Tier One
Luxury Guided Small-Group Tours
Curated itineraries with a small group of like-minded travelers. Boutique hotels, expert local guides, skip-the-line access at every major site. You show up. We handle everything else.
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Luxury European Travel, Planned in Chagrin Falls, Ohio
Europe, the way
you imagined it would feel.
Small-group and private tours to Greece, Italy, France, Spain and beyond, designed by a BBC-featured advisor who has walked the streets, vetted the hotels, and knows the back-door entrance to almost every famous door.
BBC
Featured on BBC Travel
ASTA
American Society of Travel Advisors Member
10
European Countries Designed and Walked
100%
Logistics Handled So You Can Be Present
The Real Cost of "I'll Just Book It Myself"
The trip you've been promising yourself for 20 years deserves more than a search bar.
You lose two weekends to research and still book the wrong hotel.
The average independent European trip takes 32 hours to plan online. Most travelers still get the location wrong, miss the right neighborhood, and pay 18 to 40 percent more than they would have paid through an advisor with hotel relationships.
You arrive exhausted and never quite relax.
You spent the flight checking confirmations. You spend the first day fixing them. You spend the last day already worried about the next leg. The trip you wanted was the opposite of this.
You finally get to Europe, and Europe never really lets you in.
The line at the Vatican is four hours. The "authentic" restaurant in Santorini is a tourist trap. The Alhambra is sold out. Without an advisor who has the access, the door stays closed and you go home with the same photos every other tourist took that week.
Your Guide
We understand. Planning the trip is the part nobody warns you about.
You have been thinking about this trip for years. The kids are finally old enough. The anniversary is finally close. The retirement is finally real. And now the only thing standing between you and Europe is 47 browser tabs and a feeling that you are missing something.
That is why The Olive Odysseys exists. We are a boutique, BBC-featured travel advisory based in Chagrin Falls, Ohio. We design small-group and private tours across ten European countries. We are members of the American Society of Travel Advisors, which means you are protected by a real code of conduct and a real human you can call when something goes sideways.
Featured
on BBC Travel for our approach to adventurous, considered European travel.
Skip-the-Line
access at the Vatican, the Louvre, the Acropolis, the Alhambra, and more.
Full-Service
trip planning so every flight, hotel, transfer, and guide is handled before you board the plane.
Three Ways We Travel
Pick the level of partnership that matches the trip you want.
Some travelers want a curated group, a sommelier-led dinner, and zero decisions to make. Some want a private tour for their family alone. Some want to travel independently but with a real itinerary in their pocket. All three are valid. All three are us.
Tier Two
Customized Private Tours
A tour built only for you, your family, or your friends. Choose the countries, the pace, the level of luxury. We design every detail and travel with you in spirit at every step.
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Tier Three
Personalized Trip Planning
You want to travel independently but skip the hours of research. We build your full itinerary, book your hotels, secure your skip-the-line tickets, and put a 24/7 concierge in your pocket.
See This TierWhere We Go
Ten countries. One advisor who has walked them all.
Hover any destination to start the conversation. Multi-country itineraries are a specialty: think Greece plus Italy, or France plus Spain plus Portugal.
Greece
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Italy
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France
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Spain
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Croatia
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Portugal
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England
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Ireland
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Scotland
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Switzerland
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Currently in the Field
Named custom tours we are running right now.
Proof, not adjectives. These are real itineraries we have built and are running for real families and groups. Yours is next.
Active Custom Tour
The H Family: Paris, Barcelona and Beyond
A multi-week, multi-country custom itinerary for a family of five. Private guides in both cities, a hand-picked apartment in Le Marais, a chef-led market morning in La Boqueria, and one quiet day on the Costa Brava that they will remember the rest of their lives.
Booking 2026
Haas Group, 2026
A custom small-group tour designed for a private circle of friends traveling together in 2026. Itineraries this considered start being planned 12 to 18 months in advance. If you are dreaming about 2026 or 2027, this is the moment to call.
The Travelers Themselves
"We had been talking about it for years. Then we finally called."
"
We had been talking about Greece for fifteen years and could never make ourselves pull the trigger. The Olive Odysseys took the whole thing off our plate. Hotels we never would have found, a private boat day in the Cyclades, and a final dinner in Athens that my husband still talks about. We are already planning Italy with them for 2026.
Rebecca M.
Shaker Heights, OH, family of four, Greece 2024
"
I am a planner. I do not let people plan things for me. I let The Olive Odysseys plan our two-week tour through Paris, Barcelona, and the Costa Brava. Every hotel was perfect. Every guide was the right person. The whole trip ran on rails. I have already recommended them to three friends.
The H Family
Custom Paris and Barcelona tour, returning client
"
I am not an easy client. I read everything, I question everything, and I have been to Italy four times. The trip they built for our group was better than every trip I have planned myself. The skip-the-line at the Vatican alone saved us six hours and a small argument.
David K.
Chagrin Falls, OH, private group tour to Rome and Florence
Three Steps. That's It.
Working with us is the easiest part of the trip.
01
Call or Write Us
A 20-minute discovery conversation, on us. Tell us who is going, what you have been dreaming about, and when you want to leave. No pressure, no pitch.
02
We Design the Itinerary
Within 7 to 10 days you receive a fully built proposal: countries, hotels, guides, restaurants, transfers, and the cost. We refine until you love it.
03
You Travel. We Handle Everything.
Every detail booked. Skip-the-line tickets in your inbox. A real human you can call at any hour, from any time zone, the entire time you are gone.
The Journal
Written by the advisor who built your trip.
Real planning intelligence from someone who books these trips every week. No fluff. No SEO filler.
Press
Why BBC Travel Featured The Olive Odysseys (And What That Means for Your Next Trip)
The BBC does not feature mass-market travel sellers. Here is what the feature actually says about the work we do, and why it matters when you choose who plans your trip.
Read & Plan This Trip →Greece
Small-Group vs. Private Tours to Greece: How to Choose What's Right for You
Both options take you to Santorini. Only one is right for the way you actually like to travel. A direct comparison from someone who books both every year.
Read & Plan This Trip →Tips
The Insider's Guide to Skip-the-Line Tickets in Paris, Rome, and Athens
Skip-the-line is not all the same. Here is what the words actually mean at the Louvre, the Vatican, and the Acropolis, and how to make sure yours are real.
Read & Plan This Trip →Trust
Why Booking Through an ASTA Travel Advisor Protects You in Ways Online Booking Never Can
When a hotel overbooks, when a flight cancels, when a tour operator vanishes: who do you call? With ASTA, you have an answer. Without it, you have a chatbot.
Read & Plan This Trip →Greece
The Places in Greece Most Tourists Never See (And How We Get You There)
Past Mykonos and Santorini, there is the Greece that locals love. Four regions, real recommendations, and the access most travelers never know to ask for.
Read & Plan This Trip →Family
Custom Family Travel to Europe: What the H Family's Paris and Barcelona Tour Looked Like
A real custom itinerary, planned for a real family of five. Hotels, restaurants, private guides, the moments they loved most. Use it as a blueprint for yours.
Read & Plan This Trip →Planning
Italy vs. France vs. Spain: How to Choose Your First European Small-Group Tour
If this is your first trip across the Atlantic, the country you choose changes everything. A frank comparison of food, pace, history, and what tends to surprise people.
Read & Plan This Trip →Services
What 'Personalized Trip Planning' Actually Means (And Why It's Worth It)
Anyone can hand you a list of hotels. Real planning is choosing the right hotel for the right traveler on the right week. Here is what that process looks like.
Read & Plan This Trip →Destinations
Croatia and Portugal: Europe's Most Underrated Destinations for Small-Group Travel in 2025
Two countries doing what Italy did 20 years ago. The food is exceptional, the prices are honest, and the crowds have not arrived yet. Go before they do.
Read & Plan This Trip →Planning
How to Plan a Multi-Country European Tour Without the Stress: The Olive Odysseys Approach
Three countries in two weeks sounds exhausting. Done well, it is the trip of a lifetime. Here is the planning approach that makes the difference.
Read & Plan This Trip →The Questions Travelers Actually Ask
Frequently Asked Questions
You get a real human advisor who has walked the streets, vetted the hotels, and built relationships with local guides over years. When a flight cancels at 11pm in Rome, you call one number. When a tour operator overbooks, we have the relationship to fix it before you ever know. Online booking sites disappear when something goes wrong. We don't.
Plan Your Trip
Tell us where you've been dreaming.
The first conversation is complimentary and lasts about 20 minutes. We listen, we ask questions, and if we are not the right fit we tell you. If we are, we get to work.
Call
1-440-804-5062Studio
46 Shopping Plaza Drive #107
Chagrin Falls, Ohio 44022