It was hazy and hot. The air was still. Sticky even. The seas were calm. Certainly not the conditions we were expecting for Baltic sailing as we motored down the narrow channel towards St Petersburg on the eastern edge of the Baltic which so many of us had travelled so far to visit. But the uncharacteristically warm and sunny weather was only the first salvo of what proved to be a barrage of sensory overload.

The air smelled of diesel fuel. The calm seas were the colour of hot chocolate. Then the first of many ultra-high-speed hydrofoil ferries screeched by – dangerously close in the perilously narrow channel – at well over 40 knots.

By that point, we’d already experienced a uniquely Russian combination of bureaucracy and lawlessness when we cleared Customs at the stereotypical Soviet-era dock on the fortress-island of Kronstadt, which has been protecting St Petersburg from the west since Peter the Great took it from the Swedes in 1703. Being buzzed by a steady stream of 40-knot hydrofoils was just the icing on the cake.

Our 27-boat cruising armada had reached only the halfway point of the World Cruising Club’s first-ever ARC Baltic rally. It had begun three weeks before, 800 miles to the south-east in Kiel, Germany, but we’d already become quite accustomed to the pleasant combination of sailing, sightseeing, socialising, sunny skies and logistical support that makes taking part in a rally so worthwhile.

Tommy and Anita Edlund made me welcome aboard their X412 Tomanita II

When you add in the fact that I was lucky enough to be teamed up with Tommy and Anita Edlund, highly experienced cruisers (and sweet people) who graciously agreed to take me aboard their fast X-412, Tomanita II, for the Visby-Tallinn-St Petersburg portion of the rally, any expectations I had prior to my arrival didn’t stand a chance.

It was easy to find the marina in Visby on the Swedish island of Gotland where I caught up with the Edlunds and ARC Baltic. I just needed to look for the flags flying from the masts of the recently arrived fleet and navigate through the sea of tall, blond, sunglass-sporting, high-heel-wearing beautiful people who had descended upon the quaint 12th Century walled city for a week of partying (and looking pretty) that’s called Stockholm Week.

And instead of jumping aboard and immediately heading offshore as I often do, I got to look around for a few days. In fact, this luxury, especially on well-organised sightseeing tours with lots of fellow participants, was one of the many unique aspects of rally life that I really enjoyed. And there was lots to see in Visby: fascinating Viking and Hanseatic history, stunning stone architecture, numerous churches.

The walled Haseatic town of Visby. Photo: Alamy

But it wasn’t until I got a chance to mingle with my fellow rally participants at an impromptu barbecue on the dock, when the sun dipped briefly below the horizon at around 2300, that the real magic of the ARC Baltic started to sink in. With the forecast calling for sunny skies and a blustery broad reach up to the small Swedish island of Gotska Sandon the next day, the fun was just beginning.

Rally round

You could argue that sailing in a large fleet of 35-57 footers, descending upon sparsely inhabited islands and romantic cities en masse, runs counter to the conventional ideal of self-sufficient cruisers who head out over the horizon to find new lands for themselves. And I’m not saying that one is better than the other, but when a rally is done right, it’s a blast.

That said, it was still pretty weird to gather on the beach of a virtually uninhabited island with 30 or 40 fellow explorers. But that’s exactly what happened after our glorious, seven-knot sleighride up to Gotska Sandon. Our solid block of boats left Visby Harbor as a group. We never really lost sight of each other during the fast 50-mile reach. We anchored together, and then everyone stormed the beach in their dinghies like it was an amphibious military exercise.

Rallying round – the ARC Baltic group getting a guided tour

So, rather than visiting the tiny settlement, we more or less invaded it. In fact, the operation was a well-executed rally rendezvous organised on the VHF by Joel and Cecilie – the hyper-efficient and uber-friendly World Cruising Club rally co-ordinators, who made everything happen. They gathered us all together on the beach so Hans Hansell, the official rally leader, Baltic expert and captain of the lead boat could provide a guided tour for the group.

Then everyone returned to their boats and prepared to sail the next 190 miles to Tallinn. Most boats departed the anchorage during the short period of darkness around midnight (it was dark for about four hours a night) because the winds were favourable and, as it was going to take more than 24 hours, they’d be sure to arrive during the day.

Frankly, most just wanted to stay with the lead boat – Hansell’s Jeanneau 49, Working on a Dream – which was scheduled to arrive first so Joel and Cecilie could work their advance-team logistical magic. The cool thing about the ARC Baltic is that you can take the advice and guidance when you want it, but you’re also free to do your own thing (within reason) when you don’t. In this case, I got lucky.

Tommy and Anita are Swedish. They knew the route and have sailed to Tallinn before. “We’ll have to sail through one night anyway,” said Tommy. “We may as well have a nice dinner and get some sleep on the anchor tonight.” We awoke to a peacefully empty anchorage, sunny skies and a building westerly breeze.

Spinnaker run

“What’s in the yellow bag?” I asked as the mighty Tomantia II with her carbon sails came alive in the freshening morning breeze. We’d set our course to Tallinn with the apparent wind locked in at 120°, perfect for the spinnaker in the yellow bag that I knew Tommy was just itching to set.

“Ah ha! I think you know,” he said with a smile.

But first we needed to convince Captain Anita that the spinnaker wouldn’t cause any problems with our easy passage – though since she was once in charge of VIP events for Swedish Match during the 1997-1998 Whitbread Round the World Race, it wasn’t too hard.

Soon, our wake was sizzling, our skin warmed by the strong, seemingly never-ending Scandinavian sunlight, and we couldn’t stop smiling as the spinnaker flew and the speedo hovered effortlessly over eight knots. “This is some of the best sailing we’ve had in a long time,” said Tommy after many, many hours of no-gybe, off-the-wind, yellow bag awesomeness. I couldn’t have agreed more.

And that was before we arrived in a city that was ruled by the Teutonic Knights in the 13th Century.

Totally Tallinn

If you haven’t figured out that sailing in a rally is a fantastic way to explore new cruising destinations yet, our experience in Tallinn – as it was in every destination on this Baltic circumnavigation – should do the trick. First, we were guided into the marina by one of the organisers on the radio and were greeted by rally members ready to grab our lines.

Old city of Tallinn. Photo: Alamy

Then we were given a highly detailed, destination-specific info-pack that described everything from Customs procedure and the marina wi-fi code, to where to get provisions. Anything you needed to know was covered, and if it wasn’t, Joel and Cecilia could (and did) find out.

But they couldn’t explain why there were so many wedding parties – literally dozens of brides wearing wedding dresses, purple sashes, the whole bit – around the marina when we arrived.

It was the point at which it became clear that we were simply not in the West any more, and everyone I spoke to loved the chance to explore a truly foreign place. From the centuries-old history of the city and Estonia’s complicated relationship with Russia, to the warm locals and the hopping night life, Tallinn dazzled.

This stop also gave us a chance to get better acquainted with our fellow rally crews at an organised dinner in a restaurant off the main square in the old city. Some were rally veterans; others new to offshore cruising and appreciating the security of the group. Some had signed up just to do a few legs (like me), and others were in for the whole Baltic circuit. But everyone I talked to described the chance to sail into our next destination – St Petersburg, Russia – as the reason they made the trip. It didn’t disappoint.

Surreal St Petersburg

It was one of the most extreme, entertaining and paradoxical cruising destinations I’ve ever experienced. And it goes without saying that our arrival at the foreboding Customs dock was made infinitely easier thanks to the World Cruising Club’s considerable advance work.

The stimulating nature of the place was everywhere, from the pseudo-disco-modernness of the night clubs near the marina next to large, abandoned, Communist-era factories, to the gilded excess of Tsarist St Petersburg that was only a short trolley ride away.

Fast ferry in the River Neva

The cultural immersion started almost immediately with an introductory tour of the city, which included a visit to the Peter and Paul Fortress, St Isaac’s Cathedral and the Dostoyevsky museum. But nothing could have been more Russian, or more over-the-top, than our visit to the Romanovs’ private theatre in the famous Hermitage for a performance of Swan Lake later that night – quite an evening out for a sunburned sailor who had never been to the ballet before. And the cultural cascade continued the next day with guided tours of the glittering acres of art in the Hermitage and the Winter Palace.

It takes more than a few days to appreciate St Petersburg fully, but sailing there and living in the marina at the mouth of the Neva River for several days provided a unique view of the city and Russian culture that might not have been available on a standard tourist trip.

We also got to experience the everyday St Petersburg, such as the steady stream of private helicopters that landed (loudly) in a cloud of dust next to the marina on an almost hourly basis, and the Bentleys, Ferraris, Maseratis and Bugattis sharing the dirt roads around the marina with tractors and old Ladas that had to be seen to be believed.

The ARC Baltic is made welcome in St Petersburg

As my time in St Petersburg, and on the rally, wound down, I was pretty jealous of my wonderful hosts and the rest of the fleet who had three more weeks of this kind of curated cruising ahead of them – next stop Helsinki, then on to Åland, Stockholm and back to Denmark. Any scepticism of a rally’s pack mentality I may have had before I started was gone. The sailing had been great, logistics were easy and we’d seen things I’d never thought I’d see. And that was all before the flock of Russian bikini models descended upon us in the marina.

They teetered down the uneven dock wearing shockingly high heels and tastefully colourful swimsuits. They explained in a mixture of Russian, English and hand gestures that they were doing a photo shoot for a particularly Russian brand of car racing and were wondering if they could pose on the bow of Tommy’s X-412 to promote a race?

How could we refuse?

Baltic cruising basics

• Participating in a rally is hardly the only way to see the Baltic. If you are contemplating a trip north here are some things to keep in mind:

• The summer months are the obvious times to go. The days will be long, but it can still be quite cold and rainy so be prepared (we were lucky with the weather).

• Sailing distances between all the main Baltic destinations can be significant. Plan on making at least a few extended passages.

• Navigation, especially through the Finnish and Swedish archipelagos, can be tricky. Passages are tight. It’s extremely rocky and there are many, many unmarked hazards. There’s also a significant amount of large ferry/passenger ship traffic (not to mention the fast hydrofoils of St Petersburg) to avoid.

• Clearing in for US or UK citizens did not require an entry visa for any country we visited except for Russia. In that case, visa forms must be filled out and approved well in advance. For the rally, the World Cruising Club hired a private Customs agent to facilitate the entry and exit paperwork. Having an agent definitely made the entry process easier and I’d recommend hiring one if you’re planning a visit to Russia.

• Don’t rush! Nearly all the main Baltic destinations are gorgeous and rich with history. Be prepared to spend at least several days in each port to soak it all up.

This is an extract from Yachting World February 2015 issue