Caribbean trip planner

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

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

Caribbean

Although powdery white beaches, turquoise seas, and swaying palm trees remain a common scene across the Caribbean, the region boasts tremendous cultural diversity across its numerous island nations. Great Britain, France, Spain, and the Netherlands all left their mark as colonial powers, but the Caribbean also possesses cultures all its own. You'll find it in the patois dialects, spicy and tangy foods, and energetic rhythms of its various musical styles. Islands alternate between bustling and sleepy, with a short boat ride often separating two distinct atmospheres. While many visitors spend their Caribbean vacation at an all-inclusive resort, there's also much to recommend the region to independent travelers. The scuba diving and fishing are world-class, mountainous national parks serve up challenging hikes rewarded by sea views, and small colonial towns welcome those looking for a break from sand and sea. But if it's postcard-worthy beaches you're after, it's hard to go wrong with almost any destination you choose.
Create a full itinerary — for free!

Plan your trip to Caribbean

  • 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.

Places to visit in Caribbean

Where to stay in Caribbean

Browse hotels, guesthouses, and unique homes and book your stay on the world's leading accommodation sites.
Millions of travel reviews on TripAdvisor
2 adults
Adults (12 +)
- +
teens
- +
Children (2-11)
- +
Close
Live like a local, find unique places to stay
2 adults
Adults (12 +)
- +
teens
- +
Children (2-11)
- +
Close

Recently planned trips to Caribbean

2 days in Bridgetown BY A USER FROM BARBADOS May, popular PREFERENCES: May ATTRACTION STYLE: Popular PACE: Medium 19 days in United States & Grand Bahama Island BY A USER FROM SPAIN August, culture, beaches, historic sites, popular PREFERENCES: August, culture, beaches, historic sites ATTRACTION STYLE: Popular PACE: Medium 20 days in Mexico, Central America & Havana BY A USER FROM AUSTRALIA December, outdoors, beaches, hidden gems PREFERENCES: December, outdoors, beaches ATTRACTION STYLE: Hidden gems PACE: Medium 1 day in St. George's BY A USER FROM TRINIDAD AND TOBAGO June, popular PREFERENCES: June ATTRACTION STYLE: Popular PACE: Medium 1 day in Puerto Rico BY A USER FROM PUERTO RICO May, popular PREFERENCES: May ATTRACTION STYLE: Popular PACE: Medium 5 days in Havana BY A USER FROM EGYPT December, culture, outdoors, beaches, historic sites, museums, popular & hidden gems PREFERENCES: December, culture, outdoors, beaches, historic sites, museums ATTRACTION STYLE: Popular & hidden gems PACE: Medium 7 days in Havana BY A USER FROM EGYPT November, culture, outdoors, beaches, historic sites, museums, popular & hidden gems PREFERENCES: November, culture, outdoors, beaches, historic sites, museums ATTRACTION STYLE: Popular & hidden gems PACE: Medium 4 days in Providenciales BY A USER FROM TURKS AND CAICOS ISLANDS June, popular PREFERENCES: June ATTRACTION STYLE: Popular PACE: Medium 15 days in Mexico, Caribbean & South America BY A USER FROM CANADA November, popular PREFERENCES: November ATTRACTION STYLE: Popular PACE: Medium 8 days in Havana BY A USER FROM UNITED STATES May, popular & hidden gems PREFERENCES: May ATTRACTION STYLE: Popular & hidden gems PACE: Medium 1 day in Punta Cana BY A USER FROM UNITED STATES July, teens, culture, outdoors, relaxing, beaches, historic sites, shopping, wildlife, popular PREFERENCES: July, teens, culture, outdoors, relaxing, beaches, historic sites, shopping, wildlife ATTRACTION STYLE: Popular PACE: Medium 11 days in Cuba BY A USER FROM UNITED STATES June, popular PREFERENCES: June ATTRACTION STYLE: Popular PACE: Medium
View more plans