Sailing Holiday Beginners Guide 2026

A sailing holiday sounds like a sport for professionals. Like it requires a license, years of training, and a deep knowledge of knots. That is a myth. Book a skippered charter and you need zero prior experience. The only thing that actually matters: choosing the right sailing region for your first trip.

Here is the honest beginner’s guide.

Bareboat Charter vs. Skippered Charter: Which Option Is Worth It for Beginners?

This is the first question you need to answer.

Bareboat charter means you rent the boat and sail it yourself. For this you need a recognized sailing certificate (depending on the region: ICC, SRC or equivalent). No license, no bareboat.

Skippered charter means a professional skipper handles all navigation. You and your group enjoy the sailing without touching the wheel. No certificate needed. No knowledge needed. The skipper often cooks too. This is the right option for everyone on a sailboat for the first time.

Costs: Bareboat charter from around 1,200 EUR per week for a boat accommodating 8 people, meaning 150 EUR per person excluding food and skipper. Add a skipper and the cost rises by 800-1,500 EUR per week, roughly 100-190 EUR more per person.

Total for one week skippered charter (8 people, Croatia): 2,000-3,500 EUR for the boat including skipper, plus food and marina fees. That works out to 250-440 EUR per person for a full week.

Which Sailing Region Is Right for Your First Holiday?

Three beginner-friendly regions in Europe, one for long-haul travelers.

Croatia, Dalmatia: The classic beginner region. More than 1,000 islands between Split and Dubrovnik, calm bays, well-equipped marinas, turquoise water. Most charter bases sit in Split or Šibenik. Best months: May, June, September. July and August: warm but crowded.

Greece, Ionian Islands: Between Corfu and Zakynthos. Calmer winds than the Aegean, green islands with Venetian harbor towns, excellent food on shore. Popular with families. Main base in Lefkada. Best time: May through October.

Turkey, Aegean: The Gökova coast and the Bodrum-Marmaris stretch. Cheaper than Croatia and Greece, less busy. Beautiful bays, ancient ruins right at the water’s edge. Main bases in Bodrum or Göcek. Best months: April, May, September, October.

Caribbean (long-haul): British Virgin Islands or the Grenadines. Consistent trade winds, relaxed sailing between small islands, turquoise water on a completely different level. More expensive than Europe (boat charter from 3,000 USD per week), but a genuine dream experience. Best months: November through April.

Our Croatia island hopping guide covers the best routes between Split and Dubrovnik.

What Should You Actually Watch Out for on a Sailing Holiday?

No panic about swell. The boat moves. That is normal. Most beginners have no issues after the first day. If you are prone to seasickness: eat light in the morning, keep your eyes on the horizon, stay on deck in fresh air. Ginger tablets help.

Marina fees: In Croatia 20-80 EUR per night depending on the marina and boat size. In Greece often cheaper. Anchorage is usually free, but you need an anchoring permit in national parks.

Regional licenses: For Croatia and Greece, the skipper needs local registration. This is handled by the charter company. With a professional skipper it is never your problem.

Insurance: Good charter companies include comprehensive insurance. Check the excess, which often sits at 1,500-3,000 EUR. Many providers sell excess waiver insurance for 100-200 EUR per week. Worth it.

Booking platforms: Sailing Angels and Noforeignland.com are solid starting points for vetted skippered charters in Europe. Larger platforms like Zizoo or Click&Boat offer more choice but less personal guidance.

How Much Does a Sailing Holiday Actually Cost?

Summary for one week in Croatia, 8 people, skippered charter:

Boat charter including skipper: 2,000-3,500 EUR
Food and drinks: 400-700 EUR (80-90 EUR per person)
Marina fees: 200-400 EUR
Getting there: 200-400 EUR per person (flight to Split)
Excess waiver insurance: 150-200 EUR

Total per person (group of 8): 500-750 EUR for one week, excluding flights. With flights 700-1,150 EUR. Cheaper than many all-inclusive hotel packages, but a completely different experience.

If you need a rental car for the journey to the marina, our rental car checklist has everything you need to know.

What Gear Do You Actually Need?

Very little. The boat has sleeping berths, a kitchen and a bathroom. You bring:

Light, quick-drying clothes
Good sunglasses (water reflection is intense)
High-SPF sunscreen, applied daily
Water-resistant sandals or boat shoes
Seasickness medication if needed
Personal medication

No heavy suitcases. Duffel bags or backpacks that fit into the storage hold. Hard-sided wheeled luggage does not work on boats.

Use Zercy to compare sailing regions and find charter options by destination. Save your shortlist in your Zercy Logbook so you have all options handy when booking.

Frequently Asked Questions

What sailing certificate do I need for a sailing holiday?

With a skippered charter, none at all. The skipper handles all navigation. You only need a recognized certificate (ICC, SRC or similar) if you want to sail the boat yourself on a bareboat charter.

When is the best time for a sailing holiday in Croatia?

May, June and September. Good weather, warm sea, uncrowded bays. July and August are the hottest and most expensive months. April can still be a little cool but offers very low prices.

What happens if the weather is bad at sea?

The skipper decides whether to sail. In poor conditions the boat stays in port or in a sheltered bay. This is normal and not unusual. Good skippers know the region and which bays are safe in different weather.

How far do you typically sail in one day on a sailing holiday?

Usually 3-6 hours of sailing per day, 20-50 nautical miles (40-90 km). The rest of the time is for anchoring, swimming and exploring harbor towns. The pace is decided jointly by the group and the skipper.

Read more:

Sailing Holiday for Beginners: What You Really Need to Know