September 2024

Travsessed is

heading to Greece!

  • Beach Hopping
  • Wine & Food
  • Sunsets

About Travsessed Greece

We went to Greece a few years ago and fell in love…which is easy to do because Greece is amazing!! 

This trip is all about:
Sunsets, Wine, Beach Hopping, Sailing, Cliff jumping/swimming, Culture, Food & Fun Adventures!!

We will be visiting: 

  • Athens: Because of food and culture.
  • Milos: Because Milos is the go to beach destination for those IN THE KNOW!! It’s our absolute favorite island, there are far less crowds and tourists & it’s known for its food, local vibes and BEAUTIFUL crystal blue water!!
  • Santorini: Because there is nowhere in the world like Santorini.

Mix the stunning scenery, laid back vibes, and delicious food/wine, then add lots of sunshine, sailboats, sunsets, island adventures & like minded – FUN new travel friends and you have the best trip ever!!

This is so much more than a trip to Greece. This is about creating memories & new friendships that will last a lifetime!!

Let us take care of you!!

Get yourself to Greece & we’ve got the rest covered!!!

We’ve already done all the researching, planning, organizing & heavy lifting for you.

All you have to do is show up with an open mind…a positive attitude & be ready to RELAX, EXPLORE & HAVE FUN with your new travel buddies!!! 

So much thought, love, and detail went into the creation of this trip & we hope that you are just as obsessed & excited as we are!!!!

We’ve personally curated a unique & Special itinerary that you won’t find anywhere else

trip highlights:

  • Sunset cruises
  • Incredible food
  • Lots of wine
  • Cliff jumping 
  • Sailing adventure
  • Sunset picnics
  • Local wine tour
  • Beautiful beaches
  • Off the beaten path Island adventures
  • Local Food tour
  • Volcano hot springs
  • Private and Exclusive EXPERIENCES

As with all Travsessed Adventure Trips, we partner with locally owned companies and work very closely with local guides for a true insider experience & to help support the local communities & people of the places that we travel to. 

Trip Details:

  • Travsessed Greece is an 11 day trip
  • Dates:
    • GROUP ONE: 9/5-9/15
    • GROUP TWO: 9/19-9/29
  • Do not book any flights until you’ve received the green light from us

Total Cost:


**shared accommodations Per Person

**Not including Processing Fees

**If you are interested in upgrading to a private room, please email [email protected] and we will email you a quote if a private room is available. Private rooms are not guaranteed.

What’s Included:

  • All Accommodations
  • All airport transfers
  • All English speaking guides
  • Flight from Athens to Milos
  • Ferry from Milos to Santorini
  • Private Sunset picnic dinner
  • Private sailing experience in Milos
  • Private sunset catamaran experience in Santorini
  • Private local wine tour
  • Private local food tour
  • ATV’s for island hopping
  • 6 Course foodie & wine Rooftop dinner
  • 10 Breakfasts
  • 5 Lunches
  • 7 Dinners
  • A lot of wine LOL!!
  • ALL TIPS. We will tip generously on your behalf for all guides, drivers, hotell staff, boat crew & dining experiences so you don’t have to stress or think about it on your vacation

What’s Not Included:

  • Airfare to Athens, Greece (Start of Trip Location)
  • Mandatory travel insurance
  • Other activities, meals or alcohol not listed in the itinerary
  • Personal spending money
  • International drivers license (required to drive ATV’s)

Trip Itinerary:

Subject to change…but this is the overall vibe.

We will provide a full trip itinerary, packing list, restaurant guide & more detailed trip info, once you have signed up.

Day 1


You’ll get picked up from the airport and driven to your hotel. You’ll have time to shower, nap & get settled in. We will all meet in the evening to kick off an incredible trip with a 6 course foodie & wine welcome dinner on a rooftop overlooking the city.

Meals Included: Welcome Dinner & Drinks

Day 2



The morning and afternoon is yours to enjoy & explore Athens. We will all meet up in the afternoon to explore the hidden foodie gems of Athens!! We will eat our way through this delicious city with our local guides. We will taste all the amazing food + we will learn about the history, local culture & way of living.

Meals Included: Breakfast & Food Tour

Day 3


We will depart from the Athens airport in the morning & fly the quick 40 minutes to Milos. Milos is an incredibly beautiful/foodie island. The afternoon is yours to relax and enjoy the island. We willl meet up in the evening for a beautiful sunset & dinner.

Meals included: breakfast, Dinner

Day 4


Milos is known for it’s vibrant sailing community. We will have a beautiful sailboat + full crew ALL TO OURSELVES today! 

This was one of our favorite travel experiences ever! We will sail around the beautiful Cyclades Islands, exploring hidden gems that you can only get to by boat. We will snorkel, swim, eat, drink & watch the incredible sunset!!

Meals: Breakfast, Lunch, Dinner & Drinks on Boat

Day 5


The best way to explore & experience all this island has to offer is to rent ATV’s. Today we will hop on our ATV’s and go to all of the most beautiful beaches around the island! 

We will climb down to secret coves, swim in beautiful crystal blue waters & cliff jump off moon-like white volcanic rocks. 

We will have lunch at one of our favorite spots and then the evening is yours to enjoy at your own leisure.

Meals Included: Breakfast & Lunch

Day 6


Today we will say goodbye to the beautiful Milos & take the ferry over to Santorini. Once we arrive, We will Settle into our hotel and have some free time. 

In the evening we will meet for an EPIC- Exclusive, Sunset dinner picnic overlooking the amazing caldera!
We will eat delicious food, drink local wine & have the famous Santorini Sunset all to ourselves!! This will be one of those epic moments that you will never forget!!

Meals: Breakfast, Sunset Dinner Picnic with Wine

Day 7


Most tourists don’t even leave the Caldera in Santorini…but not us, there is so much to experience on this unique & gorgeous island!! 

We are having another ATV adventure day to explore.

We will take you to our favorite beaches, local towns & the best place for lunch on the entire island. We will end the day way our favorite beach spot where we will eat tacos, relax, and watch the sunset.

meals: Breakfast, Lunch, Light Dinner

Day 8


Today we will hike along the iconic caldera, from Fira to Oia (6.5 miles). This is an amazing walk/hike that gets us away from the crowds and gives you the best views and picture opportunities. 

We will end our hike by cliff jumping into the crystal blue waters & enjoying a delicious lunch at one of our fave local spots down by the water! 

The evening is yours to enjoy.

Meals: Breakfast, Lunch

Day 9


Enjoy a free morning to sleep in and explore on your own….

We will meet in the afternoon for the most amazing & fun wine tour. We will visit multiple wineries on the island & our local guide will teach us all about Greek wines & the very unique way they grow grapes in Santorini. 

We will drink a lot of wine, eat an amazing dinner, and watch the sunset at a beautiful winery overlooking the caldera.

Meals: Breakfast, Wine Tour, Dinner

Day 10


The morning is yours to relax and chill. In the afternoon we will be back on the water for a once in a lifetime sunset cruise…because Greece! 

We will have a private catamaran & crew that will take us all around the island. We will swim in volcanic hot springs and visit other cool spots that you can only get to by boat. 

We will eat amazing food, sip wine and end the night by watching the iconic Greece sunset from our private boat, celebrating an incredible trip with all of our new travel friends.

Day 11

Today we say goodbye “for now” and either head back to Athens or continue your Greek vacay!!


While we can’t guarantee private rooms, you can reach out to us directly to check availability.

Flight from Santorini back to Athens will not be included. This is to give you more flexibility in your post-trip plans. Flights from Santorini are very inexpensive. You can also book ferries to different islands if you wish to stay in the islands longer.

We are all about location with our hotel choices. 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 & planes that can sometimes experience delays.

All activities are weather dependent


Do not book your flight until we’ve given you the green light.

All International flights will arrive and depart from Athens International Airport (ATH).


Our trip will end on the island of Santorini…You can either fly back to Athens to catch your international flight home or continue exploring the Greek islands.


Greece consists of 6,000 islands. 227 of them are inhabited.

Greece is one of the sunniest places in the world averaging about 250 days a year of sun

Local Currency


National Language


Time Zone

Eastern European Summer Time
7 Hours ahead of EST


The weather in Greece in September is fantastic!!!
Highs: 82 Degrees
Lows: 68 Degrees

Why Travel With Travsessed

We’re Kim & Erran, a healthcare traveling couple & the founders of Travsessed.

We are travelers who are obsessed with travel!! We love traveling and researching & planning and we put our heart, souls and so much love and thought into every single detail and trip that we plan!!

We create one of a kind, small group, boutique travel experiences for healthcare workers (and their friends or partners)

We plan & organize all the things…so all you have to do is show up & have a good freakin time!!

We work closely with small local businesses, friends, and local guides to create a unique, one of a kind experience that you will not find anywhere else!!

We always get off the beaten path & dive into the local culture, food, people & experiences!

We go beyond the surface & way past the “highlights” to create experiences that will give you a deeper perspective, understanding & appreciation for the places you visit.

And we have a lot of fun along the way!!!

What Other Travelers Are Saying:

My trip to Peru with Kim & Erran was packed full of the perfect amount of everything my soul needed from, adventure to relaxation to communing with some of the coolest people I’ve ever met. Truly had the time of my life and look forward to embarking on another Travsessed adventure soon! Keep on doing what your doing. Travel changes a person to their core for the better and I really believe you two are fulfilling your life’s purpose.

Lori J

Just got back from the most amazing trip to Machu Picchu in Peru with Travessesd!! It was truly an adventure trip of a lifetime! I can’t say enough good things about Kim and Erran and the whole Travessed experience- from start to finish it was perfectly planned and executed with a focus on excellent, beautiful, epic adventures where we were immersed in the local culture of Peru

Linda R

Travsessed Peru was the most well-thought-out, adventurous, incredible trip! Kim and Erran do such an amazing job at creating a culturally immersive and unique journey! The group was an instant family that motivated and inspired each other the whole way! I couldn’t have planned a better trip to Peru, and I wouldn’t trade the memories, tears, laughter and love for anything!

Emily K

Kim and Erran put on the best trip imaginable!! Not only did I get to experience a new country for the first time but I got to meet some of the most amazing people to do it with ♥️ I love that we didn’t just do “touristy” things but got to experience a lot of the culture. I would do it again in a heartbeat. 100/100

Ashley R

Spots are Extremely limited!!

Join Us In Greece: Save Your Spot Now


Don’t worry about that because 90% of our groups are ALL solo travelers too!!

You’ll meet so many cool, like minded friends on this adventure!! 

We have so many lasting friendships created from these trips.

 By the end of the trip, we will ALL be one big happy family!!! 

The adopted Travsessed motto has become: “Come as Strangers, Leave as Family”

If you are coming with a friend or partner you will be rooming with them, If you’re traveling solo, No worries, so are most people who come on Travsessed adventure Trips, so you’ll be in good company.

We’ll do our best to pair you with someone we think you’ll click with based on your intake forms.

Anyone with an open mind & a positive attitude are welcome on our trips! Our trips tend to be 90% healthcare workers just because that is who we are and the community that we talk to.

But if you have a friend or partner that doesn’t work in healthcare that wants to join…they are more than welcome:)!!!

We say that it’s always the PEOPLE that make the experiences so memorable & FUN!!

Our trips attract really fun, high vibe, open minded, down for anything kind of humans!!! 

We do almost everything together on our trips!! We get very close very fast! 🙂

This is your trip and we want you to make it exactly what you want! There’s a lot to see and experience, so we’ve tried to design an itinerary that’s a balance of adventure with some down time sprinkled in.

We always leave room for some FREE TIME, but we’re together 95% of the time!!!

That being said our trips are pretty go go go & if you need to rest or recharge you are always free to opt out of an activity for some alone time!!

We totally understand that and you are in good company because the majority of people on our trips….come alone & they don’ t know anyone when they arrive.

We create a very friendly & inclusive vibe from the beginning and we all become fast friends.

We do all the planning and organizing for you!! We plan trips based on our own experience in that destination while also using all the tips and insider knowledge from local guides and friends that we meet along the way!! 

All you have to do is get yourself there….we take care of the rest!! 

I’m nervous to book because I have never traveled outside the country before, there are lots of things that I do not know how to do, and what if I make a mistake.

When we say we have you covered, we have you covered.  We provide a FB Group, WhatsApp Group Chat, direct access to us via email, so we can walk you through anything you might not know how to do.

We also send you a packing list, places and restaurants to check out during your downtime,  how to get local currency, tips, local facts to familiarize yourself with the local area, visa information, customs information, and will provide video details of airports, and will have a driver there that we are in constant contact with and have worked with before to pick you up from the airport and bring you to the hotel where we will be there to greet you and get you checked into your hotel room.

In other words, We got you!!! 

Yes, it is mandatory for all guests on Travsessed Adventures to have personal travel insurance for the duration of the trip. We recommend you book your travel insurance as soon as you make your trip deposit to protect your investment. (We will send more info about insurance upon booking)

All payments are non-refundable. If the trip must be postponed or cancelled due to events beyond our control, you will be offered the choice between a full refund and applying your payments to a future trip.

The reason payments are non-refundable is that we start incurring costs from the moment someone signs up — from credit card fees to our local vendors & organizers coordinating and booking everything on the ground for our group and beyond.

Thank you so much for your understanding and respect of our need to enforce this policy strictly. 
We are excited to share so many incredible adventures with you.

If you have any questions please email us at [email protected]