Tried and Tested: Osprey

Welcome to the latest edition of the Best of Suffolk ‘Tried and Tested’ blog series, featuring Osprey – a pretty, pet friendly first and second floor apartment within one of Southwold’s stunning Victorian townhouses.

Tried and Tested Osprey

In this edition, Osprey was home to the Ripman family, over the Southwold Christmas lights switch-on weekend in November.  Two adults, two children and one dog!  Tim, Laura, Olly, Lily and Sky the black Labrador had a full-on festive weekend including the switch on, the Adnams 10K and a stormy winter weekend in Southwold!

Centrally located, spacious and well-equipped, Osprey is ideal for families, or groups of friends.  It can also be hired alongside Kestrel, the apartment below, creating flexible accommodation for extended families too.  Being dog-friendly means your four-legged friend doesn’t need to stay at home!  Southwold was designed with dogs in mind, with many pubs and restaurants being dog friendly, and sections of the beach open to dogs all year-round.

Lily Laura Sky Osprey

Here at Best of Suffolk, we love getting out and exploring the glorious county of Suffolk.  As a truly local top team of Suffolk experts, we know our county inside out.  It’s what makes us different from any other holiday letting agency.  It’s also why our Tried and Tested blog series is now long-running and has such a wide readership.  We love sharing our top tips, recommendations, and local knowledge, and you love hearing them!

The long-standing Tried and Tested blog series sees the team ‘try and test’ our properties with their family and friends.  Each blog provides first-hand experience of our stays and combines this with recommendations of things to do nearby.  From the property itself to knowledge of where’s good for food – we ‘try and test’ it all.

Let’s see how the Ripman family got on when they ‘Tried and Tested’ Osprey;

Osprey, Southwold

Osprey is a beautifully presented first and second floor pet friendly apartment within one of Southwold’s stunning Victorian townhouses.  Standing in a prime position in the heart of Southwold with views of the sea and lighthouse, it is within easy walking distance of the High Street shops and a minutes walk to the sea front. This is vintage chic at its best, offering groups of friends and families a stylish retreat!

Osprey Exterior

You are welcomed into a shared entrance hall with the apartment below, Kestrel.  As well as accommodating up to 8 guests, downstairs is Kestrel offering an additional 4, so there’s the potential of accommodating 12 in total with the benefit of 2 kitchens, 3 bathrooms, outdoor space & 2 dogs!

A door opens to a private entrance with stairs leading to the first-floor hall.  Directly ahead there is the master bedroom, family bathroom, and a bunk room.  Two further stairs lead to the sitting room which opens to the kitchen. Stairs from the hall lead to the second floor which has a double bedroom, a twin bedroom, and a shower room.

Osprey Sign Door Sky

The sitting room is a beautiful room with large sash bay window and window seat. There is a living flame gas fire with a large sofa and 2 armchairs, a dismantled drum kit to use as coffee tables and polished wood floors. There is a flat-screen Toshiba TV with Netflix and a Philips HiFi with iPod/iPhone connectivity.

Osprey Sitting Room


Location, Location, Location!

Southwold sunset

This self catering holiday cottage in Southwold is located in a terrace of houses, a short walk from the town’s popular shops, cafes and delis.

The sandy beach at Southwold is adorned with a string of colourful beach huts that lead along to Southwold Pier at one end and towards Southwold Harbour at the other end the town boasts several excellent pubs and restaurants as well as a range of independent shops and galleries.

There is a pretty walk through the harbour and over a footbridge to the picture-postcard village of Walberswick, home to two good pubs (The Anchor and The Bell) and a long sandy beach.  Fresh fish can be bought from the fish huts along the harbour. Southwold is home to the Adnams Brewery and the town’s excellent pubs include one of our personal favourites, The Lord Nelson where you can try a range of Adnams bitters.

Osprey: First Impressions

We arrived excited, and were welcomed by Christmas decorations, which only added to the growing 2021 festive feeling!

Osprey Tim Lily Olly External

Access was made very easy thanks to the trusty Best of Suffolk arrival details.  The key-safe had helpful automated lighting and the code worked like a charm.

A lovely extra touch was the tasty and generous welcome pack, featuring a selection of local drinks and snacks.

Welcome Pack Osprey

The kids particularly enjoying the bunk room and Lily the roll-top bath!

Osprey Bathroom

Osprey is so centrally located, at this time of year we found parking easy on Chester Road.  Once we had parked up there was no need for a car as everything could be easily reached on foot.

This stunning self-catering Southwold property is furnished to a very high standard but with added quirky stylish touches.  The wine glass lamp shade and drum coffee tables in the sitting room for example are wonderful touches that really differentiate Osprey from other self-catering holiday homes.

Dog Friendly Southwold Holiday Cottage

Sky made herself at home in Osprey almost immediately!  We put her dog bed in the sitting room, so she could enjoy cosy nights by the fire.  Southwold beach one of her ‘happy places’.

Southwold Dog Friendly Holiday Cottage

Warm and Cosy

Considering it was the coldest weekend of the year to-date, we remained warm, cozy and snug at all times.  Whether returning from a walk or bunking down to read the papers or enjoy a little TV, Osprey was the ideal home away from home.  Most of our evenings were spent by the fire, enjoying the views with a glass of delicious wine, as provided by owner in our welcome pack.

Fire Wine Osprey

The heating system was very quick to react when turning up for some extra warmth factoring in the frosts and ice outside!

Ideal Southwold Family Holiday Cottage

With a football match on the Saturday for Olly and the famous Adnams 10k race on Sunday for Laura, breakfast on both mornings were key to the days and served up in the kitchen.

Breakfast Osprey

Outside of keeping ourselves busy in Southwold, Osprey made the ideal base for quality family time.  Over the weekend, this included a chilled Saturday afternoon out of the rain enjoying the papers, games and football scores coming in from the premier league!  Both evenings it was sofa time for Strictly Come Dancing, a Ripman essential each week!

Olly Strictly

Enzos Pizza

For tea on our first night we had booked a table at Enzos, a unique pizzeria on Southwold High Street.

Tim Oly Lily Enzos

Combining Italian, football, film and celebrity themes, complete with signed shirts and memorabilia galore, there was plenty to keep the kids entertained.

Lily Enzo

We received a friendly welcome from the man himself, Enzo who is the front of house, waiter, barman and chef all at the same time!  He delivers a small but delicious menu of pizzas that tick boxes for the family, especially the ‘spicy’ special for Tim!  The pizzas are freshly made and quick to be served with Enzo attentive and making a fuss in between his many roles.

Pizza Enzo

I was impressed by the good selection of Italian beers, with wine by bottle and glass on offer too.  If the restaurant is full, take away is occasionally on offer.  You can take away and eat on the beach in better weather!

Beer Enzos

Time For Bed

After all the fun and feasting at Enzos, we headed back to Osprey and put the children to bed.  Lily loved having story time in the big, comfy bed!

Lily Bed Readng

A Leisurely Saturday Breakfast

On Saturday we Ripmans split into two teams.  The boys had a local football match to be part of, and Laura, Lily and Sky made full use of being in Southwold.  A lovely, leisurely start was enjoyed by all, making full use of the comfy beds at Osprey!

The ladies headed into town to do a spot of shopping for breakfast.  Lily picked cinnamon swirls and croissants to take back for the next day at Two Magpies Bakery.

Lily Two Magpies

Even better, Laura and Lily got to enjoy a delicious breakfast, freshly produced in the bakery itself!

Lily Laura Cafe

Life’s A Beach!

Lily and Laura took Sky for a stroll on Southwold’s beautiful beach.  Lily particularly enjoyed beach hut name spotting, finding Lily’s Lookout!  It was great to get out in the fresh air and enjoy the glorious county of Suffolk, even in the winter!

Lils Beach Hut

The beach was as popular as ever, with swimmers and surfers braving the winter sea.  From 1 October to 30 March, dogs are allowed on all parts of Southwold beach too, so there were plenty of friends for Sky to play with!

Sky Beach Hut

Southwold Winter Sun

In winter, we all know there can be rain one minute, and glorious sunshine the next!  After setting out in grey clouds, we ended our walk in warm winter sunshine, very happy to have been brave enough to have hit the beach in November!

Sky Southwold beach

Southwold Independent Shops

After our glorious walk on the beach, Lily and Laura headed back into town to purchase the weekend’s papers and pick up a few essentials for the weekend.

Lily Grocers

Southwold Christmas Lights Switch-On

Being as popular as Southwold is, the light switch-on drew in the crowds!  Locals, visitors and holiday home owners stood side by side and awaiting the big switch on from Father Christmas.

It’s a very family orientated event, with carols and prayers.  The Town Crier is master of proceedings and makes the whole event run beautifully.

Southwold Light Switch

The bustling High Street, full of independent and nationally-recognised brands take part in a Christmas window display competition.

The Sole Bay Inn

After all the festive fun of the light switch-on, we decided to head to the Sole Bay Inn to thaw out and get some tasty hot food.

Ripmans Sole Bay Inn

The Adnams pub was buzzing, with crowds gathering inside and out.  The Sole Bay is dog friendly, so Sky could join our family meal out.  There was a delicious Christmas ale on draught, a 50/50 with bitter, called ‘Mother-in-law’!  The food selection was plentiful, with two menus including a specials board.

Laura and Olly Sole Bay

The team there were friendly, and the service was efficient.  As a family we enjoyed some delicious pub classics of fish and chips and scampi and chips.  It had a real bustling atmosphere, and was busier than normal due to the switch-on event. So many hopefully coming in and looking for tables, but there was no room at the inn!

Tim and Lily Sole Bay

There are a couple of long tables, ideal for seating 10 or more.  We shared our table and enjoyed the friendly, community atmosphere.  We were surrounded by families, who were playing games amidst eating and drinking!  Outside, those brave enough to enjoy a pint under the stars!

Drinks Sole Bay Inn

Adnams 10k Race

Following a second decent nights sleep it was race day!  The Adnams 10k is a Southwold tradition, enjoyed by locals and visitors alike.  The route takes you through some of the most picturesque parts of Southwold and has a real community spirit.

It was very cold conditions, but our runners braved it anyway!  Running were Laura, Laura’s brother (and Tim’s brother-in-law) James, Harry and Harry’s Dad Matthew, plus numerous friends

Laura 10K Southwold

The race started at harbour end of the town, and finished on South Green with a couple of laps in between.  There was a real mix of elite/club runners, experienced runners, fun runners, runners with dogs, runners with buggies and walkers.  A huge well done to everyone taking part!

Laura Harry 10k Southwold

It was wonderful when the sun came out for race.  The children enjoyed giving the runners high-fives as they jogged past and cheering on their names.  We decided to stand outside Ferry Cottage in order to see runners twice before heading up to South Green to see the finish line in front of Red Lion.

The Sail Loft

After working up quite an appetitive, we decided to head out for a family lunch.  We were joined by friends for Sunday lunch at The Sail Loft.  Our mighty table for 12 people had been pre-booked to ensure we had somewhere warm and tasty to enjoy roast beef with all the trimmings!

Group Photo Sail Loft

The Sail Loft was the perfect post run pub, where we enjoyed good times with friends.  We enjoyed attentive service and friendly other diners, who didn’t seem too put off accepting noise from our table!  Afterwards, we walked into town in search of an ice cream in the winter sunshine.

If I Had More Time, I Would…

…Head to Covehithe Beach.


Covehithe is a rural beach, unspoiled by any form of development, surrounded by the Benacre Nature Reserve. There are no facilities on the beach at all (not even a toilet!), but an ideal beach for a dog walk.

….Head to Paws for Tea Tearoom.

Paws for Tea

Located on Beccles Common, Paws for Tea is a dog-friendly team room that offers a delicious range of meals and drinks, plus treats for your four-legged friend!  combine with a walk through the ‘fairy wood’ nearby, to see how many fairies you can spot!

…Visit Dunwich Heath

Dunwich Heath Purple

Enjoy both beach and heath at the National Trust site, Dunwich Heath.  Seasonal trails to follow, dog friendly and a tea room to boot!

The Verdict: Osprey

A family and dog friendly period holiday home that could not have been more ideally located for a fun-filled weekend in Southwold.  Equipped with everything we could have needed, plus very spacious for our family group, the Ripman family will definitely be returning!

Why not take a look at availability, and secure your break to Osprey?