"Remember, Travel is the only thing you buy that makes you RICHER."

2025 Leisure Trips

All you have to do is pack your bags and book your flight.

Have Questions? FAQ’s Here.

STEP BY STEP BOOKING PROCESS

Find your dream destination from any of our curated trips!
Then make sure the dates work for you & the trip fits your budget.
*TTD offers flexible payment plans & low deposits
Once you've picked your destination/meet-up you can secure your spot by paying your deposit.
YOU'RE CONFIRMED!
Make sure you're checking your emails (& spam) for important trip update
*Join the group chat!
Connect with other travelers & your travel agent
SHOW UP & SHOW OUT!
Our team will be waiting for you to arrive for your stress free fully curated trip!!
*Leisure trips does not come with a TTD Host on-site but is planned fully, just with more of a leisure vibe!

TRAVELER REVIEWS:

"Perfect travel agent to plan your trip!! From beginning to end Shay was was informative and assisted in all my trip needs. She gave great suggestions on excursions and places to visit. The website was very helpful for the guest attending the trip, they always had something they could refer to. Making payments was seamless and very reasonable. I will not be planning anymore trips myself instead having The Travel Diaries plan them for me. Will definitely be using them again for my next trip."

-Sarah
"I had an amazing experience In Puerto Rico. The Travel Diaries really provided a fun,safe and friendly environment where strangers enjoyed each other like family. Shay and her team are amazing, tentative and caring. I will recommend all my friends and family to travel with TTDL. Again thank you for a memorable vacation that I will never forget."

-Daniel
"My trip to Jamaica was the highlight of my Summer! Shay planned this trip down to the hour! Shay couldn’t have picked a better travel host than Keyz!!!! This girl is the life of the party and both ladies are down to Earth! It’s because of this trip that I’ve decided that travel is part of my culture! I’m beyond thankful for this experience with this group of people! I had such a great time that I’m already booked for Tulum in 2023!"

-Crystal
"The best way to travel for me. Amazing travel company. Feels like traveling with family. Everything is taken care of before you go. You just go and enjoy."

-Tristina (4x returning traveler)
"The Travel Diaries definitely gets a 10/10 from me . From the day i made my first deposit i received constant updates and any questions i had there was always a prompt response. For this being my first trip solo and with people i have never met i felt so comfortable even down to my roommate.Shay and Will thank you for allowing me this opportunity to step out of my comfort zone and experience the Colombian cultures and making my birthday trip beyond special. The Travel Diaries exceeded my expectations for this trip and i can’t wait to book my next vacation with you guys. If you’re looking for a safe, organized and qualified travel agent to book your next vacation, baecation, group or solo trip this is definitely the right person to book with you won’t be disappointed."

-Kareema