stunning scenery, laid back vibes, and delicious food
We start off in Milos, known for its vibrant sailing community and otherworldly rock formations. Then head to Santorini, by far the most popular and well known island of Greece to check out it's multi-colored cliffs, famous blue and white Cycladic houses, and spectacular sunsets. End the trip in Paros, located at the heart of the Cyclades and known for its crystal water beaches, vibrant nightlife and classic architecture.
for the love of
Starting at $3,499*
Athens, Milos, Santorini, Paros
Group of 14 (max) new friends
Covid-19 vaccine is required for this trip.
Masks are required in public transportation.
All accommodation in centrally-located hotels (boutique when possible, shared twin/double room)
All ferry tickets (Athens to Milos, Milos to Santorini, Santorini to Paros)
8 breakfasts, 3 lunches, and 4 dinners at curated restaurants with drinks included
Day-trip: private sailing around Milos (lunch and drinks included)
Excursion to Sarakiniko beach
Wine tasting with snacks at an island vineyard
Evening trip to Plaka for sunset and dinner
Private sunset cruise in Santorini, including swimming in volcanic hot springs
Caldera hike with views of the entire island of Santorini
Afternoon trip to Oia
Day trip around Paros with secret beach stop
Beach club access with day beds
Trip Manager throughout
DAy by day
*Itinerary is indicative for 2022 and is subject to change
Day 1 - Athens, Milos
Arrive in Athens by 10am (though we recommend arriving a day early to get settled and check out Athens as we won't be spending any time here.) Meet up with the group in Mikrolimano, the port city known for its great selection of restaurants. Enjoy an authentic Mediterranean lunch with your new travel crew before we make our way to the Piraeus port to catch a ferry to Milos.
From there, let the island hopping begin!
Once we check-in to our hotel in Milos, you'll have free time to relax, or stroll through the cute island town.
In the evening, come back together for our welcome dinner at the island's best seafood restaurant. Bond with your new trip mates and let it all sink in...you're in F-ing Greece.
Day 2 - Milos
Start the trip off right with a day of sailing on a private boat. After breakfast, we'll head off to sail around the island of Milos while working on our tans.
Take in the blue waters of Polyegos, the red and yellow landscapes of the Sulphur Mines, and secret beaches you can only reach by boat. Expect boat jumping, snorkeling, and a delicious Greek lunch!
Return for a free evening to explore or relax - up to you!
Day 3 - Milos
After sharing a breakfast together, we'll meander our way down to Sarakiniko beach, one of the most amazing places you'll visit on this trip. Catch some rays, explore the moon-like white volcanic rocks, and swim in crystal clear turquoise waters. Then we'll head to a local vineyard for a tasting of the island's homegrown wines, before making our way back into town.
Take a couple of hours to do a bit of shopping or grab some goodies at the island's famous gelato shop.
In the afternoon, wander the streets and take in the views of hilltop village Plaka before coming together for a breathtaking view of the sunset. From there, we'll make our way over to dinner at a cozy, family run restaurant and indulge in some traditional homemade dishes.
Day 4 - Santorini
After an early breakfast at our hotel, we will hop on a high-speed ferry to Santorini, one of the most popular and iconic Greek Islands. From the port, we will head over to our hotel to check-in and drop off our bags. You'll have plenty of time to explore the vibrant island at your leisure.
We recommend visiting the famous black sand beaches to soak up some Santorini sun or make a reservation at one of Santorini's wineries!
Later afternoon, we'll make our way to Oia to meander the winding pathways and enjoy a famous Oia sunset.
The evening is yours to enjoy!
Day 5 - Santorini
Wake up early for an optional guided hike of the caldera where you can really soak in Santorini's stunning views.
The rest of the day is yours to explore and hit the beach!
In the evening, we'll be back on the water for a once-in-a-lifetime sunset cruise. We'll cruise to the volcano island to jump in thermal hot springs and cover ourselves in detoxifying volcanic mud. Sip some wine and admire the cascading cliff-side towns of Santorini as the descending sun sets off a colorful display. Trust us, you won't want to miss this!
We'll dock at Thria's old port and take the cable car up to town where you'll have the rest of the night to go out Santorini style!
Day 6 - Paros
After breakfast, we will catch a ferry ride over to the last island of our trip, Paros - one of the most up and coming Greek islands.
Here, instead of the cruise ship crows that flock to Mykonos, you'll find Parisian jetsetters, festive Greek locals, and in-the-know travelers from all over.
Upon arrival, we will check into our boutique hotel and you'll have time to settle in at your own leisure. Feel free to head to the beach or explore a bit on your own.
Once you're gotten your fill of me-time, we'll come back together for dinner at a traditional tavern that serves local Greek cuisine prepared from fresh produce harvested directly from their gardens!
LIVE IT UP
Day 7 - Paros
In the morning, we'll grab a delicious homemade breakfast before heading off for a local farming experience at one of the most beautiful properties on the island.
We'll try some of their locally grown products and wine and then head to one of our favorite beach clubs where we'll relax on our daybeds, drink cocktails, and dive into the blue waters!
In the evening you'll be free to get dinner on your own at one of Paros's many charming Greek tavernas.
Day 8 - Paros
Soak it up
Today is a day of pure rest and relaxation, our last full day in the Greek islands. Make the most of your time by spending it at one of the many magical beaches of the island and exploring the streets of the charming towns.
We will reconvene for our farewell dinner at our favorite seaside tavern.
Spend the rest of the evening rehashing your favorite memories with your new friends over drinks and a gorgeous view of the traditional fishing boats.
DINE AL FRESCO
Day 9 - Athens
Today is the final day of our trip.
We will have one last group breakfast before we say farewell.
Note: Based on trip feedback, we are not including a flight from Paros to Athens, giving travelers more flexibility in their post-trip travel plans (aka in case you want to stay in the islands a bit longer!)
Work tip: Stand up. Stretch. Go to airport. Fly to Greece. Never return.
Just for Fun
Greek sovereign land includes 6,000 islands and islets scattered in the Aegean and Ionian Seas, of which only 227 islands are inhabited.
No one in Greece can choose to not vote. Voting is required by law for every citizen who is 18 or older.
Greece enjoys on average more than 250 days of sunshine a year.
Flight from Paros to Athens will not be included. This is to give you more flexibility in your post-trip plans. Flights from Paros to Athens are very inexpensive. You can also book ferries to different islands if you wish to stay in the islands longer.
Dinners in Greece are typically much later than in the US. It is not uncommon for dinner to start between 8 and 10pm.
This trip stays at more basic hotels. While clean and centrally located, some of them are no frills. This is because we devote more of the budget to included activities and meals.
About the greek islands
Welcome to Greece! This country wears its charm on its sleeves, through its lovely colorful towns, its white-washed stone ruins and marble sculptures, its delectable cuisine and secret recipes passed down from generations, and of course, its lively culture, with festivals, music and lots of socializing!
For this trip to Greece, mix the stunning scenery, laid back vibes, and delicious food, then add lots of sunshine, sail