There is a certain breed of tennis player who cannot be stopped by the weather, and the debate over winter tennis in Florida vs. summer tennis in New England resorts is one they live rather than argue.
From the prominent Coachella Valley to the breezy coastlines of San Diego and Santa Barbara, this guide covers seven standout properties that have made California one of the most celebrated tennis destinations in the world.
Kiawah Island Golf Resort has been serving unforgettable match moments from the time its first guests stepped onto the tennis courts in 1976. Fifty years later, that legacy continues to rally. In late 2025, the acclaimed Roy Barth Tennis Center added two new padel courts to its award-winning lineup.
There is a certain breed of tennis player who cannot be stopped by the weather, and the debate over winter tennis in Florida vs. summer tennis in New England resorts is one they live rather than argue.
From the prominent Coachella Valley to the breezy coastlines of San Diego and Santa Barbara, this guide covers seven standout properties that have made California one of the most celebrated tennis destinations in the world.
This guide covers six padel resorts in Italy, from a family-friendly all-inclusive village on the Calabrian coast to a five-star lakeside retreat in Veneto.Â
The TRO team has not visited this resort yet; the information provided combines our research and information taken from the resort’s website. We recommend you contact the resort before visiting to ensure its accuracy.
Rosewood Bermuda has partnered with Cliff Drysdale Tennis to offer a comprehensive racquets program, the first of its kind on the island. The program includes lessons, retreats, and clinics, providing a challenging and enjoyable experience for both members and guests. The Racquets Sports Center features a pro shop, four Har-Tru clay tennis courts, four pickleball courts, two padel and locker rooms. The program combines favorable weather with world-class facilities, enhancing the racquets experience and offering social opportunities.
Off Court
Overlooking Castle Harbor's sparkling blue waters, Rosewood Bermuda offers guests the sophisticated elegance of a spa resort with the relaxing casual ambiance of the islands.
Located only 90 minutes by air from the U.S. eastern seaboard, the island's British and African heritage give it a personality unlike anything else in the world. As Britain's oldest colony, British influence continues to dominate government, educational and legal institutions. One may spot a Bermudian judge walking through the capital of Hamilton in a powdered wig, see a bobby directing traffic or overhear a passionate conversation about a local cricket match. While subtler, African influences can be found in dance and music, especially reggae, calypso, and the rhythm of the Gombeys – magnificent dancing and drumming troupes that often take to the streets.
19 Reviews on “Rosewood Bermuda - Cliff Drysdale Tennis”
Excellent
5
19 reviews
On Court Experience
5.0
Off Court Experience
4.9
Overall Tennis
4.9
Overall Pickleball
4.7
Adult Tennis Camp Experience
4.9
Tennis Instruction
5.0
Pickleball Instruction
5.0
Adult Tennis Camp Experience
4.8
Accomodations
4.8
Resort Amenities
4.9
DL
I had a lesson with coach Terry and he was so patient with me as I had not played for a number of years. Loved the area and environment. Such a nice atmosphere created by the wonderful staff.
AF
I had a fantastic experience with Coach Brent and Coach Ashley during my stay at Rosewood Bermuda.
Coach Brent made pickleball fun and engaging, especially for my first time—his easygoing demeanor made it easy to relax and enjoy the game. I then joined Coach Ashley the next day for a tennis lesson, and her level of patience was unmatched. Even when I struggled, she gently reminded me that it’s all part of learning something new and to simply enjoy the process.
Both lessons were highlights of my stay. I would highly recommend for your next time in Bermuda!
TS
Awesome experience at Rosewood tennis. Ashley was so helpful and friendly when booking. They have really nice new padel and pickle courts.
LB
Coach Ashley is an outstanding instructor – knowledgable, friendly and extremely skilled at getting the best out of your game. The Rosewood Bermuda team are approachable, welcoming and work hard across all three racquet sports to provide a first rate service!
CS
Awesome experience with the coaches and players across the tennis, PB and padel courts! Coach Ashley did a great job with cardio tennis – I cannot believe how she remembers everyone’s names! And coach Brent and Terry really brought the energy and competitive environment to the PB sessions. Really wonderful overall experience!
KL
We love the courts and the tennis staff! Always welcoming, very knowledgeable and fun to be around. Makes all the difference that they make a point to know your name as best they can and to welcome you back if you are returning. We play tennis every day of our stays and will continue to do so. Ashley, Terry, Brent, Kayla, Jordan run a fantastic program!
CK
We had an outstanding experience with Ashley Brooks during our recent stay at Rosewood Bermuda. She’s one of those rare tennis pros who brings real enthusiasm and energy to every minute on court. Her drills were fun, challenging, and incredibly well‑structured — there wasn’t a dull moment, and our two‑hour sessions flew by.
Ashley’s feedback was clear, actionable, and immediately useful. We’ve already implemented several of her suggestions and have seen noticeable improvements in our play since. She also went out of her way to share her contact information so we could follow up, adjust future lessons, and keep building on what we learned. Her flexibility with scheduling was genuinely appreciated.
Beyond the tennis itself, Ashley was a fantastic resource for local recommendations — restaurants, experiences, and things to do around the island. It made the whole trip feel more personal and connected.
The tennis facilities at Rosewood are excellent. The four hard‑tru courts are in top condition, and while we didn’t use them this time, the property also has pickleball courts and two brand‑new padel courts — something we’ll definitely try on our next visit. The Rosewood grounds are beautiful, and although the hotel, tennis centre, and beach club are spread out, the shuttle and the quite roads for walking made it easy to get around. The beach club is also a highlight of this property.
Overall, Ashley made our tennis experience a highlight of the trip. Highly recommended for players of any level looking for high‑quality instruction in a stunning setting.
DF
Excellent tennis instruction in a luxury resort. We learned a lot and enjoyed Bermuda in the uncrowded off season.
JD
My friends and I had an unforgettable ladies’ tennis retreat at Rosewood Bermuda! Ashley was exceptional—kind, accommodating, incredibly fun, and a truly talented coach. When rain disrupted our tennis plans one day, she went above and beyond by introducing us to padel, which ended up being a highlight of the trip. I can’t recommend this destination enough for anyone planning a tennis getaway!
PC
My husband and I had an incredible time at Rosewood Bermuda. Ashley and Terry were so friendly and fun, not to mention excellent tennis instructors. I felt like I knew them forever. Al and I both loved the private lessons as well as the clinics; especially cardio tennis! Highly recommend spending a week there!
ST
Highly recommend! I regularly attend the cardio tennis sessions, which have a fantastic energy and great advice. The team is incredible, offering valuable tips on improving your game. They also host excellent tennis mixers and match-ups!
RS
I cannot speak more highly of the team of coaches at Rosewood Bermuda – Cliff Drysdale Tennis! Ashley is incredibly responsive, helping me set up lessons before I arrive on the island. Terry and Ashley are also amazing teachers who run fast-paced, enjoyable adult clinics, and Kaylah is a wonderful hitting partner. All of the coaches are great with players at any age or any level, and they create a welcoming, enthusiastic tennis environment. I highly recommend playing tennis at Rosewood!
LH
It’s more than tennis in a beautiful setting. It’s a community of tennis lovers. Pro Ashley and the team deliver a varied program for players of all ages, levels while creating an anti-snobbish atmosphere. It’s a welcoming space to meet new hitting players and the pros can guide your game to the next level. Definitely a must-play for visitors.
ME
Ashley and all of the coaches – Kaylah, Brent and Terry – are fantastic. The courts are beautiful and the atmosphere the coaches create is top notch. Everyone from beginners to advanced players is welcome. Playing tennis a must do on any trip to Rosewood and Bermuda.
CM
We loved playing at Cliff Drysdale at Rosewood Bermuda. Ashley is an amazing coach, full of helpful instructions, and so much fun, which was a bonus. We wanted to go back right away to get more of Ashely’s instructions, unfortunately we had some injuries that’s been delaying us from returning. We’re already looking forward to next time – it’s hard to beat great tennis coupled with a beautiful resort on a gorgeous beach, all just a couple of hours away from NYC! Megan was great in helping us set up the booking, thank you!
LC
Recently returned from 5 great days of tennis with the Cliff Drysdsle program at the Rosewood Bermuda resort. The tennis program there is headed by a great pro , Ashley Brooks. I played two hours of singles daily , three days with her and two with one of her several assistants. Brooks’ team go the extra mile, accommodating all sorts of requests for court time , changes in schedule, equipment and pairing with other Drysdsle customers, The excellent Har-Tru courts were a welcome change from a long winter on indoor Decoturf back home and also easier on the knees for long sessions. The tennis staff also was generous with advice about all manner of other activities , sightseeing and dining.
Rosewood Bermuda is among the very nicest resorts I’ve visited on 6 continents. Beautiful suites, four great yet casual restaurants. A beautiful beach and golf course and a highly skilled and friendly staff – to a person. I look forward to many returns to Rosewood Bermuda , to Ashley and her team and the first rate Drysdale tennis experience.
DD
My wife and I loved this place. The pros were great. Very accommodating to adjust schedules due to changes in weather conditions. Also a lot of fun to get some clinics in with local folks who were super nice and welcoming to us. We will be back for sure!
BL
I thoroughly enjoyed playing with the pros 3 or 4 times a week for 4 weeks.
AH
Another great experience booking and playing with Clif Drysdale. Megan is always responsive and easy to organize trips with. Makes the experience as a group leader smooth and hassle free.
This property is gorgeous and I can’t wait to return. The director Ashley is full of energy and a great coach. We all loved our time there!
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19 Reviews on “Rosewood Bermuda - Cliff Drysdale Tennis”
I had a lesson with coach Terry and he was so patient with me as I had not played for a number of years. Loved the area and environment. Such a nice atmosphere created by the wonderful staff.
I had a fantastic experience with Coach Brent and Coach Ashley during my stay at Rosewood Bermuda.
Coach Brent made pickleball fun and engaging, especially for my first time—his easygoing demeanor made it easy to relax and enjoy the game. I then joined Coach Ashley the next day for a tennis lesson, and her level of patience was unmatched. Even when I struggled, she gently reminded me that it’s all part of learning something new and to simply enjoy the process.
Both lessons were highlights of my stay. I would highly recommend for your next time in Bermuda!
Awesome experience at Rosewood tennis. Ashley was so helpful and friendly when booking. They have really nice new padel and pickle courts.
Coach Ashley is an outstanding instructor – knowledgable, friendly and extremely skilled at getting the best out of your game. The Rosewood Bermuda team are approachable, welcoming and work hard across all three racquet sports to provide a first rate service!
Awesome experience with the coaches and players across the tennis, PB and padel courts! Coach Ashley did a great job with cardio tennis – I cannot believe how she remembers everyone’s names! And coach Brent and Terry really brought the energy and competitive environment to the PB sessions. Really wonderful overall experience!
We love the courts and the tennis staff! Always welcoming, very knowledgeable and fun to be around. Makes all the difference that they make a point to know your name as best they can and to welcome you back if you are returning. We play tennis every day of our stays and will continue to do so. Ashley, Terry, Brent, Kayla, Jordan run a fantastic program!
We had an outstanding experience with Ashley Brooks during our recent stay at Rosewood Bermuda. She’s one of those rare tennis pros who brings real enthusiasm and energy to every minute on court. Her drills were fun, challenging, and incredibly well‑structured — there wasn’t a dull moment, and our two‑hour sessions flew by.
Ashley’s feedback was clear, actionable, and immediately useful. We’ve already implemented several of her suggestions and have seen noticeable improvements in our play since. She also went out of her way to share her contact information so we could follow up, adjust future lessons, and keep building on what we learned. Her flexibility with scheduling was genuinely appreciated.
Beyond the tennis itself, Ashley was a fantastic resource for local recommendations — restaurants, experiences, and things to do around the island. It made the whole trip feel more personal and connected.
The tennis facilities at Rosewood are excellent. The four hard‑tru courts are in top condition, and while we didn’t use them this time, the property also has pickleball courts and two brand‑new padel courts — something we’ll definitely try on our next visit. The Rosewood grounds are beautiful, and although the hotel, tennis centre, and beach club are spread out, the shuttle and the quite roads for walking made it easy to get around. The beach club is also a highlight of this property.
Overall, Ashley made our tennis experience a highlight of the trip. Highly recommended for players of any level looking for high‑quality instruction in a stunning setting.
Excellent tennis instruction in a luxury resort. We learned a lot and enjoyed Bermuda in the uncrowded off season.
My friends and I had an unforgettable ladies’ tennis retreat at Rosewood Bermuda! Ashley was exceptional—kind, accommodating, incredibly fun, and a truly talented coach. When rain disrupted our tennis plans one day, she went above and beyond by introducing us to padel, which ended up being a highlight of the trip. I can’t recommend this destination enough for anyone planning a tennis getaway!
My husband and I had an incredible time at Rosewood Bermuda. Ashley and Terry were so friendly and fun, not to mention excellent tennis instructors. I felt like I knew them forever. Al and I both loved the private lessons as well as the clinics; especially cardio tennis! Highly recommend spending a week there!
Highly recommend! I regularly attend the cardio tennis sessions, which have a fantastic energy and great advice. The team is incredible, offering valuable tips on improving your game. They also host excellent tennis mixers and match-ups!
I cannot speak more highly of the team of coaches at Rosewood Bermuda – Cliff Drysdale Tennis! Ashley is incredibly responsive, helping me set up lessons before I arrive on the island. Terry and Ashley are also amazing teachers who run fast-paced, enjoyable adult clinics, and Kaylah is a wonderful hitting partner. All of the coaches are great with players at any age or any level, and they create a welcoming, enthusiastic tennis environment. I highly recommend playing tennis at Rosewood!
It’s more than tennis in a beautiful setting. It’s a community of tennis lovers. Pro Ashley and the team deliver a varied program for players of all ages, levels while creating an anti-snobbish atmosphere. It’s a welcoming space to meet new hitting players and the pros can guide your game to the next level. Definitely a must-play for visitors.
Ashley and all of the coaches – Kaylah, Brent and Terry – are fantastic. The courts are beautiful and the atmosphere the coaches create is top notch. Everyone from beginners to advanced players is welcome. Playing tennis a must do on any trip to Rosewood and Bermuda.
We loved playing at Cliff Drysdale at Rosewood Bermuda. Ashley is an amazing coach, full of helpful instructions, and so much fun, which was a bonus. We wanted to go back right away to get more of Ashely’s instructions, unfortunately we had some injuries that’s been delaying us from returning. We’re already looking forward to next time – it’s hard to beat great tennis coupled with a beautiful resort on a gorgeous beach, all just a couple of hours away from NYC! Megan was great in helping us set up the booking, thank you!
Recently returned from 5 great days of tennis with the Cliff Drysdsle program at the Rosewood Bermuda resort. The tennis program there is headed by a great pro , Ashley Brooks. I played two hours of singles daily , three days with her and two with one of her several assistants. Brooks’ team go the extra mile, accommodating all sorts of requests for court time , changes in schedule, equipment and pairing with other Drysdsle customers, The excellent Har-Tru courts were a welcome change from a long winter on indoor Decoturf back home and also easier on the knees for long sessions. The tennis staff also was generous with advice about all manner of other activities , sightseeing and dining.
Rosewood Bermuda is among the very nicest resorts I’ve visited on 6 continents. Beautiful suites, four great yet casual restaurants. A beautiful beach and golf course and a highly skilled and friendly staff – to a person. I look forward to many returns to Rosewood Bermuda , to Ashley and her team and the first rate Drysdale tennis experience.
My wife and I loved this place. The pros were great. Very accommodating to adjust schedules due to changes in weather conditions. Also a lot of fun to get some clinics in with local folks who were super nice and welcoming to us. We will be back for sure!
I thoroughly enjoyed playing with the pros 3 or 4 times a week for 4 weeks.
Another great experience booking and playing with Clif Drysdale. Megan is always responsive and easy to organize trips with. Makes the experience as a group leader smooth and hassle free.
This property is gorgeous and I can’t wait to return. The director Ashley is full of energy and a great coach. We all loved our time there!