2023 Greece Sailing Trip

8 Days

Greece Sailing Trip for Teachers

Mykonos. Santorini. Naxos. These are just a few of the most beautiful islands in the Aegean Sea.

Mykonos island from Greece Sailing Trip for Traveling Teachers image 1. Beautiful, sunwashed buildings with blue roofs looking over the Aegean Sea.

Teachers have been asking for a Greece sailing trip for a long time, and we’re finally doing it!

Sailing is quite addictive. Anyone that’s been on one of our trips can tell you it’s become their new, favorite way to travel!

You can learn how to sail on this yacht trip, too.

Our skipper has over 15 years of experience in sailing instruction, and his experience with sailing itself far surpasses that.

The thing I love most about our skipper, is that he’s also a teacher. More specifically, he’s a member of our global Traveling Teachers community. Because of his connections and relationships with the sailing community across Europe, we’re getting an AMAZING deal on the boat rental of this trip.

Sailing trips throughout the Southern Cyclades in Greece often sell for $2,000-$3,000 per person, per week – so we’re getting a really great deal. 

Please note that this package does not include airfare between your point of origin and Greece.

If coming directly from the United States for your sailing trip, we recommend booking flights in and out of Athens, then commuting to the marina from there. More information will be given to travelers who register for the trip.

Available Dates and Spots

As of January 18th, 2023, these are the available weeks and spots:

  • June 3rd-10th, 2022 (7 spots available)
  • June 10th-17th, 2022 (7 spots available)
  • June 17th-24th, 2022 (7 spots available)

What’s Included?

The following is included in this sailing trip package:

  • 24/7 access to an on-board Trip Leader (another Traveling Teacher!)
  • Air conditioning when at port (by popular request!)
  • Electricity when available at port
  • Sailing instruction
  • Yacht charter fee
  • Transit log & end-of-trip cleaning
  • Dinghy outboard engine
  • High-speed WiFi
  • Tourism
  • Cooking gas
  • Individual bedding (note that you’ll be sharing a small-sized bed unless you rent out an entire cabin)
  • Damage insurance
  • Marina fees
  • Engine fuel
  • Continental breakfasts
  • Light lunches
  • Dinners when anchored at sea
  • Access to the full kitchen
  • Towel rental

What’s NOT Included?

  • Transportation to/from the airport, before and after the sailing trip
  • Dinners and drinks in towns

What to Expect

While every trip and group is different, we understand that knowing a bit about what to expect can reduce fear of the unknown.

So if you’re wondering what the day-to-day of a sailing trip with Traveling Teachers looks like, don’t miss this section!

What’s Sailing Like?

If you’re brand new to sailing, then this is the perfect first trip for you!

On a sailing trip, the skipper (along with the help of the crew) takes us along on the boat by working with the wind.

It’s a unique travel experience, because each traveler becomes a member of the crew.

You’ll learn how to sail from a professional sailing instructor with decades of experience, across the beautiful Aegean Sea.

How involved you want to be after learning is entirely up to you, though the skipper might ask for your help when anchoring or docking. 

When we’re staying out at sea (which isn’t often), we drop the anchor.

When we’re staying at a marina or at a port in town, we dock the boat.

Each of these processes takes about 15 minutes.

Some travelers choose to be at the helm for most of the trip, while others prefer to relax and sunbathe after learning the basics. You get to choose how to spend most of your time!

Flexibility with any sailing itinerary is a must, and this trip is no exception. We literally travel on the wind!

Changes might be made to the iinerary due to weather, high waves, or anything else that would impact the crew’s safety.

This route has affectionately been dubbed “glamping at sea,” and we think that’s the perfect description for it.

What Are Accommodations Like?

This route has affectionately been dubbed “glamping at sea,” and we think that’s the perfect description for it.

The type of boat we rent for that summer makes a big difference as far as the layout and configuration.

For the summer of 2023, we’re looking at a boat with 4 berths (cabins).

Individual travelers share the bed with other travelers, so we recommend booking with a friend or a loved one!

These cabins are pretty small; they’re usually about the size of a tent, albeit a bit taller.

Each cabin has its own, en-suite bathroom – so you’ll only share with your roomie! 

And if you book the whole cabin to yourself, you’ll get your own bathroom.

If you prefer to book an entire cabin to yourself, you can select that option at the time of booking, should it still be available.

I cannot stress enough what a deal this is!

If you’ve ever wanted to visit Greece, now is the time to book.

Cost & Payment Plans

You can pay for your trip in full using this booking page.

As of today, the cost per person, per trip is $1,400.

You also have the option of making payments.*

  • The first 30% of the trip is due at the time of booking
  • The next 30% of the total is due before Monday, January 30th
  • The total must be paid by Friday, March 24th

*You can setup a payment plan with and through PayPal.

Refund and Trip Cancellation Policy

Refunds will not be issued for trip payments or deposits.

We understand that things happen, and for this reason, we recommend and require that every traveler have personal travel insurance for the duration of their trip.

Your insurance policy should include travel to and from the marina in Greece, and we recommend insurance that includes your flight(s).

Should you need to change your plans, we can transfer your payments to another traveler if the request is made before May 31st, 2023. This is because we need to ensure that the Greek port authorities have accurate information on every traveler joining us.

You can read the full policy on trip booking terms, cancellations and refunds here at this link.

Covid-19 Restrictions and Entry Requirements

Entry requirements for American citizens into the country of Greece have changed several times throughout the pandemic.

Please bookmark the page at this link to track requirements.

I will send major updates as I receive them to travelers via email, and I’ll keep all of you updated here in the Traveling Teachers Community Facebook Group.


This is more than just a general trip to Greece.

This is your opportunity to truly explore and experience the parts of Greece most other people don’t get to see.

Yes, we’ll visit Mykonos and Santorini – because they’re beautiful and absolutely worth the visit.

But there are so many other, stunning islands and places worth visiting that get missed by most travelers.

That won’t be you, though.

Explore it on a sailing trip and see the lesser-known gems that the Southern Cyclades has to offer.

Sample Itinerary

Day 1 :

Karystos, Euboea (Evia)

Sail north from Lavrion to the second-largest Greek island - Euboea. On the southern coast of the island, nestled in a wide and well-protected bay, you will find the coastal town of Karystos. Visiting the area around the town, you will find medieval castles, ancient landmarks, miles of beautiful beaches and traditional tavernas – everything you'll need to start your Greek adventure.

Day 2 :

Start your tour of the Cyclades by visiting the northernmost island in the cluster, Andros.

The island is full of lush vegetation and a perfect place to kick back and enjoy the pristine water and breathtaking sandy beaches like Zorkos beach, Achla and Syneti beach.

If you are looking for a bit of culture, visit the town of Andros and the Museum of Modern Art, the Maritime Museum or the Open Andros Theatre.

Day 3 :

Leaving Andros, set your course south and sail to the island of Tinos.

On the southern shore of the island, you will find the coastal town of Tinos and a small marina offering protection from the northern winds.

The most interesting attraction in Tinos is the Monastery of Virgin Mary Evangelistria, a church which attracts pilgrims from all of Greece.

Beaches on the southern side of the island are more tourism-orientated with plenty of bars and restaurants, while those looking for more privacy should explore the secluded coves on the northern coast.

Day 4 :

The famous island of Mykonos is your next stop, located a short sail south from the island of Tinos.

On the western coast of the island, you will find the town of Mykonos, one of the most popular summer destinations in Greece, known for its vibrant nightlife. You will find the most remarkable and popular beaches like Super Paradise, Paradise, Platis Gialos on the southern side of Mykonos island.

As the island is a popular tourist and sailing destination, there are several marinas to choose from, including the Mykonos Marina, Tourlos Marina and Santa Marina Resort, all located near the town of Mykonos.

Day 5 :

Continuing your sailing vacation south, the next stop on your route is the island of Naxos.

The island is most famous for its long and sandy beaches, most notably the Plaka beach and the Agios Prokopios beach, located south of the capital town of Naxos.

The sea around Naxos is rich in reefs and wrecks, making diving one of the more popular activities on the island with several local diving centres organizing daily dives. In the town of Naxos, you will find a medium-sized marina offering 70 berths for vessels up to 20 m in length.

Day 6 :

The last stop on this route is probably the most famous and recognizable of all Greek islands - Santorini. Colourful architecture, combined with the spectacular blue sea and the volcanic composition of the island, create a unique setting that will sweep you away.

The island is considered to be one of the most romantic destinations in Greece and is perfect for couples and groups of friends. Strolling the narrow streets of the largest town, Thira, you will be greeted with spectacular views of the surrounding area, topped off by majestic sunsets. Santorini is a popular tourist destination so expect some traffic and crowds when visiting here.

For mooring, sail south to Vlychada Marina, a small harbour located in the city of Vlychada, offering protection from the northern winds.

Day 7 :

Most of the day will be spent sailing back north to your starting location, the town of Lavrion. Depending on your remaining time, take a stroll through the Old town of Lavrion and familiarize yourself with the rich history of this port town.

If you wish to take a breather and relax, the town is full of recently-opened taverns and restaurants, perfect for sampling the local seafood and traditional Greek recipes.

Day 8 :

Pack up, clean the yacht, and depart for home.


  • 24/7 access to an on-board Trip Leader (another Traveling Teacher!)
  • Air conditioning when at port (by popular request!)
  • Electricity when available at port
  • Sailing instruction
  • Yacht charter fee
  • Transit log & end-of-trip cleaning
  • Dinghy outboard engine
  • High-speed WiFi
  • Croatian tourist tax
  • Cooking gas
  • Individual bedding (note that you'll be sharing a small-sized bed unless you rent out an entire cabin)
  • Damage insurance
  • Marina fees
  • Engine fuel
  • Continental breakfasts
  • Light lunches
  • Dinners when anchored at sea
  • Access to the full kitchen
  • Towel rental


  • Airfare
  • Ground transportation
  • Travel insurance
  • Trip Protection/Coverage
  • Medical insurance
  • Meals and drinks when in town

Frequently Asked Questions

I've never been on a yacht before, and I've never done any sailing - can I still come?

Of course you can! And this is a great route for first-time sailors. The Adriatic Sea is very calm and safe. You’ll learn the basics of sailing and safety at sea within the first couple of days.

Is ground transportation included?

No, transportation to and from the yacht is not included. We can arrange said transportation for you at an additional fee. See the options at checkout.

Is airfare included?

No, flights and airfare are not included for this trip.

Can I bring my partner/spouse/friend/family?

Absolutely! This is a trip for Traveling Teachers and their loved ones. If you’d like to request an entire cabin instead of one shared spot, we recommend booking as soon as possible, since there are only 3 whole cabins available for booking on this trip.

Am I able to make payments for my trip?

You can! Note that 30% of the total is due at the time of booking.

Here are the available payment plans, factoring in 30% of the deposit already being paid, as well as the $100 administrative fee for payment plan setup:

6 Monthly Payments: $162.50
5 Monthly Payments: $195
4 Monthly Payments: $243.75
3 Monthly Payments: $325
2 Monthly Payments: $487.50

Can I share a room with another teacher who's coming?

Of course! If you’d like to request a particular roommate, please note their name when you fill out the Traveler Information Form. You’ll receive the link to this form after you book.

Are payments refundable?

Unfortunately, payments for sailing trips are non-refundable.

If you’d like for someone else to take your place, please inform us of this change before May 31st, 2023.

Will we spend nights in a hotel?

There are no hostel stays included in this trip. The sailing yacht has cabins, where we sleep throughout the week.

What do I need to pack?

Participants will receive a packing list soon after booking.

Important note: there isn’t storage space for large, hard-sided suitcases. A soft duffel bag or backpack would be ideal.

What will I have to do on the yacht?

Entering and exiting the yacht will often require walking across a gangplank. It looks much scarier than it us! You’ll get used to it after a few times. 😉

Leaving or entering a mooring (marina, at anchor or attached to a buoy) requires some people to throw/catch a rope, hook the buoy or drop/raise the anchor. The rest of the time, you choose, you can do as much or as little as you wish.

Our skipper can actually sail the yacht single handed!

How much money will I need to bring?

You’ll want to bring money for when we dock and go out. We often get wine, beer or other snacks and bring them back to the boat! And of course, you’ll need to bring money if you plan to buy souvenirs or post cards.

Should I bring cash, a debit card, or a credit card?

Greece uses the Euro as currency. While most places accept debit and credit cards, you’ll want to have some cash on hand for smaller shops and restuarants. We recommend waiting until you are in the EU to exchange for euros, as it can be quite pricey to do so while still in the U.S.

We also recommend downloading the Revolut app to make sending and receiving money easier, should you choose to split a bill or share expenses with other travelers.

Before you leave the U.S., make sure your debit/credit card is activated to be used in Europe.

I can't swim, will I be safe?

Paul has hosted a number of non-swimmers over the years, and he hasn’t lost one yet!

The yacht will not be heeling over at a crazy angle, and it won’t capsize.

Fun fact: Brittany, the founder of Traveling Teachers, doesn’t swim far out in open water!! So you’ll still have a great time if you can’t swim, or even if you don’t want to.

Will there be bedding and/or towels?

Although the cabins are shared doubles (two twin beds which are very close together), the bedding is individual.

Is there an age limit?

Not at all! Everyone is welcome, though we will respect the drinking laws and limitations of Croatia.

What if I have dietary restrictions or food allergies?

We’ve hosted mixed crews of vegan, vegetarian and meat eaters, along with a couple who only ate gluten free.

There is a central kitty (pool of money) used to purchase supplies. As a crew, we make sure that everyone is catered for when shopping.

Do keep in mind, however, that due to the very close proximity of the shared space, we will not be able to accommodate anyone with airborne food allergies.

Is travel insurance included?

No, and individual travel insurance is required to participate in all trips. We recommend policies that include flights, and making sure that it starts on your first date of travel (especially important if you’re traveling throughout Europe before/after the trip!).

Once you register, we’ll ensure you have our recommendations on the best travel insurance policies. Not all policies include marine activities, and/or medical evacuation!

What if something gets damaged? Do I have to pay?

Damage insurance is included in the price. But if you damage something of another traveler’s, we ask that you work it out with them privately.

Will I learn anything?

Our skipper, Paul, started sailing dinghies when he was 16, and yachts a year later. He has raced, cruised, and was an instructor for 15 years. He’ll teach you as much as you want to learn.

Will I be able to go ashore?

Lunchtime is usually at anchor or attached to a buoy, so you can have a swim. We will likelt have an outboard engine to fit on the dinghy, so going ashore in some places is an option. Certain places also have the option of taking a water taxi from the boat. Some nights will be spent in a marina, so you can eat in a restaurant, explore the city, or go sightseeing. See the itinerary for more details.

What about medicines?

There are pharmacies but, they may not stock the brands you are used to in the US. Please make sure that you have enough supply of any prescription or usual medicines.

Sun screen is an absolute must have!!!

What else should I know?

The Adriatic is a very clean sea.

There are a lot of ‘bottom feeders’, aquatic life which eat everything disposed into the sea.

This can be surprising to travelers when leftover food is thrown overboard! But we can assure you, it gets eaten. 🙂

As the water from the showers and sinks goes straight into the sea, it would be good not to use soaps or shampoos which are toxic for aquatic life.

You can send your enquiry via the form below.

2023 Greece Sailing Trip
From $ 1,400
/ Adult