Samantha Cleary, Travel Agent in Grand Rapids, MI

Samantha Cleary

Grand Rapids, MI Travel Agent

Samantha Cleary

Grand Rapids, MI · 3 Years of Experience

Always Travel Season, an independent agent with KHM Travel Group, a Travel Leaders Network Affiliate Agency
5.0
(6)
100% Recommended
We cannot recommend Samantha Cleary with Always Travel Season highly enough! Traveling with two kids under 4 isn’t always easy, but she took care of everything... Read More >
About
My Travel Specialties
Reviews
Certificates & Awards
My Places
Travel Stories & Media
Itineraries
Client Testimonials

Areas of expertise

Destinations:

Croatia, Banff, Punta Cana, Cascais, Cancun

Interests:

Adult Only, All Inclusive, European Culture, Family Vacations, Groups

Suppliers:

Funjet Vacations, Inclusive Collection – World of Hyatt, Kensington, Sandals Resorts, Classic Vacations

About Me

Travel Advisor Designing Curated Experiences

Specializing in all-inclusive vacations, cultural European travel, national parks, family vacations, group travel, and honeymoons, I offer expert guidance and tailored planning for travelers seeking stress-free, high-value experiences. With in-depth knowledge of top resorts, destinations, and travel logistics, I curate trips that match each client’s unique vision. Whether it’s a romantic honeymoon, a milestone celebration, or a multi-generational getaway. I manage every detail, from destination recommendations and resort matching to securing exclusive perks and organizing group arrangements. My goal is to simplify the planning process, provide exceptional service, and ensure every trip is seamless, personalized, and unforgettable from start to finish.

My Travel Specialties

Group Vacations, Planned by a Travel Agent

Group Vacations, Planned by a Travel Agent
Why Booking with a Travel Agent Makes All the Difference Planning a group trip is exciting, but let’s be honest, it can also feel overwhelming. Whether you’re organizing a multi-family spring break getaway, a milestone birthday celebration, a bachelorette party, or a reuni...Read More ▶

Honeymoon Vacations, Planned by a Travel Agent

Honeymoon Vacations, Planned by a Travel Agent
Your Honeymoon Should Be Unforgettable After the excitement (and stress!) of wedding planning, your honeymoon is more than just a vacation, it’s the beginning of your new life together. It should be unforgettable, seamless, romantic, and absolutely tailored to you. Whether...Read More ▶

Banff Vacations, Planned by a Travel Agent

Banff Vacations, Planned by a Travel Agent
Why Banff Needs to Be on Your Bucket List: If there’s one place in the world that truly feels like it was painted by nature herself, it’s Banff. Located in the heart of the Canadian Rockies in Alberta, Banff National Park is a destination that doesn’t just meet your expect...Read More ▶

Portugal Vacations, Planned by a Travel Agent

Portugal Vacations, Planned by a Travel Agent
The Ultimate Travel Guide to Portugal: Why This Enchanting Country Should Be Your Next Adventure Portugal is one of those rare destinations that feels like a storybook brought to life. With its golden coastlines, colorful cities, soulful music, and heartwarming cuisine, th...Read More ▶

Croatia Vacations, Planned by a Travel Agent

Croatia Vacations, Planned by a Travel Agent
Some destinations are meant to be explored by land. Croatia? Croatia was made to be discovered by sea. And just so you know...I sailed the Croatian islands by yacht, and I can honestly say it was one of the most unforgettable travel experiences of my life. From quiet morning swims in hidden coves...Read More ▶

Honeymoon, Group Travel, All Inclusive Specialist

Honeymoon, Group Travel, All Inclusive Specialist
I've spent over a decade immersed in the enchanting world of hospitality and tourism. With a profound love for travel and a passion for helping others explore the world, I've made it my mission to unveil the wonders that lie just beyond your front door. My heart thrives on the thrill of discovery...Read More ▶

REVIEWS

Rating: 5.0
6 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.
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Showing 6 reviews

Family Trip to Mexico!
Reviewed By The Rienstra Family - Holland, MI | Traveled to Mexico
We cannot recommend Samantha Cleary with Always Travel Season highly enough! Traveling with two kids under 4 isn’t always easy, but she took care of everything for us. She found a sunny, tropical all-inclusive resort that was perfect—relaxing for us, fun for the kids, and completely stress-free. From the planning stages to being in-country, Samantha was detail-oriented, well-prepared, and gave great recommendations. When we lost a purse with important documents, she immediately stepped in to help us sort it out. She was responsive and supportive the entire time. Thanks to her, we had a smooth and memorable trip. We’ll definitely work with her again!
I would recommend this agent to my family and friends.
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Great family travel experience!
Reviewed By T Family - Hamilton, MI | Traveled to Dominican Republic | Caribbean
Samantha was amazing and so on top of things! We had continuous plane delays and got deboarded when returning home from vacation. Samantha was following and paying attention to our flights and ended up getting my family on a completely different flight! I would highly recommend Always Travel Season for traveling. Samantha is excellent at making things as simple and flawless as possible.
I would recommend this agent to my family and friends.
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Amazing Beach Getaway!
Reviewed By Beachfamily - Zeeland, MI | Traveled to Florida | USA
Samantha made planning our family trip to Santa Rosa Beach and 30A a breeze! She had every detail organized ahead of time, so we could just relax and enjoy. Her quick responses and support were incredible, and her recommendations for family-friendly spots made the trip unforgettable. We highly recommend Samantha for your next family adventure!
I would recommend this agent to my family and friends.
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Stress-Free European Adventure Thanks to Samantha!
Reviewed By Jen K - Santa Rosa Beach, FL | Traveled to Bavaria | Germany | Europe
Our girls’ trip to Europe was an absolute dream, thanks to Samantha! When unexpected airline issues arose, she jumped into action with quick and effective solutions, turning what could have been a stressful situation into a seamless travel experience. Her professionalism, attention to detail, and dedication to ensuring everything went smoothly allowed us to fully enjoy our adventure without missing a beat. Samantha truly went above and beyond—she’s the reason our trip was unforgettable. Highly recommend!
I would recommend this agent to my family and friends.
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The best honeymoon in Italy!
Reviewed By Sarah - Angola, IN | Traveled to Italy | Europe
Samantha planned the honeymoon of our dreams in Italy! Every detail was flawlessly arranged, from charming accommodations to romantic activities and must-visit spots. She was always available to answer our questions and made the entire trip stress-free. Thanks to her expertise, we experienced the best of Italy and created unforgettable memories. We highly recommend Samantha for planning your perfect getaway!
I would recommend this agent to my family and friends.
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Certifications & Awards

AMA Academy
AMA Academy
AmaWaterways Specialist
AmaWaterways Specialist
AMResorts Master Agent
AMResorts Master Agent
Seacademy - Gold Certification
Seacademy - Gold Certification
Seacademy - Scarlet Certification
Seacademy - Scarlet Certification
Seacademy - Silver Certification
Seacademy - Silver Certification
Seacademy - Violet Certification
Seacademy - Violet Certification
TRACKS (Rocky Mountaineer Specialist)
TRACKS (Rocky Mountaineer Specialist)

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

Croatia
View Album

    Client Testimonials

    Corporate Incentive Trip a Huge Success!
    This is the second year we relied on Always Travel Season, Samantha and Karen, to manage our resort venue and airfare arrangements for our corporate trip. Coordinating flights from the United States is a challenging task, Samantha and Karen it flawlessly. Upon arrival, we were well-prepared with scheduled meetings and felt highly organized as we gathered to celebrate our top salesperson awards. Thank you for making it happen again!
    Ann Y Holland, Michigan
    BESbswy