A Package Holiday In Greece Vs. Sailing In Style

Greece is probably on your bucket list of places to visit, and for good reason. Turquoise waters, whitewashed villages and long lunches in the sun draw thousands of people to the mainland and its islands every year. Most travellers default to a package holiday in Greece because it feels simple and familiar, but if you’re craving something more personal, a Sailing in Style trip offers a completely different way to experience the Greek Islands.

Below, we compare a typical package holiday with our bespoke sailing experiences across five key parts of your trip.

1. Travel: Coach Transfers Vs. Cruising Between Islands

How you move around shapes your entire holiday. Travel can either feel like a chore you endure or a highlight.

On a typical package holiday in Greece, your journey is mostly fixed: airport > coach > hotel. Transfers can be crowded and slow, with everyone heading to the same few resorts. Once you arrive, most of your ‘travel’ is a shuffle between the pool, the buffet and the nearest stretch of beach. If you visit another island, it’s often through a large group excursion on a packed boat with a strict timetable.

With Sailing in Style, travel is the experience. Your catamaran or monohull is both your transport and your home, meaning no queues, no coaches and no jostling for space. You glide between islands at your own pace, stopping in hidden bays for a swim or snorkel whenever you like. The journey is unhurried and peaceful, with the sound of the water replacing crowded swimming pools.

2. Excursions: One-Size-Fits-All Vs. Tailored Adventures

Excursions can be the difference between ‘we did the same as everyone else’ and ‘we’ll never forget that day’.

On a brochure-bought holiday in Greece, excursions are designed to suit the masses. You’re often herded in large groups to must-see sights, souvenir shops and busy tavernas, following a set script on a set schedule. There’s little room for spontaneity and if you’d rather linger in a village square or swim in a quieter cove, that’s usually not an option.

On a Sailing in Style trip, every day is essentially a bespoke excursion. From the moment you get in touch, we start planning a holiday in Greece that’s perfectly matched to your group’s likes and interests. You tell us the islands and experiences on your wishlist and we’ll make them a reality. We’ll also recommend places you may not have heard of, and our insider knowledge grants you access to unique experiences not open to the average tourist — including private artist workshops, VIP restaurant areas and exclusive vineyard trips.

Your skipper can recommend walks, viewpoints, family-run restaurants and chapels that coaches can’t reach — and you decide how long to stay.

3. Food: Buffet Lines Vs. Authentic Greek Cuisine

Food is often where holidays feel either generic or genuinely local.

On a typical package holiday in Greece, meals can be plentiful but repetitive. Buffets, all-inclusive wristbands and set menus are designed for volume and predictability. You might grab a gyros or two in town, but it’s easy to come home feeling like you didn’t really taste Greece.

With Sailing in Style, Greek food is woven into the soul of your trip. Think lazy breakfasts on deck, snacks and drinks at anchor and evenings spent in high-end restaurants handpicked by our team. Ask your skipper which local dishes best represent the island you’re visiting. Expect grilled octopus, local cheeses and carafes of house wine in tucked-away courtyards and waterfront spots locals love.

4. Unique Experiences: Resort Entertainment Vs. Moments Money Can’t Script

The memories that stay with you are rarely the ones planned in a brochure.

Unique experiences on a package holiday in Greece usually mean hotel entertainment, themed nights and mass-organised activities. They can be fun, but they’re rarely personal — and your photos often look like everyone else’s.

On a Sailing in Style holiday, the magic is in the moments that couldn’t have been scripted. A pod of dolphins racing your bow, an impromptu sunset swim, stargazing from the deck or a late-night conversation in a harbour bar with locals you’d never meet at a resort.

5. Variety Of Islands: One Resort Vs. A String Of Different Worlds

A holiday in Greece shouldn’t be one destination — it should be many islands, each with its own character.

On a generic holiday, you’re usually tied to a single resort on a single island. You might manage a day trip to one nearby spot, but wider exploration is difficult. You leave having really only seen one place, from one perspective.

With Sailing in Style, variety is built into the itinerary. In a single week you might anchor off a quiet, uninhabited islet for lunch, then moor in a lively harbour lined with bars and boutiques by evening. One day you’re wandering cobbled streets and blue-domed churches; the next, you’re hiking to a viewpoint or swimming in a bay accessible only by boat. The contrast keeps every day fresh.

Let Us Plan Your Holiday In Greece

A standard holiday in Greece can be familiar and fine, but if you’re ready for a trip that feels truly yours, Sailing in Style offers something completely different. Book a no-obligation exploration call with Sailing in Style and let’s start designing your Greek island adventure.