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.

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 up to 5 free, no-obligation quotes from a travel specialist.

Get up to 5 Caribbean quotes!

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 up to 5 free, no-obligation quotes from a travel specialist and compare islands, resorts and dates.