Cayman Islands

What you need to know:  

  1. The Cayman Islands are made up of three islands:  Cayman Brac, Little Cayman, and the largest and most populated, Grand Cayman.  The capital, Georgetown, is located on Grand Cayman and is likely the city you will fly into.
  2. The Caymans are a British Territory where English is widely spoken.  They do have their own currency though, the Caymanian Dollar.  While the U.S. Dollar is widely used on the island, you’ll likely get better prices if you use the local currency.  Credit cards are also widely accepted.
  3. Cayman Islands citizens have the highest standard in of living in the Caribbean based on GDP per capita and as a result, crime rates are very low.  Their infrastructure is very modern and on par with that of the United States.
  4. Geography wise, Grand Cayman is very flat.  They do get the occasional hurricane during the June-November timeframe.  
  5. Like many places in the Caribbean, the Caymans are a scuba diving hotspot.  
  6. As far as tourism goes, the Cayman Islands are widely thought of as a resort haven.  The Seven Mile Beach area is generally considered the center for tourism on the island.  However, there are adventures to be had if you want to do more than just sit on the beach.  
  7. If you like snorkeling, consider bringing your own equipment, including a floating dive flag.

7 night Itinerary in Grand Cayman:

Thought Process:  I love to just sit and read at Caribbean resorts but my kids get bored and need something else to do on occasion.  So while we want to sit by the beach/pool a lot, we need some adventures as well.  Thankfully, the Cayman Islands deliver with numerous opportunities to make memories while still getting you plenty of time by the water via this 7 night itinerary.  

Where you’ll stay:  The Rum Point area of Grand Cayman provides a nice balance.  All of the amenities you need for a great vacation are right there yet you are not routinely subjected to the hustle and bustle of Seven Mile Beach and the cruise ship scene, which is 45 minutes away by car or ferry.  I suggest staying anywhere at or east of Rum Point beach.  There are very nice beaches and properties to the west of Rum Point Beach as well, but the wind notably picks up on that side of the island.  Also, while everyone loves beachfront, don’t feel like you have to stay right on the beach.  Being within walking distance should more than suffice in this area.  We particularly enjoyed staying at The Retreat.  One thing to note is that if you do schedule a water tour, make sure it is running out of Rum Point.  I believe all of the tour operators I linked in this itinerary operate out of Rum Point.  Check out or to find a rental property that will work well for your family.  Make sure it’s a property with a kitchen and numerous positive reviews.

How you’ll get there:  You’ll fly into Georgetown and pick up your prearranged rental vehicle.  In regards to flights, make sure to include Cayman Airways in your search.  

Day by Day Itinerary:

Day 1:  Fly into Georgetown, pick up your car and head to your rental property to unload and then go pick up groceries.

Day 2:  Hit the beach or pool.  Most likely, the place you are renting is beachfront or has a pool or beach within walking distance.  Today is a great day to take advantage of it.  If you like the idea of someone bringing you drinks and food while you lounge on the beach and the kids play with other children, make your way over to Rum Point Beach where you can lounge or even set up a tour if you like.  Be advised, that many tours make stops at this beach, including those bringing folks from the cruise ships, so the place is busy.   But if you can secure some chairs and are patient with the servers, this is a great place to enjoy a cheeseburger in paradise.  There is some snorkeling offshore, most notably a reef that is probably 100 yards out that you and the kids can handle if you are strong swimmers and have your own equipment/dive flag/snorkel vests .  

Day 3:  Stingray City and Snorkel Tour.  To this day, Stingray city is one of the coolest things I have ever done and I’ve been lucky enough to do it multiple times.  You arrange for a tour (ideally a catamaran) to take you out to this sandbar where wild sting rays swim around you like puppies looking for the squid you are going to feed them.  It is highly unlikely that you will get stung because these creatures have been hand fed by humans their entire lives.  They are aggressive about getting fed, not about stinging you (you will be blatantly felt up for squid by rays more than 2 feet in diameter).  You can even give them kisses.  I was snorkeling there once and a large one happened to swim over my back just as I was floating to the surface.  As a result, I had involuntarily lifted it out of the water with my back.  I remember thinking “I probably deserve to get stung.”  But according to my wife, it just flapped a couple times to get off me and kept on looking for food.  When you book a tour, make sure you are going to the sandbar section of Stingray city (just ask if you’ll be able to stand and feed them) and inquire about the maximum number of people on the tour.  Ideally, you won’t be on a “cattle boat.”  Also, make sure it leaves from Rum Point, otherwise you will be doing a lot of unnecessary driving.  The tour will probably include a snorkel trip to the reef as well.  Red Sail Sports has been running this tour out of Rum Point for a long time and has an excellent reputation.  I believe they provide snorkel gear if you don’t have your own.  If you would prefer to take the tour via jet-ski instead of catamaran, contact The Sweet Spot.  

Day 4:  Star Fish Point and self-guided snorkeling.  Star Fish Point is a low key beach which is very close to Rum Point.  It’s very shallow and for some reason, starfish tend to congregate there.  The number of starfish one might see on a given day tends to vary and is perhaps based on the tides but the kids will likely spot a few and enjoy searching for them.  Feel free to bring a beverage or two to enjoy while the kids are looking.  Apparently this area used to have a lot more starfish but people kept holding them out of the water, which can cause some type of infection internally which the little buggers may die from.  If you visit, make sure to only hold the starfish underwater.  This laid back activity may only take up an hour or two so if you are still looking for something to do and didn’t get enough snorkeling yesterday, consider doing a self-guided snorkel tour.  As you can see from the link above, there are plenty of snorkeling opportunities on Grand Cayman that you can access from the beach.  Just make sure you have some equipment (might be able to rent at Rum Point if you didn’t bring your own), snorkel vests, and a floating dive flag.  

Day 5:  Cayman Turtle Centre and Horseback Riding.  These two activities are located near each other just north of Seven Mile Beach.  It will take you a little more than an hour to get there by car from Rum Point.  The Cayman Turtle Centre is cool because you are able to hold and interact with the turtles.  It also sounds like they have added some additional activities since we last visited.  If you’ve done one dolphin encounter, you’ve done them all in my opinion but since you are in the neighborhood, you might consider visiting Dolphin Discovery across the street which I’m told is pretty similar to Dolphin Cove.  It is worth noting that both the Turtle Centre/Farm and dolphin places are for-profit “conservation by commercialization” places.  The dolphins aren’t being rehabbed; they’re there to entertain you and some of the turtles are being harvested for meat.  That said, both organizations actively fund and participate in conservation efforts and the animals are generally considered to be very well-cared for.  

Admittedly, you can ride horses at a lot places in the world.  But there is something cool about riding a horse on a Caribbean beach.  It’s extremely peaceful, you get to ride them in the water, and it’s a great photo opportunity.  If you like horses, it’s a wonderful way to spend the day.

Day 6:  Crystal Caves and Bioluminescence Night Tour.  Crystal Caves wasn’t open the last time I was in the Caymans but it’s near Rum Point, looks pretty cool, and has solid reviews.  Think crystal clear water plus awesome stalactites.  Tours are approximately 90 minutes and by appointment only currently so make sure you contact them ahead of time.  There is also a bioluminescent bay in the Rum Point area.  You can see this phenomenon in Puerto Rico and Mexico among other places and it’s pretty cool.  Most people take a boat or kayak tour to access the area but you may be able to do just as well accessing from shore.  You’ll want to check the moon calendar as a full moon and/or light pollution reduces the effect.  Also, apparently you only want to float on top of the water because small jellyfish are more apt to sting you if your feet are on the ocean floor.    

Day 7: Hit the beach or pool again.  You’ve done a lot.  Take some time to rest up before the trip back.  

Day 8: Go home.  

Note:  There are plenty of other activities to enjoy in the Cayman Islands that you may want to substitute for those above.  The Caymans are a great place to fish and scuba dive of course and there are opportunities to go for a helicopter ride, parasail, or rent jet-skis if you are looking for something else to do.