Winsome Transport
Winsome Transport
5
City ToursHistorical & Heritage ToursPrivate Tours
About
Winsome Tours are private and exclusive for all size groups from 1 through 50 people (or more) - Owners Ralph and Julie Richardson are both Born Bermudians. They are both semi retired and enjoy sharing their island home with their guests. The couple has increased their fleet to two vehicles as demand has required it. Both bring their unique Bermuda experiences to their tours and immediately create the feeling of family with their guests. Their incredible knowledge of Bermuda, coupled with their friendly approach, sets Winsome apart as a premier tour operation. As one of their guest has stated, "It is like a drive with family."New!! 2015 - Due to demand new associates have joined the Winsome team - all rate extremely well on Tripadvisor - Welcome: Anthony, Robert and Rene.
Warwick Parish, Bermuda

Awards
Travelers' Choice
2024

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Most Recent: Reviews ordered by most recent publish date in descending order.

Detailed Reviews: Reviews ordered by recency and descriptiveness of user-identified themes such as wait time, length of visit, general tips, and location information.

Popular mentions

5.0
5.0 of 5 bubbles343 reviews
Excellent
323
Very good
8
Average
2
Poor
4
Terrible
6

Steve F
1 contribution
5.0 of 5 bubbles
Aug 2023 • Couples
We highly recommend Winsome Tours to give you a first hand look at the many interesting sites to see in Bermuda. Our private 14 passenger vehicle was perfect for our group and having Julie, one of the owners of the company, as our guide was invaluable. Her love, knowledge, and compassion for her country was felt immediately. We were able to improvise our itinerary as we went along and spend as much or as little time as we wanted at each location. As an extra treat her 15 year old granddaughter, Taylor, sang for us a couple of times during our tour and shared some of her experiences as well. Beautiful voice and our overall review is 5 stars!
Written August 14, 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Hello SteveF, Thank you for your kind review. Julie is always happy to host our guests and meet new friends. You happened to be in Bermuda during school break so that Taylor could join her grandmother, which she loves to do. We are thrilled that you enjoyed your private tour with us. Both Julie, Taylor and our other team members are encouraged to continue what we do at Winsome because of the wonderful feedback we get from our guests like you. We hope that you choose us again someday. Cheers
Written September 19, 2023
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

Morgan
Virginia Beach, VA65 contributions
5.0 of 5 bubbles
Mar 2022 • Couples
We cannot share enough praise for our time spent with Ralph! We did a full island tour and felt him to be the most perfect ambassador for the community and culture of Bermuda. Ralph was exceedingly kind, thoughtful, knowledgeable and genuinely lovely to spend time with. Ralph beautifully wove incredible stories of his life on the island into his tour, which warmly invited us to experience Bermuda through his eyes, which we felt was the most special and unique part of our tour. We left our tour with Ralph feeling fully apprised of Bermudian history and personally welcomed into the very heart of Bermudian culture.
Written April 2, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Hello Morgan, First, thank you for your kind review. After my report on the two of you, Julie wanted to meet you both and we were able to arrange for the four of us to have delightful lunch on another day. We both hope that you will stay in touch so that we can get together when you next visit Bermuda. We wish you both all the very best with your work in helping people beyond your shores. With kind regards,
Written April 10, 2022
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

nkim29
New York City, NY2 contributions
5.0 of 5 bubbles
Jun 2023 • Family
Had a wonderful day experiencing Bermuda with our tour guide Julie. Our family of 4 had a comfortable ride in the van and we learned much about the history and culture of Bermuda all charmingly wrapped in the stories of Julie and her family's experience and legacy. She was very accommodating to our schedule and we were able to make adjustments throughout the day. We felt like we got a taste of the whole island, and were appreciative that we never felt bored by lingering too long in one place. Julie and this tour gave us the experience that we were hoping for!
Written June 29, 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Thank you, Kim, We appreciate your very kind words. We feel that it is a privilege to share our island home with guests. We are all proud of Bermuda and how it has provided us with a wonderful place to live. We try to provide a comfortable mix of information to share with our guests and your review has given us encouragement. We wish you all the best and that you have a safe and pleasant summer.
Written July 1, 2023
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

Michelle G
Del Rio, TX47 contributions
5.0 of 5 bubbles
May 2023 • Family
We had a group of 5 adults and a 2 year old, along with 4 other passengers in a very clean and comfortable van. It was an amazing experience where we were able to get a great overview of Bermuda. Brenton was a perfect tour guide, having such pride in his country and giving a very informative tour. We were able to see from Royal Naval Dockyard up to the northern tip of St. Regis Bermuda Resort. Brenton's knowledge of Bermuda and its history were incredible. We all hope to come back and visit your beautiful island for a longer time. Thank you!
Written May 19, 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Hello Michelle, Thank you for taking the time to write this review, We are extremely proud that our son Brenton has come aboard after expressing interest in the business for some time. We are also thrilled by the response to his tours and the future of Winsome. Brenton brings a long list of skills to the company including his business acumen and love for people. He also brings enthusiasm, drive, and technical expertise which is already showing results. We wish you and your group well and trust that all of you will have a safe and pleasant summer. Hopefully we will have the opportunity to share Bermuda with you. again someday. Cheers
Written May 30, 2023
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

Kate B
1 contribution
5.0 of 5 bubbles
May 2024 • Family
We chose the full-day island tour with Ralph while in Bermuda with our daughter and grandson who was celebrating his 8th birthday. Ralph was a wonderful, knowledgeable host. While we'd made two prior trips to Bermuda, we learned so much new information during our day with Ralph.

From picking us up right off the ship to sharing details of the island with us to helping us make special memories with our family, Ralph provided an excellent level of customized service.

We highly recommend Winsome Tours for anyone who wants to see the real Bermuda and learn more about it from a local.

We've taken tours in over 20 countries, and this tour is among the very best we've experienced!
Written July 9, 2024
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Hello Kate, We feel honoured by your kind words. Your response to our tour validates the work we are doing and helps us to work even harder. We continue to study more about our island home and have many stories about our Bermuda experiences. We feel that these experiences help our guests to go beyond the surface to the essence of Bermuda life. Thanks again for your kind review and we hope to see you again.
Written July 15, 2024
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

Kevin L
1 contribution
5.0 of 5 bubbles
Aug 2023 • Family
Great experience learning about he beautiful island of Bermuda with Raymond. From. The very start, Ralph and Julie were very helpful and attentive to help us create our day excursion especially with such short notice to book. Ralph was very understanding when we added another family and gave us the best island experience with the best driver to make our visit to Bermuda one of the most memorable experiences we have ever had
Written August 24, 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Hello Kevin, Thank you for your patience in arranging your tour. We were sure that you would love Raymond as your guide. He has such an amazing personality. Raymond has been assisting us this year and we are thrilled that he could assist. We trust that you will consider us on your next visit and wish you and your entire group the very best. Enjoy the rest of the summer. Cheers
Written September 19, 2023
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

csd747583
Medford, NY8 contributions
5.0 of 5 bubbles
Jun 2024 • Family
If you have the opportunity to experience Bermuda with Ralph or Julie from Winsome Transport, don't pass it up! My husband and I, and our son, daughter-in-law, and 2 grandsons, ages 5 and 8, toured with Ralph on June 28th. I had spoken with him a few times to work out an itinerary that would appeal to everyone, and it was wonderful! Ralph is a long-time Bermudan resident and his knowledge is extensive. He told us fascinating stories and took us to many beautiful and interesting places. We had a perfect day!!
Written July 3, 2024
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Marilyn B
1 contribution
5.0 of 5 bubbles
Aug 2023 • Friends
Ralph from Winsome delivered excellent customer service from the time I asked for information about Island tours to when he issued me a full refund for our cancelled trip (due to Hurricane Franklin). I plan to go to Bermuda in the future and will definitely book with Winsome. Ralph worked so hard to accommodate changing requests due to weather. I am sure we would have had a wonderful tour experience with him.
Written September 3, 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Hello Marilyn, You will have a fantastic tour when you visit Bermuda. We offer full refunds when our clients are not able to arrive on the island due to weather. We try our best to promptly respond with refunds. Of course, we hope you will try again so that we will have the opportunity to share Bermuda with you. We look forward to that. We hope that you enjoyed the revised itinerary on your cruise and that you also enjoy the rest of your summer. Cheers
Written September 19, 2023
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

Gsnogles
7 contributions
5.0 of 5 bubbles
May 2023 • Couples
A friend recommended Winsome Transport tours and it was the best decision we made! By far the favorite part of our Bermuda trip. We had a group of 11 adults ranging in age from 40 to 80. We all fit comfortably in the van and very accommodating to the older travelers in our group. Brenton was the perfect tour guide. He shared his knowledge and love for the island. From the Royal Dock Yard to St George’s Island we saw and learned about it all! He was a joy to chat with. Thank you for sharing your island with us. We can’t wait to back!
Written June 15, 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
We are thrilled that Bernton is making such an impact during his first year working with the family business. It is refreshing to have our son working with us and giving great support and input in ways to imporve. Your response will go a long way towards his new journey with us. The most important thing for us, however, is that your group enjoyed your experience, and that is our goal for each group that chooses Winsome Tours. All the very best to you and your group.
Written July 1, 2023
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

Mark R
Baltimore, MD2 contributions
5.0 of 5 bubbles
May 2024 • Friends
A friend booked this tour for us to join them on, and it turned out to be the highlight of our stay in Bermuda. Ralph was both engaging , and full of knowledge of the island and its history. Saw things from his unique perspective as we drove from Dockyard to St. George’s and back. Even stopped at Woody’s on the way home to help us get fish sandwiches for lunch. His minibus was comfortable, with a PA system that allowed us to hear his commentary easily. He gladly accommodated a request to stop at a beach known for seaglass that did not disappoint. The tour struck the perfect balance between sights, sand, shopping, and history. Would recommend without hesitation.
Written May 16, 2024
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Hello Mark, When locals drive miles (not too far in Bermuda) for a special treat, it has to be good. So why not share our secret for the best fish sandwiches? We drive there often for our favourite fish options. Of course, we love to customise our tours to focus on what our clients want. We made the decision more than a decade ago to offer private rather than mixed group tours through our website. We have become more flexible with customising tours that fit within the two tour lengths we offer, each of which can be extended if requested. Enjoy the rest of the summer
Written May 26, 2024
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

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Winsome Transport - All You Need to Know BEFORE You Go (2024)

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