with. She was attentive, responsive, and very patient. I plan on definitely using her for my next family trip!! Top Notch service !!!!!!!!!!!!! - Shenquaya C.
Amazing vacation it was def worth our money and she made everything easy for us from begin in to end ! - Ashley L.
This cruise was amazing. Lashaya and Pat were very helpful and prepared me for what to expect. I was totally prepared so I was able to totally enjoy myself on the cruise. They were very knowledgeable and was able to answer all my questions/concerns. I would definitely recommend them to plan your trip(s). I know I will be. - Pamela L.
LaShaya & Pat Bennett are so Great. They are attentive to my needs and desires. They follow through on all my questions and concerns and they always keep me updated on any special/deals that come available.
Shay is an outstanding travel agent. She is very consistent and patient. She pays attention to detail and is always looking for the best deals with options to take for your trip. I booked with Travel Fun Fly a few times already! I highly recommend Travel Fun Fly for all travels! - Andrew B.
The vacation started off amazing before I even left. My travel agent was absolutely amazing, helped my friend and I pick the perfect getaway. She definitely made us feel like we were more than just another customer. Definitely would recommend and most definitely booking again - Kathryn W.
My experience with travel fun fly was top notch! LaShaya pays attention to detail and she also went above and beyond to accommodate my requests for my family vacation. - Mirta M.
We had the pleasure of working with LaShaya to book our trip! She was great! She got back to us promptly! She responded to all of my questions I had to prepare for our first cruise! We went to the Bahamas for our son’s birthday! We had such a great time! I can’t wait to book our next cruise with her!! Thank you!! - Desiree G.
I highly recommend LaShaya. She was just a phone call away when the hotels front desk tried to up-sell our room for a higher rate stating we would not have a good view. LaShaya was there and our room and view was Great! The security that she provided, as our travel agent, makes our travel worry-free and that is why I Always book my trips with her! - Ray P.
Shaya is amazing and knowledgeable and helpful at booking us trips! - Daniel H.
Great service. Found me a great resort very quickly at a good price. I’m always going to book with them. They are very convenient for me and makes sure I got the best vacation for the money I can spent. Thank you guys once again!!! - Tre P.
My family and I enjoyed our trip. Our agent, LaShaya made sure that our accommodations were exactly as we requested. We did not encounter any problems with the arrangements.
I had an AMAZING experience with Travel fun fly ! Lashaya was easy to work with . I explained to her my ideal trip , my budget and she delivered!! We had a great room , delicious breakfast option . The pool side service was a great highlight. She was Attentive to all my travel questions and very personable. I will definitely use Travel fun fly for my travel needs in the future! - Angela L.

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