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!

Visa requirements vary depending on your nationality and destination:

  • Visa-Free & Easy Entry: Many Caribbean islands, including Barbados, the Bahamas, and Saint Lucia, allow visa-free stays for short visits.
  • eVisa or Visa on Arrival: Some islands, like Cuba and the Dominican Republic, may require an eVisa or tourist card.
  • US & UK Territories: Islands like Puerto Rico (USA) and the Cayman Islands (UK) follow their respective country’s entry rules.

📌 Pro Tip: Some islands require proof of onward travel (a return ticket), so check the rules before booking!

Asia can be as budget-friendly or as luxurious as you want! A daily budget depends on The Caribbean can be affordable or ultra-luxurious, depending on your style:

💵 Budget Travelers: $50–$100 per day (guesthouses, local food, public transport)
💳 Mid-Range Travel: $150–$300 per day (boutique hotels, excursions, dining out)
🏝 Luxury Travel: $400+ per day (resorts, private tours, fine dining)

📌 Pro Tip: The Dominican Republic and Jamaica offer more budget-friendly options, while islands like the Bahamas and Saint Barts tend to be pricier.

Transport varies by island, but here’s what you need to know:

✈️ Flights: The fastest way to island-hop—regional airlines like LIAT, Caribbean Airlines, and inter-island charters connect major destinations.
🚗 Car Rentals: Great for exploring larger islands like the Dominican Republic, Puerto Rico, and Saint Lucia.
🚕 Taxis & Rideshares: Taxis can be pricey, but some islands have Uber or local rideshare apps.
🛥 Ferries: Ideal for hopping between nearby islands like Saint Martin and Anguilla or the Bahamas’ Exumas.

📌 Pro Tip: On smaller islands, renting a scooter or bicycle can be a fun and flexible way to explore!

The Caribbean is a foodie’s paradise! Don’t miss:

🇯🇲 Jamaica – Jerk chicken, Ackee & Saltfish, Bammy
🇧🇸 Bahamas – Conch Fritters, Bahama Mama cocktail, Rock Lobster
🇩🇴 Dominican Republic – Mofongo, Sancocho, Tostones
🇵🇷 Puerto Rico – Mofongo, Lechón, Piña Colada
🇹🇹 Trinidad & Tobago – Doubles, Roti, Callaloo
🇧🇧 Barbados – Flying Fish & Cou-Cou, Macaroni Pie, Rum Punch

📌 Pro Tip: Street food is a must-try, but stick to busy stalls for the freshest and safest eats!

The Caribbean is warm and sunny year-round, so pack accordingly:

✅ Light, breathable clothing (it’s hot and humid!)
✅ Swimsuits & cover-ups (you’ll be beach-hopping)
✅ Reef-safe sunscreen (many places ban chemical sunscreens to protect coral reefs)
✅ Bug spray (mosquitoes love the tropics as much as you do)
✅ A waterproof bag (for boat trips & beach days)
✅ A power adapter (some islands use different plug types)

📌 Pro Tip: If you’re visiting during hurricane season (June–November), check the forecast and get travel insurance—just in case!

Still planning your Caribbean trip? Check out our Solo Travel Guides and Luxury Travel Guides for more inspiration!