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Caribbean Vacations: Packages & Deals*

*Some taxes, fees extra. Vacation prices are per person, based on double occupancy, unless noted.
$499 -- Puerto Rico: Waldorf Astoria Escapes from Boston
Source: CheapCaribbean.com | By Veronica Crews

This deal includes flights & four nights at a Waldorf Astoria resort for $125 per person, per night.
Select dates Oct. 1 - Nov. 12

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Source: Apple Vacations

This all-inclusive resort has a full-scale water park on site and has spa that offers beachside massages
Select departures, October-January

Source: Vacation Express

Fly nonstop from Newark and save up to $750 per person on six-night spring getaways to a 4-star resort in Punta Cana
Depart on April 23, 30

Source: Vacation Express

Save up to $350 per person on a 4-star getaway to Punta Cana that includes an upgraded junior suite
Depart on April 20, 27

Source: Vacation Express

Fly nonstop from Cincinnati to Punta Cana; this larger beach vacation sale includes multiple Punta Cana resorts
Select dates through October; December on sale

Source: Apple Vacations

This all-inclusive deal includes a three-night stay at one of the top 15 hotels in Punta Cana (TripAdvisor) and includes nonstop air from Chicago
Select dates, November-December

Source: Prestige Cruises

Sail in a balcony cabin for seven nights and receive up to $600 in onboard credit per cabin.
Depart Dec. 15; Feb. 1, 18

Source: CheapCaribbean.com

You'll see spectacular views on the plane's approach, and then it's just minutes to the beach.
Select dates October-December

Source: CheapCaribbean.com

This deal includes departures all the way into December for vacations to this Waldorf Astoria resort in Puerto Rico
Select dates Oct. 1 - Dec. 12

Source: Vacation Express

This is part of a larger sale on Grand Bahama Island vacations that includes all-inclusive beach resorts
Select dates September-October

Source: Liberty Travel

Stay at a 4-star villa beach resort in St. Lucia with this deal that includes air, a four-night stay and transfers
Dec. 4-8

Source: Friendly Planet

This comprehensive escorted Cuba itinerary includes stops in Havana, Cojimar, Las Terrazas, Varadero, Cardenas, Coliseo and Matanzas
Select December-April dates

Source: smarTours

Highlights include riding in vintage cars, cigar making and a visit to the home of Ernest Hemingway
Select dates in 2017

Source: Puerto Rico

Puerto Rico stands out as an easy Caribbean vacation with 22 nonstop flights, no U.S. passport requirement, white sand beaches, and more.
2016 Travel


More Deals on Caribbean Vacations *

Select dates September-October
Vacation Express
Through Oct. 30
British Virgin Islands Tourism Board
2016 & 2017 travel
Cayman Islands Tourism

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Caribbean Vacation Tips
Each Caribbean location has its own culture and traditions, offering everything from historical stays to relaxing beachfront escapes. Travelers can choose from popular spots like Jamaica, Puerto Rico, the Bahamas, the Dominican Republic and more.

Popular among families and people looking for an easy escape, all-inclusive packages are common here at budget-friendly as well as luxurious properties. These packages tend to include flights, hotel stays, meals and some activities.

Prices are most reasonable June-November, which is hurricane season in the Caribbean. Aruba, Bonaire and Curacao are popular during those months because they fall outside of the hurricane belt. The most popular time to visit are mid-December into April, and prices can shoot up over spring break times.

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