At just over 75 square miles, lovely Grand Cayman is the largest of the Caribbean’s three Cayman Islands. It’s also the most popular, welcoming over 600,000 tourists each year.
Home to famously beautiful beaches and clear turquoise water, a vibrant arts and food scene, upscale oceanfront resorts, world-class hospitality, and near-perfect weather year-round, it’s easy to see why this British territory is consistently ranked one of the best vacation islands in the world.
Guests can get out on the water for unforgettable boating, snorkeling, and scuba excursions along the island’s stunning coral reefs, crystal-clear shallows, and private lagoons. Hike winding trails through old-growth forests and protected land. Stroll historic George Town to take in the traditional architecture and dine on incredible local cuisine. Or spend lazy days relaxing on the world-famous Seven Mile Beach, enjoying ocean breezes, gentle waves, and walks along the shore.
With plenty of opportunities for water fun, outdoor adventure, and more leisurely island pursuits, it’s the perfect destination for thrill-seekers and laid-back travelers alike.
We asked our Grand Cayman Destination Manager, Chelsea, to share her top picks for three perfect days in this Caribbean paradise. The result is an itinerary packed with fun-in-the-sun activities, delicious food, and unforgettable underwater excursions!
DAY 1: Sunshine and Snorkeling
Start your morning off with a fresh Acai bowl or healthy breakfast wrap from Island Naturals across the street from your Equity Estates home as you wait for your guide from Fat Fish Adventures to pick you up and take you out for a thrilling day of boating and snorkeling at some of Grand Cayman’s most stunning locales.
In and on the water, you’ll have the opportunity to get up close and personal with the island’s marine life as you swim with wild stingrays along the sandbars at Stingray City, snorkel around beautiful coral reefs with turtles, eels, and schools of fish, and interact with starfish in the shallow tide pools dotting the beach at Starfish Point. Between adventures, kick back and soak up the sun on one of the island’s quiet, secluded beaches. And afterwards, grab a laid-back lunch of grilled fish or wood-fired pizza at the lovely Kaibo Restaurant or enjoy the delicious jerk chicken and Caribbean vibe while hanging out at the colorful waterside picnic tables at The Wreck Bar & Grill.
In the afternoon, spend a little quiet time at home or by the pool before walking next door for happy hour drinks at the elegant Seven at Ritz-Carlton. Enjoy a glass of their sommelier-selected wines or try one of the bar’s unique, handcrafted cocktails—the refreshing, peach-infused Fly With Me and the Pop Corn Old Fashioned are both especially tasty.
For dinner, we’ll make reservations for you at the festive Coccoloba Bar & Grill at the Kimpton Seafire Resort, a pleasant 20-minute stroll up the beach. There, you’ll wrap up an amazing first day with incredible tacos, island drinks, frozen desserts, and live music served up in a cozy, open-air dining room.
DAY 2: Beach Time
There’s more fun and sun on day two, starting with a morning kitesurfing lesson at Barkers Beach in West Bay. This is the premier spot for kitesurfing on Grand Cayman, located in the center of a protected park, a short 15-minute drive from Seven Mile Beach. With calm, shallow waters framed by white-sand shoreline and lush tropical trees, it’s a picture-perfect spot to start the day. Best of all, Kitesurf Cayman will pick you up for your adventure, provide all the necessary gear and instruction, and get you out on the kiteboard in no time.
For lunch, enjoy a light meal on the sophisticated seaside patio at Saint June. The Avocado Toast and Chili Lime Fruits are perfect for sharing, while the Blackened Fish Tacos and West of Cayman bowl are enough to fill you up without feeling too heavy afterward. Add a signature Agua Fresca or Saint June Pina Colada to your order for a true island lunch experience.
In the afternoon, it’s time to hit the beach. Considered one of the best beaches in the world, Seven Mile is a paradise of soft, white sand, blue skies, and crystal-clear water, right outside your front door. Spend the day lounging under an umbrella, strolling along the shore, picking up jet skis or paddleboards from any of the beachside vendors, swimming, or watching the sunset with a tropical drink in hand. Your personal travel concierge will arrange anything you need in advance so that you will have an unforgettable afternoon by the water.
That night, we’ll have reservations for you at Tillies, a classic seaside eatery known for excellent service, fantastic fresh seafood, and lovely views of the water from their elegant dining room or open-air patio. Share a platter of raw oysters or try the Aji Ceviche to start, order the perfectly grilled ribeye or local snapper for your main, and be sure to save room for drinks and dessert.
DAY 3: Shopping, Sightseeing, and Sunset Dinner
On your final perfect day, wake early for a scenic 45-minute drive to the island’s Northside and a visit to the recently opened Cayman Crystal Caves. Set within a lush tropical forest, the caves are one of Grand Cayman’s oldest landmarks and were once hideouts for pirates. During a 1.5-hour guided tour, you’ll explore the open-ceiling cave, roots cave, and lake cave, marveling at the unique stalactite and stalagmite crystal structures and otherworldly rock formations before heading up to the viewing deck and taking a walk along the forest paths above the caves to view indigenous trees, plants, and island wildlife.
After your morning out, cool off with a light lunch of fresh veggies and sandwiches in the lovely garden area at Mrs. Piper’s Kitchen, or dine at The Brasserie, a cozy, seasonally inspired, farm-(and sea)-to-table restaurant in the heart of Georgetown. There, you can enjoy a garden-fresh watermelon or mango salad, or try the tuna poke bowl, famous Brasserie Grilled Cheese, or fresh catch of the day.
From lunch, take a walk through town to check out some of the local shops and galleries. Stop by Heroes Square and the Fort George Ruins for photos. And pay a visit to the Cayman Islands National Museum to tour the island-focused art, culture, and natural history exhibits. Just be sure to check the cruise ship schedule with your local host ahead of time. On cruise ship days, the downtown area is filled with tourists, though it’s easy to plan around that if you want to avoid the crowds.
To round out the afternoon of sightseeing, make the three-minute drive to the high-end Camana Bay entertainment district for a few hours of duty-free shopping and fun. Take a walk up the 75-foot observation tower for panoramic views of the island; grab an icy treat from Gelato & Co. to enjoy in the shaded courtyard or by the fountain; and visit the district’s 30+ boutiques to shop for everything from jewelry and art, to clothes, home goods, books, and more. There’s also an excellent, state-of-the-art movie theater onsite—perfect for rainy days or if you want to beat the heat indoors.
That evening, you’ll end your three perfect days in Grand Cayman back in West Bay for a casual sunset meal of authentic island cuisine in a stunning, right-on-the-water dining room at Macabuca Bar and Grill, or with reservations for a romantic dinner at the beautiful Ristorante Pappagallo, with 30-foot thatched ceilings, water and forest views, and excellent Italian cuisine.
At Home in Grand Cayman with Equity Estates
Our lovely three-bedroom Grand Cayman penthouse is located on the most sought-after section of the island’s famed Seven Mile Beach, just 600 feet from the Ritz Carlton and a short, twelve-minute drive from the airport. Ranked as one of the best beaches in the world, this is a location that can’t be missed.
The home features an excellent indoor/outdoor floorplan with a gourmet kitchen, open living and dining room, and a spacious screened-in patio (and small, open deck) with unobstructed views of the property’s infinity pool, palm-lined beach, and brilliant turquoise water. With its prime, oceanfront location and cozy, sophisticated décor, you’ll have easy access to some of the best dining and outdoor activities on the island and a relaxing space to unwind at the end of the day.
Your personal travel concierge will work with you to plan your itinerary before you arrive and make sure your stay is effortless by arranging reservations for activities, transportation, and dining. Leave the details to us and arrive to a fully stocked kitchen and bar with groceries of your choice from the local market. With Equity Estates, comfort and luxury are yours.
Travel with Equity Estates for a unique and memorable experience. If you would like more information about investing with Equity Estates, please reach out to our Investor Relations team at 404.445.8501 or click to schedule a call. Your fabulous Grand Cayman getaway awaits!
