Croatia Vacations, Planned by a Travel Agent

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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 >
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Areas of expertise

Destinations:

Croatia, Dubrovnik, Split, Hvar, Korcula

Interests:

European Culture, Family Vacations, Celebration Travel

About Me

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 to sunset wine tastings in centuries-old villages, every moment felt like magic. I knew right then and there: I had to help others experience this, too. So when I say I can’t recommend this trip enough, I mean it. I’ve lived it. I’ve built connections with trusted local partners. And I’ve curated itineraries that blend the best of adventure, relaxation, and Croatian charm...so you don’t have to lift a finger (unless it’s to raise a glass of rosé).

Along its shimmering Adriatic coastline lie more than 1,000 islands, each with its own charm, character, and story to tell. While most travelers stay anchored in one city or hop between a few on the mainland, those who choose to sail unlock a completely different kind of experience: one of freedom, beauty, and unmatched connection to this magical destination.

Picture this: You wake up on a sleek yacht, sunlight streaming through the cabin windows. You wander up to the deck with a coffee in hand and glance around...no crowds, no noise, just turquoise water and an island rising in the distance. By the end of the day, you’ve swam in a hidden cove, explored a centuries-old village, tasted wine in a cliffside cellar, and watched the sun dip below the horizon with a chilled glass of rosé in hand. This is Croatia. And this is the kind of trip I plan.

As a travel advisor, I curate elevated, seamless sailing experiences for travelers who want more than a vacation...they want something transformational. If you’ve ever dreamed of island-hopping through Europe, waking up in a new paradise each day, and exploring beyond the tourist trail, Croatia by yacht might just be the adventure you didn’t know you needed.

A Croatia sailing trip isn’t a luxury reserved only for celebrities or millionaires..it’s surprisingly accessible, and totally worth it.

1. No Packing and Unpacking Ever Again

On land-based trips, you’re constantly moving...check-in, check-out, schlepping bags. On a yacht, your hotel floats with you. You unpack once, and your “backyard” changes every day. It’s a traveler’s dream.

2. Skip the Crowds and Find Hidden Gems

Yachts can go where ferries and big cruise ships can’t. That means fewer crowds and access to tiny beaches, secluded coves, and uninhabited islands most tourists never see. Your captain and crew (often locals) know all the best secret spots.

3. Wake Up Somewhere New Each Day

Imagine opening your eyes to a new island on the horizon every single morning. One day you’re in the glitzy harbor of Hvar, the next you’re anchored off a national park in Mljet. Every day is a new postcard.

4. You’re In Control of the Experience

Want to swim before breakfast? Spend all afternoon at a beach bar? Explore a medieval town or lounge on deck with a book and wine? A sailing trip is flexible and tailored to you. It can be as adventurous or relaxed as you want it to be.

WHY CROATIA IS THE ULTIMATE SAILING DESTINATION

If Italy is for art lovers and Greece is for history buffs, Croatia is for travelers who crave the blend of natural beauty, culture, and sea-kissed adventure.

1. Over 1,000 Islands to Explore

Croatia’s coastline is dotted with over a thousand islands, only about 50 of which are inhabited. That means you’ll find a perfect mix of energy and tranquility, history and nature. Sail through the famous islands like Hvar, Korcula, and Brac...and also drop anchor at lesser-known gems like Šolta, Vis, and Mljet, where quiet beaches and old-world charm await.

2. Turquoise Waters You Won’t Believe Are Real

The Adriatic Sea is known for its clarity and jewel-toned colors. On a yacht, you’re not just looking at the water...you’re living in it. Morning swims, paddleboarding sessions, snorkeling in quiet coves...it’s all part of your daily routine.

3. Unspoiled Villages & Coastal Towns

Many of Croatia’s island towns feel like stepping back in time. Think stone alleys, red-tiled rooftops, family-run konobas (taverns), and flower-filled balconies. With a yacht, you can dock right at the heart of these communities...no taxis, buses, or transfers needed.

4. Incredible Food & Wine. Often Made by the People Serving It

Each island has its own culinary story. You might dine on just-caught seafood in a quiet bay, try olive oil made by a farmer’s grandmother, or sip wine from grapes grown on a family’s steep hillside vineyard. This isn’t just food...it’s culture served on a plate.

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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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
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    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
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