Maui Travel Agent Specialist

View My Main Profile
Matthew Schaffer, Travel Agent in Chicago, IL

Matthew Schaffer

Chicago, IL Travel Agent
Super Agent

Matthew Schaffer

Chicago, IL · 7 Years of Experience

A full-service Travel Leaders Associate Agency
5.0
(47)
100% Recommended
Matthew was fantastic! He planned a last minute trip to the Grand Canyon for me and my boys age 11 and 13. He... Read More >
About
Reviews
My Places
Travel Stories & Media

Areas of expertise

Destinations:

Wailea, Maui, Maui Island, Kapalua, Maui, Kaanapali, Maui, Kahului, Maui

Interests:

Honeymoons, Couples & Romance, Adult Only, LGBTQ+ Travel, Beach Vacations

About Me

Wailea Maui Beach
Wailea Maui Beach

Maui is by far my favorite destination in the Hawaiian Islands.  If you are a beach paradise lover like me, you just can’t ask for a better place for a romantic getaway, group travel or a family vacation.  With my help, I will make your trip to Maui an unforgettable experience that lasts forever.

Maui is unquestionably at the top of Hawaiian Island vacation spots.  Also known as “The Valley Isle”, Maui is Hawaii’s second-largest island, offering excellent food, amazing snorkeling, and some of the planet’s best beaches.  It’s not as highly commercialized as Oahu, but also not as underdeveloped as Kaui, making it an excellent destination for couples and families seeking authentic Hawaiian vibes.

Another highlight that makes Maui unique is that it’s actually comprised of three islands, not one.  Romantic Lanai and uncrowded Molokai are also part of Maui, which is officially known as Maui Nui. From Maui Island, you can sail to Lanai on a scenic 45-minute ferry or hop a 25-minute view-filled flight to Molokai.

Without a doubt, some of the most gorgeous beaches in the world are in Maui.  Maui is unique in that it has a broad array of beaches ranging from white, red, to black sandy beaches.  With glorious sands and amazing views, Maui has a beach for every mood.  Amazingly there are still several secret beaches on Maui that are unspoiled and secluded from tourists, making them ideal for a private romance experience.

One of my favorite beaches is Wailea Beach, located on the south coast it is known as one of the best beaches in the U.S.  Wailea means “the water of Lea”, the goddess of canoe makers. The beach is wide, the sand perfect, and the ocean is calm, with views of Kaho’olawe, Molokini, Lana’i and sightings of whales in the winter.  At Wailea Beach snorkeling is excellent around the rocky outcroppings that define both ends of the beach. Boogie boarding and body surfing are also great options to enjoy the small waves with gentle slopes.

A drive along the coast takes you past calm snorkel coves, and some of the biggest surfable waves on Earth.  Another One the best Maui beaches is Ka’anapali Beach, which is located on the western side of the island. It’s been named America’s Best Beach and offers three miles of soft, white sand for sunbathing. kayaking, snorkeling, and swimming with sea turtles.

If you have never been on a black sand beach, Honokalini Beach will astonish you. It has been Conde Nast Traveler’s number one choice in their 20 Best Beaches in the World.  With otherworldly black volcanic sand, Honokalani Beach at Wai’anapanapa State Park is a must see.

But there is so much more to Maui than just it’s amazing beaches.  Maui is the home to one of just three volcanic atolls in the world, Molokini Crater. A snorkel trip to this watery wonderland will reveal a rainbow of coral and bountiful schools of tropical fish all within the crystal-clear crater’s waters.

Another top attraction is the Road to Hana, which boasts some of the most beautiful landscapes in Hawaii.  This scenic drive offers many includes black sand beaches, cascading waterfalls, Bamboo forests, Garden of Eden, Hana lava tube, Seven sacred pools, and much more.  In fact, there are so many attractions on this beautiful road that it is impossible to see them all in a single day.

Hiking is one of the best activities in Maui, with several great hiking trails such as Iao Valley Park, Haleakala Crater, and Pipiwai Trail.  Hikers of all ages and skill levels will appreciate the incredible trails that wind through the Valley Isle. Whether you want to explore bamboo forests, waterfalls, or a volcanic state park, you’ll find it all on Maui.

If adventure is what you are looking for, Maui is the epicenter of Hawaii’s adventurous activities. Its lush green forests, diverse terrains, and scenic mountains offer exceptional adventure opportunities. You can go ziplining above Kaanapali, take a thrilling biking tour to the 10,000ft scenic Haleakala Mountain, experience the thrill of diving with white tip reef sharks at Mala Wharf, walk through a 900-year-old Hana Lava Tube, or enjoy a waterfall trek in East Maui.

If you happen to visit during winter, National Geographic recommends Maui as the best place to catch a glimpse of the 10,000 humpback whales that migrate from Alaska every year During peak whale season, December through April, you can often catch a glimpse of the massive whales right from the shore.

For you foodies, with a large bounty of tropical ingredients and plenty of eateries, Maui boasts world-class dining in paradise. Stop by a food truck for kalua pork tacos and a plate lunch, or splurge on dinner at a five-star restaurant.  Don't forget to experience the Luau while sipping a Mai Tai and enjoying the sunset over the Pacific.

There is so much more to say about Maui, but better to experience it instead. I really hope everyone gets a chance to experience Maui at least once, and I know I can provide the perfect vacation that you deserve.

Additional Languages
Spanish

REVIEWS

Rating: 5.0
47 reviews
100% Recommended
Your trust is our priority. Every review is submitted by verified travelers after they have booked and completed their trips. Learn more about our review guidelines.
Search reviews:

Showing 47 reviews

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.
3 of 3 people found this review helpful. Was this review helpful to you?YES|NO
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. Was this review helpful to you?YES|NO
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.
6 of 9 people found this review helpful. Was this review helpful to you?YES|NO
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. Was this review helpful to you?YES|NO
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. Was this review helpful to you?YES|NO

My Places

When it comes to travel planning, real-world experience makes a huge difference. Check out the map below to see all the places I have personally visited or booked for my clients. I know these destinations well and can give you reliable guidance.

My Photo Albums and Videos

Hawaii
View Album
    BESbswy