Portland & Weymouth UK, 2023
Initially, we had low expectations for Portland, UK, viewing it merely as a jumping-off point for excursions like Stonehenge. However, our experience turned out to be a delightful surprise. Here’s why we fell in love with this charming port town during our first British Isle cruise stop.
Updates:
Overview of Portland
Portland is located 68 miles southwest of Southampton, making it either the first or last port of call on many British Isles cruises. The port itself is a commercial dock area, so don’t expect a bustling cruise terminal. Instead, you’ll find an open lot with a few buildings, an outdoor kiosk staffed by friendly volunteers with guide maps, and a small terminal building with free Wi-Fi, seating, and taxi access.
Since walking out of the port area is not permitted unless you’re on a tour or have arranged private transport, free shuttle buses operate throughout the day. These buses follow a set route, stopping first at Portland Castle and then continuing to Weymouth, before circling back. While there can be crowds returning to the ship later in the day, the frequent shuttle service keeps wait times short.
Exploring Weymouth: A charming Seaside Retreat
The biggest surprise of our visit? Weymouth! This small seaside resort town has been a beachside getaway for British royalty since the 18th century. While there’s certainly history to soak in, what stood out most was its charming, old-fashioned English seaside appeal.
Stroll the Esplanade: Enjoy a walk along the picturesque beachfront, complete with traditional carnival rides and ice cream stands.
Try a Cornish Pasty: At the Cornish Bakehouse, we savored a large pasty—a delicious, meat-filled pastry similar to a giant empanada.
Note: Be cautious on the cobblestone sidewalks, as they can be uneven.
Unexpected Surprises
1. Castletown D-Day Center
Located within walking distance of the Portland Castle shuttle stop, the Castletown D-Day Center was an unexpected gem. Portland, Castletown, and Weymouth played critical roles in D-Day operations, serving as staging grounds for thousands of servicemen before the invasion of France on June 6, 1944.
While listed on many "things to do" lists, we were blown away by just how interactive and immersive this museum was:
Climb into jeeps and tanks
Handle authentic World War II firearms
Try on uniforms and pack gear
Lift artillery shells and crank an air raid siren
Explore a replica German pillbox from Omaha Beach
Many artifacts were even used in films like Saving Private Ryan! Friendly and knowledgeable docents were available to provide insights, making this a must-visit. Though many guides suggest spending an hour here, we highly recommend allocating at least two hours to fully experience the exhibits—especially if traveling with kids.
2. Weymouth Land Train
While Weymouth is flat and easy to walk, the Weymouth Land Train provides a fantastic alternative for those who prefer to take in the sights with minimal walking. This fun, budget-friendly train loops around the main attractions and stops near vibrant restaurant and music areas. Our parents particularly appreciated this comfortable and leisurely way to explore the town.
3. Warm Hospitality
Perhaps the most memorable part of our visit to Portland and Weymouth was the incredible hospitality. From the warm and welcoming volunteers at the port to the friendly locals in town, the sense of genuine kindness was unmistakable. Despite being a tourist destination for centuries, Weymouth has maintained its authenticity—never feeling like a commercialized tourist trap.
And as we departed, we were treated to a heartfelt farewell performance by talented local singers, The Dorset Wrecks—a unique and touching send-off we won’t soon forget.
Final Thoughts
We left Portland with a desire to return. There’s so much more to explore, including Portland Castle, Portland Bill Lighthouse, and Chesil Beach. If you’re considering this port, check out our Stonehenge vs. Athelhampton House video for more excursion options.
Portland may have started with low expectations, but it quickly became a memorable highlight of our trip!
