Olegana Travel Boutique

05/24/2025

Plot twist: planning the trip wasn’t the stressful part.

When clients say things like “I don’t think I can ever travel without Anna again” or “We trusted her with everything and it was flawless,” it’s not just ego fuel (although, thank you, I will be framing that).

It’s because I don’t just plan vacations—I anticipate your chaos, manage your “what ifs,” and somehow make your entire trip feel effortless. Which, let’s be honest, is borderline witchcraft.

You get to eat pasta in Rome or float through Venice like a local, while I stay behind the scenes, making sure your driver actually shows up and your boutique hotel doesn’t randomly double-book you with a Swedish tour group.

So yeah, “seamless” is cute. But I call it the standard.

Ready to be the person in the group chat who actually pulled off the dream trip? Slide into my DMs. You bring the suitcase—I’ll bring everything else.

05/19/2025

It didn’t start as a business. It started as a search.
For freedom.
For meaning.
For places that felt like me — even when I was a world away from home. 🌍

Small group trips for women by Olegana Travel Boutique weren’t in the plan.
But after a few life-altering trips, something clicked.
I wanted other women to experience travel that’s not just about luxury, but liberation.

Now it’s a full-blown movement.
Curated journeys. Soulful escapes.
Connections that last longer than the vacation.

A friend recently wrote about how it all began. And let’s just say… she got deep. Like “did I really cry in the Milan airport?” deep. 🫠

So if you’ve ever wondered how Olegana came to be — this is it. The messy, magical, deeply personal origin story.

No gatekeeping. No fluff. Just real talk.

📖 Click the link below you want the full story (you won’t, but I love pretending).

https://oleganatravelboutique.com/blog/for-the-love-of-travel-olegana-travel-boutique-origin-story

05/17/2025

"Wow – I don’t have enough words of praise, respect, and adoration…”

That’s not marketing fluff. That’s from a real mom who came back from a three-week adventure across Italy and Greece with her husband, her five-year-old, and her eight-year-old—and somehow still had the energy to leave a glowing review.

Here’s what she said:

🧳 “Anna was all over EVERY single detail…”
🏨 “Every hotel, every meal, every private driver, every single tour, every activity – EVERYTHING was flawlessly curated.”
👨‍👩‍👧‍👦 “Our every need was thought of and accounted for.”
💌 “I don’t think I can ever take a trip without Anna’s help again.”
🫶 “She is the ABSOLUTE BEST!!!”

This is what I do: I handle every detail so families can actually enjoy their vacation. No logistics panic. No 47-tab planning spreadsheets. Just magical, seamless, memory-making across Europe.

If you’ve got kids, chaos, and dreams of a vacation that doesn’t feel like a second full-time job—I’ve got you.

DM me “FAMILY” and let’s make it happen.

05/14/2025

If you’re thinking of fall, think Andalusia.

Spain’s southern soul isn’t just a summer fling—it’s a full-blown autumn romance.

Cooler air, quieter streets, and cities that feel like poetry wrapped in stone: Seville, Granada, Cordoba, Ronda.

Flamenco echoing through courtyards, tapas shared under falling orange leaves, golden light that makes even your phone photos look like art.

Andalusia is for slow walks in the fall. Late dinners. Rooftops with wine and no rush.

It’s romance without the crowds. Culture without the overwhelm. A trip that feels like a secret passed between lovers.

We’ve been. We've wandered. We know the hidden spots, the charming stays, the tables you want to reserve before anyone else knows you’re coming.

So if you’re dreaming about disappearing somewhere beautiful this fall—go south.

We'll help you find the magic.

05/12/2025

🍷✨ Spring 2026: Sicily is Calling — Are You In? ✨🍫

What happens when you mix Sicilian sunshine, decadent chocolate, and bold local wines? Answer: you, laughing with new friends on a sun-drenched terrace overlooking the Mediterranean.

Join us for an unforgettable women’s getaway through the heart of Sicily — where every cobblestone street has a story, every glass of wine has a history, and every chocolate has zero regrets attached. Think vineyard strolls, chocolate tastings (yes, plural), charming villages, stunning coastlines, and that feeling of finally doing something just for you.

✔️ Curated boutique experiences
✔️ Zero planning stress (we’ve handled it)
✔️ Maximum wine, laughter, and gelato

🌍 Explore more and claim your spot:
oleganatravelboutique.com/womens-group-trips/spring-2026-wine-chocolate-you-in-sicily

Warning: Side effects may include chronic happiness and a refusal to return home.

April 12 - 20, 2026Spring 2026: Wine, Chocolate & You in Sicily Bella Sicilia is calling…Close your eyes and imagine the golden glow of the Italian sunset, painting the hills with hues of orange and pink. You are lounging in luxury, sipping on a glass of velvety wine and soaking in the beauty of t...

05/10/2025

Tough as a mother.

Because traveling with kids isn’t a vacation—unless someone else has done the work.

I’ve been there (with the snacks, the meltdowns, the stroller that doesn’t fit in the rental car). And I’ve also been there as a travel advisor who knows how to make family trips actually feel enjoyable.

I know where not to go. I know which “family-friendly” hotels are code for chaos. And I know how to make the whole thing smoother, smarter, and maybe even a little fun for you too.

Because when the trip is planned right?

You get to be present. You get to enjoy the destination. And you don’t have to be the cruise director and the lifeguard and the snack bar.

Tough as a mother, yes. But smarter with help.

05/08/2025

We didn’t hire a pro to plan our first family trip to Portugal.

We thought, “How hard could it be?”

Ah yes, the classic “Lisbon with a stroller” debacle—also known as CrossFit: Baby Edition.

Cut to: us in Lisbon, dragging a stroller up cobblestone hills, dodging trolleys, sweating through every layer of our naïve optimism. Oh, and stairs. So many stairs. Lisbon doesn’t believe in ramps (most of the time).

It was beautiful, yes. But it was also a lesson.

Traveling with kids is different. You have to think ahead—about terrain, logistics, naps, restaurants that don’t give you side-eye when a toddler melts down over juice.

That’s where experience matters.

Now, I plan differently—for my own family and for clients. I know how to make family travel easier, smoother, smarter. Because I’ve made the mistakes already (so you don’t have to).

So take it from me: don’t DIY your way into an uphill battle. Literally.

Hire someone who knows better.

Your knees—and your sanity—will thank you.

05/06/2025

There are Caribbean islands everyone talks about—and then there are the ones you remember.

Over the past few years, I’ve had the chance to visit St. Lucia and Grenada—both with my family, and both incredibly special in their own way.

They’re not loud. They’re not trying too hard. They’re just… right.

Lush, peaceful, full of color and rhythm and quiet corners you want to get lost in.

Perfect with kids, perfect without.

This year, I’m heading to Barbados and Antigua—curious to see how they stack up.

Different energy, different charm. That’s the beauty of the Caribbean: no two islands are the same, and they all surprise you in their own way.

If you know, you know. (And if you don’t, that’s what I’m here for.)

05/05/2025

🌸 Mother’s Day is coming… and you deserve more than brunch. 🌸

How about this instead:

✨ A massage under the open sky, surrounded by ancient olive trees and kissed by the southern Italian sun
✨ A welcome lunch straight from the earth—fresh, local, unforgettable
✨ Time with your mom, your daughter, your sister, your chosen family—making memories that actually last

We're giving you two incredible experiences FREE when you book our October 2025 women-only trip to Puglia, Italy—and bring a special woman in your life. 💕👯‍♀️

Because chocolates melt. Flowers wilt. But Italy? Italy stays with you.

🍷 Tag your mom, your daughter, your best friend—and say YES to the trip of a lifetime.

📅 Trip details + future 2026 travel dates in the comments!

05/04/2025

Some places you visit. Some places you return to.

The lake region of Italy is one of those for me.

Lake Como, Lake Garda, Lake Maggiore, Lake Orta—each with its own rhythm, its own kind of beauty.

Como is elegance with a view. Grand villas, quiet glamour, and espresso that somehow tastes better by the water.

Garda has range: lemon groves, sailboats, and charming towns that feel like they’ve never needed to change.

Maggiore is slower, a little quieter, perfect if you like your mornings misty and your afternoons on a boat.

And then there’s Orta—small, poetic, often overlooked. Which is exactly why I love it.

I’ve spent time in all four—sometimes with my family, sometimes solo. And every time, I find something new to love.

If these lakes are on your list (and they should be), don’t wing it.

Use someone who actually knows them. Otherwise, enjoy booking the wrong hotel and arguing over ferry schedules.


 
 
 
 
 
 
 
 
 


04/21/2025

Sicily: where EVERY bite tells a story! 🍋

If you're not eating your way through Sicily with us, you are missing out!

From the salty sea breeze to the sweet scent of citrus, this island knows how to serve flavor.

Must-try Sicilian dishes:
🥐 Arancini – Crispy, golden rice balls of pure joy
🍆 Caponata – A sweet-sour eggplant medley that’ll change your life
🐟 Fresh seafood – Grilled swordfish, octopus, and pasta with sardines
🍧 Granita & brioche – Breakfast that is just wow!
🍰 Cannoli – Because dessert is always a great idea

🍫 Chocolate - Deep, dark, and just the right hint of spice

Sicilian food isn't just a meal, it's a memory. Come make the most delicious memories with us!

Wine, Chocolate & You in Sicily: October 5 - 13, 2025

DM me for details!

04/02/2025

🌟 Traveling with kids? It can be a challenge, but we’ve got you covered! 🌟

Check out our latest blog post for the 3 essential tips every parent needs for smooth family trips: packing like a pro, planning around your little one’s schedule, and staying patient through the chaos. ✈️👶

✨ Must-Pack Essentials: Snacks, activity books, tablets with headphones, extra clothes, and comfort items like a favorite blanket or stuffed animal!
✨ Smart Planning: Book flights around nap times, allow extra time for everything, and choose kid-friendly accommodations.
✨ Patience is Key: Stay flexible, embrace delays, and keep a sense of humor!

Don’t miss out on these simple hacks to make your next family vacation unforgettable! 🎒✨

🔗 Read more on our website - https://oleganatravelboutique.com/blog