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Fun in the Sun in the Cayman Islands
From underground and underwater, to skimming over the surf on a kiteboard or biking along the quiet roads of the East End of Grand Cayman, everywhere you turn in the Cayman Islands, you’ll find opportunities for adventure. A plus of this seven-day itinerary is that while you are pursuing your adventures, and perhaps trying some new sports, you’ll also have opportunities to see many of the islands’ most stunning sights: beautiful caves, bays that glow at night, a sanctuary for stingrays, and some of the best dive sites in the world.
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    Day 1
    Head East
    Most visitors to Grand Cayman make their base on the western end of the island, and with good reason. That’s where you’ll find the famous Seven Mile Beach, one of the world’s most beautiful crescents of sand lined with luxury resorts, condos and top restaurants. On this itinerary, however, you’ll head to the East End, where you’ll find an off-the-beaten-path air of quiet tranquility.

    Your base for your stay will be the Wyndham Reef Resort Grand Cayman, where every room comes with an ocean view and the sounds of the Caribbean Sea are just meters away from your bed. The resort also has a long list of activities they can arrange with jet skis, kayaks, Hobie cats, and other water sports equipment available.

    The East End of Grand Cayman is also known as a kitesurfing (or kiteboarding) destination, and when the wind blows the surfers flock here. After you have settled into your room, you’ll join them with the help of a lesson from White Sand Water Sports, where the classroom consists of a sandbar that creates a sheltered area of waist-deep water. Before you know it, you’ll be up on your board and bumping over the waves, powered by your sail.

    Dine tonight at the Tides at the Wyndham—you’ve had a long day of travel and learning a new sport, and tomorrow is equally busy.
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    Stingray City
    Day 2
    Snorkel with the Stingrays
    You’ll head today to the northern coast of the island, to Rum Point, for one of the Cayman Islands’ most unforgettable experiences, swimming with stingrays. Two sandbars just off shore create a protected environment for these surprisingly friendly and curious creatures. Afterwards, you’ll also visit Starfish Point where the colorful animals dot the ocean floor beneath clear waters.

    Take a break from meeting the marine locals with lunch at Rum Point Club Restaurant, where you can meet some of the human residents of the island while enjoying a signature mudslide cocktail and a meal with ocean views.

    In the afternoon, you’ll go underground, literally. The Crystal Caves sit on the north shore of Grand Cayman, on the way back to the Wyndham. While there are hundreds of caves in the area, you’ll visit a few of them with a guide who will point out the dramatic stalactites and stalagmites and explain the geological history of the area.

    After some late afternoon pool time at the Wyndham, you’ll return to the beach near Rum Point in the early evening for a unique kayaking adventure on Grand Cayman’s bioluminescent bay. Thousands of tiny microorganisms glow in the water, brightening with each sweep of your paddle or hand in the water. The effect is most pronounced on dark nights—ideally when there’s no moon or a new one—so be sure to check out Cayman Kayaks to confirm.
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    Photo By ECO Rides Cayman
    Day 3
    Pedal Around
    You’ll get up early today for a 4.5-hour bike tour of the island’s east end with ECO Rides Cayman. On two wheels, you’ll be able to breathe in the ocean air as you ride along rugged stretches of the coast and stop at beaches that feel like a Caribbean lost in time, a world apart from the bustle of resort areas on other islands. Midway on your tour you’ll stop to visit an authentic Caymanian home where you’ll be able to refuel with coconut water from a coconut freshly picked from a palm tree.

    In the afternoon, take advantage of some of the many water sports activities offered at the Wyndham. Later you’ll leave the resort for sunset cocktails and dinner at Tukka, a restaurant where the Australian owners prepare dishes that are a fusion of Australian and Caribbean cuisines. The fresh fish is even more delicious when paired with the views of the Caribbean from the restaurant’s verandah.
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    Days 4 and 5
    Dive Deeper Into the Cayman Islands
    This morning you’ll leave Grand Cayman for a quick flight to neighboring Cayman Brac. The second largest of the three islands of the Cayman Islands, Cayman Brac has some of the most dramatic scenery in the nation with a high bluff running the length of the 12-mile island. It is the sites below the sea, however, that bring many visitors to Cayman Brac with some of the best dive sites in the Caribbean. There are some 30 dive sites right offshore, and many more accessible on day trips with local operators. From stunning wall dives to others along the reefs, they all share some aspects in common: the remarkable clarity of the water here—with visibility up to 150 feet—and an astounding diversity of corals and marine life. You’ll swim alongside sharks, turtles, and hundreds of different fish species.

    Your base on the island will be the Cayman Brac Beach Reef Resort, a no-attitude hotel with simple, understated rooms and an excellent dive operation.
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    Day 6
    Natural Adventure
    You’ll explore Cayman Brac today on a free, private guided tour that will introduce the island’s flora and fauna. A convenient resting ground for migratory birds and home to several species of seabirds, you may spot herons, grebes, warblers and more on your outing. The five different colonies of seabirds here include boobies, frigatebirds, and terns. A new boardwalk provides a walk into a tropical forest, while other paths allow access to bird nesting sites, while assuring visitors keep a safe distance and leave the feathered residents like the indigenous Cayman Brac parrots undisturbed.

    Another highlight of Cayman Brac is its caves including Peter’s Cave, long a shelter during hurricanes; Rebecca’s Cave, named after a girl who died there when her family sought shelter; and Bats Cave, named after its current residents. Many of the island’s caves are easily accessible without any special equipment beyond some good walking shoes and an LED flashlight if you intend to go deep into them.

    If you would rather explore Cayman Brac on your own, start your day at either the National Trust Headquarters on the West End or Heritage House in the Eastern Bluff where you can pick up maps and other information on the island.
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    Day 7
    Grab a mask and a snorkel, and take one last swim in the sea so you can bid farewell to the fish of Cayman Brac. It is then time to start the journey back to Grand Cayman and home. Your flight is a good time to start planning your next visit, and what adventures you’ll pursue when you return.