Physical Address
304 North Cardinal St.
Dorchester Center, MA 02124
Physical Address
304 North Cardinal St.
Dorchester Center, MA 02124

Experience the luxury of a private sailing and dining trip on Windermere’s stunning waters, combining sailing, scenic views, and a delicious locally sourced ploughman’s.
Imagine being the only group on a sleek 10-meter Oceanis Clipper yacht, drifting silently across England’s largest natural lake, Windermere. This private Sail and Dine experience promises not just a scenic boat ride but a chance to enjoy authentic sailing, spectacular vistas, and a hearty, locally sourced meal—all in one smooth three-hour package.
What truly makes this experience shine is the personalized nature of the tour. With only your group on board, and a seasoned skipper with 20 years of Windermere sailing experience, you get intimate insights and the flexibility to tailor your time to your mood—whether you want to hop aboard and help with the sailing or simply sit back and soak in the views. The highlight, without a doubt, is the extensive ploughman’s lunch served in a setting most restaurants can only dream of—on deck, with panoramic lake views.
A possible consideration? The weather can be a factor—since this outing relies heavily on wind and sunshine, rain or poor weather could mean rescheduling or a less memorable experience. However, the provider’s policy offers full refunds or alternative dates if the weather turns unfavourable.
This tour is perfect for couples seeking a romantic escape, small groups of friends craving a unique adventure, or anyone wanting a luxurious yet authentic experience of Windermere’s natural beauty.


For a more personal experience, these private Windermere tours deliver individual attention
Booking the tour typically requires about two weeks’ notice—most travelers reserve around 15 days in advance. The experience is priced at around $405.25 for your group of up to two people, making it a relatively intimate and exclusive outing. The meeting point is conveniently near public transportation in Windermere, specifically identified by a code, ensuring easy access.
The yacht itself is a 10-meter Beneteau Oceanis Clipper, a vessel known for its stability and seaworthiness, ideal for lake sailing. The skipper, with two decades of Windermere sailing experience, not only manages the boat but also shares stories and insights about the lake’s history and natural features. Reviewers consistently mention how personable and informative the skipper, often named Ian, is—adding a layer of authentic local knowledge that elevates the trip.
The experience begins with about 90 minutes of sailing, where you’re encouraged to take an active role—hoisting sails, steering, or simply enjoying the ride. If the wind is favorable, you’ll get a good feel for what it’s like to captain a yacht on Windermere’s calm waters. For those less inclined to steer, the skipper provides plenty of commentary and stories, making it a relaxed yet engaging activity.
After sailing, the boat anchors in a secluded bay—perfect for unwinding and soaking in the scenery. Here, your homemade ploughman’s lunch arrives, packed with locally sourced ingredients and served with lots of delicious homemade additions. You can opt to dine al fresco on deck, taking full advantage of the stunning views, or stay inside the spacious saloon if weather isn’t cooperating.
Reviewers like Gemma B praised the “fantastic weather and plenty of wind,” which made the sailing especially enjoyable. The lunch is described as extensive, hearty, and full of homemade touches, making the break both satisfying and relaxing. Soft drinks, tea, and coffee are included, with a well-priced bar available for those wishing to indulge in alcoholic beverages—note, you must be 18+ to purchase alcohol.
The yacht offers conveniences like a private bathroom and central heating—features that make the outing comfortable, especially if the weather turns cooler. The well-stocked bar and the provision of bottled water keep everyone refreshed, while the safety and hygiene measures align with standard expectations.

At just over $400 for a three-hour private adventure, this tour delivers a lot of value. You’re not just paying for the boat ride but for a personalized, intimate experience that combines sailing, stunning scenery, and a delicious meal. For couples, this is a romantic way to spend an afternoon; for small groups, it’s a memorable way to celebrate a special occasion or simply enjoy some quality time together.
The review from Gemma B highlights how well-organized and communicative the process is, adding peace of mind before you step aboard. The fact that most reviews rate it a perfect 5 out of 5 suggests that the experience consistently meets or exceeds expectations.
The main draw here is the combination of sailing and dining in a private, scenic setting. Windermere’s calm waters and breathtaking views make for a memorable backdrop, especially when complemented by the warm, hearty meal. The fact that you can participate in sailing or simply relax makes it accessible for a wide range of travelers.
However, the experience’s dependency on good weather is worth noting—so if you’re visiting in a season prone to rain, it’s wise to be flexible with your dates or keep an eye on the forecast.

This experience appeals most to those seeking an authentic, hands-on sailing adventure with a touch of luxury. It’s perfect for couples looking for a romantic afternoon, small groups celebrating a special event, or anyone wanting a more personal way to explore Windermere’s natural beauty. It also offers a fantastic opportunity for sailing novices and seasoned sailors alike—everyone can enjoy the relaxed, friendly atmosphere.
If you’re after something unique, memorable, and with a high level of comfort and privacy, this sail and dine experience hits all the right notes.
Is this tour suitable for children?
Yes, the minimum age is 9, making it a family-friendly option. Just keep in mind that children should be supervised, especially during sailing.
What should I wear?
Dress appropriately for the weather. Since the yacht is partly outdoors, layers and waterproofs are recommended if rain is forecasted.
Can I participate in sailing?
Absolutely. You are welcome to get involved as much or as little as you like. The skipper is happy to teach or guide you through the process.
Is alcohol included?
No, alcoholic beverages are not included. However, a bar service is available on board at reasonable prices, and you must be at least 18 to purchase alcohol.
What happens if the weather is bad?
The tour is weather-dependent. If the weather doesn’t permit sailing, you’ll be offered a different date or a full refund.
How long in advance should I book?
Most travelers book about 15 days ahead, ensuring availability for this popular private experience.

The Private Sail and Dine Experience on Lake Windermere offers a rare chance to combine a private sailing adventure with a hearty, locally sourced meal amidst some of England’s most beautiful scenery. With a knowledgeable skipper, stunning views, and the chance to participate actively or relax, it provides a tailored, meaningful way to enjoy the lake.
Perfect for those craving intimacy, authenticity, and a touch of luxury, this tour stands out as a memorable highlight for any Windermere visit. Just remember to check the weather and book early—the exclusivity and quality of this experience are well worth the investment.
Whether you’re celebrating a special occasion or simply want to enjoy Windermere from a different perspective, this sail and dine offers an authentic, peaceful escape you’ll remember long after the boat has returned to shore.