Plan a Caribbean Trip

So many islands, one perfect trip. From Aruba’s beaches to St. Lucia’s Pitons and the Bahamas’ cays, the Caribbean is easy, warm and endlessly varied — and a specialist matches the island to you.

The Caribbean is dozens of islands, each with its own character — the calm beaches and steady sun of Aruba, the lush volcanic drama of St. Lucia and Dominica, the reefs and cays of the Bahamas and Turks & Caicos, the music and mountains of Jamaica, and the French flair of St. Barts and Martinique. Choosing the right island (and the right resort or all-inclusive) for your travel style is the whole game, along with timing around hurricane season and finding the best value. A travel specialist matches the island, resort and dates to your trip — beach escape, honeymoon, family week or island-hopping cruise.

Still deciding between islands? Our sister site groups Caribbean island hotels by destination so you can compare prices side by side.

Leaning toward rainforest, waterfalls and the twin Pitons? See where to stay in St. Lucia, from Rodney Bay’s beaches to the hills above Soufrière.

Why Plan a Caribbean Trip with a Specialist?

The right island

Each island suits a different trip.

All-inclusive value

Bundled resorts & savings.

Beaches & nature

Reefs, cays & volcanic peaks.

Cruise or stay

Island-hop or settle in.

Ways to Enjoy the Caribbean

Turquoise cove at Anse La Raye, St. Lucia

Beach & all-inclusive

Aruba, Punta Cana & Jamaica.

Honeymoons

St. Lucia & the Grenadines.

Island hopping

Bahamas cays & the Grenadines.

Caribbean cruises

Eastern, Western & Southern routes.

Popular Caribbean Trip Ideas

All-inclusive beach weeks in Aruba or Punta Cana
St. Lucia & Grenadines honeymoons
Bahamas & Turks & Caicos island escapes
Jamaica resorts & adventure
Eastern & Southern Caribbean cruises

Ready to plan your Caribbean trip?

Tell us your island, dates and travel style and we’ll match the resort and bundle the extras. Get your best-value travel quote free from a true travel specialist.

Get your best-value Caribbean quote free!

Or contact a Caribbean travel specialist »

Why Smart Traveler?

Smart Traveler is a service of the travel division of Best of the USA, Inc. Entrust your trip to seasoned professionals specializing in cruises, tours, vacation packages, all-inclusive resorts and international airfares. With over 50,000 travel advisors in our growing database, we’re sure to have the experts right for your travel needs!

50+ years of expertise

Five decades fine-tuning the art of travel — every journey a masterpiece.

Online pioneers since 1995

Tradition blended with technology — book your dream trip with a click.

Exclusive proprietary rates

Insider access to rates and partnerships unavailable to the average traveler.

Planning a Caribbean Trip — Frequently Asked Questions

Which Caribbean island should I choose?

It depends on your trip — Aruba for reliable sun, St. Lucia for scenery and honeymoons, the Bahamas for cays, Jamaica for variety. A specialist matches the island to you.

Are all-inclusive resorts worth it?

For many Caribbean trips yes — they bundle meals, drinks and activities for predictable value; a specialist compares options for your dates.

When is the best time to visit the Caribbean?

December–April is peak dry season; late summer and fall are cheaper but overlap hurricane season — a specialist advises and protects your trip.

How do I get a quote?

Request your best-value travel quote free from a true travel specialist, with no obligation, and compare islands, resorts and dates.