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We actually visit the Cayman Islands at least once a year and have fallen in love with it’s calm, sleepy charm. The main island Grand Cayman isn't as lush or picturesque as Caribbean islands like St. Lucia or Dominica, but it still has some of the best beaches in the world, it’s easy to get to from most major cities in the US, and it's is one of the safest islands in the Caribbean.

We travel here for the friendly locals, the relaxing let's-hang-out-on-a-boat vibe, and the yummy food. Spend a few days here and we bet you'll be charmed, too. 

This travel guide has information on where to stay on Grand Cayman, what to see & do, and our favorite spots to eat and drink. There's also a downloadable three day itinerary available at the very end. Use the table of contents to jump around!  

sleep

Seven Mile Beach view from The Westin

Seven Mile Beach view from The Westin

The Westin Grand Cayman Resort & Spa
Seven Mile Beach | 345.945.3800Website
This is where we’ve stayed every time we’ve visited Grand Cayman. It’s not cheap, but it’s one of the nicer hotels on the island and you have your own private section of Seven Mile Beach (consistently rated one of the best beaches in the world). There are a few good restaurants, tons of equipment for water activities, and - most importantly - a swim up bar. At night you’ll hear absolutely no noise since there really isn’t a lively bar at the hotel - that means superb beauty sleep. If you are a Starwood points guy or gal, you can find pretty good deals if you go during low season (May-October). Prices start at around $259/night. Rooms were recently renovated. 
#WildTerrains tip: You might want to pay up for ocean views if you plan on spending a lot of time in the room, but if you’re anything like us you’re going to be outside most of the time anyway. Safe a few dollars and pick an island view room - more pool bar cocktails for you!  

Sunshine Suites Resort
1465 Esterley Tibbetts (Seven Mile Beach) | 345.949.3000Website
We haven’t stayed at this hotel, but their restaurant Sunshine Grill is our favorite on the island. The hotel is actually right across the street from the Westin, so it's not on the water, but it takes only a few minutes to walk over to Seven Mile Beach from the hotel. This is where we would stay if we couldn’t find a reasonable rate at the Westin. Prices start at around $150/night.

Other thoughts...

Really want to splurge? There’s a Ritz Carlton right next to the Westin. We’ve never been able to afford to stay there, but if you can, we’ve heard it’s fabulous.

There’s also a Kimpton hotel opening on Seven Mile Beach in late 2016. We haven’t stayed there either, so we can’t vouch for it, but it’s gotten a lot of hype.

If resorts aren't really your thing (albeit the ones above aren't massive resorts), there are plenty of Airbnb options to choose from.

nosh

Burger at Sunshine Grille

Burger at Sunshine Grille

Sunshine Grill - lunch or dinner
1465 Esterley Tibbetts (Seven Mile Beach) | 345.946.5848 Website
We love this restaurant so much that we eat here multiple times when we visit the Caymans. Sometimes twice in one day. It’s tucked away in the middle of Sunshine Suites Resort (next to the pool) in a little unassuming beach shack. The atmosphere, the drinks, and the food are all about island vibes. Friendly service and prices. This place is so good - if you go to Grand Cayman and don’t eat at least one meal here, we will actually be sad (and so will your soul).
#WildTerrains tip: Order the burger with fries, the shredded orange chicken tacos, or the fish tacos - or all three for the table or yourself. No judgement here. 

Calypso - dinner
#10 Morgan's Ln (West Bay) 345.949.3948 Website
Calypso is a funky little restaurant right on the water at the tip of the island. It’s a great spot for a romantic dinner, but the atmosphere isn’t too stuffy. Fresh seafood is the specialty here. Sit outside on the open air deck and enjoy a leisurely dinner with lots of wine and food. Prices are a bit high because this is a tourist and expat favorite, but that’s to be expected on most Caribbean islands.
#WildTerrains tip: Take a cab here. The roads can be a bit dark to drive yourself and the cabs aren’t too expensive on the island. There will be a few waiting outside after you’re done with dinner.

Heritage Kitchen

Heritage Kitchen

Heritage Kitchen - lunch
Boggy Sands Road (West Bay) 345.916.0444 Website
Heritage Kitchen is a rustic seafood shack with so much Caribbean charm you'll be snapping Insta pics left and right. They serve really delicious fresh fish and fritters topped with local hot sauce. It's a perfect spot to get away from the more touristy areas of town. Only open Wednesday-Sunday.
#WildTerrains tip: If you happen to be on the island on a Sunday, swing by Heritage Kitchen for their Sunday barbecue - it's a favorite of the locals!

Beach House - dinner
The Westin Grand Cayman (Seven Mile Beach) | Website
Looking for something a bit fancier? We had a fabulous dinner at the Beach House at The Westin Grand Cayman. We actually didn't order dinner - instead we got a bottle of wine and ton of appetizers to share. We sat outside a few feet from the beach and listened to the waves. The staff was super friendly and let us linger at the table all night until they closed. 
#WildTerrains tip: Looking for something off the charts fancy instead? Make a reservation for Eric Ripert's Blue at The Ritz Carlton. (Let us know how it is!)

sip

The Beach Bar - poolside bar
The Westin Grand Cayman (Seven Mile Beach) | Website
If you’re staying at the Westin or Sunshine Suites (or an Airbnb!), then the pool bar at the Westin is the spot to grab a sunset cocktail. Gorgeous views of Seven Mile Beach & strong margaritas! 
#WildTerrains tip: The drinks are reasonably priced compared with the Ritz Carlton's pool bar, but that's also an option and right next door! 

Calico Jack's - beach bar
Next to public beach, West Bay Rd (Seven Mile Beach) | 345.945.7850  | Website
Looking for something that’s a bit more lively? Walk down Seven Mile Beach to Calico Jack’s - an oceanfront dive bar with killer views. The drinks are lighter-fluid-strong and the food is sufficiently fried to soak up all the booze. It’s probably not somewhere we would bring our parents, but it makes for a fun night out with your better half, travel buddy, or BFF. 
#WildTerrains tip: The Caymans are super safe, so it’s safe to walk along the beach at night. If you’re walking to Calico Jack's from the Westin, it’s about a 10 minute walk (which is awesome at sunset). 

Kaibo Beach Espresso

Kaibo Beach Espresso

caffeinate

Kaibo Beach Espresso - coffeeshop
585 Water Cay Rd  (Rum Point) | 345.947.9975Website
There aren’t a ton of great coffee options on the island, but if you make it to Rum Point on the other side of the island there’s an adorable coffee shop next door called Kaibo Beach Espresso. A few minutes drive from Starfish Point - we made this our pit stop on our way back to the hotel.

experience

Swimming with the string rays

Swimming with the string rays

Seven Mile Beach
Consistently rated one of the top beaches in the world. The water is warm and crystal clear to the bottom with soft creamy sand. On a sunny day the color of the water will be so blue, you’ll think your eyes are fooling you. The best part is no crowds - since most of the beaches are privately owned, the only person who will bother you is a nice person asking if they can bring you a fruity beverage (dreamy, right?).
#WildTerrains tip: Don’t want to sit on the beach all day? You can rent kayaks, SUP boards, jet skis, and snorkeling gear right on the beach.

Starfish Point

Starfish Point

Sting Ray City
This is one of the coolest animal experiences we’ve had while traveling (and we’ve been on African safaris and to the Amazon!). Basically you hop on a catamaran (with a cash bar - yaaas!) and they take you to a natural sandbar in the middle of the ocean where hundreds of giant sting ray congregate. This magical place is called Sting Ray City. You hop off the boat into the water and swim around with the sting rays - if you’re lucky (and not too terrified) you’ll even get to hold them! It’s an amazing experience. Our favorite tour is led by Red Sail Cayman
#WildTerrains tip: You ask: "But aren’t sting ray dangerous? (I mean, hello, Steve Erwin…)” Good question! These sting ray are actually docile after years of human interaction - in fact, their stingers don’t even sting anymore! Follow up question: does that mean this activity is harmful for the animals? No, go with a top tour operator like Red Sail and their team will make sure you’re interacting with the animals in way that’s safe for both you and them.

Starfish Point
Rent a car and drive to the other side of the island (should take around 45 minutes to an hour). Follow signs to Starfish Point and you’ll find a gorgeous empty beach with tons of large starfish hanging out in the water. Get in the water with them! You can even touch and hold them as long as you’re very gentle and only keep them out of the water for a few seconds.

three day itinerary for grand cayman