Closing out the October 2009 issue of Sail Magazine, Vera Cole writes a great article titled “The More the Merrier – Done Right, Multi-Family Charter Leaves Everyone Smiling“.  There are some great insights for family or flotilla trips that bareboaters would find useful.  Here’s a summary:

• Families with children of similar ages are idea sailing companions – it’s important to discuss expectations before departure including activity level, pace of voyage, common interests, budget, and temperament.
• Find a boat which is user-friendly  – comfortable and some privacy, catamarans are ideal.
• Do research with regards to wind and weather patterns – consider the rainy season or paying the one-waydrop-off fee so as not to have a slog to return to base.
• Holidays and festivals – can be a blessing or curse so be sure to plan around them.
• Charter rates vary – check for internet discounts, negotiate, or work with charter brokers.
• Establish the captain – because sometimes decisions need to made quickly.
• Provisioning – when possible submit your own grocery list for the first 3 days and pay the service fee.  (I’ll add you might want to provision for all the beverages particularly water, soda, and spirits.  It’s so much easier to load up at the dock before departing.)

Other Bareboating Advice: Before Departing  Provisions  Living Aboard  Sailing Stuff