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destinations-caribbean-way_south-largeThe past year had been filled with adventures – a new boat built in England, the transatlantic passage bringing her across to our side of the Atlantic Ocean, a winter in the Caribbean, spring in the Out Islands of the Bahamas, and a fast trip home to Lake Ontario via New York and the Erie Canal.

After 19 years of sailing our old Classic 37 sailboat, Two-Step, we had to show the folks at home our new Southerly 42 sailboat, Distant Shores. With her unique variable-draft swing-keel, she draws 2 feet 10 inches with the keel up, so many new places were open for us to explore. After a great summer at home in Canada, we headed back south for another winter in the Bahamas and Caribbean

Heading back down the Erie Canal to New York and then offshore to Cape May we arrived in the Chesapeake Bay in time for the boat show in Annapolis, Maryland. It's a wonderful stop on a voyage south; there are so many great deals to be had when preparing your boat for a long-term cruise. Too many, in fact. Our credit cards were smoking and the boat was loaded with new gizmos and gear when we finally tore ourselves away to set sail down the Bay!

We love the trip south down the Intracoastal Waterway. We had planned a slow meandering trip "down the ditch" to visit all the little coastal towns and historic cities along the way, but this year the temperatures stayed at freezing for far too long and as we scraped off the frost in Beaufort, NC in early November, we said, "The heck with this! Let's just get south!"

From Beaufort, we made several offshore jumps stopping at McClellanville, SC, Charleston SC, Fernandina Beach FL, and then prepared for our crossing to the Bahamas.

Matt Heron, an Australian ex-pat working in Dubai, who is thinking of purchasing a Southerly 42 like ours, flew in to join us as guest crew to the Bahamas, as well as our upcoming offshore passage to Antigua. Matt is planning to do a lot of passage-making with his own boat in the future so he wanted to see how the boat performed offshore and get some hands-on with an experienced crew.

We had planned a few days in Florida to prepare the boat and allow Matt to get over his jet lag and get accustomed to the boat. But we had a weather window with the desired southerly winds on the day that he arrived so, with his blessing, we cast off for a night sail across the Gulf Stream immediately. This was so we could avoid a big front coming down the coast that would keep us in Florida for another week.

Conditions were fine but perky for the crossing but throughout the night the winds rose and by the time we made landfall near West End, the winds were near 30 knots with rising seas from the SW. We decided not to try to enter the harbour. Instead we headed north in the lee of the Abacos and made for Walker Cay. The winds continued to increase and by the afternoon we were seeing 40 knots with gusts of 50! We had the main sail double-reefed and were sailing over 6 knots upwind even after we furled the self-tacking jib away altogether! We were very proud of Distant Shores in these heavy weather conditions – and of Matt too. The stronger the winds blew, the happier he seemed to be. The wind was still blowing a solid 40 knots as we swung up the keel to slip onto the banks behind Walkers Cay and dropped the hook in smooth seas in the protection of the islands.

Once the wind subsided we had very pleasant conditions for the rest of the Abaco cruise as we island-hopped eastwards across shallow banks to Marsh Harbour. Matt is a kite surfer and brought his gear, so we had fun swinging up the keel and poking into shallow coves that had the perfect sandy beaches where Matt could launch his kite and play around the boat. Although Distant Shores is a monohull, she is designed to be beachable (with the keel up) so we enjoyed demonstrating this ability as we creek-crawled in the mangroves or dried out on gorgeous remote sandbars.

We have now travelled over 13,000 nautical miles aboard our Southerly 42 but the next offshore leg was one of the toughest we have had to date. We had planned an "uphill" passage of 1,100 miles from the Bahamas to get us directly to Antigua. It was early December by this time and possibly past the best time to do this (if there is a best time since the prevailing east to northeast winds are always on the nose) but if you play the winds right it's a fast way to get south to the wonderful islands of the Caribbean.

The strategy is this. Wait for an approaching front whereby the winds strengthen and go to the south, then clock around to west and northwest behind you. This gives you the opportunity to make your way east. Then, as the winds settle back into their normal trade wind pattern, turn right and head south with the winds on your beam.

We watched the weather and finally made the jump from Marsh Harbour. We faced all points of sail on the first two days, from strong south winds clocking around to west and northwest behind us as they built in strength. But throughout the pounding conditions, Distant Shores did a great job. Matt was certainly the most cheerful, tough and optimistic crew anyone could hope to have on board on a difficult passage like this. He quickly got into the routine and could always be counted on to jump in and help. This, despite such a rough ride the first few days that no one on board felt much like eating the great provisions Sheryl had laid on.

We made landfall at Nelson's Dockyard Marina in English Harbour, Antigua, where we cleared-in to customs. Since Matt would be flying home from here in another week we were instructed to come back to the office to have him officially removed from the crew list within 24 hours of his departure. We could go to any of the 3 official Ports of Call – English Harbour, Jolly Harbour or St. John's (the capital city) – to do this but the officer strongly recommended not going to St. John's since the officers are very busy there with cruise ship and ferry passengers. A good tip for all cruising sailors clearing in or out of Antigua.

Picturesque Nelson's Dockyard is one of our favourite harbours in Antigua. It is the only restored Georgian period dockyard still in active use in the world and is named after the famous English Admiral Horatio Nelson – the 26-year-old Captain of HMS Boreas, part of the Caribbean Leeward Islands fleet who served from 1784 until 1787. During Nelson's period in Antigua, the naval yard was greatly expanded.

Before Matt flew home we spent a few days relaxing here and partying atop Shirley Heights where a fabulous BBQ is held every Thursday and Sunday night. Sunday is the biggest event and we danced to the music of the steel drums overlooking both English and Falmouth Harbours, the best view in Antigua. We then finished the week cruising around the south coast of this lovely island.

Our first stop was at Indian Creek to the east, where singer Eric Clapton has a magnificent mansion on the headland at the entrance. But we hadn't come to stargaze. We'd heard Indian Creek was a good hurricane hole and wanted to check it out. The creek snakes its way deep into the mangroves offering good protection from the sea and surge we were delighted to see. It gets quite shallow at the head; this wasn't a problem for us since it would give us more space if the anchorage got crowded in a storm. Another advantage of our boat's shallow-draft swing keel is that we have more choices of safe harbours. We can also avoid the dangers of crowding since we can often go in a little closer to shore to get more space.

Continuing east, we rounded up to Nonsuch Bay and the anchorage at Green Island where once again Matt could kite surf across the protected yet expansive waters while we snorkelled on the surrounding reefs.

It was time for some downwind sailing so we headed back west along the coast stopping at Falmouth Harbour, the home of mega-yachts in Antigua. There is a huge anchorage here as well as several marinas complete with chandleries, grocery stores and restaurants. A sailor's paradise!

While there, the magnificent Maltese Falcon arrived! The Maltese Falcon is a clipper sailing luxury yacht owned by American venture capitalist Tom Perkins. It is one of the largest privately owned sailing yachts in the world at 88 m (290 ft). The ship has fifteen square sails, five per mast, stored inside the mast; they can fully unfurl into tracks along the yards in six minutes. The three carbon fiber masts are freestanding and able to rotate.

Matt still had a few more days until his departure so from Falmouth we continued on west to Carlisle Bay, then 5 Island Bay and finally concluded our cruise of Antigua at the large resort and marina at Jolly Harbour. There is a convenient dock right in front of the Customs and Immigration Office where we tied up the boat while officially signing Matt off our crew list.

We said our farewells but a new friendship had been bonded. You can't sail 1,100 miles together helping one another through tricky seas to reach a beautiful tropical island like Antigua and just say goodbye.

As we say to our cruising friends one and all, "Catch you later. We'll see you out there!"