Forget overcrowded sunset spots, budget-breaking hotels and nightmare ferry days, there’s a better way to explore the Greek Islands than the typical tourist trail through Santorini and Mykonos. Let me tell you why a Greece sailing tour should be on your travel wishlist.
After six Greece trips to five different island groups (so far), I can confidently say that seeing the magical Mediterranean by yacht is by farrrr the most authentic, most relaxing and best value for money way to do it.
From waking up to secluded swim spots without any other humans in sight, to sipping mojitos on the catamaran net with new friends, to docking at islands you’d never even heard of but now will never forget, the Greece island hopping life is simply unbeatable. 10/10, no notes.
But if you need a little more convincing, or if you’re already on board but now have to work on getting your favourite travel buddies to join you, here are 10 reasons why a Greek sailing tour deserves the top spot on your travel bucket list for your next adventure.
Huge thanks to my friends at MedSailors for hosting me on their Greece sailing tours in 2023 and 2024. I genuinely love these trips, they’re a highlight of my time in Europe every year, and I’m stoked to share my experiences with you.
1. Minimum effort, maximum reward
You have two options:
- DIY your Greece island hopping trip and figure out ferry schedules, island transport, dinner reservations, access to the best swim spots, and what activities are actually worth it
- Or jump on a boat for a week of swimming, sailing and sunsets, where the most important decision you’ll make will be whether to have a margarita or a mojito
I know what I’m choosing!
The amount of research/planning/effort you’ll have to put in during your sailing trip really depends on the operator you choose, but using the legends at MedSailors as an example, here’s what’s sorted for you:
- Accommodation sorted for six nights
- An expert skipper who can even show you the ropes if you want to learn
- Itinerary is pre-planned and the skippers will change it up if weather conditions require
- Breakfast supplies on the boat, with food storage and kitchen facilities for you to make your own lunch and dinner (or eat dinner at port, up to you!)
- BYO drinks onto the boat so drink what you want when you want, you won’t be hit with a gut punch of a bar tab upon check out
- Tried-and-true suggestions for food, drink, activities and sightseeing at each stop from the Guest Experience Leader
Too easy, and especially helpful if it’s a part of a bigger Europe trip and you just want to enjoy some time without logistical hassle.
2. Discover places you’d never go on your own
With more than 220 inhabited islands dotted around Greece’s vast waters, it’s wild to think that most visitors only visit the big five: Santorini, Mykonos, Crete, Rhodes and Corfu.
There is so much more to Greece than the white-washed buildings and overpriced beach clubs, and even if that’s exactly what you’re after, you can find them elsewhere without the crowds.
A sailing tour lets you escape the chaos and discover islands, beaches and ports you’d never even heard of, far away from the cruise ships and package holidayers.
3. Make new friends
Booking a spot on sailing tour means you’ll have a ready-made group of travel buddies to explore with, and all it takes is one late night catamaran net deep-and-meaningful under the stars to become besties.
Many sailing trips in Greece are flotilla-style, meaning they have multiple boats following the same route, and you can mix and mingle with the other crews at swim stops and at port each afternoon/evening.
Some companies have huge flotillas of 20-40 boats (too overwhelming for me personally but could be great if you’re a social butterfly), some have smaller flotillas of 3-10 boats which makes things much more manageable without being too small and awkward. MedSailors has 3-6 boats in their flotillas.
If you’d prefer to keep your social circle to your own crew, consider something like Yacht Getaways, which lets you book a cabin on a shared boat but without any other boats coming along with you.
4. Brilliant value for money
While the upfront cost of a Greece sailing tour might seem steep, a good Greece sailing tour will actually end up being better value than if you tried to replicate it on your own.
Obviously different sailing tours vary in their pricing and inclusions, but to give you an example, with MedSailors you have the budget-friendly boats costing from €133-161 per person per night (depending on the month you choose) which covers your transport, accommodation, breakfast and practically a boat tour each day.
Additional costs include lunch and dinner (cook on the boat or eat at restaurants, up to you), any activities you choose to do at the port stops, and alcohol if you want to indulge.
If you tried to plan your own Greece trip and visit a different island every day for a week, with coastal boat trips everywhere you go, you’d absolutely spend more than this. Of course you can visit Greece on a lower budget if you’re happy with hostel dorms, sticking to free activities, and not travelling between islands, but if you want the island hopping experience, a yacht tour is probably better value than you’d expect.
5. Swimming from a boat >>> swimming from a beach
Maybe this is a controversial opinion but I cannot emphasise how much better a boat swim is compared to a beach swim.
Swimming from your yacht means no sandy toes or sore feet from rocks and pebbles, you can reach bays and coves with no land access so less people to share them with, you can hop from your bedroom to the sea in 10 seconds without paying an absolute fortune for beachfront accommodation.
On most sailing tours you’ll get at least a couple of swim stops per day, plus free time at the port stops to check out local beaches too.
6. A sailing trip for every traveller
Sailing holidays used to be exclusively for people so rich they could either drop a house deposit on a week-long private charter for their friends, or proper boaties with their own yacht to explore the Med (and who knew what they were doing), but not anymore!
These days island hopping tours are far more accessible to typical travellers like us, and depending on the tour you can book a single bed for just yourself, a double cabin for you and your partner or BTFF (best travel friend forever), or even a whole boat if you’ve got enough of a crew.
Not all tours offer solo spots unless you book a double cabin for yourself (and pay for two people), but MedSailors has yacht options with single cabins as well as bunk cabins where you’ll get paired with another solo traveller of the same gender.
7. Unpack once
Greece’s cobblestone alleyways and hilly islands are no fun when you’re wheeling a heavy suitcase or lugging a big backpack around, so having a cabin as your home while you visit a different place every day is a huuuuge weight off your shoulders (literally).
As someone who lives out of a suitcase for 9-10 months of the year and moves hotels/apartments every 2.5 days on average (🫠), having a room for an entire week and being able to unpack my bags is the greatest feeling ever.
8. Choose your own adventure
Not all sailing tours are made for the same type of traveller, and the last thing you want is to be stuck on a boat for a week if it’s absolutely not your vibe. Luckily, you’ve got lots of options!
Many of the bigger operators are party-focused, with massive group events every day and onboard bars or drinks packages (no BYO) so you’re paying a pretty penny per drink. Some party cruises are backpacker-style and budget-friendly, generally with a more ‘first time in Europe’ / gap year crowd, while some are billed as luxury festivals on the water with themed parties and much higher prices. If this is what you’re looking for, fantastic, you’re going to have an epic time.
But if that sounds like your idea of hell, or if you just want to balance the revelry with some more relaxation, there are options for you too.
One of the reasons I love Medsailors is that you can pick the pace of your own trip, there’s no pressure to stay out until 3am and there’s no pressure to wake up at 7am for an island hike either. When you book you get asked about your ideal sailing holiday style and they’ll make sure you’re matched up with like-minded travellers with the same travel style, so party animals won’t be stuck with bed-by-9pm-ers and vice versa.
If you’re looking for a Greece island hopping experience without the logistical headaches, a sailing tour is the perfect solution!
Most sailing companies operate from May to September/October, with pricing dependent on demand. Shoulder season is generally better value than July/August, and your flights and any additional accommodation will be cheaper then too.
If you have any questions about sailing in Greece then let me know in the comments, check out my full blog on planning a trip to Greece for a comprehensive how-to guide, or read about my different Greece trips here:
- What it’s like to sail the Ionian Islands
- What it’s like to sail the Saronic
- A travel guide to Skopelos
- A travel guide to Alonissos
MY GO-TO TRAVEL PLANNING RESOURCES
Flights ✈️ I use Skyscanner to find the best flights for my trip and then I’ll always book direct with the airline to protect myself from having to deal with dodgy third parties if anything goes wrong.
Trains 🚂 If I’m travelling through Europe, I try to travel by train wherever possible! For an extended trip (2+ weeks) I’ll calculate if a Eurail Pass is worth it, or I’ll book point-to-point tickets through RailEurope or the local train operator.
Accommodation 🛎️ I book almost all of my accommodation through booking.com, they have a user-friendly website + app and many of their options are free cancellation, easily cancelled with a simple click of a button.
Activities 🗽I use GetYourGuide, Klook and Viator to look for activities in the places I visit, or I just Google ‘things to do in [city]’! P.S. If you book anything on Klook you can use the promocode FINDINGALEXXKLOOK to get 10% off
Travel cards 💳 I’m a Wise gal through and through, they’ve been my chosen travel card for more than five years now. You can easily top up your card from your bank account or through Apple Pay, convert your money to local currency, and spend money with minimal fees and the best exchange rates around.
Travel insurance 🩺 I use Cover-More NZ travel insurance for my own trips, I have a comprehensive policy and I’ve only had good experiences with them. Cover-More also has an Australian company, but if you’re from elsewhere then two popular insurance options for global travellers are SafetyWing (cheaper policy, lower coverage) and World Nomads (more expensive but significantly better coverage).
Luggage 💼 I travel with Samsonite Cosmolite suitcases, one 75cm check in bag and a 55cm carry on bag, and I absolutely adore them and will never travel with anything else! They are SUPER lightweight (2.8kg and 1.9kg respectively) so I have much more space for my actual stuff.
Camera gear 📸 I use a iPhone 15 Pro Max for phone photos/videos, and my camera kit includes a Lumix S9 (incredible lightweight full-frame camera, a game changer for travel creators!) with a 20-60mm lens, a Lumix G9 with an 8-18mm and 12-60mm lens, a DJI Mini 3 Pro drone and a GoPro Hero 10. I do all my writing and editing on my ASUS Zenbook 14, it’s lightweight but powerful enough for photo editing and intense blogging sessions.
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