10 Things to know about chartering a sailing yacht for a family vacation.
Let’s start with a confession. Yes, I’ve watched every episode of Bravo’s Below Deck Sailing Yacht series where Captain Glenn and a crew of eight attractive 20-somethings wait hand and foot on affluent, and often intoxicated, passengers. What I’m about to describe is not that. Mind you, chartering a crewed sailing yacht isn’t cheap, but it is a unique way to explore the beauty of the Greek Islands.
Here are 10 things to consider before setting sail:
1. Where do you want to go?
The country of Greece has six main island groups in the seas surrounding the mainland: the North Aegean Islands, the Cyclades, the Dodecanese, the Ionian Islands, the Saronic Islands, and the Sporades. Additionally, you have the island of Crete. The Cyclades are the most well-known, thanks to the party reputation of Mykonos and over-Instagrammed blue domes of Santorini. Each group has its own character, its own challenges to reach, and its own sea conditions.
That last one — sea conditions — was my biggest concern. I’m extremely prone to seasickness. Over the years, I’ve learned to pre-medicate with a prescription, but I don’t tempt fate. In doing my research for Greece, it became clear which island group had the calmest waters during June when we planned to visit: the Ionians. Fortunately, they also has some of the most beautiful water color in the Mediterranean due to the limestone bedrock. Our charter with Anko Yachting left from Patras, a two-hour drive from Athens, so the trip could easily be done in a week.
As a side note, I was extremely relieved that we didn’t book a charter in the Cyclades. After the cruise, we flew to Santorini for two nights. There we met an American family who’d just finished a week-long catamaran cruise. They described it as “scary” and said that they spent most of their sailing time below deck because of the rough seas.
2. What kind of cruise should you book?
Unless you have extensive sailing experience, you’ll need to charter a boat with a crew. Most of the charters include just a captain, leaving the cooking to you. I wouldn’t recommend that. Our charter had both a captain and a hostess. Our hostess Alicia was absolutely amazing. Polish-born and Greek-married, she and her husband run Anko Yachting with two partners.
Alicia never stopped. In the morning, she’d walk into whatever port we were anchored in and get two fresh loaves of bread from the local bakery; sometimes it was still warm when she returned to the boat. She made coffee and prepared breakfast: fresh-cut fruits, yogurt, granola, cereals, meats, cheeses and bread. One day, she even made fresh jam from apricots in her yard. After pulling lines and helping to anchor at our first swim spot, she’d make a daily cocktail and then focus on lunch, typically at least four or five traditional Greek dishes. Lunch ended with dessert and a local liqueur. Far and away, Alicia’s food beat anything that we ate for dinner at any island restaurant! She’d also brief us at each port, suggesting walks or places to see. In between her swims, she’d also do some light housekeeping.
I can honestly say that the trip wouldn’t have been the same without Alicia. You’re on vacation! Who wants the responsibility of grocery shopping, cooking, and collecting trash on holiday?
3. Who do you want along on your trip?
Our 52-foot catamaran had room for ten passengers. Unlike a private charter where you rent the entire boat, this cruise rented by the cabin. The passenger list ended up including our family of four and three other American couples. We very much enjoyed getting to know them, and everyone on the boat got along well.
That being said, I think the most ideal way to experience this type of vacation would be with other families that you know. I think that our sons would have liked to have had friends their ages on the boat.
4. What type of boat should you charter?
You basically have two choices for sailing charters: a monohull or catamaran A monohull is typically smaller with fewer passengers, so they tend to be rented by single families. They also have much less deck space, which — given the size of the cabins — you’ll come to cherish. Catamarans are wider and offer more deck space. Monohulls tend to be better than catamarans in rough seas.
5. Who’s at the helm?
If you search online for “chartering a sailing yacht in Greece,” you’ll likely come up with a bunch of brokerage sites. These are clearinghouses that connect boats and captains with would-be customers and charge you extra for the service. I spoke with one of these brokers over the phone and found him to be really pushy.
My advice: go Greek. Look for a Greek-owned and operated company like Anko Yachting. You want to sail with people who have a vested interest in you experiencing the vacation of a lifetime. These crews also have valuable local connections at the ports. The fact that Alicia was friends with the harbormaster was the difference between getting a primo portside mooring as opposed to anchoring in the harbor on more than one occasion.
6. How important is actually sailing to you?
Remember how I mentioned that we chose the Ionian Islands because of the calm waters? Well, guess what — when you have flat seas, you don’t have wind. Duh. Not sure why that caught me by surprise, but it did. In seven days on the water, we never had enough wind to sail. That’s right, we motored the entire time.
We were initially pretty disappointed by that, but after hearing about the other family’s hair-raising (and sickening) experience in the Cyclades, we decided that it was probably for the best.
7. Do you like to swim or snorkel?
If you don’t like being in the sea, this vacation is not for you. Period. The ports are not the draw; the water is the main attraction. If you’re cruising the Ionians, you don’t need to be a particularly strong swimmer. Again, the water is calm, and you can grab a float and paddle yourself to shallow water, if need be.
The water is as crystal clear as anywhere that I’ve ever been with breathtaking hues of blue. In June, it was reasonably warm — and that’s coming from someone who doesn’t tolerate cold water at all. I was in the water several times a day. In terms of snorkeling, I’d say the sea life is average. The fish are certainly more plentiful in places like the Galapagos or Australia’s Great Barrier Reef, and they’re more colorful in the Caribbean. But you will have fish, some sea caves, and beautiful landscapes to look at.
KidTripster Tip: Ionian beaches aren’t sandy; they’re stoney. Bring water shoes or flip flops.
In terms of other water activities, we had two paddle boards on deck, and I used one at every stop. By the end of the trip, I was pretty competent standing and paddling on my board. One day, Captain Stefanos hooked a paddle board to our dinghy, and my son and I did a form a wakeboarding around the cove. That was a highlight for us both.
My son is also a pretty competent diver. He did flips off the boat and rocky outcroppings, where it was safe. He even taught Alicia some new moves.
8. Can your kids entertain themselves?
There is a lot of downtime on a sailing charter. Each day, you have several hours of motoring from one spot to another. If you have younger children who aren’t able to entertain themselves with a good book or audiobook, you may want to delay this trip until they’re older.
KidTripster Tip: Unless you’re a sailing family with a great deal of confidence. I’d hesitant bringing really young children on a sailing yacht. Kids would require constant attention to make sure they don’t go overboard.
9. Are you capable of full relaxation?
I mean this question seriously. This may have been the hardest part for me, personally. I typically have a go-and-see travel style. I don’t lounge well. But that’s exactly what I needed to do on this vacation — lounge, read, and even nap! I should say that it’s exactly the kind of vacation that my husband and younger son prefer, so they had no problem falling in line.
And while most of the ports are picturesque and have lovely walks, some shopping, and restaurants, the smaller ports are better described as fishing villages. Again, it’s all part of the Greek Island experience.
10. Should I add on other Greek destinations before or after the cruise?
I have a mixed answer to this question. Since you’ll be flying into Athens, it certainly makes sense to go see the Parthenon atop the Acropolis archaeological site. But if I’m being completely honest, my family isn’t that big on ruins, especially when it’s hot and there’s a crush of people, both certainties during the summer. And we don’t particularly enjoy museums. So after less than two hours at the Acropolis, we were good and looking ahead to our sailing voyage.
On the backside of the trip, we flew to Santorini for two nights. I’ll admit to being sucked in by those too-good-too-be-true photos on Instagram. Well, the pictures don’t lie; it is a photogenic island, but I couldn’t help but feel that Instagram has negatively impacted the island’s vibe. Most tourists that we saw were so busy getting that perfect photo that they missed actually experiencing the island itself. In fact, visitors can now hire photographers who supply long flowing gowns of blue, red and orange for the sole purpose of taking glamour shots at some of the most recognizable spots, particularly in Oía, the most stunning of the island’s towns. In addition, the island is absolutely swamped by thousands of cruise passengers nearly every day from around 8 a.m. until just after sunset. On some promenades, it’s wall-to-wall people.
If you asked my sons, they’d vote for skipping Santorini. They’re not social media influencers, photographers, wine lovers, or shoppers. Santorini is not a good beach island. The towns on the west side are up on the cliffs, and the east side is rough and windy. We did do a good 10-kilometer clifftop hike from Oía to Fira and had some delicious food, but they’d had their fill of Greek island life after the cruise. Honestly, I think Santorini is a better couples island than it is a family island — and in the shoulder seasons, not summer.
[Related: 6 Must-Dos for Families in Greece]
Bottom Line
I would honestly recommend the Anko Yachting and the Ionian Islands, especially if you were planning a trip with extended family or friends. And I would go so far as to make sure that Alicia is your hostess. Just kick back, slow down, and soak in your big Greek vacation!
