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.
Live like a local, find unique places to stay
Millions of travel reviews on TripAdvisor

Recently planned trips to Caribbean

8 days in Aruba BY A USER FROM CANADA February, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular PREFERENCES: February, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular PACE: Medium 16 days in Cuba BY A USER FROM IRELAND March, popular PREFERENCES: March ATTRACTION STYLE: Popular PACE: Medium 14 days in Spain & Grenada BY A USER FROM UNITED STATES April, culture, romantic, popular PREFERENCES: April, culture, romantic ATTRACTION STYLE: Popular PACE: Medium 9 days in Dominican Republic BY A USER FROM CANADA April, teens, outdoors, wildlife, popular PREFERENCES: April, teens, outdoors, wildlife ATTRACTION STYLE: Popular PACE: Medium 7 days in Nassau BY A USER FROM UNITED STATES March, relaxing, beaches, popular PREFERENCES: March, relaxing, beaches ATTRACTION STYLE: Popular PACE: Medium 6 days in St. Croix BY A USER FROM UNITED STATES March, culture, outdoors, beaches, historic sites, wildlife, popular PREFERENCES: March, culture, outdoors, beaches, historic sites, wildlife ATTRACTION STYLE: Popular PACE: Medium 1 day in Grand Bahama Island BY A USER FROM UNITED STATES February, culture, historic sites, museums, shopping, popular PREFERENCES: February, culture, historic sites, museums, shopping ATTRACTION STYLE: Popular PACE: Medium 31 days in Central America, South America, Mexico & Caribbean BY A USER FROM ISRAEL September, culture, outdoors, relaxing, romantic, beaches, wildlife, popular & hidden gems PREFERENCES: September, culture, outdoors, relaxing, romantic, beaches, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 9 days in Curacao BY A USER FROM UNITED STATES April, popular PREFERENCES: April ATTRACTION STYLE: Popular PACE: Medium 7 days in St. John BY A USER FROM CANADA April, teens, popular PREFERENCES: April, teens ATTRACTION STYLE: Popular PACE: Medium 6 days in Puerto Rico BY A USER FROM UNITED STATES February, culture, outdoors, relaxing, beaches, historic sites, shopping, wildlife, hidden gems PREFERENCES: February, culture, outdoors, relaxing, beaches, historic sites, shopping, wildlife ATTRACTION STYLE: Hidden gems PACE: Medium 3 days in Parc National BY A USER FROM UNITED STATES July, popular PREFERENCES: July ATTRACTION STYLE: Popular PACE: Medium
View more plans