Finding the Caribbean Holiday that's Right for You: Part 5 - Flotilla Holidays

ASA Flotilla in San Juan

Flotilla Holidays are for hands-on sailors who prefer to travel in a larger group of other boats and with the security of a lead boat and skipper to help with navigation, weather assessments, route planning, daily anchoring and general boat or sailing questions.  Prices are slightly higher than a bareboat charter, but lower than a luxury crewed charter.

Who Is It For?

Flotilla holidays are ideal for those with a reasonable holiday budget, and who generally have some experience of sailing (although it's not always mandatory). It's perfect for a couple, or family with young children, or a group of friends travelling together, who are looking for some support whilst sailing and a relatively lively time in the evenings socialising with other boats and crews.  Some flotilla operators also offer 'per cabin' or 'per person' bookings which make them a possible option for single travellers. This will generally be on board the Lead boat.

Finding the Caribbean Holiday that's Right for You: Part 4 - Freelance Charter (Crewed or Skippered)

Yacht Ibis - St Kitts

Freelance yacht charter gives those with a modest holiday budget the option of chartering a yacht directly from the owner or captain.  Prices start at around $4,000 for the boat for a week, or $1,000 per person, plus some additional expenses (see later).  Boats, Captains and/or Crew vary significantly in what they offer to guests and you can choose to be as hands on as you like on this type of sailing vacation.

Who Is It For?

Freelance yacht charters are ideal for those with a reasonable holiday budget and looking for a holiday a little more out of the ordinary. It is ideal for a group of friends clubbing together, or a family holidaying together, and some boats also offer 'per cabin' or 'per person' bookings which make them a great option for single travellers. No prior experience of sailing or boating is needed, but if you're looking to get involved with sailing the boat, this is generally welcomed.

Finding the Caribbean Holiday that's Right for You: Part 3 - Luxury Crewed Charter

The 41m Valquest - available through YPI (Yachting Partners International)

When money's no object, the most beautiful yachts in the world are at your disposal.  Pay top dollar and expect the best.  Prices start at around $8,000 per week for the whole boat, and can be as much as $700,000 per week plus, dependent on the boat, the number of guest berths and the cruising area.  See below for a typical cost breakdown.

Who Is It For?

Private luxury yacht charters are ideal for those with a big holiday budget looking for a superlative standard of comfort and service.  Perfect for a special family occasion like a honeymoon, anniversary or birthday; for a family or group holiday way out of the ordinary, or a corporate retreat.  No prior experience of sailing or boating is needed.

The St Barth's Bucket - Classic Yachts Under Full Sail

Hanuman - the 42m J Class replica of Endeavour II

You've seen them in the magazines.....marvelled...and if you're like me you've probably drooled a little bit.  They're beyond the reach of mere mortals, and their names and provenance will outlive their owners, designers and builders....that's a certainty.  For the yachts chosen to sail in the Bucket Regattas are the finest, most famous and amongst the most expensive on the planet.

We can but dream of sailing on one, no less of owning one, although the cost of maintenance alone would be enough to bankrupt most of us in the space of a few months!  So the closest we might ever get to one of these yachting icons is at events like the St Barth's Bucket Regatta, where those with a golden ticket gather to pit themselves against one another under full sail and in the turquoise waters of the Caribbean under a blue sky.

How to Choose the Caribbean Sailing Holiday That's Right for You; Part 2 - Your Budget and Your Options

Adventure Sailing on Ibis V

For the price of a reasonable guest house room in the Caribbean, you could be on board your own charter yacht cruising far flung islands and remote anchorages off the beaten path.

Like everything, there are good and bad charter agents, charter companies, yachts, skippers and crew, and it's important to do a little research to find the best option for you and/or your group.  The most expensive is not necessarily the best, and the cheapest is not always the best value, however there are exceptions; for example Sailing School Courses offer exceptional value for hands-on sailors.

Budget & Experience

A good starting point is to establish your budget and your level of experience.  Whilst it's possible to undertake any type of sailing holiday with no experience at all, two options such as Bareboat Charter and Flotilla Holidays normally require one of your party to hold a certificate of competence before the company will let you loose.....