Sample group trips
Greek Islands Tall Ship Cruise 2026
Hidden Gems of the Greek Islands
Cruise dates: September 5 – 12, 2026 | 7 Nights
Pricing: from $2,600 per person, double occupancy
Trade big-ship crowds for white sails and island air. For one unforgettable week hopping Greek Islands, you will hop between quiet coves, storybook harbors, and seaside towns that feel like they were made for wandering. All of it on Star Flyer, a classic four-masted tall ship that carries you from Athens into the Sporades and back again, with time to breathe, swim, and explore at your own pace.
Built for Bliss: Why It Works
⚓ Big sails, small crowds. Star Flyer slips into little harbors the big ships skip, so you get secret beaches and quiet lanes instead of lines and loudspeakers.
⚓Greek Islands hopping that actually feels like a vacation. Swim, stroll, sip something cold, watch the sails fill, repeat. The rhythm is effortless.
⚓ Postcard towns, zero pretense. Skiathos, Skopelos, Poros, Myrina. White lanes, blue water, pine scent in the air, and cafés that welcome you like a local.
⚓ Sea days you will want. Deck loungers, a dip in the pool, breeze in your hair, and that moment when the crew hoists the canvas and everyone smiles at once.
⚓ Perfect host energy. Max keeps it friendly and easy. She knows when to plan, when to pivot, and how to turn a group of strangers into shipmates.
⚓ Just the right size. The ship feels like a private yacht with room to breathe, chat, and find your favorite spot to watch the sunset.
⚓ Pure Aegean magic. Clear water, coves you can only reach by boat, and starry nights that make you forget what time it is.
Itinerary
Piraeus (Athens) | Dikili, Turkey | Myrina, Limnos | Skiathos | Skopelos | Poros | Piraeus (Athens)
Day 1 – Sat, Sept 5 · Piraeus (Athens)
Embark in Athens’ historic port. Settle in, explore the decks, and watch the city lights fade as sails fill and you head into the Aegean.
Day 2 · At Sea
Ease into the rhythm onboard. Find your favorite deck chair, cool off in the pool, or try a gentle climb on the ship’s rigging with the crew’s guidance.
Day 3 · Dikili, Turkey
A quiet harbor town and gateway to ancient Pergamon. Think hilltop views, ages-old stones, and a calm waterfront lined with cafés.
Day 4 · Myrina, Limnos
Volcanic soils, fine local wines, and a medieval castle above town. Myrina’s promenade and sandy bays make it perfect for a swim and a slow evening stroll.
Day 5 · Skiathos
The Sporades at their sunniest. White beaches, boat-only coves, and a lively old town with narrow lanes and sea views at every turn.
Day 6 · Skopelos
All pine forests, whitewashed chapels, and glassy blue water. Film buffs know it from “Mamma Mia,” sailors love it for the bays and the bakery smells drifting through town.
Day 7 · Poros
Near-perfect island for a final day ashore. Stroll the waterfront, climb to the clock tower for views, or linger over a long lunch by the sea.
Day 8 · Sat, Sept 12 · Piraeus (Athens)
Return to Athens and disembark with sun-soaked photos and a phone full of new contacts from the deck.
Highlights Along the Way
Greek Islands Tall Ship Cruise
Skiathos
A classic island mood, dialed up. Bright harborside cafés spill onto the quay, cobbled backstreets climb to whitewashed viewpoints, and beaches shimmer from turquoise to deep cobalt. Hop a small boat to Lalaria or Castro for sea arches, pale pebbles, and water so clear it looks unreal. Finish with a lazy gelato and golden-hour stroll along the marina, pure summer.
Skopelos
Quieter than its famous neighbors, and better for it. Wander Skopelos Town’s lanes where bougainvillea drapes over balconies and tiny Byzantine chapels appear around corners. Then slip into pine-framed bays like Panormos or Kastani for that “Aegean postcard” swim — glassy water, soft sand, and the scent of pine in the breeze. Evenings are for waterfront tavernas and slow sunsets.
Myrina, Limnos
A lived-in Greek town with an easy, genuine pace. Climb to the hilltop castle for panoramic views over twin bays and terracotta roofs, then wander down to cafés where locals linger over coffee. Volcanic soils shape the island’s character, and its wines, so a tasting is well worth your time. Beaches here are wide and welcoming, perfect for a mid-day dip before a seaside lunch.
Poros
Close to the Peloponnese yet wonderfully its own. Poros is all soft light, pine-green hills, and a curved shoreline dotted with bobbing boats. Browse the marina’s little shops, then climb to the clock tower for a sweeping panorama of the channel. Cap it off with something cold at a waterside taverna, watching the yachts glide by as the sky turns peach and pink.
Why Travel with Max
Max keeps the trip easy and social. She sets a welcoming tone from day one, helps the group find great little places ashore, and reads the room so plans never feel forced. Expect thoughtful check-ins, shared sunset meetups on deck, and the kind of small touches that turn a fun week into a trip you talk about for years.
Reserve Your Cabin
September 5 to 12, 2026. Join Max for 7 nights exploring the hidden gems of the Greek islands aboard Star Flyer, a majestic tall ship made for sailing these waters.
$2,600 per person, double occupancy. Space is limited.
Complete the form below to secure your place.
We will confirm your details within 24 hours.
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About the Ship
Star Flyer is a true sailing ship with polished teak, tall masts, and a friendly crew that loves to be under canvas. Cabins are smartly designed and air-conditioned, public spaces are relaxed, and the top deck is where you will probably spend most of your time. It feels more like a private yacht than a cruise ship, which is exactly what you want in the Greek islands. (Capacity about 166 guests; four masts; classic clipper style.)
Catch the Olympic Spirit in Italy 2026
This trip is no longer accepting new bookings
Italy Ski Trip 2026
Catch the Olympic Spirit
February 14–21, 2026 | $2,800 per person, double occupancy
Bring your ski legs and your best Olympic cheer because this is not your average winter getaway. Join Max for the Italy Ski Trip 2026, a week of snow, laughter, and pure Dolomite magic. We’ll be calling the family-owned Hotel Post in San Candido home, a picture-perfect alpine village where cobblestones, cappuccinos, and mountain views collide. By day, you can glide through the Dolomiti Superski slopes or sip spritzes in the sun, and by night, we’ll gather over cozy dinners that taste like Italy itself. And just when you think it can’t get any better, remember we’re only 40 minutes from Cortina d’Ampezzo, the beating heart of the 2026 Winter Olympics. Seven nights of skiing, eating, cheering, and celebrating life the Italian way — it’s basically the gold medal of vacations.
Your Home for the Week: Hotel Post
We’ll spend 7 nights at the beautiful, family-owned Hotel Post, where tradition meets comfort in the heart of San Candido. This is one of those places where the welcome feels personal, the details are thoughtful, and the mountain charm is real. After a day in the crisp Dolomite air, you’ll return to warmth, laughter, and a hotel that feels like it was built just for skiers like us.
And because no Italian escape would be complete without food, your breakfast and dinner are included daily. Think mornings that begin with rich coffee and flaky pastries, and evenings with hearty alpine meals that set the tone for stories, wine, and maybe a little laughter around the table with the group.
Hotel Post Highlights
Daily breakfast and dinner included: hearty alpine mornings and relaxed Italian evenings.
Central location: steps from ski lifts in San Candido.
Perfect balance: close to the Olympic buzz in Cortina, yet peaceful enough to soak in village life.
Why San Candido?
San Candido (also known as Innichen) is the perfect mix of postcard-pretty village and ski town energy. Nestled in the Dolomites UNESCO World Heritage site, it offers stunning views, easy access to lifts, and a welcoming vibe that’s less crowded than the big-name resorts.
And here’s the kicker: you’re only 40 minutes from Cortina, the glamorous alpine hub where Olympic events will unfold. That means you get the best of both worlds — the peaceful rhythm of a traditional village, with the Olympic spirit buzzing just next door.
Ski, Cheer, Repeat
This week is about more than skiing, it’s about catching the Olympic Spirit. Imagine waking up to snow-dusted rooftops, skiing the Dolomite slopes, and knowing the world’s best athletes are competing just a short drive away. Whether you’re carving turns on the local mountains or soaking up the festive atmosphere, every day will feel like you’re part of something bigger.
Travel dates:
February 14–21, 2026
Included:
- 7 nights at the family-owned Hotel Post in San Candido
- Daily breakfast and dinner
- Prime location: steps from ski lifts, 40 minutes from Cortina d’Ampezzo
Why Join Max?
Because traveling with Max is like going with your best friend who just happens to know the ropes. She brings the energy, the fun, and the little touches that make the trip more than a vacation, it’s an adventure you’ll remember forever.
Ready to Go?
This is your chance to celebrate winter, skiing, and the Milano-Cortina 2026 Olympics in unforgettable style. Join Max in San Candido and get swept up in the magic of Italy in winter.
Reserve your spot today and get ready to catch the Olympic Spirit.