Home » Island Hopping Around Greece by Travelive: Your Yacht Adventure Starts Here

Island Hopping Around Greece by Travelive: Your Yacht Adventure Starts Here

by Travelive Team

Picture this. You wake to soft waves, slide into clear blue waters before breakfast, then sail toward a whitewashed village where grilled octopus and a sunset table are waiting for you. That is a week on a private yacht in Greece. Easy. A little adventurous. And with Greece by Travelive ensuring smooth sailing, simply magical.

If your clients love the sea, enjoy endless comfort, and like spending time with their favorite people on a beautiful boat, then there’s a skipper waiting for them at the helm. Looking for the best bays? Prepare to drop anchor there. Need an extra layer of ease? A private chef and hostess can serve breakfast on deck, have picnic lunches appear in secret coves, and make dinners feel effortless. And if the captain offers his hat for a photo, take it. We fully support hat selfies.

But before you set course, here are a few things to consider when navigating the waters.

The Fleet

Now let’s talk boat types. Catamarans feel like floating beach houses. Wide decks. Stable ride. Perfect for families and groups who want space to spread out and step straight into the water. Motor yachts bring speed and polish. They cover more water in less time and often come with big sun pads, plush cabins, and more toys than you can use in a week. Whatever your travelers’ style, we can match the right yachts to their dates and group size.

The Course

Greece rewards a focused route. Distances at sea add up, so a seven-night charter shines when you stick to one island group. The Cyclades deliver the postcard moments. Think Santorini, Paros, Naxos, Mykonos, and Milos. The latter is a sailor’s favorite, with pirate caves and coves like Kleftiko and Sykia that beg for a swim stop. In July and August, the local winds (Meltemia) can get lively, so we keep routes flexible and chase the best water day by day.

Looking for gentler seas? The Ionian Islands feel calm and green. Kefalonia’s Fiskardo is a classic sailor’s harbor with pretty quays and colorful houses. The Blue Caves near Zakynthos turn the water electric. It’s mellow sailing with vast swimming territory.

Meanwhile, the Saronic Gulf sits close to Athens and keeps crossings short. There, Hydra has no cars, so donkeys deliver the charm while you enjoy a cocktail by the harbor. Spetses brings chic seaside energy. And Aegina answers with pistachio ice cream and easy hop days. 

For longer adventures with a quiet vibe, the Dodecanese stretch toward Turkey. Rhodes mixes beaches with medieval walls. Symi’s pastel harbor looks like a watercolor, and the anchorages nearby feel like your own private pool.

And if you still can’t decide, perhaps our Greek Island Matchmaker can be of assistance!

When to Go

May (from mid-May onwards for warmer seas), June, September, and October (ideally up to mid-October for warmer weather) are sweet spots. Warm sea. Friendly winds. Harbors with room. July and August bring big summer energy and stronger winds in the Cyclades. If your clients’ dates fall in peak season and they want that region, a motor yacht or a flexible plan keeps the fun high. And if they want smooth sailing, the Ionian or Saronic are your best friends.

A Word on the Weather

The sea sets the rhythm, and your captain knows its moods. Routes are suggested in advance, then fine-tuned along the way for comfort or a better swim. Some of the best memories happen when the breeze shifts and you anchor in a quiet bay where the water stays calm and clear. Bring sunscreen and a good playlist. We will handle the rest.

How Costs Work

Most charters use an Advance Provisioning Allowance for fuel, food, drinks, and port fees. This is usually about thirty-five to forty percent of the weekly yacht rate and is paid to the charter company before you sail. The captain tracks everything and shares updates. Anything you do not use comes back at the end. Simple and transparent.

Sailing Off Into the Sunset

Getting started is easy. Tell us if your clients have chartered before or if this will be their first time. Share the dates, the group size, and how they would like the cabins arranged. Let us know if they prefer a catamaran or a motor yacht, and which island group feels right for their wish list. A budget range also helps hit the target faster. Most trips run seven nights, usually Saturday to Saturday, and some yachts offer flexible start days and durations in certain seasons.

Once we have the details, we’ll hold a few great yachts, sketch a route that fits the preferred pace, and send clear choices. All your clients have to do is bring swimsuits and sunglasses, and we will handle everything else. Should the sunglasses fall in, they will not be the first. Consider it an offering to Poseidon.

All Aboard!

If this sounds like the kind of summer your clients will love, then send Greece by Travelive your dates and group details, and they’ll be sailing across the deep blue seas in no time!

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