After exploring the rich local culture of Grand Cayman, it’s time to venture off and discover the mysterious caves, pure shores and unspoiled beaches of our Sister Islands, as well as the conveniently close neighbouring tourist destinations. All of which are easily accessible from Owen Roberts International Airport.

Whatever your travel fancy, Grand Cayman is your gateway to a world of Caribbean adventure and beyond.

Weekend trips to our conveniently close neighbouring destinations are always worthwhile and all offer something unique, such as the lush forests and diverse birdlife of Honduras and Costa Rica,  the beautiful Blue Mountains of Jamaica, and the history of Cuba’s La Habana Vieja (Old Havana).

Cayman’s national carrier, Cayman Airways, won the 2019 TripAdvisor Travellers Choice awards for Best Airline in the Caribbean and the Top Specialty and Leisure Airline in North America.  Cayman Airways offers non-stop flights to 12 destinations: Cayman Brac (daily), Little Cayman (daily), Miami (daily), New York, Tampa, Denver (seasonal) and Dallas in the US, Havana in Cuba, Kingston and Montego Bay in Jamaica, and finally La Ceiba and Roatan in Honduras.

JetBlue also offers direct flights to New York; American Airlines can take you to various destinations in the US, Southwest offers direct flights to Fort Lauderdale and Houston and Air Canada flies direct to Toronto.

In 2019 it was announced that Trinidad’s Caribbean Airlines will start offering a route to Kingston, Jamaica. This route provides a handy connection to other regional destinations such as Antigua and Barbuda, Bahamas, Barbados, Curacao, Venezuela, Grenada, Guyana, St. Lucia, St.  Maarten, St. Vincent, Suriname and Trinidad and Tobago.

Depending on whether you have a single weekend or an entire week to travel and with so many choices of where to go and how to get there, this chapter will help you narrow down the options by  suggesting a few places you can visit.

Important Travel Requirements

Most flights off-Island, even if the final destination is a country in Europe or Asia, will be routed through the United States. So, it is important to understand the travel requirements of the United States, including whether or not you are eligible to apply for ESTA (Electronic System for Travel Authorization) under the U.S. Waiver Programme in order to enter the country. We have provided some handy tips to help you avoid confusion at the airport.

Staycations & The Sister Islands

Each of the Cayman Islands offer something different, making them great weekend destinations that requires minimum travel stress.

Off-Island Destinations

It is a good idea to check the local newspapers for holiday weekend charters. These charters can be excellent value and often take you non-stop to places like Costa Rica, which you would otherwise have to catch a flight to Miami to get to.

We recommend booking with one of the local travel agents. They offer great packages and are invaluable when organising flights and hotels during busy travel periods.

Travel Agents & Airlines

Planning trips off Cayman is easy with plenty of airlines servicing Grand Cayman and professional travel agents who can help you with any queries you may have.

Travel Insurance

Take the stress out of travelling by ensuring you are fully covered for loss of baggage, accidents, cancelled flights and more.


Winter is a popular time for residents to take off and head to the mountains for a ski holiday. Ski resorts in North America are renowned for their spectacular scenery, spacious pistes, fantastic facilities and service and a lack of lift queues.