Tailwind Travel and Tours by Dream Vacations - Hernando, Mississippi

Julie Holden

Cathy Massey is absolutely phenomenal! She has now booked 4 trips for us and we will never book a trip without her again. She goes above and beyond and was with us every single step of the way. She is always so easy to reach and was able to guide us with every decision that comes along with elaborate trips. We are so grateful to Tailwind Travel and Tours!

Jordan Battle

Leaving this review a little late, but wanted to rave about Heather! I first connected with her based off a referral of a friend and I'm glad we did! My family had a tricky set of parameters for our all girl trip to London and Heather was patient and communicative with us throughout the entire process! She provided us with a number of hotel and flight options to accommodate our needs and her expertise was needed and appreciated. She even sent links for booking on Viator to help plan our activities! The hotel we decided on was in an ideal location, close to transportation and Central London. She stayed in communication with me and kept me updated on every part of the process which was incredibly helpful when trying to wrangle 5 women from various states and sides of the country! I would absolutely recommend Heather and Tailwind Travels by Dream Vacations. I'm already trying to figure out how to use them for my next big trip!

Dennis Ross

I tasked Jan with what I thought was the impossible, for me and my wife's 40th wedding anniversary. Jan worked for weeks until she found the perfect 14-day trip for us to Italy. She handled everything from start to finish with professionalism, relentless drive, and a LOT of patience dealing with me, the travel dunce. I can positively recommend her personal service and "I'll find that needle in a haystack" attitude! Job well done!

Jeff DeFord

Kace did a fantastic job working with us on finding the right trip, at the right time, and right price. We will definitely be using Kace and her services again. Her follow-up and communication made this trip abroad so much easier and enjoyable.

Victoria James

We booked a weekend getaway to celebrate an anniversary. Stacey Steiner made our travel experience stress free. She took care of the booking and extra arrangements for the room. We were even given recommendations for restaurants and attractions. Highly recommend her services!

Rob Watt

We booked a family vacation with Tailwind Travel and could not be happier. We started the planning about 10 months before the trip (4/19/24), soliciting input from our agent Heather on adult-only all inclusive resorts in the Caribbean or Mexico.
She did a lot of research and was great at communicating what she found, giving us quite a few options and then helping us narrow down what she thought were our best options, having asked detailed questions about the desires/priorities of my whole clan (2 parents with 4 adult children).
We ended up taking her recommendation on a lovely resort outside of Tulum, Mexico. The beach was fabulous, food consistently good, friendly staff, nice rooms. It definitely checked all the boxes for our family and we would consider going back there or to one of their other sister properties.
One of the tour guides she recommended (Memo tours) was a highlight of the trip, visiting some local Cenotes.
The only hiccup of the whole trip was due to some airport to resort transportation for two of our kids, and Heather was on it! She responded immediately and did everything in her power to make it right.
I am a very well travelled 65 year old that had not used a travel agent/planner in probably 40 years, always doing the legwork and planning ourselves. I will not hesitate to use Tailwind from now on for our future holidays.
One more thing; the co-owner of the company, Buddy, also was very solicitous, reaching out during and after the trip to make sure we were happy.
It is so refreshing to experience "old fashioned" customer service and care as a consumer. We highly recommend Tailwind Travel!

R. Watt and family.

Ben Gilluly

Let’s start with- I’m an experienced traveler and internet savvy mid 40s guy. I’m pretty good at finding good deals and jumping on them. That being said- I now only book my vacations through Tailwind Travel and Tours.

Here are my reasons:

1- prompt, attentive, responsive service

2- experience recommendations that hit the mark, every…single…time for my family

3- continued follow up on bookings, changes, and recommendations

4- price

5- they love doing this job and it shows

I could go on and on and on but I’ll give one comparison.

Booked a “cheaper by $25” vacation through Costco travel- Covid hit, got a little bit of a refund after months of emails and calls.

Booked a trip this spring through TTT - got email from cruise line saying something I requested (and paid for) wasn’t available. Called Jan. Showed up for the cruise and we were immediately upgraded to an incredible suite - and had a fabulous time - because of my stellar travel agents.

Just use them!

beth west

Stacey, Tailwind Travel and Tours by Dream Vacations, went above and beyond our expectations for our vacation. Can’t wait to book our next vacation with her. I would highly recommend.