Cayman Islands trip planner

Create a fully customized
day-by-day itinerary for free

Holiday Planner
+ Add destination
2 adults
Adults
- +
Teens
- +
Kids
- +
Close

Cayman Islands

Trip Planner Caribbean  /  Cayman Islands
(40,000+ reviews from top 30 attractions)
Adventure Beaches Wildlife Areas
Known to some as an offshore financial haven, for pleasure seekers Cayman Islands remain one of the world's top vacation destinations, offering developed beaches and pristine reefs. Water-based activities remain among top things to do on Cayman Islands, with dolphin spotting, swimming with stingrays, and scuba diving favored by visitors of all ages. With world-class accommodations and a low crime rate, the islands ensure an ideal setting for relaxing family vacations. A holiday on Cayman Islands also provides a good chance to explore a cosmopolitan culinary scene, with a range of restaurants serving everything from Indian to Italian specialties. In the build up to your vacation in Cayman Islands, plan trip itinerary minutiae using the visitor reviews, staff write-ups, and custom search fields on our Cayman Islands trip planner.
Read the Cayman Islands Holiday Planning Guide »
Create a full itinerary — for free!

Plan your trip to Cayman Islands

  • Get a personalized plan

    A complete day-by-day itinerary
    based on your preferences
  • Customize it

    Refine your plan. We'll find the
    best routes and schedules
  • Book it

    Choose from the best hotels
    and activities. Up to 50% off
  • Manage it

    Everything in one place.
    Everyone on the same page.

Plan in the cities

Visit top cities in Cayman Islands:
Adventure, beaches, spas
Visit for: 4 daysStart a plan »
Adventure, breweries, shopping
Visit for: 4 daysStart a plan »
Theme parks, adventure, wildlife areas
Visit for: 4 daysStart a plan »
Adventure, nature, historic sites
Visit for: 1 dayStart a plan »
Nature, wildlife areas, adventure
Visit for: 1 dayStart a plan »

Explore a whole region

Recently planned trips to Cayman Islands

6 days in Grand Cayman BY A USER FROM UNITED STATES June, kids, outdoors, relaxing, beaches, popular & hidden gems PREFERENCES: June, kids, outdoors, relaxing, beaches ATTRACTION STYLE: Popular & hidden gems PACE: Medium 8 days in Grand Cayman BY A USER FROM UNITED STATES October, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, popular PREFERENCES: October, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping ATTRACTION STYLE: Popular PACE: Medium 20 days in United States & Caribbean BY A USER FROM UNITED ARAB EMIRATES July, fast-paced, popular PREFERENCES: July ATTRACTION STYLE: Popular PACE: Fast-paced 60 days in Caribbean BY A USER FROM UNITED KINGDOM June, culture, outdoors, fast-paced, popular & hidden gems PREFERENCES: June, culture, outdoors ATTRACTION STYLE: Popular & hidden gems PACE: Fast-paced 31 days in Central America & Caribbean BY A USER FROM EGYPT July, teens, fast-paced, popular PREFERENCES: July, teens ATTRACTION STYLE: Popular PACE: Fast-paced 7 days in Cayman Islands BY A USER FROM UNITED STATES September, relaxing, romantic, beaches, shopping, slow & easy, popular PREFERENCES: September, relaxing, romantic, beaches, shopping ATTRACTION STYLE: Popular PACE: Slow & easy 8 days in Little Cayman & Grand Cayman BY A USER FROM UNITED STATES September, relaxing, beaches, shopping, slow & easy, popular PREFERENCES: September, relaxing, beaches, shopping ATTRACTION STYLE: Popular PACE: Slow & easy 8 days in Croatia & Cayman Brac BY A USER FROM GERMANY July, culture, outdoors, relaxing, romantic, beaches, historic sites, shopping, popular PREFERENCES: July, culture, outdoors, relaxing, romantic, beaches, historic sites, shopping ATTRACTION STYLE: Popular PACE: Medium 6 days in Seven Mile Beach BY A USER FROM UNITED STATES June, teens, popular & hidden gems PREFERENCES: June, teens ATTRACTION STYLE: Popular & hidden gems PACE: Medium 6 days in Cayman Islands BY A USER FROM AUSTRALIA July, popular PREFERENCES: July ATTRACTION STYLE: Popular PACE: Medium 4 days in Grand Cayman BY A USER FROM UNITED STATES June, culture, relaxing, romantic, beaches, historic sites, shopping, hidden gems PREFERENCES: June, culture, relaxing, romantic, beaches, historic sites, shopping ATTRACTION STYLE: Hidden gems PACE: Medium 60 days in Africa, Caribbean, Mexico & Greenland BY A USER FROM UNITED KINGDOM June, outdoors, fast-paced, popular PREFERENCES: June, outdoors ATTRACTION STYLE: Popular PACE: Fast-paced
View more plans