Hi everyone!!
Okay… this one has been a LONG time coming. Like, 12 years long lol.
The team at the Cayman Islands Department of Tourism has been inviting us to come visit for over a decade, and every single time, even though we REALLY wanted to go, the timing just didn’t work out. First we had Leo, then we had Annie, then Justin’s ankle injury and surgery… There was always SOMETHING.
But this year, we finally made it happen. And we had THE most incredible time. The timing just worked out perfectly, with work feeling manageable and the kids settling into a school that encourages travel experiences for learning… it just felt right to go now.
So, in this blog, I’m sharing all of it… where we stayed, where we ate, what we did with the kids, and our full itinerary if you’re planning your own trip to the Cayman Islands.
Our Cayman Islands Itinerary, Day by Day
I always love seeing this in travel blogs, so I’m walking you through our whole week exactly how it happened. Let’s get right into it!
Days 1 + 2: Getting to Grand Cayman
We flew Kelowna → Toronto, spent the night at the Sheraton Gateway right at Pearson, and then caught a 6:45am flight straight to Grand Cayman. It was an early wake-up call, but we landed at 9:45am, which meant we basically got a full extra day on the island. Worth it for sure. The kids are such good travellers, so it was smooth sailing.
Tip: If you’re flying from Western Canada, the overnight in Toronto is SO worth it. Way less painful than one giant travel day.
Once we landed, we headed straight to Kimpton Seafire Resort + Spa, our home base for the week. It’s right on Seven Mile Beach. The hotel was bright, spacious, and so beautiful… plus those VIEWS of the crystal clear water and white sand beaches! Wow.
We kicked things off with dinner poolside at Nana Cabana, spent the afternoon settling in, and had an early night, to get ready for a week of adventures.
Day 3: Brunch + Beach Day
Sunday morning started with a surprise boat ride on this super cool boat that looked like a sports car. Of course, Leo was OBSESSED with this. Huge thank you to Red Sail Sports for this experience.
Then… the famous Cayman Sunday brunch at AVE. It’s right at Seafire, overlooking Seven Mile Beach, with fresh seafood, hand-rolled sushi, live action stations, and a whole spread of desserts.
A lot of local businesses are closed on Sundays in Grand Cayman, so we spent the rest of the afternoon on Seven Mile Beach and at the pool.
Dinner was at Peppers Bar & Grill. It’s a local favourite spot for Jamaican jerk, and they have live music starting at 8pm. I was thrilled when they started playing some country oldies (my Grandma would have loved this). You must try the margaritas if you go here.
Day 4: Camana Bay + a Sunset Sail
Sunday brunch at the hotel was 10/10 – so many options!
We spent the morning at the beach, followed by wandering Camana Bay, climbing the Observation Tower, and shopping.
Lunch was at Agua, an Italian and Peruvian seafood spot right in Camana Bay.
After an afternoon back at Seafire, we walked down to the beach for a sunset sail with Red Sail Sports, which leaves right from in front of the hotel.
We wrapped up the day with a late dinner at Paradise Pizza, a casual, breezy spot right on Seven Mile Beach. This was one of our favourite dinner spots, the food was incredible and vibes were great!
Day 5: Stingray City + Starfish Point
Okay… this was the day. We did a private half-day charter with Red Sail Sports out to Stingray City, a sandbar where you stand in shallow water and the stingrays swim right up to you. This was a lifechanging experience that the kids will never forget.
The kids LOVED it. And I got kissed (or attacked?? lol) by a stingray. And the colour of the water was unlike anything I’ve seen before. It was so warm it actually felt like bathwater. And the sand?? The softest, whitest sand I’ve ever experienced. There are so many Conch Shells here; they’re so beautiful, and Annie was so excited to find one.
Then we stopped to snorkel and finished at Starfish Point, which was such a highlight.
That night, we had dinner at Bacaro, a Venetian-inspired spot in West Bay. We had the most incredible dinner here.
Day 6: Cassava Cake, Rum Point + Glowing Water
We started the morning with a walk along Seven Mile Beach to Bonnymoon Beach Club for breakfast (it’s only about 5 minutes from Seafire). This was such a cool spot, with the most stunning views of the beach.
Lunch was at Grape Tree Café, a classic Caymanian fish shack with local specialties. The family at this cafe were the loveliest people.
After lunch, we learned how to make Cassava heavy cake, which is the national dessert of the Cayman Islands, this is actually a free experience for locals and tourists, and it ended up being one of my favourite parts of the whole trip. For anyone wondering what Cassava Cake tastes like, it kind of reminds me of a butter tart but with a coconut undertone.
We then toured Mission House, a heritage site that was rebuilt using traditional techniques after Hurricane Ivan. Honestly, one of my favourite parts of this trip was learning about the history of the islands. It makes you really appreciate a place in a new way. Of course, I knew Cayman was going to be beautiful, but I didn’t expect there to be so much history!!
From there, we headed to Rum Point for a bit of downtime and dinner at Solis at Rum Point Club.
And then… bioluminescent kayaking. This was one of the parts of the trip that we were most excited about. Annie has been obsessed with bioluminescence, she just thinks it’s the coolest thing, so we were all really looking forward to this! We paddled out after dark with Cayman Kayaks from Rum Point into Bioluminescent Bay, where the water lights up as you move through it, and the guides point out stars and constellations along the way.
For the kids, swimming in the bioluminescence was truly another life-changing experience. It was so so cool. The guide from Cayman Kayaks was SO knowledgeable, such a steward of the land, and taught us so much about constellations, conservation, bioluminescence and more! We were so impressed.
Day 7: Botanic Park, Golf + Storybook Mocktails
We spent the morning at Queen Elizabeth II Botanic Park and the Blue Iguana Preserve. We were toured around by Earl Lewis, who walked us through the medicinal plants and things that are native to the island.
In the afternoon, Justin played 9 holes at the Ritz-Carlton Golf Course, which was of course, such a highlight for him!
We spent some more time on the beach this day, soaking in allll the sunshine.
Back at Seafire, Jim, the beverage director, hosted us at Library by the Sea. He made signature cocktails for the grown-ups and mocktails for Leo and Annie inspired by children’s books.
Dinner was at Ms. Piper’s Kitchen + Garden. This was another one of our favourite dinner spots! The vibes were so good here.
Day 8: History + Our Last Sunset
On our last day, we toured Pedro St. James, a restored 18th-century great house, and had lunch at Hotel Indigo Grand Cayman. One of the best meals of the whole trip – the best curry we’ve EVER tasted.
After a slow afternoon back at the resort, with more beach time of course, we had our last dinner at Tillies at Palm Heights, right on the beach at sunset. We truly saved the best for last, this restaurant was incredible and you can’t beat having dinner RIGHT on the beach!
I couldn’t wrap up this blog without mentioning our lovely driver, Auntie Novalette, who drove us around for most of our trip. She was such a safe driver, so knowledgeable, and took very good care of our family. Just an overall wonderful human.
Day 9: Heading Home
Grand Cayman → Toronto → Kelowna. After an amazing family trip, we were ready to get back home to our pups and back to routine!
Final Thoughts
Well, there you have it! Our full Cayman Islands itinerary. We are so grateful to the Cayman Islands Department of Tourism for hosting our family on this beautiful trip.
If you have any questions about the Cayman Islands, leave them below or send me a message. I’m always so happy to share!!
xo
Jilly
This trip was hosted by the Cayman Islands Department of Tourism. All thoughts and opinions are my own.
