Little Compass RoseCaribbean Compass   September 2015

Tip-Top Tips for First-Time Caribbean Cruisers

Planning your first Caribbean cruising experience? We asked a wide selection of experienced Caribbean cruisers for their top tips just for you. Their suggestions ranged from navigation advice to island etiquette enlightenment, and several common themes emerged.
Many thanks to everyone who so generously shared the wisdom of their experience.

• Objective Advice

Nikki Segal, Skipping Stone (Pearson 530)
Make easting! As the current generally sets to the west between the Eastern Caribbean islands, we always try to make as much easting as possible, early on in the trip.

Matthew Watters, Lady Marigot (Privilege 585 catamaran)
Make a point of checking for northerly swells. They can make many usually comfortable anchorages untenable.  Check sites such as ( and look at the “surf” animations. If you see lots of south-facing arrows and dramatically coloured bands entering the islands, then it’s time to select anchorages that are sheltered in the north and open in the south. Adjust your route to avoid any bays exposed to the north during periods when the swells are at their worst.

The Meteo France Antilles Large forecast ( will also warn of any prolonged northerly swells reaching the Eastern Caribbean. These swells are generated when major storms affect the mainland USA and roll out into the Atlantic. So if you’re hearing about major snowstorms up north, a few days later it is likely swells will be appearing in parts of the Caribbean.

Really bad swells can even make usually navigable channels untenable, as swell and surf action stirs up the bottom and makes eyeball navigation difficult.
Don Street, formerly of Iolaire (44-foot 1905 engineless yawl)
Author of Street’s Cruising Guides,

Do not enter harbors at night. When entering and leaving harbors forget about your chart plotter: use eyeball navigation. When relying on eyeball navigation do not head east before 1100 or west after 1400.
The Eastern Caribbean is a fabulous cruising area and despite what is said to the contrary it is not overcrowded if one is willing to get off the beaten track.

Rosie Burr and Sim Hoggarth, Wandering Star (44-foot custom steel cutter)
Invest in the best possible anchor(s) and gear and go at least one size up from the recommended size. Anchoring technology has improved markedly in recent years and upgrading is a big improvement if your boat has one of the older designs. Having faith in your anchor is one of the must-haves for Caribbean cruising and leaves you free to worry about more important issues (like have we got enough ice for the sundowners).

Ellen Birrell, Boldly Go (Jeanneau Sun Odyssey 40)
Be aware of anchoring. Just about the time you think you really get it, a new set of conditions arise and you get to learn more, more, more. (Mooring balls present their own set of challenges: “renter beware”!)

Ellen’s husband, Jim Hutchins, further explains:
Discuss techniques and considerations with fellow cruisers; there are many issues concerning proper anchoring. How are the other boats around you attached to the ground? All boats need space to swing, not just the big ones: basic scope should be five times depth plus one boat length.
The anchor must be set. There are several ways to set one but first you’ll need a bottom that gives it a chance. Stay with the boat until you are sure the anchor is set. I’m never sure until I’ve correctly pulled back with full throttle and then only if there is no wind shift.
After you have a proper position and a well-set anchor, stay aware of the weather at all times: aboard, onshore, awake or asleep. A good skipper awakes to a weather change like a mother to the rustle of her newborn child.

Monica Pisani, Journey (42-foot Tatoosh sloop)
Two years ago, when we started our sailing adventure, we made two technology purchases that stood out as they were used repeatedly providing information of all kinds.
One was a WiFi booster. After extensive research, we purchased the Ubiquiti Bullet from Island Times PC. It came packaged in a waterproof case with an antenna, which we mounted on our bimini support. It consistently provided us with WiFi at some of the most unexpected places.

The second item was our iPad with the Garmin Blue Chart App. The iPad has to have a GPS antenna built in, so it works via satellite signal, not needing to be connected to the internet. The iPad was our backup chart plotter and our trip planner. It is integrated with Active Captain, giving us access to detailed information on marinas and anchorages, plus reviews from other yachties. Extremely helpful, and we used it constantly.

Tony Sanpere, Cayenne III (51-foot Beneteau Idylle), Cayennita Grande (J/36), Nauticayenne (Catalina 30), et al
Carrying lots of spare parts is very important. Nothing’s worse than to be stuck in an anchorage or marina waiting for a part to arrive. Also, my boat’s shore power let me plug at both 110 and 220 volts.
Angelika Grüner, Angelos (Colin Archer steel double-ender)
If you need boat parts from Europe, there is a company in the UK called Parts will arrive in the Caribbean within three to five days for a very reasonable price.

Don Street
Equip yourself with a full set of Imray Iolaire charts of the area that you plan to cruise. Read the backs of the charts to find information on tides, anchoring, ground swells and harbor piloting directions needed to enter some of the small harbors.
Jan deGroot, Ring Andersen (114-foot 1948 ketch), et al

I have cruised the entire range of Caribbean islands quite extensively. I was the operator of a large charter yacht during the Seventies and have since returned by chartering a bareboat on many occasions. I know every rock, reef and bump in the area. My most important piece of advice is: Don’t be as cocky and arrogant as I am. Read the cruising guides.
Last February with some friends I chartered a boat in Rodney Bay, St. Lucia for a trip to Grenada. We set sail for Soufriere, where we intended to spend the night before heading for St. Vincent. When we entered the Bay, a fellow in a small speedboat came alongside and said that he would direct us to one of his mooring buoys. I said okay and followed him. After helping us tie a line to the buoy, he offered to take us ashore. I thought that would be a good idea: we wouldn’t have to go through the rigmarole of launching our dinghy and attaching the outboard motor. I asked him what the cost was for the use of his buoy and the shore ferrying. He did not answer, but I thought it would probably be a reasonable charge. That was my first mistake; I should have insisted on a price.

After we had strolled around the town, he took us back to our boat. I asked, “What do I owe you?” He answered, “Three hundred dollars.” “What?” I said, “You’ve got to be kidding!” After going back and forth, we finally settled on a price that I thought was still outrageous.

As I settled in my bunk that evening, I turned the pages of Chris Doyle’s Sailors Guide to the Windward Islands, a copy of which was part of the boat’s inventory. So far I had paid no attention to this book since I figured there wouldn’t be anything in it that I didn’t already know. I was wrong! The section about Soufriere clearly states that the buoys belong to the Soufriere Marine Management Association and Rangers will come and collect the fee, which amounts to EC$54. It also says that if you need help to tie a line to the buoy, a fee of EC$5, maximum EC$10, is the norm.
So, don’t be a know-it-all like me! Check Chris Doyle’s and other cruising guides before letting go of your mooring lines or lifting the anchor.

Kumploy Gomes, Dee (Gulfstar 45 Hirsch)
Bring enough money and some more! Get ready for high-priced items, from nautical stuff to imported food and clothes. And, if you love bread, learn how to bake it yourself.

Sean Fuller, Kaiso (Sovereign 40)
Protecting a boat’s systems against the Caribbean’s strong UV and high humidity is vital. The humidity in particular leads to much higher rates of corrosion than we are used to in the north.
After a day of sailing, or when leaving the boat laid up for a while, use a hose to wash out any salt crystals which may linger and cause problems further down the line. Keep a good selection of oil and silicon lubricants and cleaners onboard. Chandleries and auto stores tend to keep a large selection of these products, with each serving a different purpose.

Regularly hosing down and protecting exposed parts will increase service life. Get canvas covers for the wheel steering and the winches, and protect any areas more prone to corrosion, i.e. between dissimilar metals. (I once had a big problem with my steering system because the stainless steel bolts welded themselves into the aluminium casting that the compass binnacle sits on.) Lanocote, made from natural lanolin is excellent for protecting boat systems against corrosion. If you have a traditional Lewmar steering system with exposed bolts in contact with aluminum, you may find it preferable to remove the bolts, coat them in lanolin, and then re-tighten them.
Pay special attention to the stopcocks. Some European boats have stopcock handles that are made of poor quality steel and these will soon rust in the tropics. It may be best to have them changed earlier on or kept well coated in grease.
Spraying the engine with a lubricant like WD40 should help prevent surface rust, but some rusting may be inevitable.
Chrome fittings are prone to fast rates of corrosion and should be regularly washed down and polished, especially in areas such as the heads that may have less ventilation.

The strong UV will damage safety equipment and other fittings where they have plastic components exposed to the sun. All hatches made of acrylic should have canvas covers. Sails’ stitching and UV strips will break down more quickly, so keep an eye on these.
Ruth and Niels Lund, Baraka (Endurance 43)
Be aware that during their busy season, marine service companies on the islands are usually fully stretched, so book ahead and don’t assume instant attention is always possible. Waiting is hard when you want to get sailing, as is paying a little more, but it beats having to redo less than professional work and waste more time and money.

Obtain more than one quote and ask the right questions about guarantees, delivery expectations, materials and work methods. Use the local cruisers’ networks (VHF radio and internet) to confirm excellence and seek out the core of technically skilled people that exist throughout the island chain.

Ken Goodings, Silverheels III (Niagara 35)
Security is a consideration. When at anchor, never retire to bed in your unlocked boat with a dark cockpit. A moderately bright cockpit light combined with a well-secured companionway is a good deterrent to would-be boarders.

Candy Colley, Syrius (Endurance 40)
The Caribbean Safety and Security Net ( should get a mention.

Art Ross, Coaster (1966 Pearson), Stewball (Compac 19)
As a USCG Auxiliary Officer and a Certified Vessel Safety examiner, I preface my safety lessons with this:
Whether or not you’re a motor boater or a sailor, or you’ve seen the Southern Cross or have crossed the equator, the green flash or the high latitudes, we each have the opportunity to improve our lives that comes with the promise of “another day”. When teaching safe boating classes I keep this saying by Larry Pardey on the blackboard: “No amount of skill, no equipment, and no boat will keep you from disaster if you don’t develop the most important seagoing skill of all: a complete fear of falling overboard.”

• Subjective Advice

Joao Gomes, Dee (Gulfstar 45 Hirsch)
Bring a lot of patience to deal with the Caribbean time, especially if you plan to do some work while sailing and living aboard in the Caribbean.

Chris May, Troubador (Beneteau Idylle 15.50)
Patience. Island life moves at a different pace. Don’t forget why you wanted to escape when you’re waiting for an official or for your lunch check.

Nicola Cornwell, Pandora (Hanse 470e)
Have patience. You’re on island time now. Once you realize this you’ll learn to love it.

Sue Klumb, Orion (Out Island 41)
Don’t compare. Just because things are handled in different ways doesn’t make them wrong. Relax, feel the spirit of the island(s), embrace the change of pace and enjoy the culture.

Chris Doyle, Ti Kanot (42-foot catamaran)
Author, Doyle’s Cruising Guides,
After an Atlantic passage there will usually be a bunch of things broken down. But right after arrival is the worst time to get them fixed because all the other arriving boats have the same problem. If the broken bits are not that important, consider waiting to get them fixed, or go sailing and fix them somewhere else.

Meanwhile, have fun! Enjoy our beaches; they are probably what you have been dreaming about. But the Caribbean also has some magnificent rainforests, spectacular waterfalls and great hiking: explore ashore.
Get to know locals. Visit our yacht clubs, take part in informal races, maybe go on a run with the Hash House Harriers, ask about hiking clubs.
But you don’t have to do it all on the first day. Take it easy and enjoy!

Willie Haskins, Liahona (Nautical 60 ketch)
Spend enough time on each island to appreciate the people, food, music, arts, crafts, and natural wonders of each island. Too often we encounter cruisers who speed-sail through the Caribbean on their way to the Pacific, and think they have seen it all after spending a couple of days here and a couple of days there. We’ve been in the Caribbean for five years, and still have not seen it all.
A corollary to this advice is to not be put off by what others have said about someplace being “dirty” or “unsafe”. We have found each island/country we visited to be unique and worth exploring, and some of our favorite places are those that others have advised us to not bother going to visit!

Mark Denebeim, Sanctuary (Island Spirit 37 catamaran)
Get to know local people (other than tour guides, bartenders and Customs officers), and not just fellow cruisers. After all, it is a people world!

Tor Pinney, Silverheels (Pearson 424 ketch)
Remember, we’re self-invited guests here. Be friendly, be patient, be respectful, be grateful.

Devi Sharp, formerly of Arctic Tern (Island Packet 45)
Say “hello” or “morning” to islanders on the street. You are a visitor and it is expected that you will reach out first. You might be rewarded with a big smile or a return “morning”, or you might end up in a conversation with a friendly person. This simple act will open doors to the island.

Eat local food. Go to the fresh produce markets and try new fruits and vegetables. If you do not know how to prepare a fruit or vegetable, just ask the market vendor. People love to share their advice with you and you will have a new friend at the market.
Petra and JanWillem Versol, Witte Raaf (ALC40 ketch)
Don’t shoo away the boat boys. Try to give them some business; they have a right to earn a living. Always try to negotiate a fair deal. Paying too much will spoil the market for other cruisers; paying too little is unfair. If you are fair with them, they will be fair with you and once you have earned their respect, they will even welcome you at their homes and you’ll learn a lot about the Caribbean way of life — from the inside.

Angelika Grüner
Because many local people live on relatively small islands, everybody knows everybody. If you behave badly everybody will know it. Don’t think you are something special because you own a boat. 
In some islands locals come to the anchored yachts in their little boats or on surfboards, offering fruits and vegetables. Please consider that this is the only source of income for many of the islanders. Try to buy at least one thing. The produce might be a bit higher in price than at the market, but it is brought directly from the garden to you. Additionally you get a nice contact. Most locals now have a cell phone, so when sailing up and down the islands you can text your favorite veggie vendor, and when you arrive in the bay all your ordered goodies will be waiting for you.

Explore not only wind and sea, but also the people, their food, their islands. Hire a local guy who will guide you into his forest, to the waterfalls, maybe to meet his family.
Most important: People are very nice and kindly if you accept them as they are; don’t try to change them. If you are long enough in the Caribbean, it is you who will change, and get adapted to the Caribbean lifestyle.

Tom and Harriet Linskey, Hands Across the Sea (Dolphin 460 catamaran)
Get off the tourist/yachtie track and go visit a local school — the further removed from the anchorage or marina, the better. Introduce yourselves to the principal, offer to help out, and volunteer your time at the school. It’s fun and rewarding and you’ll discover the true beauty of the Caribbean: the lovely kids.

Carl and Mary Heckrotte, Camryka (Westerly 36)
Wherever in the Caribbean you may anchor or dock, get off the boat, see all that your new location has to offer and meet everyone you can, both locals and fellow cruisers. When all is said and done, the friends you meet along the way and the places you visit will become a part of your heart and soul for the rest of your life. Yes, you need to take ordinary precautions to keep yourself and your boat safe (maybe more so than 20 or 30 years ago) but keep in mind that 99.9 percent of the folks along your path are good and interesting and will respond positively to your friendliness.

Frank Virgintino, Raffles Light (65-foot Garden ketch)
Author of Free Cruising Guides,
Jumping to conclusions can destroy an adventure like cruising through the Caribbean. Reflect carefully on everything before making a decision. You are outside your culture, outside your geographic area, outside all of what you know about cruising except the actual “being on the boat” part. This advice applies to all areas of cruising in the Caribbean.
For example, do not assume that every boat boy is there to harass you or steal from you. Do not assume that for each repair, every person who comes to fix the boat is dishonest. Do not assume that just because you saw another sailboat sail out of the bay to the east that you can do it also; their draft may have been less than yours or it may have been high tide when they left. Do not assume because there is a spigot that you are allowed to take water or that the water is potable. Etcetera.

Mary Stone, M/V Ms. Astor (Californian 42 trawler)
I may not qualify as a seasoned cruiser, but it feels like I am seasoned and even overripe sometimes! I have only been cruising single-handed on Ms. Astor for 20 years. My advice is broad and related to the whole context of thriving in the Caribbean. It covers all topics, events and issues.

Mary’s 4 Laws of Thriving in the Caribbean
1) You will figure it out.
2) Then you will get over it.
3) It will always take longer and cost more.
4) But by then it doesn't matter; move on.
… and some days it is short cycle: reset, go to Number 1 and start over.
This free advice comes with a money-back guarantee. Your mileage may vary.

Bill and JoAnne Harris, Ultra (53-foot custom trimaran)
Many of our days are filled with scuba diving, hiking, exploring, making new friends, fun cruiser events, and more. However, there are the days or sometimes weeks that are full of boat repairs or projects, waiting for a good weather window, etcetera. So a positive attitude with a huge side of patience and flexibility gets us through these difficult times when they arise.

Cruising the Caribbean, you will learn much about yourself, since you will sometimes be pushed to your breaking point. An extremely long passage might end up being quite different than expected, or you might have to perform a tremendously difficult task that you have never done before. After waking up and planning an amazing day of exploration in your new anchorage, you discover a broken head that must be repaired ASAP. Since there is not an 800 number to call, you are the guy for the job. This can easily turn into an all-day project. However, at the end of the day, when you are sipping your rum and Coke, you will feel proud of yourself for what you have accomplished.
So the best advice we can give is, before you set sail, be sure to stock your “spice rack” with the most important seasoning of all, great attitude! A little dash of it every day will be the best recipe for a very happy and fulfilling life aboard.

Finally, a plug for Caribbean Compass. If there is a Caribbean cruising topic you are interested in, visit our Back Issue Archive at and use the easy “search” feature. There’s a wealth of information there, reflecting many years of Caribbean cruisers’ first-hand experiences.


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