5 Day Travel Guide to Grand Cayman

I surprised my fiance with a 30th birthday trip to Grand Cayman for 5 days, which literally felt like 5 days in paradise! We were absolutely blown away by the beaches, the food, people and of course the ever famous String Ray City. Even after a month of vacationing there, I can’t stop thinking about going back for another visit. For me, Grand Cayman tied with Turks and Caicos as my #1 favorite island in the Caribbean!

Grand Cayman is the most developed island of all the Caribbean islands. It is a British Territory with a population of around 53,000 people and is the largest of the three Cayman Islands (Grand Cayman, Cayman Brac and Little Cayman).
Situated 272 miles below Cuba, Grand Cayman is only an hour and a half flight from Miami. If you can visit sometime in January or February, you can usually find flights for under $500 roundtrip from anywhere in the US. We visited in mid January and a non-stop flight from New York City was only $350 roundtrip on JetBlue. Most people travel less after the Holidays so you can score cheap flights almost anywhere in the Caribbean during these months. We’ve made it an annual tradition to spend a week in the Caribbean this time of year because it’s so affordable and because you can’t beat spending a week in 75 degree weather when it’s 30 degrees in New York City!

The main beach on Grand Cayman is Seven Mile Beach. Most of the resorts located here are pretty expensive, but worth the money if you’re looking to lounge on the beach all day. When we travel, we typically stay in an air bnb because we spend most of our time out exploring and therefore, don’t feel that resorts are worth the expense. At the end of the day, it’s just a place to sleep! I booked an affordable air bnb in South Sound which was a 5 to 10 minute drive from Seven Mile Beach about 70% less in price than the resorts located on Seven Mile Beach. The cheapest hotel I could find on Seven Mile was around $350 after taxes and resort fees vs. our $110 per night air bnb.

I like a good mix of relaxing beach days and adventurous days when I travel anywhere, so we opted into renting a car while visiting to explore different areas of the island. You will not need a car if you plan to stay at a resort as many places are walkable on Seven Mile Beach and most resorts have fantastic bars and restaurants. However, I highly recommend a car if you plan on exploring different beaches and are looking to snorkel or do other activities around the island.
Grand Cayman itself is only 22 miles long and 8 miles wide so you can get from one end to the other in about an hour with no traffic. It’s about a 33 mile drive from the Northwest area of the island to Rum Point, the Northeast end of the island.
Side note: If you rent a car, keep in mind that you will drive on the LEFT side of the road and that you must yield to oncoming cars at round abouts. Most Caribbean islands have round abouts instead of traffic lights!

Here is my 5 day trip itinerary for Grand Cayman with a good mix of relaxing beach time, snorkeling, animal adventures, bars and restaurant recommendations. Note that we didn’t have enough time to go everywhere on my list so I included a top rated restaurant list at the bottom of this itinerary as well as other island activities. I guess that just means I’ll have to plan another visit to Grand Cayman soon!

Our nonstop flight from NYC was about 4 hours and we landed in Grand Cayman around 12:30pm, picked up our rental car, and dropped by The George Town Yacht Club for a quick bite to eat.
I recommend starting your trip here because it’s right down the street from the airport and you will most likely be starving when you arrive! The George Town Yacht Club features casual outdoor dining by the dock where you can watch boats come in and out of the club. Sip on delicious tropical cocktails while you enjoy fresh seafood and a beautiful view. I would definitely recommend the rum punch (my Caribbean go to), the conch fritters, coconut shrimp, fish tacos and fresh Mahi Mahi.
IMG_7613IMG_7618After your meal, check into your hotel or air bnb, get settled and get ready to explore Georgetown!
Tip: If you’re like me and want to stock up on snacks for your trip, drop by Foster’s Food Fair, located right by the airport before you head to wherever you’re staying.

Georgetown is the capital of Grand Cayman and is a major cruise ship port. It boasts a plethora of coffee shops, bars, restaurants and souvenir shops. You’ll want to explore this area of the island in the afternoon as most cruise ships arrive early in the morning and the area is overwhelmed with tourists. Go in the afternoon around 2pm or 3pm as most cruise ship passengers are heading back to their boat by then. It’s pretty deserted after 5pm so would not recommend this area for dinner while you’re visiting.

Grab a delicious cup of coffee from South West Collective. We liked this place so much that we came back every single morning for the balance of our trip! Not only do they have delicious handcrafted coconut milk lattes, but they also serve all natural food and fresh smoothie bowls. In addition, the view from the coffee bar is pretty unbelievable. You can see all of the cruise ships parked out in the water.
After grabbing a coffee to go, walk around and explore the many souvenir and gifts shops near the cruise port and take a photo with the “Welcome to the Cayman Islands” sign. Be sure to also pick up a Tortuga Rum Cake which Grand Cayman is famous for!
After exploring downtown Georgetown, head to Pure Art Gallery, one of the top ranked gift shops in Grand Cayman on Trip Advisor. This unique, colorful gift shop features art, gifts and accessories that are handmade by local artisans on the island! You can find jewelry, housewares, home decor, and more. Be sure to take a photo out front by their cute swing and decorated store front!
IMG_9093IMG_8724IMG_0039Following your visit to Pure Art Gallery, enjoy a refreshing sunset cocktail at Grand Ole House just down the road. This is one of the oldest establishments in Grand Cayman and features premium waterfront dining, an award winning wine list and live music. You can also have a romantic seaside dinner here following cocktails if you wish!
Unfortunately Grand Ole House was closed for a private event when we we arrived so we decided to grab drinks at Lone Star Bar & Grill before dinner instead. This outdoor sports bar was the perfect location because it was walkable to our dinner reservation at top rated Italian restaurant, Ragazzi.
Dinner at Ragazzi was one of my favorite meals I’ve ever had! You absolutely must book book a dinner reservation here during your visit to Grand Cayman.
Ragazzi is an Italian restaurant featuring wood fired pizzas, house made pastas, an excellent wine list and delicious desserts. We ordered the Lobster Penne which had chunks of fresh lobster and the creamiest, most delicious roasted garlic cream sauce. We also ordered the Frutti Di Mare pizza with lobster, scallops, shrimp and mussels, tomato and basil an it was one of the best pizzas I’ve ever had in my life! If seafood isn’t your thing, they have a ton of meat and vegetarian pizza and pasta options as well.
A huge plus for me was that they had gluten free pasta and pizza dough.

You deserve a relaxing beach day! On your way up to Seven Mile Beach, start your morning with breakfast at the Marriott hotel. Anchor & Den is a top rated restaurant on the island to have brunch and features eclectic cocktails and the ultimate comfort food menu. Enjoy breakfast classics like eggs benedict, pancakes and french toast with a modern twist.
The Marriott is located on Seven Mile Beach, but the best area to park closest to beach access is a little but further North of the Marriott, across the street from the Westin. Typically you can find parking on the street just about anywhere, but there is beach access located at Governors Beach. Make sure to pack your beach towels and plenty of sunscreen!IMG_8864IMG_7852After a long day in the sun, enjoy a beautiful evening with sunset cocktails and dinner at Camana Bay, one of the island’s newest shopping developments with plenty of bar and restaurant options to choose from. Enjoy outdoor happy hour at Karoo followed by dinner at Mizu Asian Restaurant or Agua.
If you’re looking to splurge on a special occasion or love a fantastic 5 star dinner experience, I totally recommend Upstairs at Kaibo. Upstairs has been Grand Cayman’s #1 rated restaurant from 2012 to 2018, featuring artisan cocktails and superb dishes, including locally line caught fish and fine Caribbean ingredients. Inside, the Rare Rum Bar houses Grand Cayman’s widest selection of rums.
We took a 6pm ferry from Camana Bay to Kaibo, located on the opposite end of the island and enjoyed the 6 course tasting menu, which was excellent and I highly recommend! We like to eat dinner pretty late, but if I could do it over again, I’d add the wine pairing and book a 6pm dinner reservation here to watch the sunset and enjoy pre-dinner cocktails downstairs at Kaibo’s Beach Bar.
Ferry tickets are $20 CI roundtrip. View the ferry schedule and book your reservation in advance HERE.
Note that the last ferry back to Camana Bay from Kaibo is at 9:30pm.

If you have a major sweet tooth after dinner like me, enjoy freshly made gelato at Gelato and Co. or house made desserts at Agua once you arrive back at Camana Bay on the ferry. In addition, if you want a late night spot for drinks and dancing, check out Royal Palms Beach Club, a local favorite located across the street from Camana Bay. We liked this place so much that we went back later in the week to watch the sunset on the beach. Have you ever seen a more beautiful sunset than this one?!
warm sunsetIMG_0195

Start your morning with a delicious smoothie bowl for breakfast at Island Naturals and head up to West Bay to check out the Cayman Turtle Centre, the island’s only turtle sanctuary. Here you will find a giant green turtle breeding pond (where some turtles weigh up to 500 pounds!) and you may be lucky enough to spot a female turtle’s nest.
There are turtle touch tanks where you can take a photo holding a green turtle, a butterfly garden, the island’s largest swimming pool and more. There are several great activities here, especially if you are traveling with children.

After a few hours of exploring at the turtle sanctuary, enjoy a casual, waterfront lunch at The Cracked Conch and a delicious cocktail from Macabuca Tiki Bar before heading to snorkel at Cemetery Beach, the best snorkel spot in West Bay.
We chose to snorkel at Smith’s Cove in South Sound, closer to where we were staying which is another great snorkel area to spot tropical fish and jump off of the rocks into the water. Spotts Beach is also noted as a top snorkeling destination on the island because you can often swim with turtles.
smith coveIMG_9031
End your day with sunset cocktails and dinner at Catch, one of Grand Cayman’s best waterside seafood restaurants. I highly recommend their Mahi Mahi Schnitzel, another one of my favorite meals while one the island!

Grand Cayman is famous for String Ray City, a giant sand bar where you can swim with and feed string rays! Start your day bright and early with a String Ray City & Star Fish Point snorkeling tour. We toured with Aquarius Sea Tours and our 4 hour tour started promptly at 9:30am, leaving from the Grand Cayman Yacht Club. The tour company provided snorkel gear and was $55 USD per person. The other note worthy String Ray City tour company on the island is Red Sail Sports which also offers water sport rentals.

The first part of our tour was 45 minutes of snorkeling out on the reef where the water was about 15 feet deep. We saw plenty of tropical, colorful fish along with a couple of small string rays.
IMG_8948IMG_8954IMG_8952Our second stop was Star Fish Point where our tour guide parked the boat and gathered several star fish for us to take photos with in the shallow water on the beach. It was pretty cool to hold a star fish for the first time! They were about the size of my hands. Star Fish Point is where star fish gather to procreate. The water temperature and climate are perfect for them to make babies here. During your visit at Star Fish Point, remember that star fish are animals and absolutely need to stay in the water to survive. Grand Cayman actually charges a $5,000 fine if you remove them from the water!
After 45 minutes at Star Fish Point, it was time for the main event: String Ray City. Our tour guide brought us to a large sandbar with the clearest, most beautiful blue water I’ve ever seen in the Caribbean! As soon as we jumped into the water, our boat captain pulled out fish bait and lured a friendly female string ray over that he has ‘known’ for almost 40 years. She was beautiful and BIG! Shortly after, we were surrounded by 30 to 40 string rays of all sizes which was kind of overwhelming at first. Many of them swim straight at you which made me a bit uncomfortable, but they will swim right past you and are harmless. Just be prepared that they will rub up against you! We each got to pet and feed the the string rays straight out of our hands which was pretty cool. This was definitely one of my top favorite life experiences with animals and I highly recommend you do it during your visit to Grand Cayman!
sting ray city
Travel tip: Water is provided on the boat but make sure you bring a beach towel, sunscreen and plenty of snacks!

After 4 hours of sun and snorkeling, you’ll likely be starving. Opt for a casual lunch at a local favorite: Pepper’s Bar & Grill. This was easily another one of my favorite meals on the island, so much so that I actually placed a pick up order on our way to the airport before leaving the island so I could enjoy it one last time on the plane!
Pepper’s is famous for their authentic Caribbean baby back ribs and jerk chicken. They also have burgers, grilled fish and my personal favorite, loaded disco fries!
IMG_8853After being in the sun and water most of the day, we opted into catching the sunset at Royal Palms Beach Club and relaxing instead of making a dinner reservation. The food here was just as great as the view!

Spend your last day in Grand Cayman at Rum Point. Known for white sandy beaches, picturesque hammocks and delicious food, you can sip on rum punch and snack on conch fritters, all while enjoying the view!
Be sure to also add a mudslide to your list of items to oder at Shipwreck Bar & Grill. This is where the original mudslide was invented! After exploring Rum Point, we decided to check out Kaibo’s Beach Bar down the street before heading back to South Sound.
rum point entranceIMG_9024IMG_8486IMG_9018 3FullSizeRenderIMG_8509Snapseed 4Reserve a table at The Brassiere or dinner, another one of the top rated restaurants on the island with a very unique and delicious dining experience. The restaurant has it’s own fishing boat and serves fresh daily caught local fish along with fresh ingredients from the restaurant garden. Don’t skip out on dessert!

All and all, Grand Cayman is a romantic destination for couples and would be a great honeymoon spot. It’s also very family friendly and has a ton of activities for children and adults. I can’t wait to go back!

Here are some additional top rated activities, restaurants and bars I’m saving for my next trip to Grand Cayman that I would recommend checking out. Happy trip planning!

Queen Elizabeth Botanical Park (Open from 9am to 4:30pm, $10 for Adults & Children 6-12 $5, Under 5 FREE)
Distillery Tour at Cayman Spirits Company in Georgetown (Tours are at 11am, 1pm & 3pm daily, but closed on Saturdays)
Helicopter Island Tour with Cayman Helicopter Company
Crystal Caves Tour (on the way to Rum Point)

Sunshine Grill
Sunday Brunch at Ave (Kimpton Seafire Resort)

Calypso Grill
Blue Cilanto
The Warf
Morgan’s Seafood Restaurant

Bar Jack (Beach Bar at the Ritz)
Beach Terrace (Beach Bar at the Westin)
Ave at the Kimpton Seafire Resort
Anchor & Den at the Westin

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