TSheeka Ruffin
Bolingbrook, Illinois Travel Agent
Pleasant Point Travel LLC, an independent agent with Travel Leaders Roswell, GA
Email Me
Destination Weddings and Group Specialist
“The world is a book and those who do not travel read only one page.”
– St. Augustine.
For the past 25 years, I have had the tremendous honor of serving clients in the travel industry. I deeply appreciate the privilege of sharing my expertise and knowledge to consistently deliver unforgettable experiences for my valued customers. With a profound love for travel, I have personally explored and immersed myself in numerous destinations that I proudly promote, such as Mexico, the Bahamas, Jamaica, Dominican Republic, Panama, and Costa Rica, among others. The essence of an extraordinary journey lies in the seamless alignment of my client's interests with the vibrant cultures of the destinations they visit. Whether it's savoring exotic cuisines, immersing oneself in captivating music, appreciating fine art, or embracing the genuine warmth and affection of the local people, I strive to curate experiences that resonate deeply with each traveler. Whether you seek thrilling adventures or tranquil relaxation, I would be deeply honored to assist you in crafting your own remarkable travel story. Together, let us embark on a journey that will leave an indelible mark on the pages of your life.
Here is what some of my clients had to say:
Shawn Wade reviewed Pleasant Point Travel — 5 star September 8 at 7:11 PM · PHENOMENAL SERVICE IS ALL I CAN SAY!!
Anthony Graham recommends Pleasant Point Travel. August 23 at 6:34 AM Tsheeka is professional and pleasant to work with for all your travel needs.
Lucia Hidalgo recommends Pleasant Point Travel. September 5 at 1:45 PM · Tsheeka booked our last friend and family vacation for my best friends 50th, she made sure everything was done beautifully.
Sharmaine Gales-Patterson recommends Pleasant Point Travel. August 22 at 1:46 PM · She is very professional and will work with you in regards to payments. The vacation was awesome and everyone had a great time! I will definitely use her to book my next vacation!
My Areas of Expertise
INTERESTS
CERTIFICATES & AWARDS
AM Resort Master Agent Certification.
Virgin Voyages
Princess Cruises
A TRAVEL EXPERT NOT AGENT!
Reviewed By Sunshinenchicago - Chicago | Traveled to Jamaica ~ Caribbean
First met Sheeka going on a high school group vacation. That experience and trip went extremely well. Since then I worked with Sheeka to plan several trips that didnt come to be. I've probably been a pain with all of my trip changes due to COVID and family circumstances... lol, but she's always worked with me, explained credits and made great suggestions. Her communication is wonderful and I know I don't have to worry about anything. She makes planning and traveling a breeze!
I would recommend this agent to my family and friends
2 of 3 people found this review helpful
Our trip was amazing we have a wonderful time
Reviewed By Hortense - MA | Traveled to Jamaica ~ Caribbean
She is very detailed.answer all my question.very experience.very easy to talk to
I would recommend this agent to my family and friends
TSheeka Ruffin responded:
It was such a pleasure working with you and I look forward to working with you again!
It was such a pleasure working with you and I look forward to working with you again!
1 of 1 people found this review helpful
Just wow
Reviewed By Mark - Montego Bay Jamaica | Traveled to Canada
Amazing, easy to work with
I would recommend this agent to my family and friends
TSheeka Ruffin responded:
We appreciate the opportunity to be part of your memorable experiences.
We appreciate the opportunity to be part of your memorable experiences.
1 of 1 people found this review helpful
All Trips Through TSheeka Are The Best
Reviewed By Leimomi - Chicago, Il | Traveled to Jamaica ~ Caribbean
Working with TSheeka Ruffin is Always A Magnificent Experience. TSheeka Goes Above and Beyond To Make Your Visions and Dreams Come True. Whether it’s for 1 or 2 People or For A Wedding Anniversary Birthday or Just Large Getaway Parties, It’s Done To Perfection. All Inclusive, Full Itineraries.
I would recommend this agent to my family and friends
TSheeka Ruffin responded:
Thank you for trusting our services. We look forward to working with you on your future travel needs.
Thank you for trusting our services. We look forward to working with you on your future travel needs.
1 of 1 people found this review helpful
Most memorable Trip!!!
Reviewed By opal - Chicago | Traveled to Dominican Republic ~ Caribbean
She is extremely thorough and has an astute attention to details.
I would recommend this agent to my family and friends
TSheeka Ruffin responded:
I appreciate your feeds back! It was an absolute pleasure working with you.
I appreciate your feeds back! It was an absolute pleasure working with you.
1 of 1 people found this review helpful
Awesome time no snags.
Reviewed By Natalie W - Poughkeepsie N.Y. | Traveled to Punta Cana ~ Dominican Republic ~ Caribbean
Professional, knowledgeable patient and thorough.
I would recommend this agent to my family and friends
TSheeka Ruffin responded:
I appreciate your feedback Natalie! Punta Cana was unforgettable and I cant wait for our next group getaway!
I appreciate your feedback Natalie! Punta Cana was unforgettable and I cant wait for our next group getaway!
1 of 1 people found this review helpful
A birthday trip to remember!
Reviewed By Tracy - Chicago, IL | Traveled to Cancun ~ Quintana Roo ~ Mexico
I have been working with TSheeka since 2017 and it has been wonderful! She has helped me planned solo trips as well as other trips for my birthday. She provided me with excellent choices , she's very helpful and attentive! My trip to Cancun was a blast! I decided to stay an extra day and TSheeka made sure everything went smoothly!! She's the best!!
I would recommend this agent to my family and friends
TSheeka Ruffin responded:
I appreciate your feedback Tracy! It's always a pleasure working with you. Your my inspiration when it comes to solo travelling. Can't wait to work with you on your next getaway.
I appreciate your feedback Tracy! It's always a pleasure working with you. Your my inspiration when it comes to solo travelling. Can't wait to work with you on your next getaway.
1 of 1 people found this review helpful
50@52 Awesome and Amazing Trip
Reviewed By The New Monica - Chicago IL | Traveled to Cabo San Lucas ~ Baja California Sur ~ Mexico
Tsheeka was and is awesome to work with. She went above and beyond for my 50@52 birthday trip. What travel agent do you know gets married the same week as your trip and still helps with any problems. She makes all her customers her priority.
I would recommend this agent to my family and friends
TSheeka Ruffin responded:
Thank you so much for your kind words. We look forward to working with you on your future travel needs.
Thank you so much for your kind words. We look forward to working with you on your future travel needs.
1 of 1 people found this review helpful
My travel agent for life!
Reviewed By sherrelllashay - Miami, FL | Traveled to Honolulu, Oahu ~ Hawaii ~ USA
She is phenomenal! She makes sure you are completely set for your vacation. We had a blast on each trip she planned so far. She also has great prices!
I would recommend this agent to my family and friends
TSheeka Ruffin responded:
Thank you for your feedback! Working with has been an absolute pleasure.
Thank you for your feedback! Working with has been an absolute pleasure.
1 of 1 people found this review helpful
The Best Cruise Ever
Reviewed By DJ - Lansing, Illinois | Traveled to Caribbean
One awesome person. Very patient and passionate about her work
I would recommend this agent to my family and friends
1 of 2 people found this review helpful
Big Fun celebrating my girl’s 55th from the Chi!
Reviewed By Cyd - Shelby Township, Michigan | Traveled to Cancun ~ Quintana Roo ~ Mexico
TSheeka was very pleasant, patient, professional and helpful in facilitating an extremely fun trip for my friend’s 55th birthday.
I would recommend this agent to my family and friends
TSheeka Ruffin responded:
Thank you so much for sharing! It was an absolute pleasure working with and I’m so happy that you had an amazing time.
Thank you so much for sharing! It was an absolute pleasure working with and I’m so happy that you had an amazing time.
1 of 2 people found this review helpful
Truly, the best trip so far!
Reviewed By Shekels - Stafford, VA | Traveled to Dubai ~ United Arab Emirates ~ Middle East
Excellent experience. She made the trip easy. I didnt have to worry about a thing. Her attention to detail and organization was impeccable.
I would recommend this agent to my family and friends
TSheeka Ruffin responded:
Thank you so much for the opportunity. We look forward to assisting with your next escape.
Thank you so much for the opportunity. We look forward to assisting with your next escape.
1 of 2 people found this review helpful
Living Life and Making Memories!
Reviewed By Mrs. She Ready - IL | Traveled to Punta Cana ~ Dominican Republic ~ Caribbean
If you are looking for an experience of a lifetime with a great knowledgeable agent, you have it right here. Every detail of your trip is planned out with service to you the traveler. TSheeka knows her stuff!!! Looking forward to NEXT. Thank you!!!
I would recommend this agent to my family and friends
TSheeka Ruffin responded:
We are so happy to be a part of another memorable experience. We’re at your service when next you travel ??.
We are so happy to be a part of another memorable experience. We’re at your service when next you travel ??.
1 of 2 people found this review helpful
The best trip of my life!
Reviewed By No nickname - Chicago, Illinois | Traveled to Europe
It was a pleasure.
I would recommend this agent to my family and friends
TSheeka Ruffin responded:
It was such a pleasure working with you and we look forward to assisting with your next getaway!
It was such a pleasure working with you and we look forward to assisting with your next getaway!
1 of 2 people found this review helpful
She made it easy
Reviewed By Sanya - Illinois | Traveled to Dominican Republic ~ Caribbean
I have to say that T'Sheeka helped take the stress out of planning our trip, she knew the right hotel and places to suggest based on our chosen destination. She was courteous, professional and knowledgeable. We had so much fun, definitely booking our next trip with her.
I would recommend this agent to my family and friends
TSheeka Ruffin responded:
Thank you so much! It was an absolute pleasure assisting you on this adventure! We look forward to helping you arrange your next getaway ??
Thank you so much! It was an absolute pleasure assisting you on this adventure! We look forward to helping you arrange your next getaway ??
Great Experience-
Reviewed By Missmish67 - Chicago, IL | Traveled to Cancun ~ Quintana Roo ~ Mexico
Tsheeka planned everyone. My trip was smooth all the way
I would recommend this agent to my family and friends
TSheeka Ruffin responded:
I appreciate your feedback it’s reviews like these that helps us to keep making vacation dreams a reality! We look forward to working with you on all your future travel needs ????
I appreciate your feedback it’s reviews like these that helps us to keep making vacation dreams a reality! We look forward to working with you on all your future travel needs ????
1 of 2 people found this review helpful
I had a great time really enjoyed myself
Reviewed By Freda - Chicago Illinois | Traveled to Jamaica ~ Caribbean
She was very nice, friendly, patient and attentive.
I would recommend this agent to my family and friends
TSheeka Ruffin responded:
Thank you for the opportunity and we are excited to help plan your next getaway! ??
Thank you for the opportunity and we are excited to help plan your next getaway! ??
Punta Cana Best Trip of our Lives!!
Reviewed By Ylona Cavalier Zebra Leopard Tiger Girl - Woodridge, IL | Traveled to Punta Cana ~ Dominican Republic ~ Caribbean
Great personality, reliable, timely, got alm of my questions answered.
I would recommend this agent to my family and friends
TSheeka Ruffin responded:
Thank you for your kind words. We look forward to working with you again!
Thank you for your kind words. We look forward to working with you again!
1 of 2 people found this review helpful
15 Days and 7 countries - The trip of a lifetime!
Reviewed By Teresa - Chicago, IL | Traveled to Europe
My recent European tour exceeded my expectations thanks to Pleasant Point Travel. I simply stated where I wanted to go, how long I wanted to travel and presto...I went on the trip of a lifetime! Thanks again TSheeka!!! Here are a few pics...toured 7 countries in 15 days. I would recommend this agent to my family and friends
TSheeka Ruffin responded:
Thank you so much for sharing! It was an absolute pleasure working with and I’m so happy that you had an amazing time.
Thank you so much for sharing! It was an absolute pleasure working with and I’m so happy that you had an amazing time.
1 of 2 people found this review helpful
Top Notch Travel Agency and Staff
Reviewed By David - Chicago, Il | Traveled to Montego Bay ~ Jamaica ~ Caribbean
I was a little hesitant to use a Travel Agent especially because everything is so accessible now with the internet. Boy was I wrong... Life gets in the way and then you're crunched for time to find the perfect vacation for your family. I stumbled across TSheeka's Facebook post showing this fabulous vacation to Jamaica. It was the perfect post at the perfect time. I contacted TSheeka and from the start, her professionalism stood out to me. She was so pleasant to work with. Very knowledgeable and attentive to our needs. I would definitely recommend her and her team to all my friends and family. Thanks, TSheeka Pleasant Point Travel for making this trip so memorable for me and my family.
I would recommend this agent to my family and friends
TSheeka Ruffin responded:
It was such an amazing pleasure working with you and I look forward to helping to make more amazing memories.
It was such an amazing pleasure working with you and I look forward to helping to make more amazing memories.
1 of 2 people found this review helpful
It was the most fun trip ever
Reviewed By Suzie - Newy York | Traveled to Punta Cana ~ Dominican Republic ~ Caribbean
It was such a fun trip! I had a blast and everything from flight, to ground transportation to hotel accommodations went very smoothly
I would recommend this agent to my family and friends
TSheeka Ruffin responded:
Thank you Moya! I appreciate your feedback and look forward to helping you plan your next family adventure!
Thank you Moya! I appreciate your feedback and look forward to helping you plan your next family adventure!
1 of 2 people found this review helpful
Monica's 50 plus 1
Reviewed By Dvines - Maywood, Il | Traveled to Cabo Rojo ~ Puerto Rico ~ Caribbean
Very pleasant and professional
I would recommend this agent to my family and friends
TSheeka Ruffin responded:
Thank you so much for the opportunity. It was a pleasure working with you.
Thank you so much for the opportunity. It was a pleasure working with you.
1 of 2 people found this review helpful
The Lewis Love Experience
Reviewed By Lisa G. - Chicago Illinois | Traveled to Jamaica ~ Caribbean
Tsheeka was top notch. No question was a dumb question and she was hands on not only to me but my guest as well. I salute Tsheeka because my group was large and she handle each of us professionally and with dignity.
I would recommend this agent to my family and friends
TSheeka Ruffin responded:
Thank you so much for the opportunity. It was a pleasure working with you on your Jamaica Wedding Group! Cant wait for Mr. Lewis to get here so I can help to create more adventures together.
Thank you so much for the opportunity. It was a pleasure working with you on your Jamaica Wedding Group! Cant wait for Mr. Lewis to get here so I can help to create more adventures together.
1 of 2 people found this review helpful
“Monie’s Redo at 52”
Reviewed By Marlyn - University park, Illinois | Traveled to Cabo San Lucas ~ Baja California Sur ~ Mexico
Tsheeka treated me and my friends like family. She has arranged multiple trips for us, all tailored to our specifics needs. Tsheeka is very professional, patient and personable.
I would recommend this agent to my family and friends
TSheeka Ruffin responded:
It’s always a pleasure! We appreciate your support.
It’s always a pleasure! We appreciate your support.
1 of 2 people found this review helpful
Our Best Trip to Date
Reviewed By The Cole Package - Chicago, IL | Traveled to Jamaica ~ Caribbean
What can I say about Tsheeka in one word: Professional, Reliable, DEPENDABLE! The first day of our honeymoon there was a minor mixup with our excursion to the Luminous Lagoon. I called Tsheeka (who was back in the states) regarding our situation and she handled it without issue. My Favorite Travel Agent!🤩🤩🤩🤩🤩
I would recommend this agent to my family and friends
TSheeka Ruffin responded:
Thank you for trusting our services Nedra. We look forward to working with you on your future travel needs.
Thank you for trusting our services Nedra. We look forward to working with you on your future travel needs.
1 of 2 people found this review helpful
Birthday extravaganza
Reviewed By Roy - Chicago, illinois | Traveled to Cancun ~ Quintana Roo ~ Mexico
I was excellent, she was very attentive to our travel plans and needs. I will definitely use this travel agent for future travels
I would recommend this agent to my family and friends
TSheeka Ruffin responded:
Thank you so much for your feedback Roy! Looking forward to helping you with your next adventure.
Thank you so much for your feedback Roy! Looking forward to helping you with your next adventure.
1 of 2 people found this review helpful
Jamaica
Reviewed By Samara - Chicago, Illinois | Traveled to Montego Bay ~ Jamaica ~ Caribbean
My experience working with TSHEEKA was the best. She works very hard to get you the best for your money, she makes sure you have a great time you don’t have to worry about excursions she takes care of everything. She is the best.
I would recommend this agent to my family and friends
TSheeka Ruffin responded:
Thank you so much for sharing! I appreciate your feedback and look forward to helping you with your next escape.
Thank you so much for sharing! I appreciate your feedback and look forward to helping you with your next escape.
1 of 2 people found this review helpful
Many more trips to come through TSheeka!!
Reviewed By Superior Travel experience!! - Maywood, Illinois | Traveled to Punta Cana ~ Dominican Republic ~ Caribbean
The Best at making a comfortable, fun, and memorable experience!
I would recommend this agent to my family and friends
TSheeka Ruffin responded:
Thank you Demetrius! I look forward to helping with you next getaway.
Thank you Demetrius! I look forward to helping with you next getaway.
1 of 2 people found this review helpful
The Twins Take Over 5.0 Dubai
Reviewed By katrina - Chicago | Traveled to Dubai ~ United Arab Emirates ~ Middle East
Working with TSheeka was a pleasure great communication an amazing experience
I would recommend this agent to my family and friends
TSheeka Ruffin responded:
It was a pleasure assisting you and your group with this epic getaway! I look forward to working with you on your next adventure.
It was a pleasure assisting you and your group with this epic getaway! I look forward to working with you on your next adventure.
1 of 2 people found this review helpful
Highly recommend
Reviewed By Kris - Joliet il, | Traveled to Punta Cana ~ Dominican Republic ~ Caribbean
Absolutely amazing she assisted me with my booking for a great deal and organized some fun activities for my family.
I would recommend this agent to my family and friends
TSheeka Ruffin responded:
Thank you so much for sharing! I’m so happy that you had an amazing time.
Thank you so much for sharing! I’m so happy that you had an amazing time.
1 of 2 people found this review helpful
Most Amazing Trip to the DR
Reviewed By Carla Allen - Chicago, Il | Traveled to Punta Cana ~ Dominican Republic ~ Caribbean
Working with T'Sheeka was so easy. I simply outlined what I wanted, and she exceeded my expectations!!!
I would recommend this agent to my family and friends
TSheeka Ruffin responded:
Thank you so much for sharing! It was an absolute pleasure working with and I’m so happy that you had an amazing time.
Thank you so much for sharing! It was an absolute pleasure working with and I’m so happy that you had an amazing time.
1 of 2 people found this review helpful
The best travel agent ever!!
Reviewed By Althea - Hyannis Ma | Traveled to Cancun ~ Quintana Roo ~ Mexico
Absolutely the best!!! What I admired most is her patient and understanding.
I would recommend this agent to my family and friends
0 of 1 people found this review helpful
Use a Travel Agent
Reviewed By BMO - Matteson, IL. | Traveled to Punta Cana ~ Dominican Republic ~ Caribbean
Tsheeka makes planning your trip easy breezy. She is very experienced and always has great recommendations. I’ve always relied on her to plan my vacations and was never disappointed!
I would recommend this agent to my family and friends
TSheeka Ruffin responded:
It was such a pleasure helping to create your memorable getaway. I look forward to helping you to make plenty more!
It was such a pleasure helping to create your memorable getaway. I look forward to helping you to make plenty more!
0 of 1 people found this review helpful
The best to book with 😁
Reviewed By Michelle B - Orlando FL | Traveled to Punta Cana ~ Dominican Republic ~ Caribbean
My experience with TSheeka has been absolutely amazing. My partner and I needed a quick trip away from our daily busy lives. She handled everything from our airport transfers, hotels and flights. We like a good deal but with a touch of class and nothing was lacking. At the hotel we got an upgrade which we know was her doing she went above and beyond. We are already booking our next trip with her.
I would recommend this agent to my family and friends
TSheeka Ruffin responded:
Thank you so much for sharing! It was an absolute pleasure working with and I’m so happy that you had an amazing time.
Thank you so much for sharing! It was an absolute pleasure working with and I’m so happy that you had an amazing time.
0 of 1 people found this review helpful
I had the best trip in October 2022
Reviewed By Leann - Nantucket | Traveled to Jamaica ~ Caribbean
TSheeka is reliable, answer all my question’s in a timely manner
I would recommend this agent to my family and friends
TSheeka Ruffin responded:
Thank you Leann!
Thank you Leann!
0 of 1 people found this review helpful
It was so much fun!!!
Reviewed By Khaaliyah Moncrieffe - Plainfield, Illinois | Traveled to Punta Cana ~ Dominican Republic ~ Caribbean
Me and my boyfriend had an amazing time! In the Dominican Republic, lots of swimming, Free food, and fun excursions. My favorite was Zip Lining in the mountains, beautiful view out there. T’sheeka provided very great service, and amazing Communication. Thank you Pleasant Point Travel looking forward to our Cruise to Greece 2023!!!
I would recommend this agent to my family and friends
TSheeka Ruffin responded:
Thank you so much for sharing! It was a pleasure working with you on this amazing getaway.
Thank you so much for sharing! It was a pleasure working with you on this amazing getaway.
0 of 1 people found this review helpful
Great travel agent
Reviewed By Patricia Love - Chicago | Traveled to Cancun ~ Quintana Roo ~ Mexico
It was a pleasure working with Ms. Ruffin she was very helpful and polite
I would recommend this agent to my family and friends
TSheeka Ruffin responded:
Thank you for you kind words. I enjoyed helping to make our clients dreams a reality and look forward to assisting with your next getaway.
Thank you for you kind words. I enjoyed helping to make our clients dreams a reality and look forward to assisting with your next getaway.
1 of 4 people found this review helpful