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Flotilla Cruising FAQs

Why Should You Do a Flotilla Cruise?

by Doris Colgate

One of our cruising course graduates recently asked me a lot of questions about our Colgate Sailing Adventures® flotilla cruises. We had a very lively conversation, that I think might be helpful for anyone considering participating in these fun sailing vacations. Steve and I led sailing flotilla holiday cruises for Offshore Sailing School graduates for more than 40 years, starting in 1973. That’s how we saw the world. I hope this information helps you as you consider whether to go on one with Colgate Sailing Adventures®. If I haven’t covered something that is still floating around in your mind, shoot me an email (doris@OffshoreSailing.com) and I’ll update this blog right away.

Q. Is there a hired captain and mate on each boat?
A. No you are “bareboating,” sailing and managing the boat you are assigned to with other participants. It’s sort of like renting a car, no chauffeur.

Q. What do you mean by bareboating?
A. Ah, sometimes I forget it is a very confusing word. The boats are not “bare” at all. Everything you need for your comfort and fun is aboard – sheets, blankets and pillows, towels, kitchen equipment, a dinghy so you can go ashore easily, and more. There’s just no hired captain or mate aboard.

Q. I have Bareboat Cruising Certification, but does everyone need certifications to do a flotilla cruise?
A. Great question! The short answer is no, because some sailing flotilla holiday participants like to bring a spouse along who hasn’t yet taken a certification course. But . . . you will enjoy it a lot more if you have at least the Basic Keelboat certification that comes with the Offshore Sailing School Learn to Sail (OSS 101) course. If cruising in Europe the assgned “skipper” and “mate” on each boat must have the International Proficiency Certificate (IPC). If you have US Sailing Bareboat Cruising Certification, it’s really easy to get the IPC. Later in this blog you will see how we put crews together to make sure every boat has sailors who can handle the boat well.

Q. Why should I consider a flotilla cruise when I already have certifications that supposedly allow me to start chartering on my own?
A. One of the biggest advantages of a Colgate Sailing Adventures® sailing flotilla holiday is that we do all the work for you – kinda like signing up for a trip on an ocean liner or river cruise ship. We also take the risks, not you. But perhaps the best reason is you get to explore areas under sail, hassle-free. We reserve and pay for the boats and associated costs way in advance as required, arrange for starter-packs or provisioning aboard the boats, set up itineraries, social events and then we give you all the information you need to make your travel plans at the time you sign up. All you have to do is book your flights (and we even give you a contact to do that), then pack your sailing gear . . . and show up.

Q. What sort of details do you send out? What kind of preparation do we need to do in advance?
A. Well – you don’t need to do anything but work on your travel plans and make sure you have valid passports. We send you a lot! So here goes. Many participants want to know what they should pack and we provide an easy check list for the location where you’ll be cruising. We give you details about the places you will anchor, dock or moor each night, and even restaurants and places to visit ashore. We give directions on how to get to the location, transfers like taxis and shuttles information, where to show up and when, what’s available at the base, hotels, restaurants, shops, and so much more.

Q. Who’s in charge when we get there? Who knows we are coming?
A. Most sailing flotilla holiday cruise are led by our staff cruise leaders – Nate and Heather Atwater – who have a real knack for making you feel comfortable with the trip. In fact, they go overboard with their attention to details and your needs 😊. They are at the base location where you pick up the boats at least a day ahead of you to make sure everything is set up correctly. And they are there to greet you when you arrive.

Q. Is there an instructor on each boat?
A. No, Nate and Heather are on the lead boat with some of the participants, usually the least experienced sailors, and everyone else is assigned to one of the other yachts in our flotilla fleet, based on your sailing experience.

Q. I don’t get it. How can you be sure the boats will be sailed properly and we stay out of trouble?
A. Great question. We ask for your sailing experience and any certifications you may have on a pretty detailed resume and participation form that goes out to you when you sign up. Then your cruise leaders spend hours putting the crews together, taking into account all the information provided. Sometimes they even call you.

Q. I’m not sure I want to sail with strangers, and if I bring my wife, I’m not sure she would be comfortable either. What happens if we don’t like our shipmates?
A. Wow, what a loaded question! I can tell you, because I have led over 70 of these cruises since 1973 with my husband, Steve, that rarely do we get any issues regarding compatibility. Oh, we’ve had a few quirky sailors aboard over those 44 years but, truly, everyone is there for a good time and to have fun. All the participants seem to be on their “best behavior,” and we hear all the time that new friendships evolve from those first-time meetings aboard. So much so, it seems a few people on every sailing flotilla holiday cruise make plans to start bareboating together on their own, together.

Q. What kind of boats will we be sailing on? How many boats do you usually have in these flotillas?
A. Normally we have around four to six boats in the fleet, sometimes three, and occasionally seven or more (like on the 2017 cruise in Italy). The boats are usually in the 40’ to 50’ range and depending on the charter fleets available, they may be catamarans or monohulls. In 2024 we are using monohulls in Greece and catamarans in Grenada and Belize. Most of the yachts in each fleet will have four cabins.

Q. So, do we have to share cabins?
A. No, we wouldn’t do that to you, unless you bring a friend or family member to share your cabin at the per person shared-cabin price. Pricing is based on purchasing a single private cabin, or two people sharing who are traveling together.

Q. So, back to my first question, why should I go with you rather than find some friends or charter with my family on my own? Isn’t it cheaper that way?
A. To answer your second question first – “maybe,” but a whole lot riskier. If you or someone else in your party who is sharing the costs has a medical problem (heaven forbid), or a business issue, or a family emergency at the last minute, you end up holding the bag. On our sailing flotilla holidays, I have to say again, “we take the risk.” You are ensured you have your cabin no matter how many others may cancel or change their minds.

Q. Can I bring my kids or some friends and have a private boat?
A. On some of the cruises, yes. Family members have to be at least 18 years old, however. If we allow you, as a family, to “buy the boat,” please be aware we can’t give you any refunds if someone in your party decides they don’t want to or can’t come after all.

Q. Do the boats have to stay together the entire trip?
A. The cruise leaders set a preliminary itinerary in advance and we send that with all the pre-cruise details. But they make the ultimate decision each day on where the fleet will sail. Each morning they do the rounds, visiting every boat to go over the navigation to the next destination. We ask that all the boats end up at the pre-arranged lunch and evening destinations. So, no, you won’t be going off on your own. It’s more fun when you stick together anyway.

Q. Back to how the crews are assigned, who is “captain” on each boat?
A. Great question. A sailing flotilla holiday cruise is all about having fun and sharing in a new adventure. But there needs to be one person on each boat who takes ultimate charge and reports to the cruise leaders, should an emergency occur. So, we assign one person the role of skipper on each boat when we make up the crews, and another, the role of mate, based on the information on your sailing resumes and conversations with your cruise leaders. But everyone aboard takes turns steering, crewing, preparing meals, and cleaning up.

Q. Who takes the boat in and out of harbors?
A. Everyone who wants to and has prior experience, should be able to do this, and get more experience picking up moorings or anchoring while the rest of the crew handle the lines. But anyone who wants to just lay back and do nothing, that’s fine too! However, it is not “fine” if the “designated skipper” decides only he or she will drive the boat, regardless of the abilities of others aboard. Happily, if that occurs, cruise leader diplomacy steps in 😊.

Q. Do we always have to eat on the boat or are there opportunities to go ashore, even alone if we want?
A. The itinerary has lots of opportunities to get off the boats, with places to explore and sample native food. Sometimes these are planned in advance, sometimes plans are made as the cruise progresses. There is usually a “break-the-ice” Welcome Party the first night, and a fun “dregs” party the last night or near the end of the cruise when boats get creative with their left-over provisions.

Q.  Is there a cook on each boat?
A. No hired cook aboard, remember, this is “bareboating.” All you need to prepare and serve meals (pots, pans, cutlery, plates and more) is aboard each boat. We recommend rotating who cooks the meals that you plan to have aboard, but sometimes you luck out with a participant who is a culinary expert and is happy to putter around in the galley while you sip cocktails in the cockpit 😊.

Q. Do we have to buy food during the cruise?
A. In areas like the Caribbean, where provisioning packages are available through the charter company, we order the meals in advance and this is placed aboard the morning before you take off. Two participants should inventory the goods against the list provided by the charter company and then put it all away so someone knows where each item is stowed. In some countries like Greece, we just start you off with a starter pack, a couple of breakfasts and lunches, because eating ashore in the tavernas and bistros is half the fun 😊!  Each boat crew puts together a kitty that is replenished along the way to cover shopping for goodies in local markets to cook aboard, which is also great fun. Normally, any meals and drinks ashore are on you. As are beverages other than water on the boat. And, by the way, we do encourage you to purchase whatever alcoholic beverages you like to have aboard for cocktail hour and dinner, but please, please do not drink while the boat is underway! And while we are talking about “don’ts” we ask that if you smoke, you never do it below decks and if on deck you go to the furthest point on the boat downwind, so no smoke hits the other crew members. We request no cigars on board please.

Q. How much do we have to pay up front, when is the full amount due? And how much should we plan on out of pocket during the cruise?
A. When you sign up 30% of the total per person trip fee is due, and generally speaking the final payment is due about 180 days prior to the start of the sailing flotilla holiday cruise. All of this is spelled out on the webpage and materials you receive once confirmed on a cruise. Also on the cruise webpage and what we send you is information on what your package covers, and what other expenses you should be prepared for. We even give you the exchange rate if the cruise is in an area where Euros or other currency is used. Nowadays, in Europe, you can usually find ATMs in the larger towns.

So, did I answer all your questions? Are you convinced this is a great way to see the world under sail? Which flotilla cruise appeals to you most?

Call 888-454-7015 to sign up for an exciting Colgate Sailing Adventures® Flotilla Cruise!


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