Portland: Our guide to the perfect weekend » Dream Cottages

Portland: Our guide to the perfect weekend

Posted by Sinead on November 13, 2017

Welcome to our guide to Portland.


For a little Island of just 4 miles in length and 1.7 miles in width, jutting out into the English Channel, Portland can boast an impressive history dating back over 180 million years.

Playing an integral part in Dorset’s Jurassic history, it has been a hive of activity, from Roman fortresses, to Henry VIII’s Castle and Olympic glory, there is more to Portland than meets the eye.

Here’s our guide on how to spend a long weekend. Showing, for a little Island, it certainly has a lot going on.


Portland Stone

The Isle of Portland, home to Portland Stone


Day 1. Tout Quarry sculpture park. Famous around the globe, and used in iconic buildings such as St Paul’s Cathedral in London and the UN headquarters in New York, Portland stone is one of the most widely recognisable building materials in the world. Take a wander around Tout Quarry sculpture park, a disused quarry that was lovingly turned into a sculpture and nature reserve. With sculptures from international artists including Anthony Gormley and an abundance of wildlife that has been allowed to thrive, it showcases Portland stone in a truly unique way.

Reward your tired feet in the evening with a trip to The Cove Inn, where you are literally dining on the iconic Chesil Beach. Enjoy exceptional views and dine on local seafood, caught straight from the Weymouth and Portland coast, you may even spot the fishermen on the beach bringing in their catch.


Day 2.  Portland Castle. Constructed by Henry VIII as a coastal fort in the 1540’s along with its sister castle Sandsfoot built on the Weymouth side of Portland Harbour, the castles still stand today. Boasting beautiful views, a Tudor kitchen, heritage gardens and replica cannons, this is a day out all the family can enjoy, book your tickets here. If history is your cup of tea, then a stop at Castletown D-Day museum is well worth a detour. This innovative and engaging museum gives you an authentic recreation of the busy Portland docks during World War II, where in 1944, thousands of American troops headed off to Normandy as part of the D-Day landings.  The museum actively encourages you to enjoy the original artifacts, including dress up uniforms, and a tank! Find out more here.

Round off your day with a meal at the Crab House Cafe, situated just off the Portland beach road, its renowned for the freshest oysters in Dorset plucked straight from their own oyster beds.


Day 3. The Isle of Portland circuit trail, to Portland Bill. Standing proud at the most Southernly tip of the Island is Portland Bill, a giant red and white stripped working lighthouse. It has kept sailors safe through the infamous stretch of water known as the ‘Portland race’ for over a century and is the most recent lighthouse in a history spanning back to 1761. With bracing walks, taking in stunning views to Portland Bill, it is the perfect spot to stop off and enjoy the wild and windy coast. Take a break from the trail and enjoy lunch at the Lobster Pot, which is known for its views out to the English Channel and fresh local seafood.


Day 4. A day on the water. As it’s the last day of your trip, why not treat yourself to breakfast with a view, at the Heights Hotel. Perched on the top of the Island, this restaurant commands views over the harbour and lagoon, watch Chesil beach sweep off into the distance as you sip a coffee.

As expected from an Island that can boast some of the best sailing waters in the world and an internationally acclaimed sailing academy, Portland offers a whole host of water based activities. If you are feeling adventurous why not try stand up paddle boarding, windsurfing or kayak lessons. If a relaxing boat trip is more what you are looking for, then try the glass bottom boat tour on the fleet. Run by the Fleet Observer, it’s an opportunity to see the lagoon from a whole different perspective. Did you know the reason the waters around Portland are so clear and the water quality so exceptional is due in no small part to a little know species called the ‘lump fish’, which are an integral part of the Scottish salmon industry and thrive in the Portland waters due to its cleanliness.


South west coast path Portland

Follow the South west Coast Path around Portland


There are so many more things to see and do on Portland, we believe you could fill an entire week or more and not need to leave the Island. It is a stunning location whatever the season, with activities to suit all the family, not to mention cosy pubs and restaurants with commanding views, you really will be surprised with how much this little Island can offer.

For a list of our Portland properties click here.

For a comprehensive list of Portland based activities click here.



Tempted you to come down?

We have a good selection of properties, like The Oast House or Cob Cottage (right). Don't forget to have a look at our special offers; we have some great late availability offers.

©2017 Dream Cottages

5 Hope Square , Weymouth, Dorset, DT4 8TR
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