2021 dates

June 12 - june 20, 2021

3 Gal spots + 2 Guy spots left

june 26 - july 4, 2021

Independence Day trip!

Gal spots SOLD OUT + 1 Guy spot left

july 3 - july 11, 2021

Independence Day Trip!


july 24 - aug 1, 2021

july 31 - aug 8, 2021

Limited spots left!

aug 28 - sept 5, 2021

sept 4 - 12, 2021

Labor Day trip!

2 Gal spots + 4 Guy spots left

sept 11 - 19, 2021

New trip!

9 days/8 nights

from $3,499

P.S. All payments can be broken up into a $500* deposit + 3 additional installments.


2022 dates

Use code eb2022gre for $100 off 2022 trip dates!

june 11 - 19, 2022


july 9 - 17, 2022


july 30 - aug 7, 2022

aug 27 - sept 4, 2022

sept 10 - 18, 2022

9 days/8 nights

from $3,499

P.S. All payments can be broken up into a $500* deposit + 3 additional installments.

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​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 trip is all about enjoying the sun, sea, flavors, and relaxed vibes of the Greek Islands. 

For the love of

















  • 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, 4 lunches, and 4 dinners at curated restaurants with drinks included

  • Day-trip: private sailing around Milos (lunch and drinks included)

  • Excursion to Sarakiniko beach

  • Afternoon at an idyllic beach club

  • Evening trip to Plaka for sunset and dinner

  • Private sunset cruise in Santorini, including volcano hike and hot springs

  • Caldera hike with local guide

  • Afternoon trip to Oia

  • Day  trip around Paros with secret beach stop

  • Trip Manager throughout

not included

  • Flights (fly into and out of Athens Airport)

  • Airport transfers

  • Mandatory trip insurance (budget approx. $80)

  • Meals not mentioned (budget around $200)

  • Incidental Expenses

  • Optional activities

Image by Dimitris Kiriakakis

DAy by day

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're in F-ing Greece.


*Itinerary is indicative for 2021 and is subject to change

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!

IMG_0292 copy 2.jpg


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 (pictured above). Catch some rays, explore the moon-like white volcanic rocks, and swim in crystal clear turquoise waters. We will have a picnic lunch on the beach, 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.


Day 5 - Santorini
volcano hike


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!

In the evening, we'll be back on the water for a once-in-a-lifetime sunset cruise. We'll make two stops with the boat to jump in thermal hot springs and then climb to the top of a volcanic island for 360 degree views of the Greek mediterranean. 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 dinner at one of Thira's best restaurants. 



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!


Day 7 - Paros


In the morning, we'll catch a ferry for artist-haven Antiparos, which is famous for the many movie stars who have houses here, as well as its beautiful town and impressive cave.


First we'll visit the 45-million year-old cave and then head to the town for some free time to explore, grab lunch and do a bit of shopping.


In the afternoon, we'll head back to Paros and drive to a secret beach where you can wade through the crystal clear waters, hike around a natural reserve, or just chill out at the beach bar!

In the evening you'll be free to get dinner on your own at one of Paros's charming Greek taverns.


Day 8 -  Paros
beach bum


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, exploring the streets of the charming towns, or renting an ATV for some off-road adventures. 

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.


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.

Trip notes

  • 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. 

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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