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.
Christmas in Italy: how to choose where to spend the holidays
Christmas in Italy changes from one region to the next: Krampus runs in South Tyrol, a mountainside of lights in Umbria, living nativities in Salento, and the great cities with the crowds gone. Here is how I choose, and how to pick the right December window.
Tuscany with kids: the family trip where nobody gets bored
Is there anything to do in Italy with kids? Italians have kids too, and theirs are on farms, in kitchens and in the sea. Here is the Tuscany I build for families and grandparents, one good thing a day, and the week that makes it work.
Algarve, Sintra or Comporta? An honest luxury guide to where to stay in Portugal
I just spent a week inspecting hotels across the Algarve, Sintra and Comporta. Here is my honest take on each region, the hotels I would send you to, and who each one is really for.
Why women over 50 are choosing small group travel in Europe
More women over 50 are reaching out to me to travel without their families, and not alone. Here is what I’ve learned hosting small-group women’s trips across Europe, who joins them, and where we’re going next.
Lake Garda and the Dolomites: a luxury guide to northern Italy’s lakes, vineyards and mountains
There’s a stretch of northern Italy where you can walk through a lemon house in the morning and stand under a wall of Dolomite rock before dinner. How I plan the route from Franciacorta to Lake Garda to the Alpe di Siusi, and when to go.
2027 Ryder Cup at Adare Manor, Ireland: your luxury travel guide to golf’s biggest event
Planning a luxury trip to the 2027 Ryder Cup at Adare Manor, Ireland? Our travel guide covers the best hotels near Adare, private driver bookings, VIP hospitality packages, and how to build an unforgettable Ireland itinerary around golf’s biggest event.
Best english gardens to visit: a luxury travel guide
Every great English garden has one week when it is exactly right. Not a season, a week. Most visitors arrive a fortnight too late and never know it. A luxury travel advisor’s guide to the great gardens of England, and to when you should be standing in them.
Portugal with kids: the best spring break trip in Europe
Six and a half hours from Newark, only five hours ahead, and warm enough in April for castles, cliff walks and boat days without the summer crowds. Here's how I build a Portugal spring break for families, including the one thing I always warn parents about before they book.
Hidden gems in Portugal: 5 places most visitors never reach
Lisbon and Porto are wonderful, and they are also where everyone goes. These five places sit an hour or two off the main route, from a fishing village with the biggest waves on earth to Portugal's only national park, and they are the ones my clients end up talking about a year later.
Cooking classes in Italy: the one day my clients never stop talking about
Five families, five regions of Italy, and one line I keep hearing: the cooking class was our favorite part of the trip. Here is where the great classes actually are, what each region gives you in the kitchen, and how I choose the right teacher for the right traveller.
Europe by rail: the most scenic train routes worth building a trip around
There is a reason the best European itineraries have a train in them. From the GoldenPass Belle Epoque climbing through Swiss vineyards to the Bernina Express crossing from glaciers to Italian palm trees, the right rail route turns a travel day into the part of the trip people describe for years.
Luxury Milan travel: the Italy you haven't seen yet
A family embroidery atelier that supplies the fashion houses. A 1930s villa with a swimming pool and a winter garden. Verdi's Milan, told by a musicologist. If you think you've already done Italy, you haven't met this city yet.
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.
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.
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.
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.