Are you headed to the Caribbean for a tropical reprieve mid-March?
Here is my Grand Cayman itinerary, including all my favorite eats and drinks.
Day 1
Arrive midday and check in to your accommodations in West Bay. Relax, unpack and freshen up to walk to dinner at Calypso Grill. The Calypso Crabcakes are CLAWsome and so is the view!
Day 2
Wake up and relax in the poolside hammock before brunch. Head to the beach for the day. Wander up the beach to Calico Jacks Bar & Grill to grab a cocktail. Cherry bikini top and a piña colada in hand, life is good! Once sunned out and ready for dinner, muscles, garlic bread and cool white wine await you at Catch Restaurant & Lounge.
Day 3
Day 3, the day you finally start to really inch your way into vacation mode. Time to visit Starfish Point. Catch a cab to Camana Bay and then a ferry to Starfish Point. Hang with the five point cuties for the day. Wander back toward the ferry pick-up and have a cocktail at Kaibo. Hold off on food, Kaibo isn’t the move. Upon arriving back at Camana Bay pick a patio and wine and dine. Shop around and catch some live music to end the day.
Day 4
Start the day poolside at your accommodations. Wander to the beach midday, stopping at Calico’s for a snack before the beach. Stay for sunset.
Day 5
Today we are swimming with sea turtles at Spotts Beach. Be sure to get there early morning or you will miss them! Have a photoshoot on the pier. After a long day of snorkeling and lounging on the beach it’s time for a gorgeous meal and sunset on a patio. House Made Coconut Shrimp with Mango Chutney from Alfresco, a local hole in the wall, are to die for!
Day 6
Off to the famous Stingray City! I highly recommend Red Sail Sports. We went on 3-4 excursions with them and loved every single one. We did the Stingray Sandbar and Rum Point Sail from 10 a.m. to 3:30 p.m. Amazing experience and staff, Stingray City is an experience of a lifetime! When you return from an exhausting day of kissing Stingrays and drinking Prosecco on a luxury catamaran, catch a cab to The Cracked Conch for a fun view, snorkeling and sub par food and drink.
Day 7
Today is a beach day with a dinner cruise planned for the evening. Get your hair braided by the local woman wandering the beach, ride the banana boat, drink a piña colada and eat a shrimp cocktail from none other than Calico’s! Head home to get fancy for a night out with Red Sail Sports. Catamaran Ferry Service to Rum Point Beach BBQ is the evening we booked. It was fabulous, I 100% recommend this excursion while visiting Grand Cayman.
Day 8
After a late night, it’s time to spend the morning lounging at the pool before a spa day. Spa courtesy of the Westin; a massage, pedicure and facial always completes a beach vacation. Yoshi Sushi to top off the evening. I would give anything for that sushi at this very moment! Absolutely to die for!
Day 9
Today it’s back to our new favorite spot, the Westin, for a beach day. Did we go eat lunch across the street at Yoshi Sushi again? Of, course! With no shame!
Day 10
On our second to last full day on the island we did our third Red Sail Sports excursion, Kittiwake and Reef Sail; hung out on the beach; and had the most fantastic Italian meal. It rivaled that of Italy itself! Ristorante Pappagallo is an absolute must while visiting Grand Cayman. Limoncello Tagliatelle and Maltagliati were two of our favorites.
Day 11
For our last day on the amazing Grand Cayman Islands, we opted for a beach day at the Westin and a Sunset Sail with Red Sail Sports. We met a family from Miami celebrating a birthday on the catamaran, ate burgers together and spent our last night out dancing with our new friends.
Book a trip to Grand Cayman, you won’t regret it!
Hannah Rene Brown 