Solo 5 Day Grand Cayman Itinerary
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The Cayman Islands is a Caribbean destination known for beautiful beaches, nature encounters, and laid-back yet luxurious hospitality. Instead of stressing over planning, copy my exact Grand Cayman itinerary for five fun-filled days in tropical paradise!
Best Time to Visit
The Cayman Islands are truly a year-round destination, though you’ll get slightly different experiences depending on when you go. For example, May is the best time to go for a Caribbean carnival experience as this is when Cayman Carnival Batabano occurs.
The weather is warm all year, with the rainy season lasting from June through November. Don’t let this deter you, though because I visited in early August and had beautiful sunshine almost the entire trip. The rainy months are also when you’ll see more diverse wildlife.
Though a lot of Grand Cayman things to do are marketed for tourists, there are plenty of non touristy hidden gems to enjoy off the beaten path.
Getting There
There are currently no Grand Cayman visa requirements for US citizens (and permanent residents) but you need a passport. The Caymans Islands is a British territory so no passport needed for UK citizens.
I flew into Owen Roberts International Airport from Houston, Texas, with a stopover in Fort Lauderdale. The airport was easy to navigate, clean, and uncrowded. There was also no line to get through immigration and customs. When I visited, leisure travelers staying fewer than 30 days and Caymanian residents and their spouses children holding US and UK passports were able to use automated entry kiosks that made entry quick and easy.
Here’s how I use my travel credit card for free Global Entry membership!
The Grand Cayman airport is about 20 minutes from Seven Mile Beach and about 35 minutes from the former capital, Bodden Town, where I stayed for the first couple days of my trip. In August, they were aligned with Central Daylight Time so I had no jet lag or time difference to mind.
Check out all my tips for catching flight deals and traveling on a budget to any destination!
How to Get Around
You will need wheels for getting around Seven Mile Beach and certainly beyond. I rented a car and was able to explore the entire island from early morning excursions to nightlife and highly recommend it. Here’s all you need to know about driving in the Cayman Islands.
Grand Cayman also has a public mini-bus system that runs through all districts of the island. The buses are actually large vans holding up to 14 passengers each and driven by contracted drivers. Cash is the only accepted method of payment and you can use either KYD or USD.
Taxis are probably the most popular mode of transportation for tourists because they are uninformed about the buses and apprehensive to drive on the left side of the road. But they can be quite expensive. My cousin took a Grand Cayman vacation just a few weeks before I did and found it more convenient and practical to hire a private driver than traveling by taxi.
Where to Stay
I initially stayed at Sea Palm Villas, a small vacation rental complex in Bodden Town. It was conveniently located for getting to local eats and activities away from the Georgetown, however, I would not recommend it for a few reasons.
While beachfront, the water was full of smelly seaweed. I woke up with bed bug bites on my second day and decided to change my accommodations at additional expense. Lastly, communication from the owner also left much to be desired.
I do, however, highly recommend the Kimpton Seafire Resort and Spa, which is where I moved over to and thoroughly enjoyed for the rest of my trip.
Here’s my detailed honest review of the Cayman Islands Kimpton hotel!
Grand Cayman Island Itinerary
Bodden Town
I arrived early in the afternoon on a Friday and checked into my rental in Bodden Town off Governor’s Beach. After getting settled, food was the first order of business!
Chill Spot is a casual authentic Caribbean restaurant in the Bodden Town district serving Caymanian versions of staples like oxtail, curry shrimp, and conch stew. I hit them up multiple times during this trip and made sure to get a carrot juice or coconut water with every meal. Highly recommend!
Smith’s Bracadere is a picturesque and popular local swimming and snorkeling spot right off the side of South Church Street. There are tables and rustic grills for cooking out and eating. I saw roosters and chickens running around the sand and little fish in the water. The ground is a bit rocky and can be uncomfortable closest to the water so I recommend water shoes if you have delicate feet! Parking is across the street.
Pepper’s is a touristy bar & grill located in the Seven Mile Beach area. I drove out for a late dinner. It was not my favorite meal by far but the Pepper’s punch (rum punch) was on point. Due to its popularity, it was tough to find a parking spot and there was a bit of a wait even to sit at the bar.
Here are Grand Cayman Island restaurants I do recommend adding to your itinerary!
Crystal Caves and Cocktails
Crystal Caves Experience was my first excursion on the island and something that I think sets Grand Cayman apart from other Caribbean destinations I’ve visited so far! This guided small group tour went through several underground quartz cave.
Read my full Crystal Caves Grand Cayman review for more details on this excursion!
Afternoon Tea at the Ritz is a luxury bucket list Cayman Islands activity, in my bougie girl opinion. I spent the afternoon being catered to with classic tea service with champagne and British bites infused with tropical flavors.
Though the weather is generally sunny and bright, indoor experiences like this one are great for riding out passing rain.
There’s a dress code here so make sure you read my full breakdown of the Grand Cayman Ritz tea experience so you know what to expect!
Next Door – I ended the day in the upscale Camana Bay complex for drinks, dinner, and live music at this speakeasy. This was recommended to me for adults only nightlife places to go with a sexy and chill vibe.
I thoroughly enjoyed myself as a solo diner but would definitely go back with my partner for date night or my friends for girls night out!
Seven Mile Beach
Tillie’s – I mistakenly hit them up for brunch, which wasn’t actually a thing when I went, so I had a fabulous lunch instead. Although it was quite hot, the view of Seven Mile Beach couldn’t be beat and my meal was delicious. Five stars for service, too, from the waitstaff to the valets.
Seven Mile Beach Day – I spent some time on the beach near Tillie’s, the Kimpton, and the Westin and the water was consistently crystal clear, warm, and shallow. There were rocks in some places but no seaweed. I see why it’s a favorite family friendly beach!
The beach is dotted with hotels but there are public access points as well. For one point, I parked at the Marriott and walked a couple of minutes to the beach. People were doing all kinds of water sports like jet skis, kayaking, and kiteboarding.
I will note that there was plenty of space on the Palm Heights and Kimpton strips of Seven Mile Beach but the Marriott has experienced significant beach erosion so there’s very little sandy area to lounge on.
Ice Cream between beach hopping, I refreshed myself with ice cream from Cayman Scoops.
Library Bar – Since I was completed settled into the Kimpton by this day, I made my first of two (or three) stops into the Library by the Sea cocktail bar located inside my new digs. The bartenders were excellent and I had a hard time deciding which cocktails and mocktails to imbibe. Everything I tried was tasty and smooth. Hence, me making multiple visits!
Marine Life Encounters
Room Service Breakfast – I started the day slowly enjoying breakfast on the balcony of my ocean view room and was shook by how tasty the food was and how quickly it came.
Cayman Turtle Farm seemed to be a family and kid centered thing to do but I (and my inner child) had fun. I wouldn’t say it’s one of my must-do Grand Cayman activities but it was a cool experience.
I booked the adventure tour option. So I watched feeding time for the large turtles, swam with the babies, visited the hatchery, and walked through the aviary to try to get a look as some local birds. No luck on that last endeavor. Their gift shop is a good place to shop if you have turtle fans in your life like I do. Budget 1 1/2 to two hours of time for this.
Souvenir Shopping with this being my second-to-last day on the island, I stopped into a few different souvenir shops around the resort area and in George Town to find gifts for family and mementos for myself. I liked Treasure Teez most and purchased most of my items there.
Bioluminescent Bay Tour was the last structured piece of my Cayman Island itinerary a super memorable way to go sightseeing on the water. I highly recommend the public tour I booked, which included stops at Starfish Point, Jellyfish Point, and the Bioluminescent Bay with education along the way.
Starfish Point is a shallow area near Kaibo where starfish naturally congregate and it’s open to the public. Jellyfish point was full of mosquitoes and we got torn up! Bug spray is not allowed as it poisons the sea creatures so this stop our or tour was cut short.
Bioluminescent Bay is shallow (about 4-6 feet deep) and we arrived after dark in order to see the glowing particles in the water. I even got to hold a jellyfish!
This was all made even more dreamy by the glittering stars in the sky above, unencumbered by any smog.
Our crew was really fun and helpful and we embarked on a nice clean boat that looked brand new. Light refreshments and snorkeling gear were included. The meeting point is just five minutes from the Kimpton–practically across the street.
Nightcap – And, off course, I toasted to my final night in town a the Kimpton Library Bar!
Pool Day and Patties
Island Taste came highly recommended for the best patties on the island so I had to go twice–once for breakfast and again for the journey home! It’s located in George Town so accessible even if your just visiting for a day from the cruise port.
Kimpton Seafire Pool – I soaked up the last little moments of rest and relaxation by the pool enjoying patty filled cocoa bread and a good book. The vibe was just right for final reflection.
Solo Grand Cayman Travel Tips
When planning a trip to Grand Cayman, I didn’t see anything marketed specifically to solo travelers but my experience was still awesome. I had no concerns exploring Grand Cayman on my own as a solo female traveler.
A common question I’ve been asked since getting back is is Grand Cayman worth visiting? and my answer is absolutely yes. It’s certainly not the most affordable but I have zero regrets.
These are my top tips for women traveling solo to help you make the very best of your trip!
Frequently Asked Questions
The U.S. Department of State advises visitors to exercise normal precautions with a Level 1 travel advisory. This is the safest destination designation. I personally, did not have any safety issues during my trip.
It really depends on how much you want to see. For me, four or five days are enough but I wouldn’t turn down one week.
More Favorite Caribbean Destinations
I hope this Grand Cayman Island travel guide helps you plan the most memorable visit soon and very soon. And sharing is caring so be sure to pin this post for later and follow me over on Pinterest. Thanks for reading!
