Every November The Cayman Islands hosts their biggest and most exciting event, Pirates Week!!! This celebration filled with music, food, culture, and of course lots of pirating; expands over three weekends on their three different islands. The body of the festival and main attractions happen on the capital, George Town, Grand Cayman. This is the weekend that we attended. I will get into more details in the “Things to Do” section.
#Funfact I had been thinking about attending Pirate’s Week for about 8 years. The festival always happens around my birthday, but for one reason or another I never got to it. But I trusted my timing, and I was glad that I was able to experience their 42nd annual celebration with an amazing group of individuals.
Getting There:
If you decide that you want to attend Pirates Week, make sure to book your flights as early as possible. We bought ours in late June for a decent price. By the beginning of November, the price had almost doubled. It’s a very popular festival, with about 35,000 attendees across all 3 islands.
As mentioned in previous blogs, unless that I am making a recommendation, I don’t like to call out any companies by name. Even when I have a bad experience. I write them the review that they deserve on their page. The flight down was not very pleasant. You really can’t control bad weather. But the aircraft was a really outdated, the food was not good, and they had no entertainment. For the prices that they charge, I am sure they can do better. All I’m saying is, stick to a familiar airline when flying down there.
We flew back to the USA through JetBlue, where my boyfriend and I have have Mosaic status. That was a breeze and a much different experience. We didn’t fly down with them, because they only travel there a few days a week and those days didn’t align with our plans.
Getting Around:
Cayman Islands do not have Uber/Lyft and taxis are expensive. We rented a car ahead of time, which we picked up right outside of the airport. It cost about $100USD for 5 days. We used a company called “Dollar/Thrifty”. It wasn’t fancy at all, but we were able to get around at our leisure. Just a heads up, they drive on the opposite side of the road, the steering wheels are on the right, and they have lots of round-abouts. So make sure that someone in your group is comfortable driving like this. Also, gas is expensive just like any other Caribbean island.
Insurance Disclosure: If you don’t get car insurance and you get into an accident, you cannot leave the island until you pay for the damages done to the vehicle. We booked the rental on our American Express card, which offers car rental/loss and damage insurance. Check with your credit card company to see if they have something similar. Otherwise, make sure to pay for the car insurance when you book a rental.
Where to Stay:
As mentioned above, the main festivities happen in George Town, so ideally this is where you want to book your stay. Although that Grand Cayman has many beautiful areas. George Town itself has many neighborhoods. I believe that I mention this in all of my blog post, but safety is my main priority. Grand Cayman overall felt very safe at all times of the day and night. The Cayman Islands is a British overseas territory. So you know that the queen doesn’t play when it comes to obeying rules.
Read my AirBNB review below:
We had the most lovely time at Samantha’s place in George Town. She was very responsive and attentive, and gave us great recommendations of things to do. The town house is in a gated community, with a private and secluded feeling, yet close to everything. Downtown George Town is at about a 10 minute ride. It is a beautiful and modern place and everything was impeccably clean. My favorite place is the rooftop overlooking the property where you can catch the amazing sunset.
The pool at San Sebastian was under renovations the week that we were there. Samantha was kind enough to let us spend the second half of our stay at her Rum Point property. The unit there is smaller, but the area is beautiful. We were able to enjoy some peace and quiet at her water front property after the Pirates Week madness. I would certainly book with Samantha again.
See AirBnB listings:
Grand Cayman AirBNB from thesocialbutterfly on Vimeo.
Rum Point Grand Cayman AirBNB from thesocialbutterfly on Vimeo.
(Click Here) to sign up and save money on your first booking.
*Tell Samantha that I sent you!
What to do:
The possibilities are endless at Cayman Islands. There is so much to do even when the Pirate’s Week Festival is not going on. So bring your walking/swimming shoes.
Our Itinerary:
Day 1:
Pirates Week Welcome Party at Royal Palms – This waterfront beach club is very live at night. Not sure if it was because the party was sponsored by Bacardi, but they make some really good mojito pitchers. Great ambiance right on Seven Mile Beach. Shoutout to our friend Nora @Mom_Muggin for these shirts.
Day 2:
Rum Tasting at Cayman Spirits – Fun activity. Was def feeling that Caribbean rum by end. The tour itself is not really a walking tour. They just take you to the back and explain how they make their liquor. FYI, it is very hot back there.
Seven Mile Beach – This beach is just stunning, and literally seven miles of beautiful blue water, white sand, restaurants, bars, shops and hotels. The water is a little rocky when getting in. But once you’re in, you won’t want to get out.
Pirates Week Fire Works – Caught these beautiful fireworks after my birthday dinner from The Lobster Pot restaurant. The fireworks take place at Harbour Drive (Hog Sty Bay). But you can watch from anywhere along the waterfront.
Day 3:
Pirates Landing “Invasion” – We didn’t make it to this event. But I heard it’s pretty awesome. Basically, the Pirates pull ashore in their ships. They fight the king’s soldiers and take the Governor prisoner. They are eventually defeated. But the festive mood is set up for the parade.
Pirates Week Parade & Festival – Decorated floats flow through the streets of George Town. The pirates show off their best outfits and spectators join in the fun by dressing up as well. The parade is followed by a street festival with local food, music, dancing, drinks and games.
Day 4: Rum Point Beach – This place is absolutely breath taking. They have water sports, but they also have a completely separate area for relaxation. You can walk along the long white pier, grab a drink or food. A visit to Rum Point for a least a day trip is a must. They have a ferry that travels from George Town to the other side.
Day 5: Souvenir Shopping water front- The water front has a few souvenir shops, as well as an outdoor market since the ships come in through there. Don’t forget to pick up your rum cake to bring home! The Tortuga Rum Cake factory has rum cake tasting and they’re pretty good. (This is not at the water front). They do have a small souvenir shop at the water front though.
Other Popular Attractions:
Swimming with Stingrays
Snorkeling, Scuba Diving
Water Sports
Crystal Caves
Hell ( Literally the name of a place there.)
Where to eat:
We made breakfast everyday at the AirBNB to save money. Make sure to stop by the the local super market. We stopped at Kirk Market, and they are well stocked.
Lunch:
Guy Harvey’s Bar & Grill – Make sure to eat at the bar downstairs.
Royal Palms Beach Club – Great lunch menu. They also have a pool to lounge while enjoying drinks.
Dinner:
The Lobster Pot – Birthday dinner place. Great food and drinks. Loved the atmosphere, and they had the most attentive customer service. Make sure to sit outside to catch the beautiful sunset.
“Upstairs” at Kaibo Yatch Club – Rum Bar and fine dining (Rum Point)
Fast Food:
Burger Shack – Yummy place for after a night out or quick bites.
FYI:
Their currency is weighted heavier than the US dollar. Unless you’re at the airport or at certain shops/restaurants they always list the price in their currency. So expect to pay a higher amount than what you see. As of the publishing of this article, $1 Cayman Island Dollar (KYD) equals $1.20 US Dollar (USD). But keep in mind that rates change. So just do your research right before you go. (Here) is a calculator, but you can also google it.
Also in general, this is an expensive island. Everything is imported, and they have a good amount of wealthy citizens. They are the second richest country in the Caribbean.
The Cayman Islands is one of the five largest offshore financial centers worldwide, and the biggest in the Caribbean. “They have no income tax, no corporate tax, no estate or inheritance tax, and no gift tax or capital gains tax, making it a pure tax haven.” – Investopedia
But best of luck trying to open up a bank account there. The process takes about six months and multiple background checks.
Please don’t let this discourage you from visiting. If you’re curious there are a bunch of cruises that stop by. Maybe you can take a quick peek first.
Additional Info:
Website
https://www.piratesweekfestival.com/
Email
info@piratesweekfestival.com
Facebook Groups
https://www.facebook.com/CaymanIslandsPiratesWeekFestival/
https://www.facebook.com/groups/ilovecayman/
I hope that this travel guide motivates you to partake in some Pirate themed festivities in the Cayman Islands. Let me know if you have any additional questions or have any Cayman Island suggestions in the comments below.
-Mari
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