By Sheryl Shard, copyright 2016. All rights reserved.

Deep Bay, Antigua

It was amazing how, immediately following Antigua Sailing Week (April 23-29, 2016), cruising boats, race boats and mega yachts alike cleared out of Antigua. The event definitely marked the end of the boating season on this Caribbean island.

Many sailors began their voyages south or north following the event to be out of the Hurricane Belt by June, race boats set sail to various destinations to participate in other regattas and mega yachts headed to sea to make their annual transatlantic crossing to the Mediterranean for the summer months.

Like us, some cruising sailors prepared to carry on their exploration of the Caribbean having organized safe hurricane storage of their boats in approved boat yards, in our case Bobby’s Boat Yard Airport Road in St. Maarten, or having plans to run to a hurricane hole or make a quick passage out of the Hurricane Belt when early warning forecasts were given. But there was still a month of safe cruising time left and we were going to enjoy every minute of it.

Distant Shores II at Jolly Harbour, Antigua, a good place to provision before a passage.

We’d had a great cruise around Antigua (see previous newsletter) which we concluded at Jolly Harbour anchoring in the outer harbour so we could easily leave in the dark to make a night sail north to our next destination, Anguilla. It would be a 95 nm passage and we wanted to sail overnight so that we would be approaching the island and arriving in Road Bay, the Port of Entry, in daylight. (Blowing Point on the south coast is also a Port of Entry but the anchorage is rolly and is a busy ferry port so it's not recommended for visiting yachts.)

We raised anchor at midnight in Jolly Harbour after a brief rest and set sail. Conditions were good throughout the night and day. Distant Shores sliced through the sapphire blue sea passing St. Kitts and Nevis, Stacia, St. Barths, Saba and St. Maarten/St. Martin arriving late afternoon on May 5th at Road Bay, Anguilla.

Road Bay, Anguilla

There are lots of moorings in Road Bay but they are all privately owned so visiting yachts are requested to anchor. No problem. It's a large anchorage and there is always lots of room however in the winter months, when there is often swell from the north, there could be a bit of a roll in here but we had peaceful conditions.

It was late afternoon when we dropped the hook, too late to clear in with Customs and Immigration so we stayed on board with our yellow “Q” flag flying on the starboard halyard to indicate that we still had to clear in and enjoyed a sunset meal in the cockpit before calling it an early night. Tomorrow was the start of the annual Anguilla Regatta and we wanted to be well rested to film it.

Anguilla, is a British overseas territory. The name Anguilla is taken from an earlier Spanish word anguila, French anguille, or Italian anguilla, all meaning “eel” due to the island's shape. It’s 16 miles long with a population of 13,450. Anguilla is a small quiet island famous for its very high-end hotels and restaurants and the most exquisite beaches. However, we discovered there are lots of great options for mid-priced travel here too.

The clear water, golden sand and open horizon at Mead's Bay Beach, Anguilla

You can see Anguilla easily from the French side of St. Martin. It takes less than 2 hours to sail from St. Martin as opposed to 12 hours from Antigua so most of the yachts participating in the Anguilla Regatta were coming over from St. Martin and St. Maarten. Cruising yachts from other countries also participated with all proceeds from the regatta going to the Anguilla Youth Sailing Association. Sailing is the national sport of Anguilla and scholarships are made available so that every child can learn to sail if they want to.

Anguilla Youth Sailing Association, Road Bay, makes sure every child can learn to sail.

The next morning we took the dinghy to the large dinghy dock which is in the middle of the beach. There is also a large commercial dock to the left with a marked channel where cargo ships come to so is restricted. However if you need water you can call the port authority "Road Bay Port" on VHF 16 and arrange a time to come over for water. We didn't ask about fuel but this seems difficult. Top up before you sail over is the best advice we got.

The Anguilla Customs, Immigration and Port Authority offices are all conveniently located right by the dinghy dock and all the officers are charming.

"Welcome to Anguilla. Welcome to Paradise," the Immigration officer greeted us as we walked in.

Although super friendly, Anguilla has the most restrictions for yachts on where you can cruise, specific hours you can sail to certain places, where you can anchor and where mooring balls must be used as compared to any other island we have visited in the Caribbean. This is an attempt to protect their small but remarkable marine resources but it can be frustrating and expensive if you don't plan carefully.

Paul swimming off the beach at Road Bay, Anguilla

Please don't be put off! If you anchor in Road Bay, which has a truly lovely crescent beach with charming beach bars, and explore Anguilla by rental car or taxi you pay no cruising fees or entrance/departure fees. This is well worth doing. The island is pristine with the most beautiful beaches with wide open horizons and the clearest water you have ever seen.

If you want to sail out to the little out islands such as Sandy Island (you can also take a little ferry there for $10 US return/person), Prickly Pear Cays or Dog Island or any of the other bays around the island, day permits must be purchased. For our Southerly 49 sailboat a day permit was $50 US per day and expired at midnight.

Beach at Sandy Island with boats in mooring field in distance.


Paul enjoying a Margarita at the Sandy Island Beach Bar

Once cleared in you are only allowed to sail in daylight hours, defined as between the hours of 6:00 a.m. to 7:00 p.m.

There is one other anchorage where you can stay overnight in your boat in Anguilla besides Road Bay and that is Crocus Bay, just one bay east from Road Bay, but since day permits expire at midnight, you pay for 2 days to stay overnight in Crocus Bay. i.e. $100 US. We didn't bother and drove there instead.

Cruising permits are also available for one week, one month and one year.

After we'd been in Anguilla for a few days we learned that if you call ahead and have an Anguilla Marine Agent clear you in (required for mega yachts but not cruising boats) you may be granted permission to stay overnight in Rendezvous Bay on the south coast which is quite lovely. (Rates are about $150 US per hour however.)

Cruising sailors are generally free spirits and are put off by these kinds of restrictions not to mention the complication and cost involved so just don’t go there. To be honest, we have been put off by this ourselves and have changed our minds several times when we considered sailing to Anguilla. There are so many other great Caribbean destinations you can sail to and explore freely and inexpensively. However, we knew Anguilla was a special place (we had cruised there 20 years ago before the restrictions were brought in and also stopped for a couple of nights in Road Bay in 2008) so were determined to check it out and learn how things worked these days when you arrive by boat and were glad we did.

There is talk of a marina being built in Road Bay (where the old salt pond is located behind the beach) so work is being done to make Anguilla more boater friendly while still protecting their the beautiful but limited marine resources of this small nation.

More on cruising Anguilla in the next newsletter…

Have you sailed to or visited Anguilla? What was your experience? We'd love to hear all about it in the comments below. Thanks!

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Sheryl and Paul Shard have now been cruising internationally for over 25 years. They are sailing authors, instructors/consultants and the fun-loving hosts of the Distant Shores sailing adventure TV series (AWE TV, Nautical Channel and Vimeo on Demand). The Distant Shores series profiles the world's best sailing destinations and provides insights into the joys and challenges of living aboard a cruising sailboat. The shows are also available on DVD and as HD downloads.

By Paul Shard, copyright 2016. All rights reserved.

From Falmouth Harbour Antigua we set sail in 18-20 knots for one of those dream Caribbean sailing days. Perfect breezes aft of the beam, sparkling blue seas, sun and the dramatic coast of Antigua in the background.




We are on a broad reach and then jibe to come in closer to admire the coast past Jolly Harbour and the beaches on the west side of Antigua.

We drop anchor in Deep Bay on the west of Antigua.


In the mouth of the bay is the wreck of the Andes, and we dive to investigate.

The Andes was carrying a load of pitch, which caught fire as she was approaching Antigua. She was denied permission to enter St John's (so as not to set others on fire). She sank in nearby Deep Bay in 1905 in less than 10 meters of water. Her funnel breaks the surface and she is easily seen by snorkelers.

Deep bay is a very calm and pretty anchorage.
Overlooking Deep Bay are the fortifications of Fort Barrington, built in 1779 to defend the approaches to the harbour and town of St John's.

Its a relatively easy 10-minute hike to the well-preserved fort…

Friends Ken & Lynn on Silverheels III shot this as we sailed along the coast of Antigua.


Anchored for the night off Bird Island on the North Eastern corner of Antigua. A wild and remote spot where the reef and these tiny islands break the big Atlantic swell for a nicely sheltered spot. There is a lot to see sailing Antigua!


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By Sheryl Shard, copyright 2016. All rights reserved.


The Antigua Classic Yacht Regatta (ACYR), held every April in the Caribbean island of Antigua, is an event that, for many years, Paul and I have been hoping to attend. This year we made it happen, sailing down from the British Virgin Islands (see previous newsletter), for the 29th annual ACYR.



Every year in April between 50 and 60 yachts participate in the Antigua Classic Yacht Regatta including traditional craft from the islands, classic ketches, sloops, schooners and yawls, together with beautiful modern yachts built in the Spirit of Tradition, occasionally J Class yachts and a few Tall Ships.



Based in Falmouth Harbour at the Antigua Yacht Club Marina, headquarters for the ACYR with many after-race parties held at the historic Nelson’s Dockyard in English Harbour, you feel as if you have travelled back in time seeing all these period yachts arriving and departing to sail as a spectacular fleet around the daily race courses.





Carriacou yachts are traditional island sloops and have a class of their own in the regatta. These boats, once used as island traders, are still built in the Grenadian island of Carriacou.





One of the after-race events this year was an outdoor screening at Nelson’s Dockyard of the award-winning documentary “Vanishing Sail” about one of the last boat builders of Carriacou yachts. (The film has since inspired his sons to continue the tradition.) Watching this beautiful film under the stars amongst the old barracks and workshops of the former British Naval Base for the West Indies built in the 1700’s with the standing-room-only crowd of classic and traditional yacht sailors was a moving experience. The film will soon be available on DVD through the Vanishing Sail website where you can view the trailer.



We were fortunate to get a spot at the quay in Nelson’s Dockyard for the week of the regatta.





Nelson’s Dockyard Marina is just a 10-minute walk to Falmouth Harbour and the Antigua Yacht Club Marina from there where all the yachts participating were based for the duration of the regatta.



Having the yachts berthed all together in one place at the Antigua Yacht Club Marina created a convivial atmosphere and made it easy to dock-walk to view these floating works of art. It was also a great way to meet the special people that sail them and care for them.



Before we went out to film the races and events each day for the Distant Shores sailing TV series, Paul and I would get up early to enjoy morning walks along the forested trails around English Harbour and through ruins of the old fortress. Good spots to watch the races from if you are shorebound.






One morning we had a close-up encounter with a young mongoose.



Tropical showers brought out colourful flowers that bloomed brightly along the trails and hillsides overlooking the sea.



Working with other marine photographers and videographers on the press boat at events such as the Antigua Classic Yacht Regatta is always a special time for us since, not only do we love the events we’re documenting for the Distant Shores sailing TV series, it’s a great time to catch up with fellow marine journalists and partners in the marine industry who sponsor the regatta.



The wind was generally light during this year’s ACYR which was unfortunate for participants but nice for spectators since it meant that all the yachts were flying maximum sails creating a sight to behold.







The Antigua Classic Yacht Regatta marks the end of the Caribbean sailing season for many of these beautiful yachts and several were preparing to cross the Atlantic Ocean following the regatta to sail and/or charter in the Mediterranean for the summer months. If you’re curious about what it’s like to sail in the Med check out the Distant Shores TV YouTube Channel where we’ve posted full 30-minute episodes from season 1 and 2 of Distant Shores about sailing in the Mediterranean.



During the regatta, Paul also spent a day sailing aboard the lovely schooner S/V Heron, built, owned, and captained by Bonnie Schmidt and Nigel Bower. You can buy a berth by on this fine vessel to sail on various legs from the New England coast all the way south to the Grenadines. Paul interviewed some of the charter guests aboard S/V Heron who were living their dream to sail aboard a classic yacht in the tropics, including journalists from WoodenBoat, a magazine for wooden boat owners, builders and designers.

Schooner S/V Heron

When we first arrived in Antigua for the start of the Antigua Classic Yacht Regatta we were pleasantly surprised to find that many long-time cruising friends, who we have shared anchorages with over the years, come each year to crew aboard these classic yachts or to work as volunteers to keep the Antigua Classic Yacht Regatta running smoothly. Even if you aren’t racing there are lots of ways to get involved as volunteers and it is such a good time!

Attending the Antigua Classic Yacht Regatta became quite a social occasion for us as we got caught up with friends and colleagues we hadn’t seen for a while, danced to the great bands in the evenings and, of course, shared a drink or two after a day of filming. Every afternoon there was free Mount Gay Rum Tasting along with other events such as cocktail making contests, BBQ’s and daily prize-giving.

The last day was especially fun with Gig Races at English Harbour. A gig is a small rowboat or sailing boat generally used to taxi the ship’s captain ashore.

This was followed by a Cream Tea at the Admiral’s Inn, Nelson’s Dockyard. It was a great opportunity for me to wear the hat my British sailing friend, Elizabeth Pattison, made for me. You meet Elizabeth in the Chichester Harbour episode of Distant Shores in season 7, episode 1.









As the ACYR website says, “The sailing combined with Antiguan hospitality, plenty of rum, sunshine, and great camaraderie in a friendly relaxed atmosphere, places the Antigua Classic Yacht Regatta, in a class of its own.”

Next year the Antigua Classic Yacht Regatta celebrates its 30th anniversary so be sure to mark your calendar. It will be held April 19-25, 2017.


Sheryl and Paul Shard have now been cruising internationally for 25 years. They are sailing authors, instructors/consultants and the fun-loving hosts of the Distant Shores sailing adventure TV series (AWE TV, Nautical Channel, Vimeo on Demand). The Distant Shores series profiles the world's best sailing destinations and provides insights into the joys and challenges of living aboard a cruising sailboat. The shows are also available on DVD and as HD downloads.