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 +)
- +
Children (2-11)
- +
Infants (Under 2)
- +
Close
Live like a local, find unique places to stay
2 adults
Adults (12 +)
- +
Children (2-11)
- +
Infants (Under 2)
- +
Close

Recently planned trips to Caribbean

1 day in Mayreau BY A USER FROM UNITED KINGDOM March, outdoors, popular PREFERENCES: March, outdoors ATTRACTION STYLE: Popular PACE: Medium 3 days in Trinidad BY A USER FROM TURKEY August, culture, outdoors, relaxing, romantic, beaches, historic sites, fast-paced, popular & hidden gems PREFERENCES: August, culture, outdoors, relaxing, romantic, beaches, historic sites ATTRACTION STYLE: Popular & hidden gems PACE: Fast-paced 12 days in Havana BY A USER FROM NETHERLANDS July, culture, outdoors, relaxing, historic sites, hidden gems PREFERENCES: July, culture, outdoors, relaxing, historic sites ATTRACTION STYLE: Hidden gems PACE: Medium 15 days in Cuba BY A USER FROM CZECH REPUBLIC November, outdoors, beaches, historic sites, wildlife, popular PREFERENCES: November, outdoors, beaches, historic sites, wildlife ATTRACTION STYLE: Popular PACE: Medium 8 days in Mayaguez BY A USER FROM UNITED STATES October, outdoors, relaxing, beaches, historic sites, museums, popular PREFERENCES: October, outdoors, relaxing, beaches, historic sites, museums ATTRACTION STYLE: Popular PACE: Medium 15 days in United States & Havana BY A USER FROM UNITED KINGDOM July, teens, kids, popular PREFERENCES: July, teens, kids ATTRACTION STYLE: Popular PACE: Medium 14 days in Punta Cana BY A USER FROM GERMANY April, teens, popular PREFERENCES: April, teens ATTRACTION STYLE: Popular PACE: Medium 15 days in Caribbean BY A USER FROM HUNGARY January, popular PREFERENCES: January ATTRACTION STYLE: Popular PACE: Medium 22 days in Saint Thomas Parish BY A USER FROM UNITED KINGDOM September, slow & easy, popular & hidden gems PREFERENCES: September ATTRACTION STYLE: Popular & hidden gems PACE: Slow & easy 8 days in Jamaica BY A USER FROM SOUTH AFRICA September, popular PREFERENCES: September ATTRACTION STYLE: Popular PACE: Medium 11 days in Negril BY A USER FROM UNITED KINGDOM September, culture, outdoors, relaxing, romantic, beaches, historic sites, wildlife, slow & easy, popular & hidden gems PREFERENCES: September, culture, outdoors, relaxing, romantic, beaches, historic sites, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Slow & easy 13 days in Cuba BY A USER FROM HUNGARY December, culture, beaches, historic sites, museums, wildlife, popular PREFERENCES: December, culture, beaches, historic sites, museums, wildlife ATTRACTION STYLE: Popular PACE: Medium
View more plans