InsureMyTrip Insiders Share Their Favorite Caribbean Islands!

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From the sandy beaches and crystal blue waters to the colorful cultures and beautiful harbors, the Caribbean is a region filled with vacation bliss.

The halls of InsureMyTrip are filled with travelers, people who vacation just like you! Here are a few of their favorite islands and experiences.

Bradford, Travel Insurance Sales & Service Representative

Jamaica is at the top of my list. I have stayed at Secrets St. James in the Montego Bay Area. The service at this resort is top notch! Secrets offers so many unique experiences and inclusions included in their booking costs. The area is gorgeous, with so many unique excursions and experiences, and it captures the spirit of a Caribbean vacation.”

Maryellen, Travel Insurance Sales & Service Representative

“I have visited many of the Caribbean Islands, and I even lived on the island of St. Croix!  My most recent trip was to St. Thomas, where we stayed at the Frenchman’s Reef. St. Thomas has beautiful sandy beaches with the clearest bluest water, and if you can pull yourself away from the shore you’ll find excellent places to dine and shop! The island makes a great Caribbean vacation spot to relax and recharge!”

Zac, Assistant Training & Quality Assurance Specialist

“I recently spent time at the Grand Palladium in Montego Bay, Jamaica. The resort is beautiful, safe, and fun! We danced the nights away, ate like kings and queens, and spent time off the resort to take in the local scene. I highly recommend Jamaica for anyone looking for a Caribbean vacation.”

Vikki, Travel Insurance Sales & Service Representative

“I spent my honeymoon in Grenada, where we also cruised the US and British Virgin Islands on a bare boat charter. Grenada is my absolute favorite island in the Caribbean. We stayed at the Blue Horizons Cottage Resort, which offers self-catering apartments, lovely tropical gardens and a short walk to Grand Anse beach. The resort allows the use of their beach chairs, Hobie cats, and other equipment, including gear that belongs to their sister resort, Spice Island.”

Lucy, Travel Insurance Sales & Service Representative

“My most recent trip to the Caribbean brought me to Aruba. The weather was perfect! 8 days of heaven, filled the sun and breezes. We stayed at the Casa Del Mar Resort which overlooks Eagle Beach. The resort offers fantastic views, and plenty to do, including an on-site casino. I’ve had the opportunity to visit nearly a dozen Caribbean islands, and Aruba is truly the friendliest.”

Lynne, Director of Product

“I’ve been to Jamaica six times, and always stayed at the Sea Wind Resort in Montego Bay. The weather is always perfect, and the local faces are always smiling! People are so friendly, and people come from all over the world to experience the island. Your dollar goes a long way in Jamaica, making this the perfect destination for your Caribbean vacation.”

Jeremy, Marketing Communications Specialist

“I love the Dominican Republic. We recently stayed in Punta Cana, at the new Excellence EL Carmen. The resort was all-inclusive, which we prefer! People are friendly, and the beaches are breathtaking. We upgraded to a swim up room, and would highly recommend that to anyone who has the opportunity.”

Cindy, Manager of Customer Care Day Operations 

“I won a free trip to Paradise Island! I had submitted a recipe to a local restaurant as part of a contest and was rewarded with a three-night stay in the Caribbean. We rode bikes, visited ruins, and took plenty of great photos. The day we left, a hurricane was headed to the island, which was CRAZY! However, we had a great trip filled with awesome reggae music!”

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