Royalty, Racing & Rigging
Cowes and East Cowes
The twin towns of Cowes and East Cowes, situated on either side of the River Medina, share a history centred on shipbuilding, sail and rope making, alongside their long-standing royal connections. The maritime and royal histories of the towns have developed hand in hand.
History Bite
In 1545, Henry VIII, who built ships on the Isle of Wight, watched in horror from across the Solent as his flag ship the Mary Rose sank just off the Island. (for The Mary Rose, see Portsmouth section) One century later, Peter the Great visited the Isle of Wight and was so impressed with its shipbuilders that he took a couple of the best of them back to Russia with him to build his fleet. In more recent times however, seaplanes, flying boats, hovercraft, Red Jets and Thames Clippers have been built in East Cowes.
Royalty, Racing & Rigging Day Tour (good to go)
East Cowes
Osborne House – Queen Victoria’s favourite home and place of her death
The Royal Church (St. Mildred’s, Whippingham) built for Queen Victoria
The Folly Inn (lunch) beautiful riverside pub/restaurant
Cross the River Medina to Cowes – using the Floating Bridge is an exciting way to do it!
Cowes
Visit the Classic Boat Museum – a must for anyone interested in the maritime history of Cowes!
Guided walking tour of Cowes and/or shopping time or harbour cruise
Tour finishes in The Garden (café/restaurant)
Royalty and Radicals tour
Brand new! Good to Go - 3-day scheduled tour
Wednesday September 23rd – Friday 25th, 2026
An exciting three-day tour, mainly based around Cowes in the north - with its strong connections to the Russian Imperial family, and Ventnor in the south-east, where the same could be said for their (Russian) Radical opponents. How simply fascinating that all this happened on Victorian Isle of Wight – do join us on this exquisitely-themed tour to learn more!
This premium tour is all-inclusive: the high-class accommodation, food and drink, transport (on the Island) and full programme is arranged and provided by us (excluding Osborne entrance and any food or drink there).
Please speak to me for full details, and please book early!
Romanov Collection, General Collection, Beinecke Rare Book and Manuscript Library, Yale University
Day 1
Royalty and Radicals Tour – Introductory talks and Imperial-themed dinner
14.00 - 16.00 – arrival at Albert Cottage, East Cowes.
We suggest that you take the Red Funnel ferry from Southampton to East Cowes. If you are not bringing your own car to the Island, taxis can be pre-booked to meet you on your arrival at East Cowes (these will be at your own expense). Your accommodation will be at the prestigious Albert Cottage, East Cowes (left). This was the home of Princess Beatrice, the youngest daughter of Queen Victoria and Prince Albert, and is a splendid Victorian era building with extensive gardens (originally belonging to Osborne itself). Car parking is available on site should you require it.
17.00 - 17.45 - tea and cake served in the Victoria Room. Welcome by Annie Horne (owner of Albert Cottage), Stephan Roman (Author of ‘Isle and Empires - Romanov Russia, Britain and the Isle of Wight’) and Jane Richter (Isle of Wight Guided Tours).
18.00 - 19.00 - illustrated talk by Stephan Roman on Anglo-Russian relations during the period of the Tsars, with a special focus on the Isle of Wight.
19.30 – 21.30 dinner at Albert Cottage. The menu will draw inspiration from that offered to the Tsar of Russia, Nicholas II, and Empress Alexandra Feodorovna by King Edward VII and Queen Alexandra during the Russian Imperial visit to Cowes in August 1909.
Day 2
In the footsteps of Russia’s Radicals
Breakfast
10.00 Depart for Ventnor. Drive along the east coast of the Isle of Wight passing through Sandown and Shanklin. Sandown was the favourite seaside resort of the German Imperial family and famous Germans such as the composer Richard Strauss also holidayed there. Shanklin is famous for its historic village centre and ‘Chine’ valley with waterfalls and sub-tropical vegetation. It was the first place on the Island ever to become a tourist destination and was visited by the great and the good – including Victoria herself, even before she became Queen.
11.00 - 1130 Ventnor - coffee at ‘The Terrace Rooms & Wine’ (shown right - formerly known as St Augustine Villa), where Alexander Herzen, a leading opponent of the Romanovs, used to stay in the 1850’s.
1130 - 11.45 a talk by Lesley Telford from the ‘Ventnor Heritage Centre’ about Ventnor and its general history.
11.45 - 12.30 a talk by Stephan Roman about the Ventnor Radicals who actively opposed Russia’s Imperial rulers in the middle years of the nineteenth century. The political, literary and social thinking that emerged from Ventnor helped lay the foundations for the Russian Revolution of 1917.
1230 - 14.00 lunch at The Terrace, Ventnor
14.15 - 15.00 guided walk along the Esplanade in Ventnor, passing where many radicals stayed including Count A.K Tolstoy and the writer, Ivan Turgenev.
15.15 – 15.45 visit Ventnor Heritage Centre
15.45 – 16.45 return to Albert Cottage, driving along the Military Road (scenic road that runs along the south coast of the Island). You will pass Blackgang Chine, associated with Ivan Turgenev and his most famous novel ‘Fathers and Sons’, and St Catherine’s Down, with its unique monument to Tsar Alexander I.
16.45 – 18.00 free time at Albert Cottage. A light tea will be available in the Victoria Room.
18.00 depart for Cowes. Cross by the Floating Bridge to Cowes, following in the footsteps of the Russian Grand Duchesses Olga and Tatiana, the eldest daughters of the last Tsar, Nicholas II.
18.30 – 19.30 visit Medina Bookshop, Cowes. Welcome by Peter Harrigan, Director of Medina Publishing.
1945 – 22.00 dinner at the Smoking Lobster, one of the top seafood restaurants on the Isle of Wight (non-seafood dishes also optional).
Day 3
In the Footsteps of Russia’s Imperial Family
Breakfast
09.30 -10.00 briefing in the Victoria Room by Jane on Osborne House and its history.
10.00 - 10.30 visit to Romanov Memorial, East Cowes.
10.30 – 11.30 visit to Queen Victoria’s Royal Church at Whippingham.
11.30 -15.00 visit to Osborne House (English Heritage). This was the home of Queen Victoria and Prince Albert and was well known to the Romanov family.
Please either pre-book tickets online or buy at the venue upon arrival. (Price for these not included in the package.)
You will have a chance to explore the Queen’s state and private apartments and then walk through the grounds to the Queen’s private beach and visit the Swiss Cottage, where the royal children played (including the future Empress of Russia, Tsarina Alexandra).
Jane will give a talk before you enter the House and both she and Stephan will accompany the group around Osborne and its grounds. Coffee and lunch can be enjoyed at Osborne where there are several cafes offering a choice of sandwiches, cakes and hot dishes.
Food and drink at Osborne house are at your own expense.
15.00 return to Albert Cottage.
15.00 - 16.00 light afternoon tea available in the Victoria Room before departing for the Red Funnel Ferry in East Cowes.
(Should you wish to stay on for the weekend, this is of course entirely your choice - indeed, the timing offers the perfect opportunity for you to do so!
And if you require any further assistance of any kind - including guiding - over the weekend, please let me know, we will be more than happy to oblige.)
The Royal Yacht Squadron is one of the world’s most prestigious yacht clubs and highly exclusive. Among other races and events, it organises Cowes Week, held in early August, one of the largest and best-known sailing regattas in the world. The ‘Round the Island’ race is incredibly popular too. This race was started, and is still run by the Island Sailing Club.
Maritime Museums in Cowes
Classic Boat Museum
Two equally superb but very different maritime museums can be found here. One is the Classic Boat Museum which has its premises in the Medina Yard, Cowes. Boat lovers and anyone else who is generally interested in the maritime history of Cowes will be fascinated! Here you will be introduced to a wealth of pivotal characters in the history of the town’s maritime history, including that of the Americas Cup (first ever raced in Cowes). Most locals are enthralled by Ben Ainslie’s present day all-consuming attempts to win it for the UK for the first time ever. A senior in-house guide will always give you an exclusive tour if desired.
We work closely with this museum, and they will gladly arrange exclusive tours and even events for us on request. If you are interested, please let me know.
Hammerhead crane
Sir Max Aitken Museum
This museum, housed in a beautiful former sail loft, focuses on the eclectic private maritime collection of the somewhat unconventional sailor and internationally known personality bearing its name. This is another place we have worked with for years and our tours here are always exclusively led by an expert in-house guide.
You can also hire this stunning venue for a more formal dinner party, or we can arrange a speaker to give you a talk alongside drinks and canapes or whatever you would like.
‘Dear Osborne’ (as Queen Victoria called it)
Osborne (House and Gardens), is a complete ‘must see’ when on the Island. Favourite home of Queen Victoria, it is also the top visitor attraction on the Island (along with the Needles). With us, you won’t just have an ordinary visit, but a right royal experience. We will regale you with tales of Victoria and Albert and their nine children, as they conducted their daily lives here. It should not be forgotten that this was NOT a mere holiday home as is often quoted – it wasn’t! Victoria ruled the Empire from here when she was in residence, very ably aided by her husband Albert, who was indispensable to her.
St. Mildred’s Church, Whippingham
Nearby St. Mildred’s (often just known as ‘Whippingham Church‘) was commissioned by Prince Albert for Victoria. He also helped with its design. It is often described as a ‘Gothic fantasy’, partly inspired by his northern Bavarian hometown of Coburg. Sadly, he lived just long enough to see it completed but not to experience the first service ever held there. Learn about the four royals buried here – two inside the church and two outside in its pretty churchyard, which nestles on the peaceful banks of the River Medina.
Northwood House
Northwood House is a largely unoccupied grade II listed Georgian manor around which the town of Cowes was expanded.
It is set in superb grounds and could have become the home of royalty. Victoria and Albert certainly took a look, but Osborne won them over.
Instead, of which, if not actually home to royalty, Northwood became a house totally dedicated to entertaining them (both our own and international) and how!
Not only royalty, but other domestic and international movers and shakers partied here to an excess that we can hardly imagine today – these were parties that didn’t just last an evening – they could last a month!
Its large network of secret tunnels, accessed by a flight of rickety stairs, have inevitably led to speculations which, while partly based on fact, have to an extent been mixed with a dollop of previously mentioned Island folklore, or what is sometimes endearingly referred to as ‘Isle of Wight truths’!
But even without these, the 100% factual stories of the varied use of the house over time, will prove more than enough to keep you captivated.
The house is not generally open to the public that often, but Tim Wander (pictured below), its Director, trustee, project manager and house historian, with whom we have worked for many years, has rarely been unable to oblige when it comes facilitating a visit.
His own credentials know no bounds, and you will become familiar with his name on this site.
It needs to be said that he is as entertaining as he is knowledgeable – he never fails to amaze, inform and amuse our clients in equal measures!
St. Mary’s Church in grounds of Northwood House
Tim Wander shows clients underground
Tim Wander (left) with fellow author Amy Harmon and husband
Medina Bookshop
Peter hosting VIP clients at Island Sailing Club
Cowes is also home to the Medina Bookshop, run by singer songwriter Paul Armfield. Peter Harrigan of Medina Publishing (owner, who is also based here), is another partner with whom I often work. He (together with Paul) has hosted various events at The Bookshop over the years and has given several riveting talks for us on different aspects of Island life. He has also worked with and entertained various Isle of Wight Guided Tours clients with me (see also Literary & Musical Wight).
The Medina Bookshop supply the books for the Isle of Wight Literary Festival, which has now earned itself a place as one of the country’s finest (again, see Literary & Musical Wight). Should you choose to visit us in October, you will be able to bear witness to this for yourselves!
Peter Harrigan hosting one of our private events in the Medina Bookshop
On another occasion, Amy Harmon and her mother being hosted by Peter and myself at the Island Sailing Club
Other things to do in Cowes
Harbour Cruise
We can really recommend taking a harbour cruise- a very enjoyable way to spend an hour or so as well as being informative in the extreme. We are more than happy to arrange this for you.
Shopping
Cowes is an amazing place to shop. Very exclusive little boutiques – stylish and ‘non-touristy’. Those on walking tours are always anxious at the end of the tour to rush back to certain shops that caught their eye along the way!
Superb art gallery – take a peek inside, opening hours permitting!
Library – they also have a little museum where we think you might enjoy spending a little time poking around.
Accommodation and Eateries
(You will meet several of these places again on our ‘Eat, Drink and Stay’ page).
As the contents of this page refers entirely to one area - I am including below some suggestions for accommodation and eateries in the area (in no particular order).
Villa Rothsay Hotel
A very Victorian boutique hotel, so intriguing that it almost has a museum-like quality, at the same time as being completely homely.
Owner Maggie Ankers couldn’t be more friendly and hospitable as well as incredibly knowledgeable.
She has fantastic tales to tell, and many of our clients have debated with her long into the night!
Its location, set just above the Royal Yacht Squadron, commands magnificent sea views from several of its rooms.
The sitting room has an absolutely captivating sea view as does its garden and terrace.
The whole house has that ‘certain something’ – it is quirky and definitely a one-off!
If a minimalistic and modern hotel is your thing, then this isn’t for you. But if you are a fan of all things Victorian, you will simply adore it!
Smoking Lobster
Delectable food in a thoroughly modern yet intimate setting – it oozes an ambience which is both exciting and modern.
The staff are simply wonderful – exceptionally so.
That they believe in the place and what they do just can’t be more evident.
One of the Island’s top restaurants, you certainly won’t be disappointed!
The Coast
Another great place – this restaurant/bar is very relaxed and informal and offers a large variety of lovely food and drink (both indoor and outdoor seating).
It somehow has a very ‘nautical’ feel to it, without really trying.
To the right – sharing an ‘off duty’ Pimm’s with author Susanna Hoe (you will meet her again on the Literary & Musical Wight page).
The Garden
More informal still – another very lively venue with a modern vibe and great to visit any time of day from breakfast time through to evening.
With indoor and outdoor seating, they also have a vibrant pop-up restaurant in summer which is directly on the waterfront, next to the Island Sailing Club.
Jolliffe 1853
Not least in its favour is the historic building in which it is housed. Originally a shoe shop (established by Henry Jolliffe in 1853), it catered for royalty back in the day – selling shoes to Queen Victoria and her daughter Princess Beatrice, who in turn, later bought her own children’s shoes here.
Destroyed by fire in 1915, the current magnificent Grade II listed Art Nouveau building was built 2 years later.
Several original features remain and the current owners pay tribute to its former life by displaying cute miniature ornamental shoes on bookshelves – a lovely touch!
Albert Cottage Hotel - East Cowes
If you want to stay right next to Osborne, in a house which once belonged to the royal family and was part of the estate, then this place is for you!. If you care to imagine yourself as a member of royalty, you will simply love the old home of Princess Beatrice (Victoria and Albert’s youngest child). It also has a popular restaurant, which is open to non-residents as well as residents. Its location lends itself well to a lunch, morning coffee or afternoon tea stop in conjunction with a visit to Osborne.
The Folly Inn - East Cowes
Situated right on the banks of the River Medina, this place commands terrific views. It also has an interesting history.
With a large amount of seating both inside and out – you have ample opportunity to observe life on the river – for example, the transportation of wind turbine blades made close by at Vestas (shown below).
The staff are both friendly and ultra efficient and the very large selection of both hot and cold food is truly delicious.
Just a few minutes from Osborne, it’s a great lunchtime choice to combine with visiting both Queen Victoria’s home AND church.
Whether you are visiting those in the morning or afternoon – you are perfectly situated here, on the same side of the river for a lovely lunch - whether before your visit(s), after, or indeed, half way through!
Wind turbine blades made close by at Vestas
The Floating Bridge
Which reminds me to say – if you are not ‘on the right side of the river’ – no problem – simply cross it!
There are two ways of doing this – either by our ‘Floating Bridge’, which is a chain ferry that only takes three minutes to get over to the other side OR travel by road.
It’s fun to use and a bit of a novelty, there aren’t many of them about!
You can use this as a foot passenger or in a car – however, the minibus is already too big to use it, so it will need to drive into Newport and back along the opposite riverbank, thus taking a little longer.
Plan your Royal & Maritime Island experience
From Osborne and royal connections to waterfront life, embracing sailing and society, this is an Island story full of history and change.
If it has caught your interest, we would be delighted to shape these elements into a personalised Isle of Wight experience, at a pace that suits you.
Explore our Tours, or get in touch to begin planning your own.