Sailing

Set sail on a Sabbatical: wind, water and freedom

No traffic, no fixed plans—just wind in the sails, sun on the water, and maybe a cold drink at anchor. Whether joining a crew or taking a boat yourself, it’s a unique way to have experience your sabbatical.

Why sailing is perfect for a Sabbatical

• Every day feels like a small adventure
• Swim, snorkel, and sleep under the stars
• Change locations without unpacking your bag

Two ways to sail: join a trip or rent your own boat

1. Join an organized sailing trip

No license, no problem. Joining a crewed or skippered sailing trip is an easy entry into boat life. Just bring curiosity and sunscreen.

Top picks:

• Belize – Calm seas, tropical islands, and incredible snorkeling
• San Blas Islands (Panama) – Crystal-clear waters and remote island hopping
• Turkish Riviera – Gorgeous coastlines, hidden bays, and incredible food, all from a traditional gulet or sailing yacht

Organized trips are social, flexible, and often include everything—meals, route planning, and a seasoned skipper. Great for solo travelers, couples, and small groups.

2. Charter your own boat

For those with experience (or the right license), skippered freedom is hard to beat. Charter companies like Sunsail offer everything from bareboat charters to flotillas where you sail your own boat with support nearby.

Beautiful locations for independent sailing:

• Sicily or the Amalfi Coast (Italy) – Combine sailing with incredible food, dramatic coastlines, and charming port towns
• Croatia – Clear waters, smooth sailing, and medieval towns right on the dock

What you need to rent a boat

If you’re looking to captain your own adventure, here’s what’s typically required:

• A valid sailing license or certificate (RYA Day Skipper, ICC, ASA 104, or equivalent depending on location)
• VHF radio license (required in some countries, like Greece)
• Experience level – Charter companies often ask for a sailing resume or proof of logged hours
• Security deposit – Expect to pay a damage deposit or take out extra insurance

No license yet? A sabbatical is also a great time to take a skipper course and get certified. Many places offer liveaboard courses where you learn while exploring new waters.

Good to know

• Sailing seasons vary – The Mediterranean season runs roughly May to October; Central America’s dry season is November to April
• It’s not a cruise – Expect teamwork, basic showers, and close quarters. But that’s half the charm