A Sailing Holiday for Beginners — With Plenty to Do Ashore

 

For new sailors, I’d recommend a week sailing around the Greek Ionian Islands. It’s a wonderful introduction to sailing: beautiful turquoise bays, short hops between islands, pretty harbours, traditional Greek tavernas and plenty of opportunities to swim, explore villages and enjoy life ashore.

You don't need to be an experienced sailor. You can charter a yacht with a professional skipper, learn a few sailing skills along the way, and enjoy the holiday without the pressure of being responsible for the boat.

Day 1 — Arrive in Lefkada

Easy start · Marina and town

Arrive, meet your skipper, settle into your yacht and learn the basics of safety and life aboard.

Onshore activities: Explore Lefkada Town's colourful streets, browse local shops and enjoy your first Greek dinner at a waterfront taverna.

Day 2 — Meganisi

Short sail · Swimming and village life

Sail towards Meganisi, with a stop in a sheltered bay for a swim. Your skipper can show you how to steer, handle ropes and understand the sails.

Onshore activities: Wander around Vathy harbour, visit a traditional café or take a walk up to Spartochori for lovely views over the bay.

Day 3 — Ithaca

Island scenery · Walking and culture

Head towards Ithaca, the island associated with Homer's Odyssey. Enjoy the coastline and practise sailing under supervision.

Onshore activities: Explore the pretty harbour village of Kioni, walk its narrow lanes, find a beach or enjoy a long lunch overlooking the boats.

Day 4 — Discover more of Ithaca

A flexible day · Walking and local food

Keep this day relaxed, with a short sail to another bay or harbour depending on the weather.

Onshore activities: Walk inland through olive groves, visit Vathy's waterfront, browse local shops or take a taxi to a scenic viewpoint. This is also a good day for a longer lunch ashore.

Day 5 — Fiskardo, Kefalonia

Pretty harbour · Coastal exploring

Sail to Fiskardo, one of the Ionian's most attractive harbour villages, known for its colourful buildings and waterfront.

Onshore activities: Browse boutiques and galleries, take a coastal walk, find a beach or settle down for a seafood dinner. If conditions permit, explore a nearby cove by dinghy.

Day 6 — Kastos

Quiet island · Snorkelling and relaxation

Enjoy a quieter stretch of the Ionian, with time for a swim and perhaps a little more hands-on sailing.

Onshore activities: Explore the small village on foot, have a leisurely coffee, snorkel in clear water and enjoy a relaxed meal at a local taverna.

Day 7 — A final swim and return

Gentle sailing · Farewell to Greece

Sail back towards Lefkada, stopping for one last swim if time and weather allow. Your skipper will manage the return passage and yacht handover.

Onshore activities: Enjoy a final coffee or lunch ashore before departure, depending on your travel arrangements.

The itinerary is flexible rather than a fixed passage plan. The skipper will adjust destinations and sailing distances for the weather, daylight and the crew's comfort. The route above is a proposed outline, not a guarantee that every stop will be possible.

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The Aeolian Islands are superb for a Sailing Adventure

 

The Aeolian Islands are superb for a sailing adventure because you can combine short, enjoyable sailing legs with volcanoes, swimming, snorkelling, villages, food and plenty of time ashore. A week gives you a lovely balance without spending all day at sea.

⛵ My suggested 7-day Aeolian adventure

I'd recommend starting and finishing at Lipari or nearby Milazzo/Portorosa, depending on the yacht charter. The route below concentrates on the islands that offer the best combination of sailing and activities. Most passages are only around 2–4 hours, leaving plenty of time for exploring.

Day 1 – Lipari → Vulcano

Sail: ~3–5 nautical miles

Start gently with a short sail across to Vulcano.

Onshore adventure:

Climb Gran Cratere for spectacular views across the archipelago.

Explore the volcanic landscape.

Relax on the black-sand beach.

Try Vulcano's famous thermal mud baths and hot-water area.

Dinner ashore overlooking the harbour.

The crater walk is particularly worthwhile early or late in the day when temperatures are lower.

Overnight: Vulcano.

Day 2 – Vulcano → Lipari → Salina

Sail: ~15–18 nautical miles in total

Head north to Lipari for a morning stop.

Lipari activities:

Walk through the old town.

Visit the castle and archaeological museum.

Browse the little shops and cafés.

Stock up on local food and provisions.

Then sail on to Salina, the greenest and arguably most beautiful of the Aeolian Islands.

Evening: Wander around Santa Marina Salina and enjoy a relaxed Sicilian dinner.

Salina is particularly good for families because it feels less developed and hectic than some of the other islands.

Day 3 – Salina: island exploration day

Sailing: short coastal sailing/swimming stops

I'd deliberately make this a slower day.

Sail around the island and stop at Pollara, the spectacular collapsed volcanic crater made famous by Il Postino.

Onshore activities:

Walk through the old village.

Explore the volcanic coastline.

Visit vineyards.

Taste local Malvasia wine and island produce.

Have a long lunch overlooking the sea.

Swim and snorkel from the yacht.

For a family trip, I'd make this one of the more relaxed days rather than trying to tick off another island.

Day 4 – Salina → Panarea

Sail: ~11–14 nautical miles

Panarea is completely different: tiny, beautiful and rather glamorous.

Anchor around Cala Junco or another suitable bay depending on the weather.

Afternoon adventure:

Dinghy exploration around the little islands of Basiluzzo, Lisca Bianca and Dattilo.

Snorkelling in crystal-clear water.

Swim from the yacht.

Walk the narrow lanes of Panarea.

Ice cream and cafés in the village.

Evening: Dinner ashore and watch the sunset.

Day 5 – Panarea → Stromboli

Sail: ~12–13 nautical miles

This is your big adventure day.

As you sail towards Stromboli, the volcano dominates the horizon.

Spend the afternoon swimming and exploring the village before preparing for the highlight of the trip.

🌋 Stromboli after dark

Head offshore in the evening and watch the volcano's activity from the sea, particularly around the Sciara del Fuoco.

The glowing eruptions against the night sky are one of the great Mediterranean sailing experiences.

If conditions and current volcanic restrictions permit, you could also arrange a guided volcanic excursion ashore. I would treat this as optional rather than building the whole itinerary around it because access and restrictions can change.

Overnight: Stromboli or, if conditions dictate, return to Panarea.

Day 6 – Stromboli → Filicudi

Sail: ~20–25 nautical miles

This is your proper sailing-adventure day.

Filicudi is much wilder and quieter than Panarea.

Activities:

Snorkel around the volcanic coastline.

Take the dinghy to Grotta del Bue Marino.

Visit the prehistoric settlement at Capo Graziano.

Walk up into the hills for panoramic views.

Have dinner at the tiny harbour village of Pecorini a Mare.

This would probably be my choice for the quietest and most adventurous evening of the week.

Day 7 – Filicudi → Lipari

Sail: ~20–25 nautical miles

Enjoy a final morning sail back towards Lipari.

I'd stop for a final swim and snorkel along Lipari's spectacular western coast before returning to the harbour.

Final afternoon:

Explore Lipari's old town.

Visit the castle.

Enjoy a long Italian lunch.

Buy local food/wine for the journey home.

Finish with a sunset dinner overlooking the harbour.

🌋 The week at a glance

Day Island Main adventure

1 Vulcano 🌋 Volcano + thermal baths

2 Lipari → Salina 🏛️ History + island life

3 Salina 🍇 Villages, vineyards + swimming

4 Panarea 🤿 Snorkelling + hidden coves

5 Stromboli 🌋 Night-time volcano spectacle

6 Filicudi 🧭 Wild island + caves

7 Lipari ⛵ Final sail + Italian evening

⭐ Why I particularly like this itinerary

It gives you three different types of adventure:

Active: crater walks, island walks, snorkelling, caves and dinghy exploration.

Sailing: enough genuine passages to make it feel like a sailing holiday rather than a boat-based island tour, but without exhausting everyone.

Family time: plenty of afternoons where you can simply swim, paddleboard, snorkel, eat ice cream or explore a village.

One important point: the Aeolians are more weather-sensitive than somewhere like the Ionian Islands. There are relatively few all-weather harbours and many anchorages are exposed to particular wind directions, so I'd use this as a framework rather than a rigid itinerary. Local skippers routinely alter the order according to wind and swell.

For a family holiday, I would also strongly favour a skippered yacht or catamaran unless you're already very comfortable with Mediterranean island sailing. Italy's tourism guidance specifically recommends professional local skippers for a relaxed and safe Aeolian itinerary.

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A Family Sailing Adventure around the Ionian Seas

 

For a family sailing adventure with plenty to do ashore, I’d look at the central Ionian — starting from Lefkada and exploring Meganisi, Kastos, Kalamos, Ithaca and Kefalonia. It gives you a lovely balance of sailing, swimming, beaches, villages, walking and a little adventure, without spending every day making long passages. Recent 2026 sailing guides also identify this area as particularly suitable for families because of the relatively short hops and sheltered anchorages

Day 1 — Lefkada → Meganisi

Sail: ~8–12 nautical miles

Start gently. Pick up the yacht in Lefkada and head across to Meganisi, perhaps anchoring in beautiful Vathy Bay.

Family adventure:

Swimming and snorkelling straight off the boat

Paddleboards/kayaks around the bay

Walk into Vathy for ice cream and dinner

Explore the little lanes and waterfront

Meganisi is particularly good for a first day because there are lots of sheltered bays and short sailing distances.

Day 2 — Meganisi → Kastos

Sail: ~15 nautical miles

This is where the holiday starts feeling like a real adventure. Kastos is tiny and wonderfully unspoilt.

Onshore:

Hire bicycles or walk around the island

Swim from the little beaches

Snorkelling expedition from the yacht

Explore the small village

Sunset dinner overlooking the harbour

I'd make this a slow day rather than trying to pack in too much.

Day 3 — Kastos → Kalamos

A short sail north brings you to Kalamos, another beautifully green island.

Family activities:

Morning swim from the yacht

Kayaking around the coastline

Walk through the pine forest

Find a traditional taverna for lunch

Evening swim and paddleboarding

The children can have a genuine feeling of exploring an island rather than simply visiting a resort.

Day 4 — Kalamos → Ithaca

Now head for Ithaca, the legendary home of Odysseus.

I'd aim for Vathy, the main harbour.

Onshore adventure:

Explore Vathy

Visit the archaeological/museum sites

Hire a car or scooters for an afternoon island exploration

Walk to one of the viewpoints

Have a proper Greek family dinner ashore

Ithaca adds something different to the trip: you're no longer just moving between beautiful swimming spots, but getting a sense of Greek mythology and island history. Discover Greece specifically highlights following in Odysseus' footsteps as an experience on Ithaca.

Day 5 — Ithaca → Kefalonia

Sail: approximately 10–15 nautical miles depending on your chosen stop.

Head across to Fiskardo, one of the prettiest harbours in the Ionian.

This is a good place for a shore-based adventure day.

You could:

Explore Fiskardo

Hire a car

Visit Melissani Cave

Visit Drogarati Cave

Go to a beach for the afternoon

Find a traditional Kefalonian restaurant

There are also established boat-excursion operators around Fiskardo if you want to add an activity without taking the sailing yacht. For example, Crystal Clear Cruising Sailing Trips operates from the harbour, while Ionian Discoveries is based in Fiskardo.

Day 6 — Kefalonia → a deserted bay

I'd deliberately make this your "no plans" day.

Find a beautiful secluded anchorage and spend the day:

🏊 swimming

🤿 snorkelling

🛶 kayaking

🏄 paddleboarding

🎣 fishing

🚤 exploring in the dinghy

📚 reading in the shade

For a family sailing holiday, these unstructured days can end up being the most memorable.

Day 7 — Kefalonia → Meganisi

Start heading back towards Lefkada, stopping somewhere such as Meganisi.

Make this your family challenge day:

Morning sailing competition

Children navigate using a chart

Anchor in a new bay

Snorkelling treasure hunt

Paddleboard race

Cook dinner together on board

Sunset swim

It turns the children from passengers into part of the crew.

Day 8 — Meganisi → Lefkada

A relaxed final sail back to Lefkada.

I'd allow plenty of time so you can stop for a final swim before returning the yacht.

🌴 The really nice thing about this route

You get five different types of holiday in one trip:

Experience Where

🏖️ Beautiful beaches Meganisi & Kefalonia

⛵ Proper sailing Between the islands

🏝️ Deserted-island adventure Kastos & Kalamos

🏛️ History & mythology Ithaca

🍋 Greek villages & tavernas Everywhere!

🤿 Snorkelling & watersports Almost every anchorage

🕳️ Caves & exploration Kefalonia

🚲 Walking/cycling Kastos, Kalamos & Meganisi

The Ionian is particularly attractive for this style of family trip because the islands are relatively close together and the sailing tends to involve manageable daytime passages rather than long open-water crossings.

🛥️ What boat would I choose?

For a family, I'd seriously consider a 4-cabin catamaran rather than a monohull.

You get:

Much more living space

Two hulls/greater privacy

Large cockpit

Easy access to the water

Plenty of room for children

More stable platform at anchor

Excellent space for paddleboards, snorkelling gear and the dinghy

If you have 6–8 people, a 4-cabin catamaran would be particularly attractive.

⭐ One variation I'd consider

If you have 10–14 days rather than just a week, I'd extend the trip substantially rather than sailing faster.

You could do:

Lefkada → Meganisi → Kastos → Kalamos → Ithaca → Kefalonia → Zakynthos → Kefalonia → Ithaca → Meganisi → Lefkada

This starts to feel like a proper family expedition through the Ionian, with sailing interspersed with beaches, caves, hiking, kayaking and Greek villages.

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What Makes a Luxury Catamaran Charter a Truly Unforgettable Experiences ?

 

Luxury catamaran charters take the inherent advantages of the platform and add the things that turn a week on the water into the week someone talks about for years.

1. The Bow Net, Which Is What Everyone Actually Remembers

Ask anyone who's done a catamaran charter what they remember most. Not the sailing. Not the restaurants. The catamaran netting. The mesh trampoline that stretches between the twin bows is where the good hours happen. It sits close to the water. It moves with the boat. Spray comes through when the sailing's good. Lying there watching a headland appear in the distance while the hull moves underneath is the kind of thing that's essentially impossible to recreate elsewhere, and it's the reason people book a second charter before they've disembarked from the first.

A well-maintained net has proper tension and clean mesh. A saggy, tired one is immediately apparent. Luxury vessels treat this as a priority rather than an afterthought, because experienced charter guests know the difference before they've even sat down.

2. Stability That Changes Who Can Enjoy the Trip

Seasickness is the silent spoiler of sailing holidays. Not everyone gets it. But on a monohull, some percentage of any group will spend the first passage day horizontal and regretting their life choices. Catamarans are fundamentally more stable. The twin hulls and wide beam produce a motion that most people handle without difficulty. This matters more than it sounds because it changes the composition of who can realistically join a charter. Mixed groups where some people are experienced sailors and others aren't so sure suddenly become more viable. That's not a small thing when someone's trying to plan a family trip or a group holiday.

3. Anchorages Worth Getting There For

Most charter vessels need depth. Catamarans don't ask for much, typically a metre or less, which opens up anchorages that everything else has to sail past. A small bay, clear water, sand visible on the bottom, no other boats. Nobody else made it in because nobody else could. These are the spots that end up in the photographs and the stories told at dinner parties two years later when someone asks how the trip was.

Good captains know where these spots are and how to build a week that reaches them. It's knowledge that doesn't appear on a charter specification but absolutely determines what the trip feels like.

4. Crew Who Run Everything Without Making It Obvious

The best charter crew is invisible in the best possible way. The captain who knows which anchorage will be sheltered tonight without being asked. The chef who figured out on day two what everyone actually likes. The crew who appear when something needs doing and disappear when the guests want to be left alone. Charter reviews consistently mention crew over vessel. The catamaran with the right people aboard outperforms the newer boat with indifferent service every time.

Final Thoughts

What makes a luxury catamaran charter stick in the memory isn't one thing. It's the trampoline at sunrise, the anchorage nobody else found, the meal that was better than expected, the day the sailing was genuinely good. None of those things happen by accident. They happen because the vessel, the crew, and the itinerary were all chosen by someone who understood what the week was actually supposed to feel like.

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Top Three Winter Sun Sailing Options

 

🥇 1. British Virgin Islands — my first choice

If you want a 7-day sailing holiday where the sailing itself is a major part of the experience, I'd put the BVI at the top.

You get:

Short, enjoyable sailing legs

Lots of sheltered anchorages

Warm water around 26°C

Reliable trade winds

Fantastic snorkelling

Beautiful beaches

Plenty of good restaurants and beach bars

Very little need for long passages

January–March is particularly good, although February is often considered one of the best months.

Ideal itinerary: Tortola → Norman Island → Peter Island → Cooper Island → Virgin Gorda → Anegada → Jost Van Dyke → Tortola.

🥈 2. Seychelles — spectacular tropical sailing

The attraction is that the sailing is combined with extraordinarily beautiful islands: granite cliffs, enormous boulders, jungle, deserted beaches and excellent snorkelling.

December–March brings warm temperatures around 29°C and generally lighter winds, typically around 5–15 knots, with occasional short rain showers.

Best for: a relaxed luxury catamaran + swimming + exploring ashore holiday rather than hard-core sailing.

🥉 3. Grenadines — perhaps the most romantic

Ideal itinerary: 

St Vincent → Bequia → Mustique → Canouan → Tobago Cays → Mayreau → Union Island.

The Tobago Cays are a major highlight — turquoise water, reefs, turtles and small uninhabited islands.

I'd choose the Grenadines over the BVI if you want the holiday to feel more remote and less developed.

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🌴 Our suggested 8-day family Thailand sailing adventure

 I'd start and finish around Phuket, travelling through Phang Nga Bay, Koh Yao, Krabi, Railay and Phi Phi, with plenty of time off the boat.

Day 1 — Phuket → Koh Yao Noi

Sailing: 2–3 hours

Settle aboard the catamaran and sail east into the wonderfully sheltered waters of Phang Nga Bay.

Family activities:

Swimming and paddleboarding

Snorkelling from the yacht

Take the dinghy ashore

Explore a small fishing village

Thai dinner on the beach

Koh Yao Noi is particularly attractive for families because it feels much more relaxed and authentic than Phuket. The island is known for quiet beaches, coconut plantations and traditional villages.

Day 2 — Koh Yao → Phang Nga Bay

This is the big adventure day.

Sail among the extraordinary limestone pinnacles of Phang Nga Bay.

Activities ashore/on the water:

Kayak through sea caves

Explore hidden hongs (lagoon caves)

Visit James Bond Island

Visit Koh Panyee, the spectacular village built on stilts over the sea

Have lunch in a local restaurant

Swim from the yacht in the afternoon

The combination of kayaking, caves and the floating village makes this one of the best days for children.

Day 3 — Phang Nga → Koh Yao Yai

A deliberately easy day.

Sail south through the islands, stopping whenever you find a beautiful beach or snorkelling spot.

Once ashore on Koh Yao Yai:

Hire bicycles

Cycle through coconut plantations

Visit a local village

Stop for a Thai lunch

Visit a rubber plantation

Have a beach afternoon

Sunset dinner overlooking the bay

This is the day I'd keep relatively unstructured—the children can have some independence while the adults enjoy the scenery. Cycling and exploring the villages are among the activities commonly suggested for the island.

Day 4 — Koh Yao Yai → Koh Hong → Railay

Sailing: around 3–4 hours, broken up with stops.

Stop at Koh Hong for a morning swim and kayak into the spectacular lagoon.

Then sail towards Railay Beach.

Afternoon ashore:

Explore the beaches

Walk through the jungle

Visit the famous caves

Try introductory rock climbing with an instructor

Explore the little restaurants and shops

Railay is particularly good if you have teenagers—it adds a genuine adventure/sport element rather than simply another beach stop.

Day 5 — Railay → Phi Phi

Head south towards the famous Phi Phi Islands.

I'd avoid spending the whole day around the busiest areas and instead have the skipper look for a quieter anchorage.

Activities:

Snorkelling

Paddleboarding

Cliff jumping where safe and permitted

Beach exploration

Sunset from the boat

The journey from Krabi to Phi Phi is roughly 25 nautical miles on typical itineraries, making it a proper little sailing adventure without being an enormous passage.

Day 6 — Phi Phi exploration day

This would be your no-sailing day.

Take the dinghy or a local boat to explore:

Maya Bay

Phi Phi Leh

Monkey Beach

Hidden coves

Snorkelling reefs

Viewpoint hike

For younger children, I'd concentrate on swimming and snorkelling; for teenagers, the viewpoint hike and kayaking make the day more adventurous.

Day 7 — Phi Phi → Koh Racha

This is your tropical-island finale.

Sail towards Koh Racha Yai.

Spend the afternoon doing absolutely nothing—or:

Snorkelling

Paddleboarding

Swimming

Beach football

Fishing from the boat

Sunset barbecue

I'd make this a particularly relaxed evening aboard the yacht.

Day 8 — Koh Racha → Phuket

Have one last swim after breakfast and sail back towards Phuket

If your flight isn't until the following day, I'd actually recommend adding one night in a Phuket hotel rather than going directly from yacht to airport. It gives everyone a chance to have a proper shower, explore Phuket and recover from the sailing adventure.

The important thing is not to make it a sailing holiday where everyone is stuck on the boat all day. Thailand is at its best when you alternate short sailing passages with genuinely interesting things to do ashore.

⛵ What I'd choose for the boat

For a family I'd look for a 40–50 ft crewed catamaran with:

3–4 cabins

Air conditioning

Large shaded cockpit

Good dinghy

Kayaks or SUPs

Snorkelling equipment

Plenty of water toys

Experienced local skipper

Cook, if budget allows

A catamaran is especially appealing here because it gives you shallow-water access, lots of deck space and considerably more stability than a monohull.

There are already 5–8 day itineraries operating around essentially this route, including Phang Nga, Koh Yao, Krabi, Railay, Phi Phi and Racha.

☀️ When I'd go 

For this particular family adventure, I'd choose November to April. The Andaman Sea is generally much more settled during this period, with clearer water and better conditions for family sailing, although the exact weather always needs checking before departure.

My personal sweet spot would be February–March: warm, relatively dry, and excellent for swimming and snorkelling.

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Our Top 6 Areas for a quiet Mediterranean Sailing Holiday

 

If peace and quiet are your priority, there are still some wonderful parts of the Mediterranean where you can sail for hours, anchor in empty bays and avoid the big flotillas. The trick is to avoid the famous hotspots and, if possible, avoid July and especially August. June and September are generally much quieter.

🥇 1. Alonissos & the Sporades — my favourite for tranquillity

This would be very high on my list.

The Alonissos Marine Park is particularly special: there are numerous small islands and islets, exceptionally clear water and secluded bays, with very little development. It's also a protected area for Mediterranean monk seals.

A lovely week could be:

Skiathos → Skopelos → Alonissos → Peristera → Kyra Panagia → Skopelos → Skiathos

You get considerably more greenery than the Cyclades, beautiful swimming spots and some wonderfully peaceful evenings at anchor.

🥈 2. Datça & Bozburun, Turkey — best for secluded bays

If your definition of a perfect sailing holiday is:

Sail for a couple of hours → find a completely quiet bay → swim → lunch on board → swim again → sunset → barbecue

…I'd seriously consider south-west Turkey.

The Datça peninsula is relatively remote and has a coastline packed with little bays accessible primarily by boat. Bozburun is another particularly peaceful area.

It also has a big advantage over the Cyclades: more sheltered sailing and fewer big charter crowds.

🥉 3. Lastovo, Croatia

If you like the idea of Croatia but don't want Hvar, Split or Dubrovnik crowds, look much further south.

Lastovo is one of Croatia's more remote inhabited islands, with a very different atmosphere from the busy Dalmatian hotspots. You can combine it with Mljet, Korčula and the Lastovo archipelago.

The drawback is that Croatia's most popular islands can become busy in July/August, so this is particularly attractive in June or September.

4. Small Cyclades, Greece

For a classic Greek sailing experience, I'd look at:

Naxos → Iraklia → Schinoussa → Koufonisia → Kato Koufonisi → Amorgos

Rather than the big-name Cyclades.

The tiny islands have a much slower pace, beautiful beaches and plenty of opportunities to anchor away from the main villages. Koufonisia is particularly lovely, although it has become more popular in recent years.

One caution: the Meltemi wind can be strong in July/August, so this is better suited to experienced sailors.

5. Dodecanese — Tilos, Lipsi & Astypalea

This is the Greek option I'd investigate if absolute tranquillity matters more than seeing the famous islands.

I'd particularly look at:

Kos → Nisyros → Tilos → Chalki → Alimia → Rhodes

or, for an even more remote feeling:

Kos → Lipsi → Leros → Patmos → Arki → Marathi

You can have lovely little harbour evenings without the scale of tourism found on Santorini/Mykonos.

6. Menorca

Don't overlook Spain.

Menorca is considerably more relaxed than Ibiza and much of Mallorca, with numerous beautiful calas and a more natural feel.

I'd concentrate on the north and east of Menorca, rather than basing the trip around the busiest southern beaches.

One important point: when you go matters almost as much as where

If you're able to choose your dates, I'd rank them:

🥇 September – warm sea, lovely weather, noticeably fewer boats

🥈 June – excellent combination of warmth, wind and relatively low crowds

🥉 May – wonderfully quiet, but sea can still be cool

😐 July – perfectly possible, but increasingly busy

❌ August – hardest month to achieve genuine solitude

The difference can be enormous. The Med in September can feel like a completely different place from the same anchorage in August.

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Cuba Sailing Adventure

 

For a 7-day sailing holiday in Cuba, I would suggest the south coast from Cienfuegos, rather than trying to circumnavigate the island. You get a lovely combination of sailing, deserted beaches, snorkelling, wildlife and—most importantly—time ashore in Trinidad.

There are established sailing itineraries from Cienfuegos through the southern cays, and the area is well suited to catamarans because many of the cays have very shallow water.

Day 1 — Cienfuegos

Cienfuegos → Punta Gorda / overnight aboard

Fly into Havana and transfer to Cienfuegos, or arrange your trip around Cienfuegos if flights work.

Spend the afternoon exploring the wonderfully preserved French-influenced city before boarding your catamaran.

Highlights

Cienfuegos historic centre

Palacio de Valle

Punta Gorda

Welcome dinner aboard

Short evening sail if conditions allow

Cienfuegos is a particularly good starting point because it gives access to both the southern coastline and the offshore cays.

Day 2 — Cienfuegos → Guajimico → Casilda

A beautiful coastal sailing day.

Stop at Guajimico, where you can:

snorkel

swim

explore caves

have lunch ashore

Then continue towards Casilda, the port serving Trinidad.

Overnight: at anchor near Casilda.

This is broadly the route used by established Cuba sailing itineraries.

Day 3 — Trinidad

This would be my big cultural day.

Take a taxi or organised excursion into Trinidad, one of Cuba's great colonial towns.

Spend the morning and afternoon:

wandering the cobbled streets

visiting Plaza Mayor

exploring the old churches and mansions

having lunch in a local paladar

visiting the Valle de los Ingenios if you want an excursion

Then return to the boat for a swim and sunset.

Evening: I'd definitely arrange a night in Trinidad for Cuban music and dancing.

Day 4 — Casilda → Cayo Blanco de Zaza

Now the holiday changes character completely.

Leave civilisation behind and sail towards the small offshore cays.

Cayo Blanco de Zaza is ideal for:

deserted beaches

snorkelling

kayaking

swimming

paddleboarding

a barbecue or seafood dinner aboard

Spend the night at anchor beneath the stars.

This section of the south coast is particularly attractive because it receives relatively little cruising traffic. One experienced Cuba sailing account describes sailing roughly 250 nautical miles around the southern coast in a week and encountering remarkably few other sailboats.

Day 5 — Cayo Blanco → Cayos Machos de Fuera

A relaxed sailing day between the cays.

I'd deliberately keep the schedule flexible rather than trying to cover huge distances.

Spend the afternoon:

snorkelling over reef

exploring the beach

kayaking through mangroves

looking for iguanas and other wildlife

fishing from the boat

Then enjoy a sunset dinner on deck.

Day 6 — Cayo Machos → Cayo Blanco de Casilda

Another relatively short sailing day.

This is your "Caribbean paradise" day—no sightseeing agenda whatsoever.

I'd spend the morning sailing, then anchor somewhere beautiful for:

swimming

snorkelling

paddleboarding

lunch aboard

beach walk

afternoon nap!

The Cuban government tourism site highlights the excellent snorkelling, coral reefs, beaches and private-charter possibilities around its northern cays; similar shallow-water conditions are found throughout Cuba's island cruising grounds.

Day 7 — Cayo Blanco → Cienfuegos

Set sail early for the return to Cienfuegos.

Make the most of the final morning with one last swim or snorkel before heading back.

Arrive in Cienfuegos in the afternoon, allowing time for:

a final wander around the city

dinner overlooking the bay

Cuban music

final night aboard or in a hotel

Then transfer back to Havana the following morning.

The real attraction is the combination: you get one fantastic Cuban town (Trinidad), one interesting colonial city (Cienfuegos), and five days of increasingly wild islands and beaches.

⛵ Catamaran or monohull?

I'd choose a 40–45 ft catamaran for this trip. The shallow water around the Cuban cays makes a shallow-draught catamaran particularly practical, while giving you much more space for swimming, eating and relaxing.

One caveat: Cuba requires a little more logistical planning than Greece, Croatia or the Seychelles. Provisioning can be unpredictable, and customs/coastguard formalities are part of sailing there.

For weather, the traditional cruising window is roughly November–April, with December–April generally regarded as the strongest period for chartering.

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Why would you sail around Crete ?

 

Sailing around Crete is fantastic , particularly if you want a holiday that combines sailing with plenty to do ashore.

This is why Crete works so well for a week of sailing.

1. Dramatic coastline and clear water

Crete has beautiful turquoise bays, caves, beaches and rugged cliffs. The northwest coast around Chania and the Gramvousa peninsula is particularly rewarding from a boat.

2. A good mix of sailing and exploring

You can alternate sailing days with time ashore for:

Ancient ruins and archaeological sites

Mountain villages and traditional tavernas

Hiking gorges and coastal paths

Snorkelling and swimming

Local food and wine

Historic Venetian harbours

3. Excellent food 🍋

Crete is arguably one of Greece's best food destinations. Sailing lets you reach small coastal tavernas that aren't necessarily convenient by road. Expect grilled fish, lamb, dakos, fresh vegetables, local cheeses and excellent olive oil.

4. Beautiful small harbours

Places such as Loutro, Chora Sfakion and Agia Galini give you a very different experience from staying in a resort. Arriving by boat makes these places particularly special.

5. You can combine famous sights with quieter anchorages

A seven-day route doesn't have to mean moving every day. You can spend a morning swimming in a remote bay, sail a few hours, then have dinner in a village harbour.

The important caveat !!

Crete is large, so I wouldn't try to sail around the entire island in seven days. You'd spend too much time covering distance.

For a first 7-day sailing holiday, I'd suggest either  :-

Option A – Western Crete ⭐

Chania → Gramvousa/Balos → Kissamos → Paleochora → Loutro → Chora Sfakion → Chania

This gives you spectacular scenery, beaches, swimming, villages and some of Crete's best-known attractions.

Option B – Eastern Crete

Heraklion → Dia → Agios Nikolaos → Spinalonga → Mochlos → Kouremenos → Sitia

This is better if you want more history, archaeology, traditional villages and quieter eastern coastline.

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The Seychelles -- one of the world's finest sailing destinations

 

Here is a  relaxed 7-day sailing itinerary covering the beautiful Inner Islands, starting and finishing on Mahé.

Day 1 – Mahé to Praslin (26 nautical miles, 4–5 hours)

Morning

Depart Eden Island Marina on Mahé.

Enjoy your first sail across turquoise waters to Praslin.

Afternoon

Anchor at Baie Ste Anne or Anse Lazio.

Swim or snorkel straight from the yacht.

Onshore activities

Visit the UNESCO-listed Vallée de Mai nature reserve.

See the famous Coco de Mer palms and endemic black parrots.

Enjoy dinner at a local Creole restaurant.

Day 2 – Explore Praslin

A leisurely day with minimal sailing.

Onshore activities

Relax at Anse Lazio, regularly ranked among the world's finest beaches.

Optional visit to Anse Georgette.

Short hike through coastal trails.

Water activities

Paddleboarding

Snorkelling

Sunset drinks aboard your yacht

Day 3 – Praslin to Curieuse Island (4 nautical miles)

Curieuse is a protected national park.

Onshore activities

Walk among hundreds of free-roaming Aldabra giant tortoises.

Follow the mangrove boardwalk.

Visit the restored Doctor's House museum.

Afternoon

Snorkel around St Pierre Islet, famous for colourful reef fish and clear water.

Day 4 – Curieuse to La Digue (7 nautical miles)

La Digue has a wonderfully relaxed atmosphere.

Onshore activities

Hire bicycles (the best way to explore).

Visit the spectacular Anse Source d'Argent.

Explore traditional vanilla plantations and coconut groves.

Browse local artisan shops.

Evening

Fresh seafood barbecue or beach restaurant.

Day 5 – La Digue and Coco Islands

A short cruise to some of the Seychelles' best reefs.

Activities

Snorkelling with turtles.

Optional scuba diving.

Kayaking around granite boulders.

Onshore

Visit Grand Anse or Petite Anse.

Watch the sunset from one of the island's quiet western beaches.

Day 6 – La Digue to Mahé (approximately 35 nautical miles)

A longer but rewarding sail back towards Mahé.

Afternoon

Anchor at Beau Vallon or Sainte Anne Marine National Park.

Onshore activities

Explore Victoria, one of the world's smallest capitals.

Visit Sir Selwyn Selwyn-Clarke Market.

Sample Creole cuisine and local rum.

Day 7 – Mahé

Spend your final day exploring the largest island.

Options include -

Hike the Copolia Trail or Morne Blanc for panoramic island views.

Visit Takamaka Bay.

Relax at Anse Intendance or Petite Anse.

Browse local craft markets before departure.

Wildlife you may encounter-

Aldabra giant tortoises

Hawksbill and green turtles

Reef sharks 

Eagle rays

Dolphins

Flying fish

Hundreds of tropical fish species

Best time to sail =

April–May: Light winds, calm seas, excellent visibility.

October–November: Another superb period with warm weather and outstanding snorkelling.

June–September: Stronger southeast trade winds make for livelier sailing.

December–March: Hotter and more humid, with occasional tropical showers.

This itinerary strikes a good balance between sailing (generally 1–5 hours per day, except for the return to Mahé) and plenty of time ashore to enjoy the Seychelles' beaches, wildlife, hiking, and Creole culture. If you're interested in a more adventurous trip, I suggest suggest a route that includes the remote islands of Cousin, Aride, and Silhouette for even better birdlife, diving, and secluded anchorages.

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Summer Sailing Hotspots

 

If you're looking for the best European sailing destinations this summer, the ideal choice depends on whether you want lively nightlife, secluded anchorages, reliable winds, or easy island hopping.

Here are some of the standout hotspots to consider :-

🇭🇷 Dalmatian Coast

One of Europe's most popular sailing regions.

Highlights:

Island-hop between Hvar, Brač, Vis, Korčula, and Mljet.

Hundreds of sheltered coves and historic harbours.

Crystal-clear water and relatively short sailing passages.

Best for: First-timers, flotillas, families, and mixed groups.

🇬🇷 Cyclades

Famous for whitewashed villages and stronger summer winds.

Highlights:

Mykonos, Paros, Naxos, Milos, Santorini.

Reliable Meltemi winds in July and August.

Spectacular scenery and authentic tavernas.

Best for: Experienced sailors seeking exciting sailing.

🇬🇷 Ionian Islands

The gentler Greek option.

Highlights:

Lefkada, Kefalonia, Ithaca, Paxos.

Warm, calm seas with predictable afternoon breezes.

Plenty of protected anchorages.

Best for: Beginners and relaxed cruising.

🇮🇹 Amalfi Coast and Aeolian Islands

Amalfi Coast

Positano, Amalfi, Capri.

Dramatic cliffs and luxury atmosphere.

Can become crowded in peak season.

Aeolian Islands

Active volcanoes including Stromboli.

Excellent swimming and unique overnight anchorages.

Best for: Food, scenery and memorable cruising.

🇪🇸 Balearic Islands

Includes Mallorca, Menorca, Ibiza and Formentera.

Highlights:

Beautiful turquoise coves.

World-class beach clubs alongside peaceful anchorages.

Excellent marinas and charter infrastructure.

Best for: Combining sailing with nightlife and beaches.

🇫🇷 French Riviera

Highlights:

Nice, Cannes, Antibes and Saint-Tropez.

Luxury marinas and glamorous ports.

Great restaurants and events.

Best for: Luxury yachts and vibrant social scene.

🇹🇷 Turquoise Coast

Although partly in Asia, it's one of the Mediterranean's premier sailing destinations.

Highlights:

Göcek, Fethiye, Marmaris.

Pine-covered bays and ancient ruins.

Excellent value compared with much of Western Europe.

Best for: Longer cruises and excellent value.

Best by interest,  then go to...

Easy island hopping Croatia

Reliable sunshine Greece

Calm sailing Ionian Islands

Stronger winds Cyclades

Luxury French Riviera

Nightlife Ibiza & Mykonos

History Croatia & Turkey

Best value Croatia & Turkey

Food & wine Italy

When to go

June: Warm weather, fewer crowds, good prices.

July: Peak season with excellent weather and busy marinas.

August: Hottest and busiest month; book berths well in advance.

September: Often considered the sweet spot—warm sea, settled weather, and fewer crowds.

For a one-week charter, Croatia and the Ionian Islands are often the easiest and most rewarding. If you're after more adventurous sailing the Cyclades offer some of the Mediterranean's best wind conditions.

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