Caribbean trip planner

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

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

Caribbean

Adventure Nature Beaches
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.

Plan in the cities

Visit top cities in Caribbean:
Nature
Visit for: 1 dayStart a plan »
Historic sites, sightseeing, museums
Visit for: 4 daysStart a plan »
Beaches, adventure, casinos
Visit for: 2 daysStart a plan »
Beaches, adventure, outdoors
Visit for: 1 dayStart a plan »
Historic sites, sightseeing, museums
Visit for: 4 daysStart a plan »

Where to stay in Caribbean

Browse hundreds of hotels and read guest reviews on the world's leading online travel agency website.
CHECK IN - CHECK OUT
Best Deals Guaranteed

Recently planned trips to Caribbean

2 days in Punta Cana BY A USER FROM DOMINICAN REPUBLIC August, culture, outdoors, relaxing, beaches, popular PREFERENCES: August, culture, outdoors, relaxing, beaches ATTRACTION STYLE: Popular PACE: Medium 7 days in Curacao BY A USER FROM UNITED STATES April, culture, outdoors, beaches, historic sites, museums, shopping, popular & hidden gems PREFERENCES: April, culture, outdoors, beaches, historic sites, museums, shopping ATTRACTION STYLE: Popular & hidden gems PACE: Medium 3 days in Trinidad BY A USER FROM TRINIDAD AND TOBAGO August, popular PREFERENCES: August ATTRACTION STYLE: Popular PACE: Medium 1 day in Santa Barbara de Samana BY A USER FROM BELGIUM October, popular PREFERENCES: October ATTRACTION STYLE: Popular PACE: Medium 14 days in Trinidad BY A USER FROM TRINIDAD AND TOBAGO August, popular PREFERENCES: August ATTRACTION STYLE: Popular PACE: Medium 13 days in Cuba BY A USER FROM CANADA August, popular PREFERENCES: August ATTRACTION STYLE: Popular PACE: Medium 3 days in Puerto Rico BY A USER FROM U.S. VIRGIN ISLANDS August, kids, culture, outdoors, historic sites, museums, popular PREFERENCES: August, kids, culture, outdoors, historic sites, museums ATTRACTION STYLE: Popular PACE: Medium 6 days in Puerto Rico BY A USER FROM UNITED STATES September, culture, outdoors, popular & hidden gems PREFERENCES: September, culture, outdoors ATTRACTION STYLE: Popular & hidden gems PACE: Medium 1 day in Grand Etang National Park BY A USER FROM CANADA October, popular PREFERENCES: October ATTRACTION STYLE: Popular PACE: Medium 13 days in Caribbean BY A USER FROM UNITED STATES December, popular PREFERENCES: December ATTRACTION STYLE: Popular PACE: Medium 7 days in Grenada BY A USER FROM BELGIUM September, popular & hidden gems PREFERENCES: September ATTRACTION STYLE: Popular & hidden gems PACE: Medium 15 days in Dominican Republic BY A USER FROM DOMINICAN REPUBLIC December, culture, beaches, historic sites, museums, popular PREFERENCES: December, culture, beaches, historic sites, museums ATTRACTION STYLE: Popular PACE: Medium
View more plans