Chartering your own sailboat from $25 a day

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Ah, sailing!

Everyone dreams of sailing the Caribbean, cruising around the Mediterranean or Aegean Seas on a sailboat, or exploring the Florida Keys in their own chartered bareboat (landlubbers: that means there is no crew; you sail it yourself).

Sadly, most people also assume this is the sort of a vacation reserved only for the rich and famous.

Not so.

Hey: if my Boy Scout troop can do it on their tight budget can do it, anyone can. That boat in the picture above to the left? My troop chartered it (and another) to spend a week sailing the keys in the summer of 2010, and it cost us only about $400 per person for the full seven days—and that was in high season.

How much does chartering a boat cost?

  • It can cost as little as $700 per week to charter a 31-foot sailing yacht with two cabins and six berths. That means two couples could afford their own sailboat for as little as $25 per person per day. Of course, that’s in the off-season.In high season (in the Caribbean, roughly November to March; in Europe, usually mid-July through early September) you’re looking at a starting price of around $1,100 per week.
  • That said, the average range of prices is $1,200 to $3,000 a week for most standard sailboats and motor yachts, depending on (among many, many other factors) season.
  • 38-foot catamaran sleeping nine runs around $4,400 in high season—still decent once you break it down: Go with a group of, say, four couples and it’s less than $80 per person per day.

How much does having a captain, crew, cook, or hostess on a boat charter cost?

If you’re not feeling up the idea of captaining your own boat, most charter outfits will also rent you a skipper for around $150 per day. Taking along a hostess or cook would run another $100 to $150 per day.

What about cruises?

Prefer to leave the driving and the schedule to someone else? You needn’t board an enormous cruise ship to go sailing.

There are plenty of small sailing ships out there, as well as loads of private yachts looking for a few extra bodies to fill berths and haul sheets for as little as $700 per person for a week’s sailing.

How can I sign on to crew a boat and sail for free?

You could also hire yourself out as a deckhand on a boat—sometimes just for free passage and the chance to sail around Europe, sometimes even to make a few bucks. » Full Story

Resources for chartering sailboats and finding cruises

  • Boat Bookings ( – Charter sailboats, motorboats, and luxury yachts all around the world.
  • ( – Loads of info and one-on-one contacts between yacht owners and charter groups. Some excellent info covering all the basics of sailing and chartering boats and the process of renting and sailing a yacht.
  • ( – Another great general sailing and boat-chartering resource.
  • Ocean Blue Yachts ( – Britain-based charter service offering bareboats and charters on the Mediterranean and the Adriatic Seas.
  • Odyssey Sailing ( – Thousands of bareboat charters, crewed sailings, and set cruises both high-end and economy, msot in Greece. Nice site; good selection; not always the cheapest.
  • Small Ship Cruises ( – Loads of links, tips, and resources for all sorts of boating and sailing trips around the world.
  • ( – Online site to find more than 50 sailing trips in nearly 60 countries.
  • InfoHub ( – Order hundreds of brochures for sailing and boating programs, both major cruise lines and small, local charters and tour companies around the world.

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