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If you’re planning a weekend break in Weymouth, this post walks you through what we did across three days — where we stayed, what we loved, and what I’d do again.

Weymouth. A seaside resort with a beautiful sandy beach and clear sea.

I found it on Google Maps while I was looking for a new town to move to — and it stayed in my mind for almost a year before I finally booked a trip.

There was one big issue, though: the journey was meant to take around six hours and involved four different types of transport. That’s a lot. I hate long journeys, but luckily I could extend my holiday and combine an already planned trip to London with a weekend in Weymouth. Splitting the journey in half was such a good idea.

Weekend break in Weymouth

For the purpose of this post, we’ll start at London Waterloo, where we boarded the 9:30am train. The journey took around three hours and was full of beautiful landscapes. If you live in London, Weymouth is definitely one of the best spots for a day trip or weekend staycation.

In this post, I’m going to run through the best things to do in Weymouth and Portland — in the order we did them. Let’s go.

Day 1: How to spend a day in Weymouth

After arriving in Weymouth, I couldn’t resist and went to the beach immediately. We hadn’t lived by the sea for years, so I was impatient — I just wanted to see the water.

Our hotel was close to the beach, so we could admire the views on the way. I honestly don’t think I’ve seen sea water that clear in the UK before.

This time round, we stayed at the Premier Inn Weymouth Seafront. I’m hesitant to stay in local B&Bs, unfortunately, and Premier Inn is usually my go-to. I know I’m probably missing out because of it!

Weymouth Beach

After we checked in, we headed straight back to Weymouth Beach. The water was icy, so swimming was a definite no for me — although I did see a few people in the water, which felt wild.

Just around the corner, a man was trying to take off on a paraglider. People seemed to be having the best time.

Weymouth Harbour

We did what we enjoy most: wandered around with no real plan. That’s how we found ourselves at Weymouth Harbour.

I was surprised that even though it was early Friday afternoon, the cafés and pubs we passed were packed. The harbour itself is really charming.

You can also see the Town Bridge here — a lifting bridge that operates on a schedule. I’d love to see it in action one day, but we didn’t catch it this time.

Chesil Beach

Later in the afternoon, we headed out to Chesil Beach — one of the major shingle beach structures in the UK. It’s 18 miles (29 km) long and runs from West Bay to the Isle of Portland.

It looks spectacular, especially from Portland.

We saw plenty of people fishing, which surprised me — I didn’t expect there to be fish so close to the shore. I didn’t feel comfortable walking right by the waterline, so we sat on the pebbles and enjoyed the sunshine instead.

And that was our first day in Dorset: walking, wandering, and soaking up the sea air.

It was our first holiday in years that we didn’t spend visiting family or running errands, so it felt genuinely restful.

Day 2: What to do in Portland, Dorset

We started early. The plan was to walk around the Isle of Portland.

We took bus number 1 from the town centre towards Southwell and spent around half an hour enjoying beautiful views of the isle and the sea on the way.

Lunch at Heights Hotel

We got off near Heights Hotel, where we stopped for an early birthday lunch. The food was delicious and the views were mesmerising — from the restaurant you can see Chesil Beach, the harbour, and more.

We spotted the Olympic Rings stone sculpture nearby, so we took a few photos before heading back to the bus stop to catch the bus towards Tesco.

After grabbing snacks and drinks, we followed Southwell Road to see if it was possible to get closer to the cliff edge.

South West Coast Path

We saw signs for the Coast Path, but it looked like it led down the cliffs. Not knowing the area (or where it would take us), we stuck to the road at first.

With the high tide coming in, it felt risky to go down to the beach.

A bit later, we joined the South West Coast Path, which let us walk closer to the cliff edge.

The views were truly amazing. The colour of the sea mesmerised me — I’ve never seen water that blue before. The sky was clear, the sun was shining, and the weather felt perfect for a long day out.

High grey cliffs towered above the sea, and we kept finding quieter spots where we could just stand and stare for a while.

Cave Hole

Continuing along the cliff edge, we came across Cave Hole. Two guys had attached a line to the cliffs and were trying to walk on it. Loads of people stopped to watch.

After taking far too many photos, we headed towards the lighthouse.

I was tired by that point, so I was very happy to sit down for a bit. We grabbed ice cream from The Lobster Pot and sat on the cliffs enjoying the views.

The sea honestly didn’t stop surprising me all day.

Touring Portland Bill Lighthouse

We reached Portland Bill Lighthouse just in time for the last tour of the day.

Going up was scary for me — narrow steps ending in a ladder makes me anxious every time. I genuinely considered giving up at one point.

But the views were worth it.

Our tour guide was an older man who talked about how everything works with so much passion. As we were the only people on the tour, he also chatted with us about his family. It turned out he has Polish roots, which felt like such a lovely small-world moment.

The sun was shining straight into our faces throughout the tour, so taking photos from the top was tricky.

After the tour, we headed back towards the hotel. We were determined to go back to our starting point on foot, so we followed the South West Coast Path again.

The western side of the isle felt totally different, and the views weren’t as appealing to us. We decided against hunting for another cliff-edge route and ended up on a path surrounded by high grass and not much else.

We were so exhausted that we changed plans and went to the nearest village to find a bus stop instead.

The Isle of Portland is hilly, which I didn’t expect at all. In the end, catching the bus felt like the right call.

Overall, we walked around 14 kilometres that day.

Day 3: Going home

The last day in Weymouth felt bittersweet. Even though I was ready to be home, I really loved our time there. I would’ve stayed longer if I could.

We took the train back to London around 1pm, hoping to get home in the early evening.

Unfortunately, our journey home was eventful and we had to switch trains in Woking. As a result, the full trip from Weymouth station to home took about nine hours. I was exhausted.

Top 6 things to see in Weymouth, Dorset

Sandworld

Have you ever seen sand sculptures? If not, add Sandworld to your “things to do in Weymouth list”. It’s a seasonal attraction and it’s one of the few sand sculpture festivals held in the UK.

SEA LIFE Centre Weymouth

Another attraction that works for pretty much any age: sharks, seals, jellyfish, octopus, otters — and loads more. It’s the kind of place where you lose track of time (in a good way).

Weymouth Beach

Weymouth Beach is an award-winning sandy beach with clear water.

It’s also very family-friendly thanks to the central location, nearby attractions, and lifeguards in season. If you’re happy to explore, there are lots of brilliant beaches near Weymouth as well.

Weymouth Harbour

Weymouth Harbour (also known as the Old Harbour) is home to pleasure boats and private yachts. It opens out into Portland Harbour, where sailing events for the 2012 Olympics and Paralympics were held.

A lifting bascule bridge separates Weymouth Harbour from the inner harbour (Weymouth Marina). It operates on a schedule, so you can see it in action if you time it right.

While walking around Weymouth, you might notice plaques referring to the Black Death. In 1348, sailors arrived here bringing the plague to the UK, and it spread quickly.

Nothe Fort

Nothe Fort is one of the best heritage attractions in Weymouth. There’s a maze of underground passages, a museum, and plenty of family-friendly bits too.

It sits on a hill at the entrance to Weymouth Harbour, which makes it a brilliant place to admire the Jurassic Coast. You’ll also find Nothe Gardens and Nothe Beach nearby.

Chesil Beach

This 18-mile (29 km) shingle barrier beach runs from West Bay to the Isle of Portland. Behind it lies the Fleet Lagoon, one of the few remaining undisturbed brackish lagoons left in the world.

Bathing at Chesil Beach can be dangerous, but it’s a brilliant spot to sit, breathe, and take in the views.

If you want a great photo of the beach, Heights Hotel in Portland gives an incredible viewpoint.

6 amazing things to do in Portland, Dorset

Portland Castle

Portland Castle is an artillery fort built by Henry VIII in the early 1540s to protect against French and Spanish invasion.

The audio tour covers its history (including the World Wars), and you can also enjoy sea views from the gun platforms and walk through the Contemporary Heritage Garden.

Fancy’s Farm

Fancy’s Farm is home to rare Portland Sheep. There’s also a playroom and outside toys, so it’s a great place with children.

You can feed animals, there’s no entry fee, and it’s close to the High Angle Battery and The Verne Local Nature Reserve — so you can easily spend a whole afternoon in one area.

Verne High Angle Battery

This 19th-century gun battery is a popular tourist attraction near the Verne Citadel. It was built in 1892 to protect Portland Harbour and was decommissioned just 14 years later.

It’s one of the best-preserved monuments of its type in the country.

Cave Hole

It’s hard to miss Cave Hole if you walk along the coast in Portland. It’s around half a mile (800 m) from Portland Bill Lighthouse and has a history tied to smuggling.

Now it’s also used for climbing, snorkelling, and Deep Water Soloing. We saw people climbing and two guys walking a rope line too.

Portland Bill Lighthouse

There are three lighthouses on the Isle of Portland, but only one is still in use: Portland Bill Lighthouse.

It’s the major attraction on the isle, and it’s open for tours.

Even though the climb can feel scary (narrow stairs and a ladder at the end), it’s worth it for the views over the English Channel — and you can spot the Trinity House Obelisk and Pulpit Rock from above.

South West Coast Path

If you like active days out, walking the South West Coast Path is one of the best free things to do in Portland.

It’s the longest waymarked long-distance footpath in England — 630 miles (1,014 km) from Minehead in Somerset, around Devon and Cornwall, to Poole Harbour in Dorset.

The Isle of Portland circuit is doable in a day: about 13 miles (20.9 km).

FAQ

How to get to Weymouth?

From London, the easiest way is to take a train from London Waterloo. The journey takes around three hours.

You can also take a National Express coach from London Victoria, which is often cheaper, but slower (around 3 hours 40 minutes).

Driving is usually the fastest option — around 2 hours 30 minutes, depending on traffic.

How to get to Portland?

The easiest way is to take bus number 1 from Weymouth town centre towards Southwell. It takes around 40 minutes.

If you want a longer coastal walk, consider getting off at Easton Square and starting from there.

Is Weymouth nice for a holiday?

Yes — Weymouth works well for a weekend by the sea, especially from London. There’s plenty to see, and it’s easy to mix relaxing beach time with sightseeing.

Where are Weymouth and the Isle of Portland?

Weymouth and the Isle of Portland are in Dorset, on the southern tip of the Jurassic Coast. Portland Bill is the southernmost point of Dorset.

Summary

Even though I hate long journeys, this was probably my favourite trip so far — and I’ve been dreaming about going back ever since.

If you’re looking for a seaside weekend with beautiful views, plenty to do, and a proper “reset” feeling, I really recommend Weymouth.

I mentioned I first discovered this town when I was looking for a place to move to, didn’t I? It wasn’t possible at the time (lack of flats to rent), but… who knows. Maybe one day.