At Cayman Routes we offer the best tour options for singles, couples, families, and small groups.

All of our tours combine a special blend of culture, history and sightseeing for a taste of Cayman that you don't want to miss!

See the most popular sites, or venture off the beaten path, enjoy the local flavour of a traditional lunch or dinner, mingle with locals, take lots of pictures and make happy Cayman memories without breaking your budget! If you want to get away from the touristy crowds come and go local with us! 

Meet your guide

Shirley Roulstone

Owner & Operator

Award Winning Generational Caymanian Tour Guide.

Pickups and Drop Offs

Cruise Port

George Town

7-Mile Beach

Custom Place

Tours & Services


Cayman Sampler

This is our most popular tour which is a scenic, cultural and historic tour to the Eastern end of Grand Cayman with stops at the Pedro St. James historic site, the Queen Elizabeth 2 Botanic Park, a Cayman style lunch at Vivine’s Kitchen or similar and the Blow Holes.

  • Includes all entrance fees, lunch, and bottled water.
  • .

Personal Transport

Need Personal Transport? Get in touch to see how we can facilitate your custom needs.

Times, prices, or itinerary may be subject to change without notice due to circumstances beyond our control.

  • Special requests for additional stops or combo tours can usually be accommodated in advance. Check with us for availability and pricing.
  • Tours operate daily except Christmas Day and Good Friday. Morning and afternoon tours are available except for Cayman Sampler and Rum Point Routes and tour times are pretty flexible.
  • We also provide custom tours, guided Mastic Trail tours, personal transport service and guided day trips to Little Cayman and Cayman Brac.
  • We are pleased to offer Military Personnel and spouses a 10% discount. Not available with other discounts.
  • Check out our Excellent reviews and photos on and LIKE our Facebook page Cayman Routes Island Tours then call or email us today!

What Others Are Saying

Based on 152 reviews
Penner M
Penner M
Cayman Sampler Tour a Must We did the Cayman Sampler Tour with Shirley (approx 5 hours) Besides stopping at some historic sites we had a wonderful lunch in a small local town. Shirley is friendly and knowledgeable and we had a great time with her.
Kim E
Kim E
Amazing island transportation- great rates Shirley welcomed us with a hug at the airport and gave us a mini tour and tons of recos on the way to our condo. Highly recommend Shirley for any of your transportation or tour needs on GC. Can’t wait to come back and will use CR again! Thnx Shirley and happy new year!
Antonio Arch
Antonio Arch
You Won't Find a More Informed, Engaging. or Entertaining Expert than Shirley... Nobody (and I mean Nobody!) knows the landscape, sights, flora, fauna, and history of Cayman like Shirley does....
Sarah M
Sarah M
Cayman Routes Isand Tours - Day Tours Shirley is an expert on all things Cayman Islands & its history; in addition to being a very interesting story teller. Shirley will make your private group feel like a local by the end of the day! Shirley goes above & beyond, on her VIP Cayman Island Tour! She picks you up & drops you off from your hotel. We had amazing fresh Mango & other delights! In addition to a fun informative tour day, Shirley let us know if needed feel free to call her while we were on our stay. Shirley’s tour was a highlight of our trip! We definitely recommend Shirley!
Jane L
Jane L
Shirley Roulstone: "Tour Guide Extraordinaire" Shirley took us on a very informative tour of Grand Cayman which included stops at the Pedro St James historical landmark and the Queen Elizabeth II Botanical Park. Shirley's love of her native homeland was evident as she shared stories of Cayman's history and her own ancestry and lineage dating back to the island's earliest settlers. Her knowledge of the island's flora is exceptional. Shirley made many recommendations for dining, from seafood and steaks, to local spirits and ice cream, her suggestions never disappointed. From the moment she picked us up at the airport to the time she dropped us there two weeks later, Shirley provided us with transportation services wherever and whenever we requested them. We had a great vacation in Grand Cayman and Shirley Roulstone made it possible. We will be forever grateful to her!
Shirley is the best you can have to enjoy Grand Cayman! Shirley made our two week vacation perfect at Grand Cayman. From the time she picked us up at the airport to taking us to her suggested two dozen restaurants to returning us to the airport, our experience with her could not have been better. Her full day tour of the island was fabulous due to her knowledge of everything past and present of the island. She took us to the grocery store, to the liquor store, to the ice cream store, and everywhere we needed to go. Shirley is a native of Grand Cayman and seems to know most of the vendors in the island. She was always prompt for every outing, and charged what we thought were bargain prices. In her heart she loves Cayman and we love her!
BEST TOUR EVER Of all of the trips we have taken - this is top of the list. Shirley is AMAZING! My husband wasn't so sure he wanted to take a tour - but it was the highlight of our cruise. She really goes over and above to cater to your wishes. She knows everyone on the island and everyone speaks highly of her. The knowledge she has and the heart she puts into the tour is the best. She asked what we wanted to do and where we wanted to go. She took us to eat lunch and try Cayman food which was so relaxing sitting on the outdoor patio right on the water. You will not regret this experience. It is a MUST if you are visiting the Cayman Islands.
The Kindness of Strangers: A Gem on the Island We weren't on a tour. This review is all about Shirley. We were lost and as luck would have it Shirley was out in her yard as we were walking by. My husband decided to ask directions which led to her offering to take us where we wanted to go! SHE was one of the highlights of our cruise. Her kindness, honesty and generosity were unbelievable! She ended up taking us on a quick spin of the town, offering to drop us off anywhere, and at the same time sharing her deep Caymanian Roots and wisdom. All this... and refused compensation. Next time we are on the island, we will definitely hire her for a full on Grand Cayman experience. STRONGLY recommend contacting her for any of your Grand Cayman needs.
Jason R
Jason R
Unbelievable Island Tour We had the pleasure of having Shirley as our tour guide. She picked is up at the airport and brought us to the B&B we were staying at on the east end. A couple days later she took us for an island tour. Along the way, she would point out different spots and educate us and provide details on each. It was awesome having her with us. We felt like VIP on her tour. She took us to a cliff that overlooked the ocean, Seven Mile Beach, Botanical Gardens, grocery store, anywhere we wanted to go! Shirley is an experienced and knowledgeable tour guide. We got to know more of her personal life on the way back to the airport. She gave up some tips for our pepper plants and banana trees back home. We will be coming back next year for another tour of the island! Do yourself a favor and take a guided tour with her.
Excellent tour Shirley is a very experienced guide and a true Caymanian. Her tour provided plenty of island history, which is fascinating. Her personal knowledge and experience contributed greatly to the tour. We enjoyed a local spot for lunch, The Caboose. Wonderful food, not the least bit touristy. Well worth the price!

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