Activities while sailing: 6 ideas for active sailing trips

Sailing sounds romantic – until the wind doesn't come for two days or blows from the wrong direction. That's when it's decided whether a sailing holiday will be stressful or the best trip of the year. I've been sailing for over ten years, overseen more than 500 collaborations with tourism boards and luxury brands, and now spend half the summer living on a yacht. In this guide, I'll show you the best activities while sailing – the water-based highlights, the land-based spots, and the quiet moments of luxury on board. No theory, just what worked on my own trips in Portugal, Spain, Italy, Greece, and the Caribbean.

1. Foiling – the best activity on the water (even without wind)

E-foiling is the activity that completely transformed my summer on the boat. You stand on a board with an electric motor and hydrofoil underneath, control it via radio remote, and fly just under a meter above the water's surface. No wind is needed, no noisy combustion engines, no dependence on waves – all you need is calm water and ideally a mothership to launch from.

I drive that SiFly Stellar S, And I can honestly say: after about an hour, you're standing up. For the first five minutes, you lie on your stomach and get used to the thrust, then kneeling, then standing. Once you're on the foil, you glide along so silently that you hear the dolphins and sea turtles beside you before you see them. For me, foiling is the ideal sport during a sailing trip because it perfectly fills the gap that sailing leaves: calm mornings at anchor, still afternoons, warm evening sun over the bay.

2. Kitesurfing – the plan B when there's too much wind

When the wind blows stronger than 25 knots, almost everyone anchors in the sheltered bay and waits. I use these days for kitesurfing. The Algarve, Fuerteventura, Sardinia, Tarifa in Spain, and many islands in Greece have reliable wind spots right next to classic sailing areas. From the anchorage, you can often reach the beach in fifteen minutes.

A clear warning: Don't start kitesurfing during a sailing trip. This is the fastest way to injure yourself or someone else. Book a complete course two weeks in advance at a location like Tarifa, Fuerteventura, or Leucate in France. Once you're confident with the kite and bar, your sailing trip will be more flexible: Calm day? Foil. Too much wind? Kite. Perfect sailing wind? Sail. You'll never be dependent on a single weather pattern again.

3. Marina hopping – experiencing harbor life as an activity in itself

Underrated, but for me one of the best parts of sailing: time spent in the marina. Vilamoura in Portugal, Saint-Tropez in France, Porto Cervo in Sardinia, Hvar in Croatia, Mykonos in Greece, Palma de Mallorca in Spain – each of these marinas is like a small town in its own right. Superyachts right next to fishing boats, restaurants open until late at night, chandleries for spare parts, sauna and pool with a marina guest pass.

On a two-week sailing trip, I always plan at least two nights in a marina. Not just for refueling and laundry, but because conversations with fellow skippers returning from the Caribbean or the Mediterranean are irreplaceable. If you're chartering a boat, ask the harbor master for the best place to eat seafood – it's never the one most prominently listed on Google Maps.

4. Beach and cliff stops – the bay as a retreat

After three hard days of sailing, neither your body nor your mind wants anything more than to lie in a sheltered bay. My absolute favorites: Praia da Marinha and Praia de Benagil in the Algarve, the Blue Cave on Biševo in Croatia, the limestone bay of Formentera in Spain, the pink sand beaches of Sardinia in Italy, the Shipwreck Bay in Zakynthos, Greece.

Find an anchorage, dinghy ashore, snorkel mask in. Praia de Benagil is notorious among day-trippers – but those arriving by water can have the grotto all to themselves very early in the morning. And honestly: an hour on the cliff path, followed by a dip in the turquoise water, beats any spa day.

5. Shore excursions – why you should regularly leave the boat

The biggest mistake first-time sailors make: staying by the water the whole time. Yet the most spectacular destinations are often just a half-hour drive away. From Portugal, I drove to... Bom Jesus do Monte in Braga, in the Peneda-Gerês National Park and drove to waterfalls behind Monchique. In Italy, you can drive to the Supramonte mountains from any Sardinian port. In Greece, a trip to the Samaria Gorge from Crete is worthwhile.

My rule of thumb: For every third sailing day, I plan a day ashore. Rental car, Vespa, or e-bike, depending on the region. And a hiking trail, a church, a viewpoint with a drone spot, a homemade dinner in a small taverna. Back on board, you love sailing again because your perspective has changed.

6. On-board rituals – the quiet luxury on board

What distinguishes a sailing trip from any other vacation? The rituals that only exist on a boat. Hammock between bow pulpit and mast, The boat rocks gently in its anchorage, you lie horizontally fifty centimeters above the water's surface, watching the sunset paint the rigging red. I take a lightweight ultralight hammock with me on every trip. Setup: five minutes. Reward: priceless.

Then there are the established evening rituals: a sunset aperitif in the cockpit, dinner together under the deck saloon, counting stars after midnight without light pollution. On a yacht off the coast of Sardinia or somewhere in the Caribbean, you see constellations you've never seen from home. The simultaneous lapping of the water against the hull is what every meditation app tries in vain to simulate.

The best sailing areas for active trips compared

Not every region is equally suitable for all activities. I've ranked the top destinations according to how they feel in practice:

My personal ranking for diversity: Algarve for Efoilen plus land program, Sardinia for the interplay of bay and mountains, Croatia for novice skippers because of the many protected islands and Caribbean as a winter escapade with guaranteed trade winds.

Packing list for active sailing activities

What always accompanies me during an active yachting week, whether in Portugal or Greece:

• Wakeboard/Efoil shorts with UV protection – not just swim trunks, otherwise the seatbelt will cause chafing.
• Lightweight neoprene vest – at 21°C water, the vest will keep you in the water for two hours longer.
• Waterproof bag 20–30 liters – for dinghy trips to beaches without infrastructure.
• Trekking sandals – Flip-flops break on the first cliff path.
• drone – I fly the DJI Mini 5 Pro, compact enough for transport in a dinghy, powerful enough for coastal panoramas.
• Power bank 20,000 mAh – two full days of drone and camera operation without onboard power.
• Ultralight hammock – 200 grams, saves every calm afternoon.
• Snorkel set – not the cheap plastic kind, but a set with tempered glass and a silicone mask.

Frequently asked questions about sailing activities

What activity is most worthwhile when there is no wind?

Foiling. It's the only watercraft that doesn't require wind, hardly needs waves, and is quick to learn. Kayaking is the analog alternative.

Is it possible to learn kitesurfing during a sailing trip?

No. Kitesurfing requires five to ten days of instruction in a shallow, standing-water area. Book this as a separate trip – otherwise you endanger yourself and others.

Which sailing area offers the best combination of activity and relaxation?

The Algarve in Portugal and Sardinia in Italy offer both: impressive underwater coastlines, good winds, spectacular hinterlands and relaxed marinas without the touristy atmosphere of Ibiza.

How many sailing days should I alternate with activity days?

My ratio is 2:1 – two days sailing, one day ashore or doing activities in the bay. On two-week trips, that equates to four to five "rest days." That's enough to keep both body and crew fresh.

Are activities like foiling allowed on every charter yacht?

Not automatically. Ask the charter company specifically about Efoil, Seabob, or jet skis beforehand. Some insurance policies do not cover the transport of motorized water toys.

Which shore excursions are specifically worthwhile in the Algarve?

Bom Jesus do Monte in Braga, the Peneda-Gerês National Park, Monchique with its Caldas thermal baths, and the historic old town of Lagos. You'll need a rental car for all four.

What is the most affordable active sailing activity?

Snorkeling. Cost: a one-time fee of 60–80 euros for decent equipment, then nothing. In Greece, Croatia, and the Caribbean, you'll see more fish without an oxygen tank than at most dive sites in German-speaking countries.

About the author

Max Haase

Travel Content Creator · Drone Photographer · Visual Storyteller

Since over 10 years professional travel creator with over 4.2 million followers. Specializing in high-end tourism board collaborations and visual travel storytelling.

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