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Matthew Schaffer

Chicago, Illinois Travel Agent
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Matthew Schaffer

Chicago, Illinois Travel Agent
A Full-Service Travel Leaders Associate Agency
39 Reviews | 100% Recommended
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Jamaica Travel Agent Specialist

Blue Hole Jamaica

Whenever I hear a Bob Marley tune streaming in my ears, my mind instantly goes that that magical place, Jamaica!!!  The birthplace of reggae and jerk, the Rastafari movement and some of the best beaches in the Caribbean, it’s no wonder to many, Jamaica is the heart of the Caribbean.

More than another other Island, Jamaica is really a state of mind. No rush, no stress, just an easy-going vibe with a lot of music, singing and dancing.  Reggae tunes make you jump out of your chair and dance and sing like a real Jamaican.  In addition, Jamaicans are very helpful, spontaneous, friendly, and their positive attitude makes you feel right at home.

As the third-largest island of the Caribbean, Jamaica is hard to cover in one trip. Rather, it's best to choose your activities and vacation priorities, and then decide where to stay.  Of the three main tourist pockets on the island, westernmost Negril is popular for its beaches and upscale accommodations; northwestern Montego Bay is well-liked by golfers; and Ocho Rios in the northeast appeals mostly to adventurous types who might be interested in climbing waterfalls like Dunn's River. Some visitors choose the eastern area of Port Antonio to try the top-notch surfing at Boston Beach, the hiking along the Blue Mountains, and the river rafting along the Rio Grande.

Jamaica is a paradise for beach lovers, home to some of the Caribbean’s most famous beaches. Near Ocho Rios are two of the best-known beaches in the world.  Seven Mile Beach in Negril, consists of a highway-long strip of platinum sand, backed by palm trees and five-star hotels.  James Bond Beach, the backdrop of Dr No, is a touristy beach surrounded by clear waters on three sides. It has water sports centers, bars, restaurants and a variety of accommodation. Moreover, James Bond Beach, is an area where jazz and reggae artists also exhibit their skills. For those who want to enjoy sun, other notable spots include celebrity favorite Frenchman’s Cove and the lively Doctor’s Cave Beach in Montego Bay.

Aside from the beautiful beaches, one of the best parts about Jamaica is the Blue Mountains area north of Kingston. The region has the world’s second largest butterfly population and was recently included in the UNESCO World Heritage List. The area is covered with walking trails, including a hike that takes you to the top of Jamaica’s highest point, Blue Mountain Peak, 7,402ft above sea level. This part of the island is a coffee heartland, too. Coffee farms are dotted all over, and many of them welcome visitors for guided tours and tastings.

Another gem of Jamaica is Dunn’s River Falls, a magnificent waterfall flowing above the country’s Ocho Rios city. One of the most famous waterfalls in the Caribbean, white water cascades down a 180ft flight of natural rock stairs. Visitors can climb the stairs, stopping to soak in natural pools and shower in the falls’ foamy water along the way. If scaling the falls isn’t adventurous enough for you, there’s also a zip-line circuit that features seven zip-lines and four hanging bridges.

But if one great waterfall isn’t enough, there is also Mayfield Falls, a community of waterfalls that come from the 21 wide-spaced little waterfalls on the Mayfield River. Moreover, you can see the excellent waterfalls flowing in the bosom of the lush vegetation cover from the surrounding suspension bridges. Furthermore, this area of natural beauty, which people often use to cool off, is one of the most important holiday destinations in Jamaica.

What could top waterfalls?  Well, how about some of the most amazing caves in the world like Green Grotto Caves.  Located on the northern coast of Jamaica, these caves have turned into one of the country’s major tourist attractions. Its predecessor is known for its many different names such as Runaway Bay Caves, Hopewell Caves and Discovery Bay Caves. While only 12 meters deep, the length of the cave is 1,525 meters is almost a mile!

For the history buffs out there, who can forget Port Royal, the legendary port city, has remained an important symbol of Jamaica for nearly five hundred years. Furthermore, the legendary pirate city was founded in 1518; it was considered to be the most desperate city in the world at a reasonable level. For many years corruption and violence had been dominant over there. Pirate ships came from all over the world, even from Madagascar. In 1692 an earthquake occurred in the island and the pirate town sank under water, and all of its remains lie in the bottom of Kingston’s harbor.

With my help, I hope I can give you the experience of a lifetime in this Caribbean wonderland.  I think it’s pretty obvious, once you’ve tasted all Jamaica has to offer: the culture of the Rastafarians, nature with its waterfalls, coves, caves and fruit trees, the chill vibes, music and history, there is only one thing that is going to bother you, leaving!  

CERTIFICATES & AWARDS

Certified ASTA Travel Agent

My Reviews

Rating: 5 39 Reviews | 100% Recommended

Good Times

Reviewed By Chelsea - Los Angeles, CA | Traveled to Cabo San Lucas ~ Baja California Sur ~ Mexico
Matt made my trip to Cabo the best! My friends and I had so much fun doing all the activites Matt set up for us. Can't wait for the next one.
I would recommend this agent to my family and friends
5 of 7 people found this review helpful
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Last minute Grand Canyon adventure

Reviewed By Heather - West Chester, PA | Traveled to Grand Canyon ~ Arizona ~ USA
Matthew was fantastic! He planned a last minute trip to the Grand Canyon for me and my boys age 11 and 13. He was so helpful and knowledgeable and made great suggestions with my boys in mind. He was a pleasure to work with and very communicative throughout the process. We are going to plan another trip to the area and will definitely use Matthew again. I would highly recommend his services!
I would recommend this agent to my family and friends
2 of 2 people found this review helpful
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Awesome!!!!!

Reviewed By Debbie - Chicago, IL | Traveled to Jamaica ~ Caribbean
Matt was always available for me no matter when I contacted him. He was able to find the perfect places and activities for all of my requests. I'll be using his services for a long time to come.
I would recommend this agent to my family and friends
3 of 4 people found this review helpful
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Hole in one!!!

Reviewed By Mark - Chicago,Il | Traveled to Kiawah Island ~ South Carolina ~ USA
Matt was so great to work with! I love golfing, but I knew nothing about Kiawah Island. Matt gave me the best golfing trip of my life. I can't wait to take another trip with his help.
I would recommend this agent to my family and friends
5 of 8 people found this review helpful
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Viva Las Vegas!!!

Reviewed By Kyle - Chicago,Il | Traveled to Las Vegas ~ Nevada ~ USA
I have always wanted to go to Vegas but wasn't sure how to make it great. Matt listened to every request I had and made every idea come true. I have never had such a great time in my life! I can't wait to travel with Matt's help again.
I would recommend this agent to my family and friends
5 of 8 people found this review helpful
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Best time ever!!!

Reviewed By David - Chicago, IL | Traveled to Los Cabos ~ Baja California Sur ~ Mexico
We had the best time ever in Cabo. The resort was great and everything we hoped for. I can't wait for Matt to plan another trip for us!!!!
I would recommend this agent to my family and friends
2 of 3 people found this review helpful
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Viva Mexico!!!

Reviewed By Julie - Chicago, IL | Traveled to Los Cabos ~ Baja California Sur ~ Mexico
What can I say but everything was great. I will use Matt again in the future and highly recommend his services.
I would recommend this agent to my family and friends
1 of 1 people found this review helpful
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Honeymoon of dreams!!!

Reviewed By Sarah - Chicago, IL | Traveled to Cancun ~ Quintana Roo ~ Mexico
Matt was on top of everything from day 1. He did an amazing job and gave us an unbelievable honeymoon.
I would recommend this agent to my family and friends
2 of 3 people found this review helpful
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Soooo Relaxing!!!

Reviewed By Jason - Chicago, IL | Traveled to Zihuatanejo ~ Guerrero ~ Mexico
From start to finish the whole experience was great! I will definitely use Matt's services again.
I would recommend this agent to my family and friends
2 of 3 people found this review helpful
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Knowledgeable, Expert in his Craft

Reviewed By Kat - South Bend, Indiana | Traveled to Cancun ~ Quintana Roo ~ Mexico
Matthew was so impressive!!! I have used many travel agents in the past, but Matthew is unlike anyone I ever used. With what he knew about Cancun, you would think he grew up there. He helped answer all my questions (and I had a ton hehe), and booked us all we needed to have a fantastic trip. After this experience, Matthew feels like a brother to us!
I would recommend this agent to my family and friends
1 of 1 people found this review helpful
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5 Star Customer Service and Dedication

Reviewed By Kerri - Evanston, IL | Traveled to Jamaica ~ Caribbean
Matthew helped my sister and I plan our first family vacation for the first time in over a decade, so as you can imagine, we had very high standards!

Matthew met us for an initial phone call after business hours, planned our trip exactly the way we wanted, and was there for us when the resort was trying to mess with our trip! I have another trip coming up and will be using Matthew again. I would recommend him to anyone who is new to traveling, or travel agents.
I would recommend this agent to my family and friends
1 of 1 people found this review helpful
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A worthwhile and amazing travel agent

Reviewed By Paul Smith - South Bend, Indiana | Traveled to Cabo San Lucas ~ Baja California Sur ~ Mexico
Matthew was dedicated to making sure my family and I had a wonderful vacation. He worked nonstop to answer all of our questions and provide us with the best possible vacation packages. I recommend him to everyone!
I would recommend this agent to my family and friends
2 of 3 people found this review helpful
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The Best!!!

Reviewed By Mary - Chicago,Il | Traveled to Zihuatanejo ~ Guerrero ~ Mexico
Matt was so great to work with. He listened to everything I wanted and delivered an amazing vacation. Two thumbs up!
I would recommend this agent to my family and friends
3 of 5 people found this review helpful
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Time of my life!!!

Reviewed By Lillian - Washington, D.C. | Traveled to Cancun ~ Quintana Roo ~ Mexico
Matt is simply the best. He made my whole family have the experience of their lives. They all thought I was the reason everything was so great, thx Matt.
I would recommend this agent to my family and friends
4 of 7 people found this review helpful
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Zihua was Paradise!!

Reviewed By Dannielle - Chicago, IL | Traveled to Zihuatanejo ~ Guerrero ~ Mexico
Matt is incredible! Our trip to Zihua was a dream come true. I loved all the tours and activites Matt set up. I think I will try Cabo with him next, I can't wait.
I would recommend this agent to my family and friends
4 of 7 people found this review helpful
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Best Travel Agent!

Reviewed By Tyler - Little Rock, Arkansas | Traveled to Cabo San Lucas ~ Baja California Sur ~ Mexico
Matt went above and beyond for me. He was always available anytime I needed him. My trip to Cabo was everything I wanted and more!
I would recommend this agent to my family and friends
3 of 5 people found this review helpful
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Amazing Trip!!!

Reviewed By Patty - Chicago,Il | Traveled to Hilton Head Island ~ South Carolina ~ USA
Wow!!! Thats the only way I can describe what Matt did to make my vacation to Hilton Head so perfect. I had never been to islands of South Carolina and had no idea what I was in for. I loved everything and had never been so relaxed in my life. I will use Matt every time from now on.
I would recommend this agent to my family and friends
2 of 3 people found this review helpful
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Only Way to Travel

Reviewed By Lily - Chicago,Il | Traveled to Sedona ~ Arizona ~ USA
Hands down this was the vacation experience I have ever had. Matt was so helpful any time I had questions and took care of everything so quickly. I can't wait to take another trip with Matt's help again.
I would recommend this agent to my family and friends
5 of 9 people found this review helpful
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Paradise!!!

Reviewed By steve - Chicago, IL | Traveled to Zihuatanejo ~ Guerrero ~ Mexico
Matt made everything a piece of cake. I can't wait for our next trip.
I would recommend this agent to my family and friends
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Honeymoon of dreams!!!

Reviewed By Laura - Chicago, IL | Traveled to Jamaica ~ Caribbean
Matt was so great to work with. I would recommend his services to anybody looking for a great honeymoon.
I would recommend this agent to my family and friends
1 of 2 people found this review helpful
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Great adult only vaca!!!!

Reviewed By Juan - Chicago, IL | Traveled to Cancun ~ Quintana Roo ~ Mexico
Matt gave us everything we asked for and more!!!
I would recommend this agent to my family and friends
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Top notch service!

Reviewed By Mark - Chicago, IL | Traveled to Cabo San Lucas ~ Baja California Sur ~ Mexico
everything was perfect!!! Matt was always available to answer questions and give us exactly what we needed.
I would recommend this agent to my family and friends
1 of 2 people found this review helpful
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Made My Vegas Trip Flawless

Reviewed By Nick - Downers Grove, IL | Traveled to Las Vegas ~ Nevada ~ USA
Matthew was very cool. He made sure the guys and I got to and from Vegas for our bachelor party. He helped us lock in the best hotel I ever stayed at. Highly recommend.
I would recommend this agent to my family and friends
1 of 2 people found this review helpful
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Amazing for small or large destination weddings!

Reviewed By Serenity - Skokie, Illinois | Traveled to Hawaii ~ USA
Matthew offered complete and thorough support for my wedding party and guests. He was able to offer immediate support and provide solutions, as needed. Thank you Matthew for making our wedding amazing. We cannot wait to use you again!
I would recommend this agent to my family and friends
1 of 2 people found this review helpful
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LGBTQ+ Friendly and Tailored Travel Services

Reviewed By Dominic - Chicago, Illinois | Traveled to Puerto Vallarta ~ Jalisco ~ Mexico
My partner and I were initially skeptical about using a travel agent, as we were specifically looking for someone who was LGBTQ friendly and able to locate travel destinations that were welcoming of LGBTQ individuals.

Matthew made my partner and I feel comfortable, and tailored his service and customer service to ensure we had a safe/LGBT-centered travel experience.

I will be using Matthew for all future travel plans.
I would recommend this agent to my family and friends
1 of 2 people found this review helpful
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Spring Break 2023

Reviewed By terrie - Laurel, Maryland | Traveled to Arizona ~ USA
From our initial contact explaining what kind of experience we were looking for with our extended family on Spring break, Matt was extremely helping with suggestions and advise on where to stay and what to see and do. He was very quick to respond to any questions we had along the way and offered some great ideas on working with our party of 11. Would highly recommend to anyone wanting to coordinate a successful adventure.
I would recommend this agent to my family and friends
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Soooo Relaxing...

Reviewed By Karyla - Chicago,Il | Traveled to Sedona ~ Arizona ~ USA
Just Amazing!!! I had never been to Sedona and Matt made everything simple for me. He gave me the most relaxing trip of my life.
I would recommend this agent to my family and friends
3 of 6 people found this review helpful
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Perfect Anniversary!!!

Reviewed By Phil - Orlando,, FL | Traveled to Maui Island ~ Hawaii ~ USA
Matt planned the perfect wedding anniversary trip for us. My wife and I were so happy the whole time of our trip to Maui. All I can say, is Matt is the best!
I would recommend this agent to my family and friends
2 of 4 people found this review helpful
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So luxurious

Reviewed By Abby - Skokie, IL | Traveled to Zihuatanejo ~ Guerrero ~ Mexico
I loved everything about my trip. Matt crossed every t and dotted every i. All the extras made me never want to come home.
I would recommend this agent to my family and friends
3 of 6 people found this review helpful
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Loved everything about it!

Reviewed By Vic - Highland Park, IL | Traveled to Cabo San Lucas ~ Baja California Sur ~ Mexico
Matt is the best!!! I always wanted to go to Cabo and have a luxurious vacation. Matt fullfilled all of my wishes and more. I will have to take a trip like this more often. I highly recommend using Matt to make your vacation the best!!!
I would recommend this agent to my family and friends
3 of 6 people found this review helpful
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Vegas Baby!!!

Reviewed By Mark - Chicago, IL | Traveled to Las Vegas ~ Nevada ~ USA
We had the best time ever. Matt gave us everything we asked for and made everything a breeze. Can't wait for the next one.
I would recommend this agent to my family and friends
0 of 1 people found this review helpful
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Thank you For Being Our Family Travel Agent

Reviewed By Elaine Katz - Wilmette, IL | Traveled to Italy ~ Europe
This is the 3rd time we have used Matthew as our family's travel agent. My husband and I spent years trying to locate a quality agent, and this will be the only agent we will ever use again.

Matthew value's customer service and punctuality, and he is detail-orientated and empathetic. All of his traits are why we continue having wonderful family vacations and why we will always come back to him.

I would recommend this agent to my family and friends
0 of 1 people found this review helpful
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Great Travel Agent

Reviewed By Tyler - St. Louis, Missouri | Traveled to Nashville ~ Tennessee ~ USA
Matt is legit. I could not have traveled to Nashville without him. Matt helped my cousin and I find our flight, hotel, and even gave us some cool things to see while we were there. I appreciated his customer service, sense of humor, kindness and patience.
I would recommend this agent to my family and friends
1 of 3 people found this review helpful
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Heaven on earth!

Reviewed By Jess - Chicago, IL | Traveled to Cabo San Lucas ~ Baja California Sur ~ Mexico
What else can I say but everything was great. My trip to Cabo was the thing of dreams. I can't wait for Matt to plan my next vacation.
I would recommend this agent to my family and friends
1 of 3 people found this review helpful
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Perfectly Perfect in Every Way!!!

Reviewed By Sybil - Northbrook, IL | Traveled to Zihuatanejo ~ Guerrero ~ Mexico
My husband and I love going to Mexico, but this trip to Zihuatenejo was by far better than any trip we tried to plan ourselves. Matt must have spent so much time working on every little detail. We enjoyed every moment together and will definitely use Matt for future vacations.
I would recommend this agent to my family and friends
1 of 3 people found this review helpful
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The Perfect Trip!

Reviewed By Ina - Chicago,Il | Traveled to Puerto Vallarta ~ Jalisco ~ Mexico
My trip to Puerto Vallerta was absolutely perfect! I have gone to Mexico before but I have never had such an amazing experience. I will use Matt for every vacation I take from now on.
I would recommend this agent to my family and friends
2 of 5 people found this review helpful
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Good Times!

Reviewed By Nancy - Chicago,Il | Traveled to Cancun ~ Quintana Roo ~ Mexico
Matt was so amazing. Planning trips used to stress me out, but Matt made everything so easy and got me everything I wanted, and more!
I would recommend this agent to my family and friends
1 of 4 people found this review helpful
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I love Hawaii!!!

Reviewed By Nakia - Chicago,Il | Traveled to Maui Island ~ Hawaii ~ USA
OMG! My vacation was so amazing thanks to Matt. He got me everything I wanted and made my experience in Hawaii with my husband unbelievable. I can't wait to do it again!
I would recommend this agent to my family and friends
2 of 6 people found this review helpful
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Swimming with the Dolphins!!

Reviewed By Jana'e - Los Angeles, CA | Traveled to Puerto Vallarta ~ Jalisco ~ Mexico
I had such a great time in Puerto Vallarta thanks to Matt. He set up an amazing trip for myself and 5 friends. I think the swimming with the dolphins was the highlight for all of us.
I would recommend this agent to my family and friends
1 of 5 people found this review helpful
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My Travel Experience

Places I’ve personally traveled to or destinations I’ve booked for my clients.