Cast Off: A Beginner’s Guide to Sailing Holidays

The ultimate island hopping experience is having your own boat. No ferry schedules, no packing and unpacking. Your hotel moves with you to a new bay every day.

Many people think chartering a yacht is only for the super-rich or experienced sailors. In 2026, neither is true. The “AirBnB of boats” platforms (like Click&Boat or Borrow A Boat) have democratized sailing. Here is how to do it.

Option 1: Bareboat Charter (You Sail)

  • The Deal: You rent the boat alone. You are the captain.
  • Requirement: You need a valid license (ICC, RYA Day Skipper, or equivalent). In the Mediterranean, this is strictly checked.
  • Pros: Total privacy and freedom. Cheaper.
  • Cons: You do all the work (anchoring, navigation, stress).

Option 2: Skippered Charter (You Relax)

  • The Deal: You rent the boat AND a professional skipper.
  • Requirement: Money. A skipper costs approx €150-200 per day (plus their food).
  • Pros: Zero stress. The skipper knows the hidden bays, the best restaurants, and handles the weather. You just sunbathe.
  • Cons: Less privacy (there is a stranger on board, though they are usually discreet). You lose one cabin to the skipper.

Option 3: Flotilla (Social Sailing)

  • The Deal: You sail your own boat (or hire a skipper) but travel in a group of 10-15 boats led by a “Lead Boat” with engineers and hosts.
  • Pros: Safety in numbers. Social parties at night. Great for families.
  • Cons: Fixed itinerary.

Best Places for Beginners in 2026

1. The Ionian Islands, Greece

  • Why: “The Nursery.” No tides, steady afternoon wind (Maestro), and islands are close together (line of sight sailing).
  • Route: Corfu -> Paxos -> Lefkada -> Meganisi -> Kefalonia.

2. The British Virgin Islands (BVI)

  • Why: The sailing capital of the Caribbean. Consistent trade winds, mooring buoys everywhere (easy parking), and beach bars.
  • Route: Tortola -> Virgin Gorda (The Baths) -> Jost Van Dyke -> Anegada.

3. Croatia (Dalmatia)

  • Why: Thousands of islands. Historic towns (Split, Dubrovnik) to dock in. Modern marinas with showers and electricity.
  • Route: Split -> Hvar -> Vis -> Korcula -> Brac.

Monohull vs. Catamaran

  • Monohull (Classic Sailboat): Heels over (tilts) when sailing. feels like “real” sailing. Cheaper. Small cabins.
  • Catamaran (Two Hulls): Stable (doesn’t tilt). Huge net to lie on. Massive space. More expensive (and costs double in marinas). Best for beginners/families.

The Cost (It’s Cheaper Than You Think)

Let’s do the math for a Skippered Catamaran in Greece (June):

  • Boat (4 cabins, sleeps 8): €5,000 / week
  • Skipper: €1,200
  • Fuel/Port Fees: €500
  • Total: €6,700
  • Per Person (8 people): €837 for a week. That is comparable to a hotel, but includes your transport and activity.

What to Pack

  • Soft Bag: Do not bring hard suitcases. They can’t be stored in cabins. Duffel bags only.
  • Deck Shoes: Non-marking soles. Or go barefoot.
  • Jackets: It gets cold at sea at night.

4. The Whitsundays, Australia

  • Why: Whitehaven Beach. You can anchor right next to it. The Great Barrier Reef protects the islands from ocean swell.
  • Route: Airlie Beach -> Hamilton Island -> Whitehaven -> Hook Island.

5. Seychelles (Inner Islands)

  • Why: Granite boulders and giant tortoises. It is the most photogenic sailing in the world.
  • Route: Mahé -> Praslin -> La Digue -> Curieuse.

Life on Board: The Reality

  • Water: Is limited. You shower fast (“The Navy Shower”: wet, soap, rinse).
  • Power: You can’t use hair dryers unless you are in a marina or have a generator.
  • The Dinghy: This is your car. You use the small rubber boat to get to shore for dinner. Learning to drive it is half the fun.
  • Cooking: Boat galleys are small. Cook simple meals (pasta, salads). Eating on deck under the stars is better than any Michelin restaurant.

Booking Tips for 2026

  1. Shoulder Season: Sailing in May or October in the Med is 40% cheaper than August.
  2. Saturday to Saturday: Most charters run on a strict weekly schedule. Flights need to align.
  3. Insurance: Pay for the “Damage Waiver.” It reduces your security deposit liability. It gives you peace of mind when docking in tricky winds.

Sailing is freedom. Waking up, jumping off the back of your boat into crystal clear water before coffee… there is nothing like it.