Olegana Travel Blog
Tailored tips and inspiration for honeymoons, luxury trips, family vacations, and exclusive European group tours.
Explore the best of Europe with our expert guidance.
Best places to visit in Europe in fall: where I send clients in September, October, and November
The best version of Europe is not the summer one. It is the one that arrives in fall, when the harvest is on, the light goes gold, and the places you have dreamed of feel like they are yours again. Here is where I send clients in September, October, and November.
Extraordinary travel experiences worth building an entire trip around
Sleep inside a 1,200-year-old monastery. Float between two tectonic plates. Sit three metres from a wild gorilla family. These are the rare, access-driven experiences worth crossing the world for, and how a luxury travel advisor makes them real.
West Liguria: the luxury Italian Riviera beyond Cinque Terre
Monet's bridge in a medieval village. Taggiasca olive oil from centuries-old trees. Rossese wine almost no one outside Liguria has tasted. And a twenty-kilometre coastal cycling path on a former railway line. This is the Italian Riviera for travelers who have outgrown Cinque Terre.
Luxury Croatia travel guide: the Dalmatian coast, islands, and Istria
Most people plan Croatia around Dubrovnik and stop there. But this country has an extraordinary coastline, a food and wine culture that rivals Italy, and more than a thousand islands most visitors never see. Here’s what a well-planned Croatia trip actually looks like.
Set-Jetting: how to travel to the TV and film locations you can't stop watching
A single season of TV can make you want to pack a bag. Set-jetting, traveling to the real places behind the shows and films you love, is one of the biggest reasons people book right now. Here's how I bring you White Lotus Sicily, Emily's Paris, the Mamma Mia islands, Outlander's Highlands, and the England of Bridgerton and Downton Abbey, with the beauty turned up and the crowds turned down.
Malta: the luxury travel guide to Europe’s best-kept Mediterranean secret
Malta may be the most underrated destination in the Mediterranean. Eight thousand years of history, Michelin-starred restaurants, turquoise coastline, the original King’s Landing, and a brand-new nonstop from JFK. Here is what a luxury trip to Malta actually looks like.
Can AI plan a luxury trip?
ChatGPT can build you an itinerary in 30 seconds. It will list the top-rated restaurants, suggest a hotel near the Colosseum, and give you a day-by-day schedule that looks perfectly reasonable on a screen. Here's what it can't do: know that the top-rated restaurant stopped being good two seasons ago, negotiate a room upgrade because you're traveling for your anniversary, or pick up the phone when your flight is canceled and you're standing in an airport with two kids. That's the difference between AI-generated travel planning and a luxury travel advisor who knows your name. Let me walk you through exactly where the line is.
Luxury Veneto Italy: a rare evening at the Marostica Living Chess Game
I've secured 26 Tribune Silver seats to the Marostica Living Chess Game on 12 September 2026, a biennial Veneto spectacle staged by more than 650 performers in Renaissance costume. Here's the luxury Italy journey I'm building around it.
Checked in, checked out: 6 European hotels I’ve actually stayed in
From a 100-year-old palace on Lake Annecy to a Sicilian masseria where the bees own the pool. Honest luxury hotel reviews from a travel advisor who gushes about a hotel and gently roasts one quirky detail.
Why women are so exhausted, and why a trip might be part of the answer
A reflection on nervous system exhaustion, invisible labor, and why restorative women-only travel may be part of the answer. Written by a luxury travel advisor after attending a talk on mental health and the invisible load women carry every day.
Luxury travel by month: where to go for every season
There is no universally good month to travel. There are months that work for specific destinations, specific kinds of trips, and specific kinds of travelers. A luxury traveler's guide to twelve right answers.
Make time for you! Podcast episodes every woman 50+ should hear before planning her next solo trip
Travel is more than movement. It’s a return to yourself. And for women 50+, it starts to mean something deeper. It becomes about clarity, confidence, wellbeing, and finally saying yes to the things you’ve been putting off for years. That’s exactly what Olegana Travel Boutique's acclaimed podcast for women solo travelers 50+, Sign Your Own Permission Slip, speaks about.
The best luxury weekend getaways near New York City: 5 properties worth knowing about
A Victorian castle on 40,000 acres. A private lake with a deliberately tiny guest count. A Rockefeller Great Camp with 11 rooms and black-tie dinner. Five luxury properties near NYC, five completely different experiences and how to choose the right one.
Farm-to-fork travel in Europe: the luxury food experiences you can’t find on any booking site
A truffle hunter and his dog in the Piedmont woods. A Viscountess cooking in her ancestral kitchen. A chef who cooks your lunch on a cliff above the Atlantic from shellfish you just picked. These are the food experiences that make a European trip unforgettable.
Why smart travelers work with a luxury travel advisor in 2026 (especially right now)
The world is louder than usual right now. But the clients who are traveling the best this year are the ones who stopped planning alone. Here is what a luxury travel advisor actually does in a moment like this.
The 2026 solar eclipse: Why Iceland is the most extraordinary place on earth to watch the sky go dark
On August 12, 2026, the sky will go dark over Iceland and Greenland for a few extraordinary minutes. I've been planning this for my clients since the path was first confirmed, and what I can tell you is this: there's no more powerful place on Earth to watch a total solar eclipse than standing on the edge of an Icelandic lava field, or sailing through a Greenlandic fjord, as totality arrives.
Luxury travel in the Dolomites: your guide to Trentino and South Tyrol
Most people picture Tuscany or the Amalfi Coast when they imagine luxury Italy. The Dolomites are a different kind of extraordinary: wilder, quieter, and layered with Alpine culture, world-class food, and a landscape that genuinely earns every superlative.
Santorini honeymoon guide: How to experience Greece’s most romantic island the right way
A private sunset catamaran through the caldera. Assyrtiko wine tasted barrel to barrel. A cave hotel with a plunge pool overlooking the Aegean. And a 3,600-year-old city buried under volcanic ash. Here’s how to plan a Santorini honeymoon that goes deeper than the Instagram version.
Furore Grand Hotel on the Amalfi Coast: the luxury stay that could shape your entire Italy trip
35 rooms, a Michelin-starred restaurant with 18 seats, the largest spa on the Amalfi Coast, and a location that makes you forget Positano exists. Here’s why I’m recommending it to every couple heading to Italy. If you’re dreaming of the Amalfi Coast but want something that feels more refined than frantic, Furore Grand Hotel deserves your attention.
Verona, Italy: the luxury city break that surprises everyone
Opera in a first-century arena. Amarone in the winemaker’s cellar. Shakespeare brought to life in the streets. Verona has everything Rome and Florence have — without the crowds. Here’s why it’s the Italy trip that surprises everyone.