If you’re in need of one of those “reality check” vacations — you know, the ones that help you reconnect with natural beauty and the charm of a community far from home — three days in Grand Cayman will get the job done. But before you start daydreaming of white-sand beaches and fresh seafood, you’ll have to make some advance preparations to get the most out of your trip.
Secure a rental car, book inter-island plane tickets on Cayman Airways and make an early-morning booking for Stingray City with Red Sail Sports. You’ll also need to make reservations for the ever-popular Sunday brunch. But once that’s taken care of, resume your daydreaming, because you’re about to head off on an adventure.
As always, check for travel restrictions and closures before planning your trip.
Friday: Explore Stingray City and Seven Mile Beach
On your first day in Cayman, be prepared to set sail at 7:30 a.m. for an early-morning breakfast aboard a luxury catamaran, which will take you to Stingray City, Cayman’s most popular natural attraction. Make sure you pack a waterproof case for your smartphone, because you’re going to be snapping a ton of photos today.
Located in North Sound, some 25 miles offshore, Stingray City is a group of waist-deep sandbars where you can interact with and feed Atlantic stingrays in their natural habitat. And because they’ve gotten so accustomed to humans, you can be sure that the magnificent creatures — some as large as 6 feet across — are not only friendly, but incredibly affectionate, frequently molding themselves to the bodies of their human visitors in a warm embrace. Tours, ranging from three to five hours, also offer reef snorkels and refreshments.
Once you’ve finished spending time with the rays, you’ll have certainly worked up an appetite. Head west to the Westin Grand Cayman Seven Mile Beach Resort & Spa, where you can enjoy a light lunch and tropical drink alfresco from your very own beachside cabana (reservations recommended) or poolside at the Tortuga Beach Grill & Bar.
Around 5 p.m., after you’ve gotten your fill of food and the white powder sands of Cayman’s award-winning Seven Mile Beach, take a cab over to Camana Bay, where you can shop for housewares and clothing at both locally owned boutiques and luxury brands, indulge in mouthwatering Italian gelato or take a casual stroll around the upscale waterfront town.
Plan to remain in the area until dinnertime, where you will enjoy a delicious meal at one of the on-site restaurants. The Edgy Vedge is the perfect stop for a plant-based dinner (think: crab cakes made with hearts of palm, jerk tofu, and a whole menu of topping-heavy pizzas). Agua is a waterfront restaurant loved by locals for its refreshing mix of seafood, pasta and share plates. Pay a visit to the nearby West Indies Wine Company to wrap up the day with a toast.
Saturday: Island-Hop to the Sister Islands
You’re on the move today, but the flights you’re about to embark on double as sightseeing opportunities. Plus, hopping from island-to-island is simple when the in-air time is less than an hour. After a quick breakfast at your hotel, take the first Cayman Airways Express flight out of Owen Roberts International Airport in Grand Cayman and island-hop to Little Cayman. The smallest of the three Cayman Islands, it’s only 30 to 40 minutes away.
On arrival, rent a scooter from Scooten! Scooters! and take a leisurely ride around the 8-mile island. Don’t miss a stop at Seahorse Boutique & Coffee Shop, which is open early and offers a great spot for a snack. Plus, today’s lunch plan is a scenic picnic, so stock up here and pack it for later.
When you’re ready for a change of scenery, rent a kayak from Sunset Cove and head over to Owen Island, an 11-acre islet just off the southwestern coast, where you can enjoy the stillness of what will feel like your very own private island.
If you’re looking for less kayaking and more scenic views, consider swapping a visit to Little Cayman with a quicker flight (we’re talking 10 minutes in the air) from Grand Cayman to Cayman Brac, also known locally as “The Brac.” No trip to this 14-square-mile island is complete without a visit to the 140-foot limestone cliff and caves known as the Bluff. For the best views in the Cayman Islands, head to the top of the lighthouse on the edge of the Bluff — this is the highest point on the island.
After you’ve taken in the views, enjoy a leisurely stroll on one of several hiking trails, such as the National Trust Parrot Reserve & Nature Trail, or the Lighthouse Footpath, a 2.5-mile trail along the edge of the Bluff.
On your way back to Grand Cayman from Cayman Brac, visit Ms. Rosie at Pioneer Bakery, widely reputed to bake Cayman’s best bread, made fresh daily with no additives or preservatives. Once you’re back, get a table at the Lobster Pot for a post-adventure dinner near the airport. Operated by the same family for nearly 50 years, the catch of the day is always a good idea.
Sunday: Brunch Like a Local and Go Sightseeing
Take in the sunrise, head for an early-morning swim or relish the opportunity to sleep in until about 10 a.m., after which you’ll make your way to a local restaurant for brunch.
If you are looking for a true island vibe with a farm-to-table ethos, head over to either Cayman Cabana on the waterfront in George Town or Thatch & Barrel at Pedro’s Castle in Bodden Town. For fish lovers, the Westin Grand Cayman Seven Mile Beach Resort & Spa is your best bet. For those interested in continental favorites, Anchor & Den at the Grand Cayman Marriott Beach Resort is another popular option.
With no schedule to chase, this is the perfect day for a casual drive through the Eastern Districts. For heritage lovers, Cayman’s original capital of Bodden Town offers a host of must-see spots. Foremost of which is Pedro St. James, the oldest building on the island with history as the primary meeting place for local leaders — today, it’s known as Cayman’s “birthplace of democracy.” Hope out and witness one of Grand Cayman’s most dramatic views, and if you’re up for it, take a tour of the more than 200-year-old property.
Hit the road once again and lose yourself as you pass the iconic “blowholes,” where sea spray adds some drama to your relaxed coastal drive. If you’re in the mood for a midafternoon snack, get in line with the locals at one of the many fish fries scattered along the coast.
Continue to follow the picturesque coastline as you make your way to Northside, home of the famous Rum Point. You’ll know you’ve arrived when you see the massive barrels in the road and a white-sand beach dotted with hammocks. Order a drink, grab a hammock or take a walk on the jetty, where you can relax on a bench.
Before you finish your Northside experience, you’ll want to head five minutes north to the secluded Starfish Point, where you can typically see about 10 to 15 starfish on the shallow seafloor at any given time.
By 5:30 p.m., you’ll want to start heading back in the direction you came. Pull over at Kaibo near Rum Point for dinner. Here, you’ll enjoy an Indigenous oceanside dining experience featuring the fresh seafood Grand Cayman is known for: conch, Caribbean lobster (when in season), seafood chowder, seafood boil and turtle stew. Once you’re finished, take a quick walk down to the sand and end the trip on a high note, taking in one last beach scene.
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