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

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 tripadvisor.com and LIKE our Facebook page Cayman Routes Island Tours then call or email us today!

What Others Are Saying

EXCELLENT
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Based on 161 reviews
Posted on Tripadvisor Tripadvisor
GoPlaces63912276669 profile picture
GoPlaces63912276669
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A beautiful day! We had the most incredible day with Shirley! She is so very knowledgeable about her island and her love for it, shines through! We learned so much more than if we were to tour the island on our own!! She has the best personality and kept us smiling!! If you are on the island, look her up! I know you’ll love her too!
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5thgirl profile picture
5thgirl
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A+ Experience! We highly recommend this company and Shirley, our guide. Loved spending the day with her, seeing the whole island and the best part was just gaining her perspective of life on the island, being a local from generations of family that settled there. We visited Pedro St. James, the Botanic Garden, Starfish Point, Rum Point, the Blowhole and had a very delicious local lunch and tasted different beers! Shirley is friendly, flexible, accommodating and super knowledgeable. By the end of day, we were like old buddys!
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ollie843 profile picture
ollie843
Tripadvisor star 1Tripadvisor star 2Tripadvisor star 3Tripadvisor star 4Tripadvisor star 5
The Best Way to See Grand Cayman ⭐⭐⭐⭐⭐ Cayman Routes Island Tour was one of the highlights of our trip. The local recommendations were professional, honest, and perfectly tailored, and the transportation was safe and comfortable throughout. We truly felt listened to and well taken care of. Shirley is the best—knowledgeable, attentive, and a joy to tour with. Five out of five stars. Exceeded expectations. I highly recommend!
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Cheryl profile picture
Cheryl
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Touring with extremely experienced guide with drinks and ac We had Shirley take us on a day of touring from Georgetown. Everything during the tour was great. We went to the turtle exhibit and saw large green turtles, saw some sites of the city, went to Hell to mail postcards, had a very good lunch at a Heritage Kitchen, took I some more sites then went to Cayman Distillery at Shirley’s recommendation vs Tortola. She was a wealth of knowledge and has lived on the island all her life. We were able to modify the tour as we went which made things even better. She is very flexible and wants you to have a great experience. She also brought a variety of drinks (waters and sodas) for along the trip. Her van was super clean and ac was cold. She is a one woman company with a family lineage going back to the first recorded settler, that knows how to treat her customers. We highly recommend her for your tour of the island. We hope to go back again and will use Cayman Routes again.
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Dana K profile picture
Dana K
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Wonderful tour guide. Just like family! We just cannot say enough good things about Shirley! We originally booked a few hours with her to get away from the SMB tourist zone and see the other side of Grand Cayman, but we enjoyed spending time with her so much that (even though we rented our own car) we asked her to pick us up again to see all the places we missed earlier in the week. Her van is comfortable and spacious and she’s an excellent driver - we were completely relaxed bringing our 4 year old (and his grandma!). That said, the absolute best part about Shirley is her incredible kindness, patience, sense of humor, and profound knowledge of the islands. Our son bonded with her so completely that it was like spending our time with an adopted auntie. We will absolutely be calling her the next time we are headed to Grand Cayman!
Posted on Tripadvisor Tripadvisor
Amy G profile picture
Amy G
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Excellent Experience with Shirley at Cayman Routes Shirley Roulstone at Cayman Routes Island Tours - Absolutely awesome! We originally heard about her from fb posts & contacted her to book a 6 hour land tour. We wanted to make sure we had smooth travel for my knee so I could see a lot of the island. Shirley tailored the tour to exactly what we wanted to see & was so helpful in planning the tour we also asked her to for airport transportation to our hotel. As soon as she picked us up at the airport we knew we were in excellent hands. Shirley was friendly, very knowledgeable about the island & made great suggestions on what we could do considering my recent surgery. We ended up hiring her to transport us every day & she was fabulous to work with. Highly recommend.
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Camper44830702318 profile picture
Camper44830702318
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Excellent Tour Guide Shirley Roulstone We were recently on Grand Cayman and was fortunate enough to have Shirley from Cayman Routes provide taxi service for us. She was reliable, friendly and shared a wealth of information of the island with us which we found very enjoyable. I would recommend Cayman Routes to anyone visiting Grand Caymans.
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reuben2009 profile picture
reuben2009
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Best tour guide ever! Honestly, our family is pretty sure that Shirley has to be the best tour guide on the island! We spent part of a day exploring the island with her (QE2 Botanic Garden, the Blowholes, frigate bird feeding at Tukka East, etc.). She was very accommodating to our schedule, has SO much knowledge of the island (can’t imagine going through the Botanic Garden without her!), was very professional, gracious, and easy to talk to! We had a great week in the Cayman Islands, but this might have been the best part of it!
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K S profile picture
K S
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To Say Cayman Routes Exceeded Expectations Would Be An Understatement! If you are looking for a knowledgeable local guide who really cares about your experience, then Shirley at Cayman Routes is the guide for you. My husband and I booked a tour in advance of our one day (cruise ship) stop in Grand Cayman. For two years in the mid 1990s I called Grand Cayman home, and was curious about how the island had changed. Shirley, who can trace her Cayman roots back to the first settlers of the island, was the perfect person to reacquaint me with this beautiful place. She took us everywhere, from Georgetown to West Bay, East End and ...to Hell and back (please go to Hell and visit Mr. MacDoom, who will stamp your postcard and be very glad for the visit). There are still those magical Caymanian places; Seven Mile Beach, and Pirate's Cove for example, and classic Cayman snacks. Shirley sussed out the perfect Conch fritters and local beer and then....(drumroll please) Shirley reconnected me to my old co-worker with whom I had lost touch. When I mentioned Cindy B.'s name (as in "I wonder where she is now?") Shirley said "I know Cindy B." and promptly called her. Cut to: emotional reunion with former co-worker made possible by Shirley's attention to detail, connection to people, and unparalleled knowledge of the island. (and thanks to THAT reunion, we were able to meet up with another dear and long lost friend Teddy E.) OK not everyone is going to be tracking down the past, but if you are looking for the best tour guide in Grand Cayman, Shirley Roulston is your woman. I cannot believe in the two years I lived there we never met. She's a gem, dear reader. I cannot say enough about her, and look forward to riding in her spotless van again soon. Shirley is the real deal, a true Caymanian with a love of people and her country. Five Stars!
Posted on Tripadvisor Tripadvisor
Penner M profile picture
Penner M
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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.

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