Distant Shores Sailing Newsletters

Caribbean Sailing Strategies

Do you dream of sailing the Caribbean someday? Are you looking for your next tropical sailing destination?
Come along with us as we explore the Leeward Islands of the Caribbean and show our process for route planning. We show how we use the PredictWind app for weather forecasting and route planning to design a comfortable cruise in the Caribbean as we sail from St. Martin to Anguilla, St. Barts, Saba and then do a nightsail to the British Virgin Islands.



Two devastating hurricanes - Hurricanes Irma and Maria - hit the British Virgin Islands in 2017. In this video (in 2019), we return to sail the BVI and get an update on recovery efforts before making a fabulous 3-day offshore passage to the Turks and Caicos.

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Distant Shores Meet SV Delos

This time on Distant Shores we run our boat up on the beach in Antigua. We get invited to a pirate birthday party, change the zinc on our Varifold propeller and meet up with YouTubers aboard SV Delos.

Drone footage beaching Distant Shores courtesy of SV Delos
Additional Footage Courtesy SV Delos
Additional Footage Courtesy of Endless Playtime



This time on Distant Shores sail from Antigua to Montserrat… Nevis… Statia and St Barts - and talk gadgets with Brian and Karin on SV Delos…

Check out Delos Channel Here https://www.youtube.com/svdelos
And thanks to Brian for the excellent aerial drone shot of the Antigua anchorage :-)

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Sailing Antigua to Anguilla - Clearing in and Cruising Permits



By Sheryl Shard, copyright 2016. All rights reserved.


antigua-deep-bay - 2Deep 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.

antigua-jolly-harbourDistant 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.
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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.

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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.

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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.

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"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.

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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.

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

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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.

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