Reviewed July 27, 2017

You Winsome, you win some!

Ralph is organized, professional, thoughtful, and insightful. He has exceptional knowledge of Bermudian culture, history, geography and nature and will tailor your tour to your group's unique needs and interests.

We had the privilege of touring with Ralph for 2 days. The highlights for me were:
1) Ralph's walking tour of the beautiful St. Georges, and the captivating stories behind it's landmarks and sites.
2) The gorgeous beaches - Horseshoe Bay stood out as being the most pristine and calm (Tobacco Bay was incredible as well).
3) Ralph's tour in his van will not disappoint. He will point out the most notable sites and will pass around interesting photographs and documents to supplement his descriptions (I won't ruin the surprise but he'll share lots of fun facts and fascinating personal connections to the island).

Ralph will go above and beyond to ensure that you have the most fun and uniquely Bermudian experience possible. If you're planning a tour, Ralph's your guy!

Absolutely the Best Tour Guides

My husband and I attended a tour with Winsome Tours in early May as part of a group cruise. Our driver, Julie, was absolutely the BEST. Her informative 6 hour tour was well worth the whole trip, as we had not so good weather for the remaining time in Bermuda. She spoke of every thing she could while driving, telling everyone stories both personal and about the land. Her stories made you feel part of her family. If anyone had any questions, she would answer. I do not think there was a road unturned from her tour. I would have done it again just to see the beautiful land they have.

Reviewed June 22, 2017

The Best Tour Guide For Bermuda

I can honestly say if you are looking for a tour guide for Bermuda this is the company you want. Julie picked us up right at the terminal and greeted us with a big hug. The tour was amazing. Since she was born and raised in Bermuda she was so knowledgeable about every aspect of the island. We feel that we got so much more than what we paid for. Her stories were just as interesting as the island itself.

June 25, 2017 via mobile

Fabulous tour!

We were greeted at the cruise ship terminal by Julie and she hugged each of us as if we were old friends. She was absolutely charming, and so passionate about Bermuda and its history. This was our third trip to Bermuda and I can honestly say I learned so much about this beautiful island from Julie. If you go to Bermuda, make sure you arrange a tour with Winsome tours. You will not be disappointed!!

Reviewed September 11, 2017

Multi generational tour of entire island

Ralph was simply amazing. We have been talking about all the things we learned from him over the past several days. I have such a new found respect for Bermuda and her people now. I highly recommend Winsome Tours as an extremely professional and knowledgeable tour. Ralph catered to my 90 year old parents and took care of them like family. He was adaptable, helpful and caring, not to mention extremely well educated and informative. I feel lucky to have had him personally do our tour. His timing to catch the beautiful sunset on the most westerly side of the island was spot on!

Bayside, New York


Reviewed September 17, 2017

Ralph is amazing!

We just came back from a cruise to Bermuda. On the 2nd day we had a private tour with Winsome tours. We had Ralph, the owner. He showed us EVERY part of Bermuda from the dockyard to, St. George, to Hamilton and every little town in between. We stopped for the reenactment in St. George, very funny. We did the Crystal Cave ( beautiful) and the aquarium and zoo. Ralph came in with us and explained all the Bermuda fish and animals in detail. He was so proud of his and his wife's Bermuda heritage and it shows in his tour. Thank you so much Ralph for a wonderful day!

Reviewed September 25, 2017

Absolutely a fantastic experience!

Julie was an amazing guide to take us on our 6.5 hour private tour of the island. She customized the points of interest and stops according to what we wanted to see. What better way to learn about the island than someone whose family has inhabited it for centuries. When we return, which we will, we will definitely hook up with Winsome Tours again. If you are looking for a comfortable ride and to enjoy the highlights of the island this is the tour for you. Thank you Ralph for communicating with me about our trip so many times - I was comforted in knowing that you would respond almost immediately to my questions.

“The best up close and personal Bermuda tour”

Reviewed June 24, 2015 NEW (TripAdvisor Review)

Mr. Richardson (Ralph) was very personable and knowledgeable about Bermuda. There were 6 of us and we were made very comfortable from the moment that we entered his vehicle. He took us all around the island and areas that we know a regular tour coach could not enter due to the roads being extremely narrow. He talked about history of the island, had photos, even a sample of the pink sand as 2 of us had limited mobility and could not get to the beach. He took us to a restaurant that everyone is still talking about the Wahoo sandwiches. I would recommend his company to anyone and everyone. We also had the opportunity to meet his wife Julie who also does tours and I am sure is just as knowledgeable of the island. It was a pleasure to have spent the day with such a gentleman and learning about his island Bermuda. If we have the opportunity to go back we will definitely book another tour with Winsome Transport. I hope that our paths will cross again. Thank you for a Wonderful Day!!!!!

Visited June 2015

“Excellent Private Tour”

Reviewed June 23, 2015 NEW (TripAdvisor)

Prior to my cruise to Bermuda I emailed Winsome Transport with a request for a private tour for 7 people. The communication was quick and excellent. Julie was our tour guide and she was very knowledgeable. For 6.5 hours she took us around the island and shared history as well as other information the entire time. She made us feel like a part of her family. I would book another tour with her without hesitation.

Visited June 2015

“Accommodating and knowledgeable.....”

Reviewed June 1, 2015 (TripAdvisor Review)

Based on prior reviews, I booked Winsome Transport and can now add my 100% total satisfaction. From my first email communication until being dropped back off at my cruise ship, I felt royalty being in the escort of Julie. Vehicle was extremely clean and comfortable and her passion for the island and its people could not have been more apparent. She exceeded our expectations and gave 100% to our enjoyment of touring Bermuda. We loved all her stories including her being raised on the island and her 2,000+ relatives still living in Bermuda. You won't be disappointed hiring Winsome!!

Visited May 2015

Visited July 2013

“Best Tour!”

5 of 5 stars Reviewed July 14, 2013 NEW

I booked a tour directly with Ralph and not our cruise line for a family of 8 after reseaching online. We wanted a private tour and the flexability of customizing a tour just for us. We ranged in age from 17-88. Julie, Ralph's wife was our guide. She was prompt, extremely knowledgeable and fit right in with our family. We went from one tip of the island to the other and back. Our 5 1/2 hours flew by and we were sad to end our day. We were beyond happy and recommend them highly! It's the best way to see this beautiful island. Thanks Ralph and Julie!

Visited July 2013

“"Awesome Tour"”

5 of 5 stars Reviewed July 10, 2013 NEW

My husband and I were invited on this tour with family members for his birthday and his daughter's 2nd wedding anniversary . . .What a Joy ! This is definitely the way to enjoy the quaintness of Bermuda. You will get personalized service at it's BEST !!

“The way an island tour should be!”

5 of 5 stars Reviewed July 9, 2013 NEW

One word to describe our experience, OUTSTANDING! My husband found this tour by researching on tripadvisor. I sent them an email with our contact info and asked if our date was available. We received a phone call that evening from Ralph and he wanted to know what we would like in a tour (what we wanted to see, do etc.). We were traveling with young children so we knew we did not want to be cramped in a large bus with a lot of people for 8 hours. We wanted our children to have a chance to get out and run/climb. We also told Ralph that we do not want to do the "touristy" attractions. When we visit an island, we like to see how the locals live. We traveled to Bermuda by a cruise ship and Ralph was at the dockyards at 9:00 AM to pick us up. We wanted to see the whole island and left it up to Ralph to design our tour including an add on hour for lunch. Ralph had us immersed in all of his stories. He even had our 4 and 9 year olds involved in all of our discussions. We made many stops and he had our boys running and climbing throughout our journey. We stopped for lunch at the Royal Bermuda Yacht Club. You can only dine here if you are a member (which Ralph is). We had a lovely lunch and the best fish and chips! We have been on many tours on many islands and this has been the best island tour we have EVER been on! We left this tour with a new favorite island and a new friend (Ralph)!

Visited July 2013

“Amazing Tour”

5 of 5 stars Reviewed July 1, 2013 NEW

We have just returned from a trip to Bermuda, and I couldn't wait to submit this review. We stumbled upon Winsome Transport while searching online for a private tour of the island. Upon leaving our ship, Ralph was right at the dock to greet us. We hopped in his van for a five hour tour of the island. The tour was FABULOUS! Ralph was an amazing person to talk to, as he has had a ton of life experiences that he willingly shared with us. We asked many questions, which he answered willingly. He even added personal touches about his family and wife Julie, who he introduced us to when our tour crossed paths with one that she was giving. I had been to the island before, but had only seen a small fraction of what I was able to discover under Ralph's guidance. It was clear to us that Ralph knew almost everyone on the island, and it felt as if we were being guided by a friend. We never felt rushed, and were completely satisfied by the tour. You MUST take this tour if you want to learn about Bermuda's beauty and history.
-The Reisner/Ravena family.

Visited June 2013


“Delightful Tour of Bermuda”

5 of 5 stars Reviewed June 10, 2013

Full Island Sunset Tour & Dinner at Tom Moore's Tavern:

My husband and I signed up for this tour through our cruise ship. We had already taken a daytime Island tour and were a little nervous that it would be similar. The main attraction, for us, was getting to have dinner at a Tavern that was built in 1652. That being said, we could not have been more pleased with this tour. Yes, we saw some of the same things we saw on the daytime tour (through a different company), but here is where it differs: The Winsome tour is for smaller groups. Unlike our daytime tour, it was much more personal and intimate. We toured parts of the island that tour buses can't access, and we got a detailed historical account of the island. A short (easy) walking tour of St. George's was included, which was a plus for a history buff like myself. Ralph, our guide, was incredibly knowledgeable and a great storyteller.

Dinner at the Tavern was a wonderful way to end the tour. A four-star meal that, no doubt, would have cost as much as the entire tour itself. Beautiful presentation and delicious to boot!

If ever we get a chance to return to Bermuda, we will most likely take this tour again. I would highly recommend it for anyone looking to get a real taste of the Island.

“Knowledge beyond belief”

5 of 5 stars Reviewed May 22, 2013 NEW

On May 15th off the Norwegian Breakaway we had a tour of Bermuda with Winsome Tours. The extensive knowledge of Julie, one of the owners, gave us not only the history of the island but her families own personal life in Bermuda. We travelled through the entire island, stopping not only at the historical locations, but whenever we wished to take a picture of the beautiful island.
We got to St. George in time to witness the "dunking" of the wench by the Town Crier. She also told us of some special events on the island during our stay. Our promissed 5 hour tour actually lasted 90 minutes longer as Winsome tours does not believe in rushing their guests. I would strongly recommend them for a private tour for individuals and groups since their vehicle holds up to 14.

Visited May 2013

In on May 24, 2013 (2 comments)

1) A comment from one of last week's 5 hour full island tours (emailed to Ralph):

Many thanks for the follow-up Email. I note my ancestor's name, Stephen Hopkins, on the Sea Venture's passenger list that you appended. Standing on Building Beach where he came ashore in 1609 was a very special occasion for me (and for my wife, who loves collecting sea glass).

The Island Tour on Sunday May 5th was exceptional! We've travelled all over the world and have never come across a more knowledgeable and congenial guide. But it was the personal touch that vividly set it apart. Your ability to weave your family's history into the story of Bermuda really made the island come alive. My friend's partner is an avid yachtsman. He was most interested to hear that you had shown us over the Royal Bermuda Yacht Club, of which he has fond memories as a participant in past Bermuda races.

Bermuda certainly exceeded our (already high) expectations in every way. We are already considering a return trip next year. Best wishes as regards your business expansion plans. This can only be a win-win situation for Bermuda and visitors.
We will certainly recommend WINSOME TRANSPORT to one and all with unreserved enthusiasm.

Best Regards,

Raymond L. Candage, Jr.

N.B. Please feel free to use me as a reference, or this communication as a Testimonial

2) A comment about our Dinner Tour available at:





Lana says on Trip Advisor:

Just took a cruise to Bermuda in April and hooked up with Ralph and Julie from Winsome Tours for a 6 hour FABULOUS tour of their island. Met right at the dock and taken on comfortable van on a tour from the Dock Yard, to St. Georges, The Lighthouse, the oldest home on the island, the beaches, tours of homes and because we had been in Hamilton the day before the city was was not included in our tour per our request. Their were 6 of us and we had a GREAT time!!!! Spoke to Ralph a few times as he responded to my e-mail immediately by phone. Julie was a Delight and explained so many things, but not so fast that we couldn't absorb the information. I had been to the island many years ago, but never got the good feeling I got on this tour! Check them out as they have an American toll free number 909-271-3322. Would recommend this couple quite highly. Julie even explained about her 1200 relatives who live mostly on the island and even showed us where she and her grandchildren went to school. She is very family oriented and expressed that to us. What a beautiful island and what a beautiful lady. Would love to go back just to see her again. They only take cash as payment, but it was US currency so no problem converting money. You can have lunch at the Yacht Club or go to the Gardens or the Caves.

Visited April 2013

Janet on Cruise Critic Says:

We just returned from Bermuda on the 21st. Had a wonderful 5 hour Island tour with Julie Richardson of Winsome Transport, www.winsometransport.com. We inquired late regarding this tour and Ralph Richardson was already booked but he actually called me the same night I e-mailed him and arranged to charter another taxi (actually a van that held 12 but we were only 6) to accommodate us. His wife, Julie (both are born & raised in Bermuda) personalized our tour to our requests combined with her suggestions. We hit all the highlights plus more. We can't recommend them enough. Wonderful people and fantastic tour guides.


May 24, 2012

Thank you, Ralph, for providing an excellent Bermuda day tour for my group of 38 friends from Washington, DC. It was great that you met us on-time at Dockyard. Our group appreciated very much your wonderful plan to see the beauty of Berm
uda from Dockyard to St. George. Your nice presentation of Bermuda history, natural, and economic was a great class for us. I would like to thank Julie and Winston’s help too. I will certainly recommend you to anyone visiting Bermuda.

The Best Tour Ever!
Hi Ralph and Julie, I wanted to thank you again for the best tour ever !!!!!!! I dont know how you did it, but you managed to talk for almost all of the 5 hr. tour and filled our time with much insight on Bermuda, its history, culture, and people. I plan to go on the Cruise site and post a blog on what a fantastic tour you gave us at such a reasonable price.

- Diane and Gordon Cooper, New Jersey

You did a fabulous job showcasing the island...
"It was so much fun meeting you and spending the day touring your beautiful island home. We hope to revisit Bermuda next year... maybe on another cruise! You did a fabulous job showcasing the island and pointing out all the sights of interest. You are both very knowledgeable about your home, and we enjoyed learning about the history of the island - much of which we didn't know!! Thanks so much."

- Mike & Nancy Polisin, USA

Julie you were Special!

One of the highlights of our 55th wedding anniversary cruise to Bermuda was our delightful afternoon spent with Julie in her spick and span limo-bus. Hers was a top-drawer excursion experience for our group of thirteen (ages 7 to 77)!! Julie was articulate, interesting and informative as she told us of her Bermuda--its history, geography and culture. Both adults and children were most favorably impressed by her. We give Julie and Winsome Transport our highest recommendation!!

- Beverly and Bill Van Winkle of New Jersey, USA

I highly recommend Winsome Transport...
If you’re looking for a great tour of Bermuda, I highly recommend Winsome Transport. On our recent Bermuda Cruise, we arranged for Winsome Transport to provide a 4-hour circle-island tour for our group of 46-passengers. Owners Ralph and Julie Richardson arranged for one 25-passenger mini-bus and two 15-passenger luxury vans at a very reasonable price of $10 per person per hour ($40 each for the 4-hour tour). Ralph and Julie served as our driver/guides during the tour and shared many interesting stories about the history and culture of Bermuda from St. George’s to Hamilton to Royal Naval Dockyard and all points in between. Their pick-up location was flexible. We just happened to begin our tour in St. George’s as that was the first port-of-call during our cruise. The tour provided a wonderful introduction of all that Bermuda has to offer and an insider’s view of the many secret treasures that could easily be overlooked by the casual observer. Having served on many local committees, and as the current Commodore of the Royal Bermuda Yacht Club, Ralph and Julie provided a wealth of knowledge about their homeland and the people that make Bermuda such an outstanding vacation destination. Ralph and Julie also offered reasonably priced transportation later in the week, however most of our group took advantage of the fast ferry and bus system to get around the island during the remainder of our stay. You can reach Ralph or Julie to make arrangements for your tour. Trust me, you’ll be glad you did!

- Kelly Shannahan, Travel Agent in MD USA