Portugal 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 >
About
Reviews
My Places
Travel Stories & Media
Client Testimonials

Areas of expertise

Destinations:

Cascais, Lisbon, Porto, Sintra

Interests:

European Culture, Family Vacations, Honeymoons

Suppliers:

Kensington

About Me

Ponte de Dom Luis I Bridge
Ponte de Dom Luis I Bridge

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, this charming country effortlessly blends old-world charm with modern vibrance. Nestled on the western edge of Europe, Portugal offers the perfect mix of cultural richness, natural beauty, and laid-back living, making it a must-visit for any traveler seeking something truly special. Whether you're a history buff, a beach lover, a foodie, or a romantic soul chasing sunsets, Portugal has something unforgettable for you.

Lisbon: The City of Light and Layers

Start your Portuguese adventure in Lisbon, the nation's capital and cultural heart. Built on seven hills and overlooking the Tagus River, Lisbon is a city of color, music, and movement. Stroll through the cobblestone streets of the Alfama district, where Fado music spills from candle-lit taverns. Visit the historic Belém Tower and Jerónimos Monastery, both UNESCO World Heritage sites. Ride the iconic yellow Tram 28 through neighborhoods bursting with azulejos (ceramic tiles), and don’t miss the panoramic views from the many miradouros scattered across the city.Café culture is big here. Order a bica (espresso) and a pastel de nata at one of Lisbon’s historic cafés, like Café A Brasileira. As day turns to night, explore the vibrant Bairro Alto and Cais do Sodré districts for music, food, and unforgettable nightlife.

Sintra: Portugal's Fairytale Town

Just 40 minutes from Lisbon lies Sintra, a UNESCO-listed town that looks like something straight from a fantasy novel. Perched in the forested hills of the Sintra Mountains, this town is dotted with whimsical palaces and mysterious gardens. Sintra is the kind of place where every corner begs to be photographed. Take your time wandering, and don’t forget to try the local pastries, travesseiros and queijadas.

Porto: Wine, River Views, and Timeless Charm (My Favorite City)

Travel north to Porto, a city defined by its charm, grit, and incredible views. Famous for its port wine, Porto sits along the Douro River, with colorful houses cascading down the hillsides.Walk the Ribeira district and cross the Dom Luís I Bridge to Vila Nova de Gaia, where you can tour wine cellars and sip on world-renowned port. Explore the Livraria Lello (rumored inspiration for J.K. Rowling’s Hogwarts), the Clérigos Tower, and the ornate São Bento train station.Porto is also a food lover’s paradise. Try francesinha, a decadent sandwich layered with meat, cheese, and spicy sauce, and pair it with local wine or a cold Super Bock beer.

The Douro Valley: Wine Country at Its Finest

A short drive from Porto, the Douro Valley is one of Europe’s most picturesque wine regions. The terraced vineyards that climb the valley’s slopes are not just scenic, they’re also home to centuries-old wine traditions.Take a river cruise down the Douro, visit historic wine estates (quintas), and sample robust reds and sweet ports. The town of Peso da Régua makes a great base, and autumn is an especially beautiful time to visit, as the vines turn golden.

Madeira & The Azores: Portugal’s Island Escapes

Looking for something even more off the beaten path? Portugal’s island regions offer untouched nature and wild beauty.

  • Madeira: Known as the "Island of Eternal Spring," Madeira features lush mountains, levada walks, and ocean views. Don’t miss the capital, Funchal, and a cable car ride to Monte.
  • The Azores: This volcanic archipelago in the middle of the Atlantic is a haven for hikers, whale watchers, and hot spring seekers. São Miguel, the largest island, is home to crater lakes, geothermal cuisine, and vibrant green landscapes.

When to Go & Travel Tips

  • Best Time to Visit: Spring (April to June) and fall (September to October) offer pleasant weather, fewer crowds, and vibrant festivals.
  • Getting Around: Portugal’s train system is reliable, and renting a car is great for exploring regions like the Douro or Algarve.
  • Language: Portuguese is the official language, but English is widely spoken in tourist areas.
  • Currency: Euro (€)
  • Tipping: Not obligatory, but appreciated (5-10% is standard)

More Than Just a Destination

Portugal is more than a place, it's a feeling. A blend of warmth, nostalgia, joy, and discovery. Whether you’re standing on a clifftop watching the waves crash below, sipping wine by a vineyard sunset, or dancing in the narrow alleys of Lisbon at midnight, Portugal leaves a lasting mark on your heart. It’s the kind of place that welcomes you in, slows you down, and reminds you what travel is really all about: connection, culture, and moments that take your breath away.

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.

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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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