This practical guide explains what types of boats you can choose whether you need a skipper, how much it costs, and what to consider when planning your first sailing trip.
If you’re reading this, chances are you’ve already been thinking about trying something new - something a little out of the ordinary, maybe even a bit adventurous. Yes, we’re talking about life on a boat.
Waking up not in a hotel room, but on the water - surrounded by silence and the rhythm of the waves. Sounds tempting? It truly is. But it also raises a lot of questions: is it only for experienced sailors? Is it expensive? Is it safe?
This beginner-friendly guide will walk you through what kind of boats you can rent, whether you need a skipper, what the prices are, and what to keep in mind when planning your first sailing holiday. You might discover it’s not as complicated as it seems.
🛥️ Why Choose a Boat Holiday?
We always tell our friends: “A boat is a mobile home on the water - with a view that changes every day.” And that’s just the beginning.
When you choose a sailing holiday, you get:
- Freedom: today in a quiet bay, tomorrow in a lively harbor.
- Privacy: no crowds, no reserving sunbeds at 7 a.m.
- Authenticity: discover hidden coves and small islands most tourists never see.
- Connection: sailing brings people together - family, couples, or friends.
Where to Sail? Top Destinations for Beginners
Croatia – a beginner’s paradise
- Islands are close to each other – short, easy routes.
- Modern marinas and plenty of safe anchorages.
- Gentle winds and clear navigation paths.
Greece (Ionian Sea) – turquoise bays without the stress
- Calm winds, easy navigation.
- Islands like Corfu, Ithaca, Lefkada – postcard-perfect.
- Ideal for travelers seeking both relaxation and beauty.
Italy (Sicily, Aeolian Islands, Sardinia) – flavor and culture
- Harbors near historic towns and UNESCO sites.
- Ideal climate for sailing.
- Italian cuisine – a new taste experience at every port.
Spain (Balearic Islands) – endless summer
- Mallorca, Ibiza, Menorca – from tranquil to vibrant.
- Long sailing season and very little rain.
- Excellent marine tourism infrastructure.
When Is the Best Time to Sail?
|
Season |
Advantages |
Disadvantages |
|
May / September |
Pleasant weather, fewer tourists |
The tourist season just starting or ending |
|
June – August |
Full summer, lots of entertainment |
Higher prices, more crowds |
|
April / October |
Peaceful, cheaper, less traffic |
Unpredictable weather, fewer activities |
With or Without a Skipper?
First time? Choose with a skipper - for both safety and comfort.
With skipper:
- No experience required
- Local recommendations and insights
- Less stress, more relaxation
Without skipper (bareboat):
- Only if you have a skipper license and experience
- More freedom, but also more responsibility
What Type of Boat to Choose?
|
Boat Type |
Recommended Size |
Best For |
Advantages |
Price (from, €/week) |
|
Sailing Yacht |
35–40 ft (3–4 cabins, up to 8 people) |
Couples, romantics |
Authentic, economical, quiet |
1,500–2,500 |
|
Catamaran |
38–42 ft (4 cabins, 8–10 people) |
Families, groups |
Spacious, stable, plenty of room |
2,500–4,000 |
|
Motor Yacht |
30–40 ft (2–3 cabins, 4–8 people) |
Speed & comfort lovers |
Fast, easy to handle, stylish |
3,000–5,000 |
When to Book Your Boat Holiday?
|
Period |
Benefits |
Recommendation |
|
November – January |
Best prices: 10–20% early booking discount |
Perfect time to plan your summer trip |
|
February – March |
Great post-boat-show offers, still wide selection |
Book while options are still plenty |
|
August |
Last-minute autumn deals |
Ideal for spontaneous travelers |
|
June – August (High Season) |
Most popular months – boats book up fast |
Reserve at least 6 months in advance |
How to Organize It All?
Planning your sailing trip is easier than you think:
- Contact us – the Travel Boat team will answer all your questions and help you choose.
- We’ll send you a few tailored offers – based on your dates, budget, and preferences.
- Book your boat – once the deposit is paid, we confirm everything officially.
- We handle the rest – you just pack your swimsuits!
A Few Practical Tips
- Choose a round route (start and finish in the same marina).
- Ideal group size: 6–8 people (on a 3–4 cabin boat).
- Plan no more than 15–20 nautical miles per day.
- Bring cash – cards aren’t accepted everywhere.
- A waterproof phone or document case will come in handy.
- Pack sea-sickness tablets - just in case.
- Download Navionics or Windy – very useful apps for sailors.
Our Promise
The Travel Boat team will make sure your first sailing holiday is not only simple but truly unforgettable.
We don’t just find you a boat – we show you how “trying something new” turns into “we want to do it again.”
Get in touch – we’ll answer all your “what if?” questions.
🌊 www.travel-boat.com – your starting point for a different kind of holiday.
Fair winds and calm seas!
This article was created in collaboration with boat rental experts with over 10 years of experience organizing sailing holidays worldwide. If you have questions or would like to receive a personalized offer, don’t hesitate to contact us!