Caribbean Travel Itineraries – Your Perfect Trip, Sorted!
So, you’re planning a trip to the Caribbean? Excellent choice. Whether you’re dreaming of sipping rum on a white-sand beach, getting lost in the colorful streets of Old San Juan, or dancing to reggae beats in Jamaica, I’ve got you covered.
Here, you’ll find handy, no-nonsense itineraries to help you make the most of your trip—whether you’ve got 48 hours, a week, or something in between. No more doom-scrolling through travel forums or ending up at an overpriced tourist trap. Just solid plans, great experiences, and zero stress.
How to Use This Page:
✔️ Pick a destination from the list below (Jamaica, the Bahamas, Puerto Rico, and more).
✔️ Choose your itinerary based on how much time you have—quick island getaways or week-long escapes.
✔️ Click, plan, pack, and go live your best tropical travel life.
Still can’t decide? Flip a coin. Or, you know, read through the itineraries below and see what speaks to your adventurous (or beach-loving) soul. Either way, happy travels! ✈️
Looking for itineraries beyond the Caribbean? Check out our Travel Itineraries Guide for Asia, Europe, Oceania, and more!
🏝 Aruba
48 Hours in Aruba – A 2 Day Itinerary – Think white-sand beaches, turquoise waters, and a touch of adventure! This two-day itinerary covers the best of Aruba, from snorkelling at Baby Beach to exploring the colourful streets of Oranjestad. See the full 2-Day Aruba itinerary →
Countries
Explore Caribbean‘s Top Destinations
Every Caribbean island has its own vibe—whether it’s the rhythmic beats of Cuba, the postcard-perfect beaches of the Bahamas, or the lush rainforests of Saint Lucia. Some islands are built for adventure, others are all about pure relaxation, and a few offer the best of both worlds.
Ready to plan your island escape? Click on any destination below for travel guides packed with expert tips, must-see spots, and itineraries that’ll have you daydreaming about sandy toes and ocean breezes in no time. Let’s get exploring!
Caribbean Travel FAQs: Everything You Need to Know Before You Go
Planning a trip to the Caribbean? Whether you’re lounging on the beaches of Aruba, hiking through Puerto Rico’s El Yunque Rainforest, or diving into Jamaica’s jerk chicken scene, we’ve got you covered! This FAQ guide answers all the big questions travellers ask—from visas and budgeting to transport and must-try foods.
Whether it’s your first time in the Caribbean or you’re a seasoned island-hopper, these tips will help you plan smarter, travel smoother, and make the most of your tropical escape!
Still planning your Caribbean trip? Check out our Solo Travel Guides and Luxury Travel Guides for more inspiration!