Girls Trip Guide to Grand Cayman

Charter a private boat for the ultimate island day

If you want one experience that feels completely unforgettable, this is it. Chartering a private boat lets you and your friends spend the day hopping around the island’s dreamy North Sound lagoon and stopping wherever the water looks too beautiful not to jump in. The best captains create an easy, relaxed itinerary that can include swimming with stingrays, snorkeling over coral reefs, and beach stops for lunch or cocktails. It’s your own private Caribbean day club on the water.

Swim with the stingrays

This is Grand Cayman’s most famous experience, and it lives up to the hype. The stingray population on Grand Cayman has become one of the most studied wild stingray communities in the world, and it has changed how marine biologists think about wildlife tourism and animal behavior.

We had the unique experience of going to a little-known area where over 100 stingrays live. With water depth at about 12–15 feet and located about a mile away from the popular Stingray City sandbar, few boats and few tourists will be present. The rays naturally swim through the water rather than gathering in a circle. Instead of standing on the sand, you will have the opportunity to swim, float, or snorkel, and watch the rays glide around you. Many locals say this version feels closer to what Stingray City was like decades ago before tourism exploded. I can truly say the “stingray kiss,” where you gently hold a ray and lean in for a lucky kiss was exhilarating and I have felt the luck ever since! Seven years of good luck, they say.

A fun bit of history: Stingray City exists because fishermen used to clean fish in that area. Over time, the rays learned boats meant food and began gathering there regularly. Eventually, tour operators started bringing visitors, and the spot became one of the most famous wildlife encounters in the Caribbean.

Discover Starfish Point

One of the most peaceful stops on the island is a little cove called Starfish Point, tucked away near Cayman Kai. The water here is shallow and looks like glass, with soft seagrass beds where bright red starfish rest on the sandy bottom. Walking through the water searching for them feels like a treasure hunt. Walk twenty or thirty yards away from the crowds and you’ll often find starfish resting undisturbed in the calm water. Be sure to hold the starfish underwater—they breathe through the water and it is now illegal to hold them out of the water

Stop for cocktails at Kaibo Beach Bar

After a morning on the water, there’s no better stop than Kaibo Beach Bar. Kaibo sits on the quiet north side of the island and feels like a secret island beach club. Boats pull right up to the dock, and the restaurant sits beneath dramatic blue shade sails with views across the North Sound. Order a round of drinks and sink into shaded tables or colorful chairs in the sun overlooking the water. Be sure to order the Cayman rum punch, a frozen mudslide, and fish tacos with conch fritters!

Boutique shopping highlights

Grand Cayman has numerous adorable boutiques for you and your friends to enjoy a shopping day or quick break from the water!

• Check out Seafire Supply Co. located inside the Kimpton Seafire Resort. It’s a beautifully curated boutique that perfectly captures the island’s relaxed luxury vibe.

• Indigo Boutique: Just below the elegant restaurant Indigo, you’ll find a boutique space featuring elevated fashion and curated accessories. This carefully curated selection of clothes, jewelry, and gifts will leave you feeling like you have discovered a hidden shop and wanting to return to buy what you didn’t the first time.

• Camana Bay: The Island’s Walkable Shopping Village Camana Bay is the beautiful waterfront town center just minutes from Seven Mile Beach. Camana Bay blends boutiques, cafés, art galleries, and restaurants along shaded streets and a marina promenade. Boutiques like NKY, Sand Angels, and other local designers sell both resort wear and items you will wear at home but always remember you bought on your Grand Cayman vacation!

Many visitors do not realize that there are so many luxury and boutique shops and that Grand Cayman is duty-free! Visit Cabana Bay in the early evening for shopping before grabbing a cocktail and dinner on the waterfront!

The Bioluminescent Bay (Bio Bay)

Grand Cayman enjoys one of the Caribbean’s most magical natural phenomena. After the sun disappears and the lagoon goes completely dark, the water itself begins to glow. Every paddle stroke, every swirl of your hand, ignites thousands of tiny sparks of light. It feels like swimming through stardust. This is the island’s bioluminescent bay, and it is one of the most extraordinary nighttime experiences in the Caribbean. Grand Cayman’s bio bay sits in the North Sound near Rum Point and Cayman Kai. The result is a glow so intense that when you move your hand through the water, it leaves a trail of light behind it.

Spend a morning on Seven Mile Beach

Seven Mile Beach is the Caribbean postcard you imagine when someone says “perfect beach.” The hotels I recommended are all on Seven Mile Beach, so you will likely spend many mornings enjoying the view and walking the beach. The sand is brilliantly white and soft. The water is calm, warm, and perfectly clear. Everyone will instinctively pull out their phones for photos to capture the moment.

Start the morning with a beach walk, grab lounge chairs, and swim between cocktails.

Beachfront lunch spots like Tillie’s or The Wharf make it easy to spend an entire day here.

Snorkel the reef at Coral Gardens

Just a short boat ride from Stingray City lies Coral Gardens, one of the island’s best snorkeling areas. The reef sits in shallow water, making it easy for beginners, and the marine life is vibrant—schools of tropical fish, colorful coral formations, and sometimes even sea turtles gliding past. Even people who normally prefer lounging end up snorkeling here because the water is so clear it feels like swimming in an aquarium.

Explore the Crystal Caves

For a break from the beach, the Crystal Caves offer a stunning change of pace. Hidden in the tropical forest, the limestone caves contain dramatic stalactites, underground pools, and rock formations shaped over millions of years. Walking through the cool cavern air after a hot beach morning feels almost surreal.

Tillies

Located at the chic Palm Heights Hotel on Seven Mile Beach, Tillies is one of my absolute favorites. The beachside setting is perfect for lunch or dinner and drinks under the stars. The atmosphere is magical day and night.

Taikun

Taikun at the Ritz-Carlton offers one of the island’s most elevated dining experiences with an intimate sushi and omakase bar. The chefs serve pristine fish flown in from Japan, including freshly grated wasabi from the root—something rarely experienced outside top sushi restaurants. It’s a memorable splurge night where incredible food and a sophisticated setting create a truly special evening. Be sure to stroll through the Ritz’s stunning collection of stunning art!

Calypso Grill

Calypso Grill is one of Grand Cayman’s most beloved classic seafood restaurants, perched right on the water near Morgan’s Harbour. The setting is relaxed yet elegant, with breezy ocean views and a menu full of fresh local seafood and Caribbean flavors. Be sure to try the famous Escovitch (crispy fish of the day), lobster and shrimp, and sticky toffee pudding.

Ragazzi Ristorante & Pizzeria

Ragazzi is a lively Italian favorite known for its warm hospitality, great wine list, and delicious pastas and pizzas. The atmosphere is energetic and welcoming, making it the kind of place where groups of friends can laugh, share dishes, and enjoy a long, relaxed dinner together. It’s the perfect casual night out when everyone wants great food and a fun atmosphere without anything feeling too formal.

Bacaro

Bacaro is a fabulous waterfront Italian restaurant tucked along the quiet North Sound, Bacaro feels like discovering a hidden Venetian wine bar in the Caribbean. The menu is built around small plates meant for sharing—think handmade pasta, seafood crudo, and elegant cicchetti paired with beautiful wines. It’s the perfect place for a relaxed evening with friends, watching the sunset over the water while lingering over several courses.

Library by the Sea: The Kimpton Seafire’s hidden cocktail gem

Tucked inside the Kimpton Seafire Resort, the Library by the Sea is a must! The bar feels like stepping into a private study with floor-to-ceiling bookshelves, unique seating, fun craft cocktails, and ocean views.

The Library by the Sea special is its cocktail “menu of stories.” Each drink is inspired by literature or historical narratives, and the bartenders treat mixology almost like storytelling. Inventive ingredients, dramatic presentation, and cocktails that feel more like experiences than drinks. Be sure to roam the hotel lobby to see the art collection throughout!