A Perfect Cayman Islands Itinerary

A few weeks ago, in August, I spent the most beautiful week alone in the Caribbean. It was a truly dreamy little escape from life, after which I returned home safe and sound while hurricane after hurricane decimated many of the gorgeous nearby islands, leaving people without electricity, shelter, or even water. The Cayman Islands were shielded from the brunt of the devastation, and in typical Caymanian fashion sent their resources to help. The Cayman Islands are absolutely beautiful, I had a chance to visit two of the three and I’d like to tell you about my trip, and hopefully inspire you to visit this beautiful country with a perfect Cayman Islands itinerary. They say #CaymanKind, and they mean that the people of the islands are welcoming; I found this to be very true.

I started my trip flying through Miami to Grand Cayman, where I rented a car. I forgot that they drive on the left! Oops! But the streets are designed with travelers in mind – most of the right turns are roundabouts which makes it easy to just follow the car in front of you. Which is what I did, and checked into the stunning new Kimpton Seafire Resort + Spa, which gets 12 out of ten stars from me. It’s truly luxurious and on a beautiful slice of perfect white sand along Seven Mile Beach. Seven Mile Beach

When I woke up and saw the view from my room I was in awe. The Kimpton also had a great selection of in-room amenities (your own yoga mat! a salon quality blow dryer! free bottled water!) and a whole host of included activities like stand-up paddle boarding and snorkeling equipment. Kimpton Seafire Resort & Spa

Even the walkways were gorgeous. Kimpton Seafire

On my first morning I headed over to the Atlantis Submarine to take in the reef and the amazing sea life. We took a ferry out to the sub, Atlantis Submarine Grand Cayman where we boarded the sub and went 100 feet underwater! I enjoyed the Atlantis Submarine when Scarlet and I were in Oahu, but this one was even more stunning. The reef is not bleached, which was so lovely to see, and we even got to spy some turtles! The light underwater omits any red from entering and I don’t have the photography skills to capture the beauty, but here’s the sub surfacing. Atlantis Submarine Grand Cayman

After that I wandered around George Town, bought some flip flops and admired the jewelry, before having an amazing fresh seafood lunch at Guy Harvey’s Grill. The sushi was perfection. Guy Harvey's Grill Sushi

That evening I did what everyone should do in Grand Cayman – watched the gorgeous sunset over Seven Mile Beach. I did mine with a coffee-based cocktail and some Mexican fusion cuisine at Coccoloba, where I also met some friendly locals and just had an all around great time.Seven Mile Beach Sunset

The next morning I had to have the quintessential Caymanian experience of swimming with wild sting rays at Stingray City. Stingray City is a sand bar in the middle of the ocean where sting rays gently swim around you and even give you hugs. Sting Ray City Grand Cayman

I got a kiss from one, which means seven years of good luck! We got there early, so it was deserted. Sting Ray City

It quickly fills up with visitors, so I really recommend the tour company I used, Red Sail Sports, for getting us there before the crowd. Sting Ray City

Once back at my resort, I headed straight for the spa, where I had an amazing massage on a bed of quartz crystals! I’d never heard of this before, it was wonderful. The spa itself was stunning, and all guests can visit it and use the hot tub even without booking an appointment, so don’t skip it. Kimpton Seafire Spa

After this I headed over to the National Gallery of the Cayman Islands. This museum is small and I think many visitors miss it – you should not! It is a stunning collection of works by Caymanian artists, and it walks you through progression of styles and artworks over the years as the island has grown and changed. It is a beautiful insight into the spirit of the country.

For dinner I did the most interesting thing – a flavor tour of the town of Camana Bay. This town is a sort of development, with apartments and retail stores, but it is also feels really special. It’s full of amazing restaurants, and with the flavor tour you get to visit a new one for each course, starting with wine and ending with desert. It was a fun way to meet new people and have some great conversations. The evening here was charming too, as kids played in the fountain. Camana Bay

I slept like a baby after that giant meal, then woke up early to head back to the airport for a quick flight to Cayman Brac on Cayman Airways. The little plane has the best logo (a pirate turtle?).Cayman Brac

Cayman Brac is stunning. Most of the south side of the island is a limestone bluff, with a few beaches scattered here and there. I stayed at one of my favorite resorts to date, Le Soleil d’Or. This boutique resort has just a few rooms, a beach club, and an on-site farm. The grounds are stunning, Le Soleil D'Or Le Soleil D'Or Le Soleil D'Or but the highlight of a stay here is the true farm to table dining. What you eat is grown on the bluff above the hotel, strategically planted into the limestone – it’s a site to behold. I toured the farm with the head farmer and tasted all of the fresh fruits and veggies before settling in for the most amazing fish dinner I think I’ve ever had. It was local fish roasted en papillote with a slew of vegetables, I savored every morsel. Le Soleil D'Or 5 copy Le Soleil D'Or Le Soleil D'or Le Soleil D'Or My favorite moments at Le Soleil d’Or were definitely relaxing at the beach club, Le Soleil D'or 10 copy where I finally finished The Goldfinch and enjoyed a farm-to-beach cocktail. Le Soleil D'Or Cocktail

I also took a tour of the small island, where I got to experience the amazing views from the bottom of the bluff, Cayman Brac Bluff and from the top. Cayman Brac Cayman Brac

We saw some local wildlife Cayman Brac and hiked up to the caves, where residents have hidden during hurricanes (and also hang out during teenage parties, I was told). Cayman Brac Cave Cayman Brac cave

The view of the North Shore, where most locals live, from outside the caves was lovely. Cayman Brac

After my magnificent 24 hour sojourn to Cayman Brac, I flew back to Grand Cayman and did a little more stand up paddle boarding, before a gourmet dinner at Avecita. If you enjoy molecular gastronomy or just trying new and interesting things, this shouldn’t be missed.

I met up with a friend I met online for drinks at Calico Jacks, a super fun party bar on the beach next to the Kimpton. It’s so fun to meet people in person after you’ve met online!  Captain jacks

Another sunset over Seven Mile Beach was the perfect end cap to a beautiful week. Kimpton Seafire Sunset

I recommend you all put the Cayman Islands on your must-visit list. I am looking forward to going back with my family, hopefully this winter!
A Perfect Cayman Islands Itinerary




Thank you Jaime for the wonderful article of the beautiful islands I call home. I am very happy you enjoyed our Cayman Kind hospitality.

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Thank you for sharing this great post with us!!!

We will be visiting Grand Cayman Aug 2022 via ship and would like to know favorite but not to spendy shopping spots after tendering on shore.


Thanks for the itinerary and recommendation for provider to get to Stingray City before the crowds! I’m starting to plan my trip now and it was really helpful.


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