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2023 DATES


*Trip availabilities change throughout the day and may not be accurately reflected here. To see if space is available for the date you are interested in, please click through to the booking form.

Aug 26 - Sept 3, 2023

SOLD OUT - Waitlist only

Sept 2 - 10, 2023

SOLD OUT - Waitlist only

Sept 9 - 17, 2023

SOLD OUT - Waitlist only

9 days/8 nights

starting at $3,999 USD

Payment can be broken down into a $500 deposit + 3 additional installments.


A girl jumps into the water off of a Greek island.

2024 DATES


$200 off with


May 25 - June 2, 2024

Memorial Day trip - likely to sell out

June 1 - 9, 2024

June 8 - 16, 2024

June 15 - 23, 2024


June 22 - 30, 2024

June 29 - July 7, 2024

July 4th Trip - likely to sell out

July 6 - 14, 2024


July 27 - Aug 4, 2024


Aug 3 - 11, 2024

Aug 31 - Sept 8, 2024

Labor Day trip - likely to sell out

Sept 7 - 15, 2024

9 days/8 nights

starting at $4,399 USD

Payment can be broken down into a $500 deposit + 3 additional installments.



Page Menu


​Mix stunning scenery, laid back vibes, and delicious food - then add sunshine, sailboats, and some fun-loving new friends and you have our Greek islands trip. 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, vivid nightlife and classic architecture. This is more than Greece group travel, it's all about enjoying the sun, sea, flavors, and relaxed vibes of the islands with new friends. 

For the love of

















  • All accommodations in a shared room with one other person with the option to upgrade to a private room (limited availability)

  • In-country transportation from Athens to Milos, Milos to Santorini, and 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

*All activities are weather dependent; in the unlikely event that we are unable to run an activity, we will have a suitable alternative in place.

not included

  • Flights (fly into and out of Athens Airport)

  • Airport transfers

  • Mandatory trip insurance

  • Meals not mentioned (budget around $200)

  • Incidental Expenses

more details
Homes on an island in Greece.

DAy by day

*Itinerary is indicative and is subject to change

Day by day
Day 1 - Athens, Milos

Meet your group in Athens before heading to our first island: Milos! Enjoy an authentic Mediterranean lunch with your new travel crew before we make our way 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're in F-ing Greece.

Travelers on a boat off 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!

Girls on a boat in the Greek islands.


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.     

Greek food served for breakfast.



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!

A guy on a sailboat off of Greece.


Day 5 - Santorini
Volcanic springs


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! 

Fresh fruit served on a boat near islands.


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!

A group of travelers drink cocktails as the sun sets.


Day 7 - Paros
beach club


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.

Jumping off of a white rock cliff into the ocean in Greece.


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.

Travelers eating outside in Greece.


Day 9 - Athens


Today is the final day of our trip. 


We will have one last group breakfast before we say farewell.


If you’ve got some more time to spare, well, this beautiful country has plenty more in store for you. Cruise on over to Crete and check out some more magical Mediterranean beauty.


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.



Fast facts

Just for Fun

Greek islands group travel for young professionals, young adults, and 20 somethings

Greek sovereign land includes 6,000 islands and islets scattered in the Aegean and Ionian Seas, of which only 227 islands are inhabited. 

Greek islands tours for young adults, young professionals and singles 20s

No one in Greece can choose to not vote. Voting is required by law for every citizen who is 18 or older.

Greek islands travel tours for young adults, young professionals and singles 20s

Greece enjoys on average more than 250 days of sunshine a year.

Trip notes

  • While we can’t guarantee private rooms, you should book your trip earlier if you prefer one, as they usually fill up.

  • 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. 

  • On European trips, we stay as close to historic city centers as possible. This means your accommodations will often be on the small side, quirky, and unique (we love this!).

  • This trip uses ferries that can sometimes experience delays.

  • All activities are weather dependent; in the unlikely event that we are unable to run an activity, we will have a suitable alternative in place.

  • More information regarding visa requirements and Covid restrictions can be found here.

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, sailboats, and some fun-loving new friends and you have the best vacation ever!


  • The national language is Greek

  • The national currency is Euro

  • Some restaurants in Greece will round up the bill, so you should check this before tipping. You can tip between 5% and 10%, but make sure the restaurant allows their staff to receive tips first.

  • The closest airport is Athens International Airport (ATH)

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Fly into Athens (ATH)

You'll need to be in Athens by 9am on Day 1, and with the recent amount of flight delays we recommend planning to arrive a day early just to be safe.

Fly out of Paros (PAS)

We recommend booking a roundtrip ticket from Athens and hopping on a one-way flight from Paros back to Athens.

Want to check out flights for your trip?

Feel free to also set up flight alerts to Athens so you can grab the best deal!

*FTLO is not responsible for any fees or costs related to flights. We strongly suggest that all travelers wait until they receive the official FTLO Greenlight Email to book flights. This will be sent 3-4 months prior to the start date of your trip.

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Alumni Reviews


We know how much you'll love the Greek Islands trip...
but don't take our word for it! Check out some of our alumni reviews. 


Learn More

Interested in learning more about our Greek Islands trip?

We're here to answer any and all questions you might have! Leave us your information below and we'll be in touch with you as soon as possible.

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