A Weekend in Weymouth - The Perfect Itinerary for First-Time Visitors

Whether you’re travelling as a couple, with friends, or bringing the whole family, there’s plenty to see and do. And with Waterside's Dorset parks - Bowleaze Cove, Chesil Beach and Osmington Mills - all close to the heart of Weymouth, you’ll be perfectly placed to enjoy it all.

Here’s our guide to the ultimate weekend itinerary in Weymouth for first-time visitors.

Morning: Weymouth Beach & Esplanade
Start your trip with a stroll along Weymouth Beach, one of the UK’s best-loved stretches of sand. From traditional donkey rides and deckchairs to modern cafés and water sports, it’s the perfect spot to soak up the coastal atmosphere.

Afternoon: Explore the Harbour
Head over to Weymouth Harbour, just a short drive from Chesil Beach Holiday Park. Wander along the colourful harbourside, watch the boats come and go, and pop into one of the independent shops or galleries. If you’re up for an adventure, you could even book a boat trip to see the Jurassic Coast from the sea.

Evening: Dinner with a View
There’s no shortage of places to eat in Weymouth. Try one of the harbourfront restaurants for fresh seafood, or enjoy a relaxed evening with a Waterside Takeaway or at Drift Bar & Grill at Bowleaze Cove Holiday Park & Spa, where you’ll find family favourites with sea views.

Morning: Nothe Fort & Gardens
Discover Weymouth’s history with a visit to Nothe Fort. This Victorian fort offers incredible views over the bay and fun, interactive exhibits - a great option for families. After exploring, relax in the Nothe Gardens with a picnic.

Afternoon: Coastal Walks & Country Pubs
For stunning Jurassic Coast scenery, take a walk along the South West Coast Path. From Osmington Mills Lodge Park, you can join a trail that winds past dramatic cliffs and hidden coves. After your walk, reward yourself with a hearty meal at The Country Club at Osmington Mills, a cosy pub-style restaurant serving seasonal dishes.

Evening: Relax and Unwind
If you’re staying at Bowleaze Cove, why not enjoy the fun of Southside Funfair or a sunset drink at The Shack? Or if you’re near Chesil Beach Holiday Park, take in the panoramic views across Portland Harbour as the sun goes down.

If you’ve got a little more time before your weekend ends, squeeze in a family activity. Weymouth Sealife Adventure Park is a favourite with children, while Dorset’s countryside offers everything from archery and segways to woodland walks. Many of these activities are also available at our parks, meaning you don’t need to travel far to keep the whole family entertained.

The best way to make the most of a weekend in Weymouth is to stay somewhere close to both the town and the coast. With three holiday parks in Dorset, Waterside offers the perfect base for your getaway:

• Bowleaze Cove Holiday Park & Spa - a lively family-friendly park with restaurants, activities, spa facilities and direct beach access.
• Chesil Beach Holiday Park - perfectly positioned for Weymouth Harbour and Portland, with panoramic views and great facilities.
• Osmington Mills Lodge Park - a peaceful, countryside retreat with luxury lodges and a traditional country club restaurant.

Whether it’s your very first visit or you’re rediscovering old favourites, Weymouth has everything you need for a memorable seaside break. From beaches and history to coast path walks and delicious dining, you’ll never run out of things to do.

Ready to start planning your weekend in Weymouth? Explore our Dorset holiday parks and book your stay with Waterside today.