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What to do in Grand Cayman: The Best 7-Day Cayman Islands Itinerary

What to do in Grand Cayman: The Best 7-Day Cayman Islands Itinerary

Wondering about some of the most memorable things to do in Grand Cayman on your upcoming vacation? We’ve curated what we think is the best 7-Day Cayman Islands itinerary for the most picturesque days you can have on our Islands. If you love taking amazing photos as memories of your experiences, read on for some of the hippest, chicest, and most beautiful spots the Cayman Islands have to offer. We promise, your memories will thank you!

We love our islands, we love design, and we love to travel too. We’re the team from Isy B., the award-winning design brand from the Cayman Islands. When we travel, we want to live like the locals, even if it’s just for an hour, to enjoy the most authentic and unique experiences. Enjoy the top picks from our team for the most fabulous 7 days of your island life!

INSIDER’S TIP: If you’re traveling to the Cayman Islands during the off-season (August through October), some restaurants may be not open and not all experiences may be available, so we advise you to call ahead.

The Best Cayman Islands Itinerary

Day 1 - Arrival in Grand Cayman

  • Arrive at Owen Roberts Airport
  • Enjoy sunset dinner and drinks at Tillie's - Breathe in that salty island air. You’ve arrived. Once you’ve checked in and dropped off bags. You’ll be ready to greet the sunset with a cocktail or two and indulge in a little celebrity spotting. Vogue, W, and Harper Bazaar have all featured this hip spot on Seven Mile Beach. The iconic striped umbrellas and vintage palm-fringed swimming pool make a gorgeous backdrop for selfies, just ask Gigi Hadid! You’re able to book your first picturesque sunset dinner and drinks at Tillies on their website.

Day 2 - Enjoy Grand Cayman’s natural beauty

  • Breakfast at resort
  • Visit the Crystal Caves - Jump in your island jeep. It’s time for an adventure to the north of Grand Cayman, where you’ll travel back in time. The Crystal Caves feature dramatic formations that are millions of years old. Don’t miss the other-worldly blue glow of the crystal lake. Pose for a picture. Book tickets through: 

BONUS ADVENTURE TIP: Depending on how much time and energy you have, you can incorporate a stop to explore the Mastic Trail or at the Queen Elizabeth Botanical Gardens on your way both offer fabulous nature walks in Cayman's unique landscape.

  • Lunch at Allora Cafe - On your way back to George Town be sure to stop at Allora, a recently opened hip dining spot. It’s a restaurant, bakery, and gelateria combined, with an all-day menu of Italian favorites to die for. The decor is as fabulous as the food. Take a photo of both before you tuck in!
  • Late afternoon drinks at the resort pool
  • Sunset dinner at Saint June - For dinner, watch the sunset at Saint June - an elegant beachfront dining destination known for its delectable cuisine and picturesque views. With each bite, drink in the beauty of the balmy Caribbean evening and capture the memory on your phone.
  • The Wharf for salsa night and after-dinner drinks on Tuesdays - Add a touch of Latin rhythm to your evening, head to The Wharf for their lively salsa night and after-dinner drinks, which are a Tuesday tradition in Cayman. What better way to finish your day than dancing under the starry Cayman sky, surrounded by the vibrant energy of locals and fellow travelers with Havana, Cuba only a short one-hour plane ride away from Grand Cayman. If you’ve never danced to salsa before, don’t sweat it. They offer a free lesson at the start of the evening. To reserve your waterfront table for a fun dance night or check out other exciting events that they host, visit The Wharf’s website.

Day 3 - Explore the Camana Bay area

  • Breakfast at Jessie's Juice Bar - Start this new exciting day with a refreshing breakfast at Jessie's Juice Bar and ensure that you’re fuelled, energized, and ready for today’s experiences with nutritious and delicious smoothies, bowls and wraps made with local ingredients. The fun decor is also photo-worthy!
  • Browse shops at Camana Bay - With your appetite satisfied, slowly make your way into the heart of Camana Bay, where modern style and Caribbean charm seamlessly merge. Here, take your time to explore the various shops in the area, browsing for local and international fashion and accessories, and unique souvenirs, and take in the vibrant atmosphere. Wander over the bridge to take a photo in one of the hammocks on the palm-fringed mini-island. 
  • Take a charter from Camana Bay dock - Once you're done shopping, get ready for the highlight of your day. Book a charter from the Camana Bay dock for a half-day cruise. The most popular companies you can book your charter are Sail Cayman, Crazy Crab Cayman, and Nick's Private Charters, each offering different experiences based on your preferences. Snorkel in Caribbean crystal-clear waters, explore Starfish Beach, or visit the stingrays. Get the crew to capture a photo of you kissing the stingrays or sipping a mudslide, you’ll never forget the first time you try either! 

INSIDER’S TIP: Depending on the charter and your chosen experience, lunch may or may not be included in the charter package. Make sure to check that beforehand so you can pack your own lunch if needed.

  • Sunset dinner and drinks at Kaibo - As the day transforms into the evening, conclude your day's adventures by heading to Kaibo for sunset dinner and drinks. The restaurant boasts its own private beach on the edge of the North Sound and provides the perfect setting to savor a delicious meal while watching the sun dip below the horizon. You can check out the Kaibo website for a detailed menu
Raise your hand if you love to decide what you’ll be ordering one month before going to the restaurant. 🙌



Day 4 - Spend the day in Georgetown

  • Breakfast at Blue Stone Lane Cafe - Start your day with a delightful tiktok-worthy breakfast at Blue Stone Lane Cafe, the hip Australian-inspired coffee chain. Housed in the brand new Fort 51 Building, the Blue Stone Cafe is the perfect place for setting the tone for a day filled with shopping, cultural discoveries, and culinary delights in Cayman’s capital - Georgetown. 
  • Historic Georgetown - Take in local history, and visit Heroes Square, just opposite the George Town Library built circa 1929, and the Parliament Buildings. In the harbor, you’ll find the site of Fort George, and a little further along stop in at the Cayman Islands National Museum located in the old courts building to learn more about the fascinating history of the islands.
  • Jewellery stores and local shops in Georgetown - Georgetown is famous for its duty-free jewelry stores, making it a great place to indulge in some jewelry retail therapy or if shopping local is more your style, explore the craft market and spend some time admiring the craftsmanship of local artisans.
  • Lunch at Grand Old House - Hungry? Make your way to the historic Grand Old House restaurant for fresh, local, and international menu options in the charming interior of an old Plantation House (great for vintage-style photos!). It also has a shaded waterfront deck with relaxing views of the Caribbean Sea. Book your table at the Grand Old House
  • Browse Local Art - Cayman’s most famous international artist and award-winning marine biologist, Guy Harvey has his studio upstairs at the Guy Harvey store. If you’re lucky you might catch him finishing off a piece. If not you can always buy one of his cult souvenir t-shirts. Also, make sure to stop in at 3 Girls and a Kiln to view and buy pieces from local artists. Want more? Wander 15 minutes South of George Town, and to find Pure Art, a local institution for the island’s artists and artisans for over 30 years to find an Aladdin’s treasure trove of art and handcrafted island souvenirs. On your way stop in at the Avril Ward Gallery for a dose of artistic inspiration. It’s a small gallery showcasing the artwork of Avril Ward and some other hand-crafted gifts from local Caymanian artisans. It’s located upstairs at Sunset House, the legendary waterfront bar and restaurant where locals meet for sundowners at sunset. Definitely worth coming back!
  • Finish off your day in Georgetown with dinner at Casanova - To conclude your day on a culinary high note, head to Casanova - The restaurant has been around for more than 25 years serving fine Italian cuisine. The service by the primarily Italian wait staff is exceptional and the sunsets from the upper deck are legendary. Book ahead as they are always busy.

    Day 5 - Go ‘Island Hopping’ to Cayman Brac

    • Breakfast at resort
    • Plane to Cayman Brac - Why a plane? Because no ferries are operating between Grand Cayman and Cayman Brac, access is possible only by air. Is Cayman Brac worth visiting? The answer is: yes, yes, and definitely YES! Cayman Brac has a completely different vibe from the big Island. You’ll be traveling back in time to experience island life 50 years ago on “The Brac” as the locals call it.
    • Rock climbing - The majestic cliffs and rugged terrain of Cayman Brac offer the perfect backdrop for rock climbing. You can book your rock climbing adventure through Climb Cayman, ensuring a safe and guided experience that will allow you to conquer new heights and witness breathtaking views from the highest cliff faces in the Cayman Islands.
    • Tour of the Le Soleil d'Or Garden and Farm-to-table lunch - Take a tour of the lush beauty of the Le Soleil d'Or gardens. It’s a tiny but super-chic Caribbean Farm Inn tucked in between the cliff and the sea on the Brac. The vibrant colors and fragrant harvests of their thriving vegetable gardens are a true feast for the senses. Afterward, enjoy a farm-to-table lunch served in the hotel restaurant with dishes made with produce picked fresh from the gardens.
    • Travel back to Grand Cayman for dinner and drinks at Paradise Pizza - Well, everything good has its end, so it is time to bid farewell to Cayman Brac and make your way back to Grand Cayman. For a fun but chilled dinner opt for Paradise Pizza - a cozy eatery known for its delicious pizza and laid-back atmosphere. It is the perfect place to wind down and reminisce on your island-hopping adventure. Other fun but chilled great pizza spots on the Island include Ragazzi and Le Vele.


      Day 6 - Go West and Get Adventurous

      • Breakfast at Vivo - Start your morning with a scrumptious vegan breakfast at Vivo, it’s one of the best on the island and we love that it serves up vegan variations of local island specialties to energize yourself for an adventurous day ahead.
      • Kittiwake diving or snorkeling adventure - The first thrill of the day awaits you beneath the unbelievably blue waters of the Caribbean sea. You’re heading out on a Kittiwake diving or snorkeling adventure, an opportunity to explore the Kittiwake shipwreck and discover an underwater marine world. There is so much marine life to see, and learning the intriguing history of the shipwreck makes this experience truly unforgettable. Book your adventure through Red Sail Cayman.
      • Lunch at Pappagallo - After your exciting morning, it’s time for lunch at Pappagallo - known for its delectable cuisine and parrot sanctuary overlooking a saltwater lagoon. The beautiful wooden building with a dramatic thatch roof provides a unique island photo opportunity.
      • Visit Cemetary Beach - This afternoon, it’s back on the water, heading to the serene Cemetery Beach. This tree-shaded spot on Seven Mile Beach is a local favorite and is often quiet during the weekdays. Walk beyond the cemetery to access the unspoiled beach. The best secret of this beach is that its reefs are very close to the shore, and are also teeming with marine life so it’s perfect for relaxed snorkeling and quiet beach time at the end of your day.
      • Dinner at Morgan’s - As evening descends, it’s time for yet another island sundowner. This time at Morgan’s, a beautiful Caribbean-style restaurant set within a charming garden that’s strung with fairy lights beside a lagoon. The restaurant's menu offers a tantalizing fusion of Caribbean flavors.

      Day 7 - Seven Mile Beach Recharge 

      • Breakfast at Sunshine Grill - Begin your day with a hearty and delicious breakfast at the laid-back Sunshine Grill to fuel up for a day filled with sun, sand, and relaxation.
      • Water Activities and Beach Sports at Kimpton and Public Beach - With the Cayman sun shining brightly, there is no better way to spend the morning than indulging in water activities and beach sports. Whether it is beachfront yoga (Book through, paddleboarding, jet skiing, or a banana boat ride (Book through Red Sail, there are activities to suit every mood.
      • Lunch at Cocoloba - With toes in the sand and a delectable Mexican-inspired menu at beach-front Cocoloba, it is the perfect spot to relax after an active morning. The tacos are to die for!
      • Spa at Kimpton Seafire Resort - Post-lunch, a visit to the spa at the Kimpton Seafire Resort is a must for a soothing massage or rejuvenating treatment that offers the ideal respite and recharge.
      • Dinner and drinks at Ms.Piper’s Kitchen and Garden - Inspired by the Caribbean backyard of the world-traveling fictional Ms. Piper and hidden away in the heart of Seven Mile Beach. It’s a completely charming little spot, so don’t resist the urge to photograph everything in sight, from the decor to the menu, and the food itself. The presentation is sublime and provides a fitting setting for your final evening on the island.

        Whether you’re in search of adventure, relaxation, or a blend of both when you’re planning your Cayman Islands itinerary, we hope you’ve enjoyed our mini-guide to some of the most beautiful spots for your 7-day itinerary in the Cayman Islands. We can’t wait to see your photos! Tag us for a shout-out. Enjoy, and as we say, see you on da road in Cayman!

        Join our newsletter to get 10% off with your first online purchase.

        BONUS: Get a free Isy B. Beach Vacation Style Guide & printable packing checklist to look fabulous on the beach.