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Boston Cruise Guide > Cruise Destinations > Caribbean

Boston to Caribbean Cruises

There are only a few Caribbean cruises from Boston, with island destinations including Aruba, St Maarten, St Kitts, Antigua, Martinique, Puerto Rico and Jamaica. In 2018 there are two cruises from Boston to Cuba. The ports of call in Cuba include Havana (the famous city with historic Habana Vieja, the Malecon, colonial forts, and Fusterlandia public art) and Cienfuegos (an elegant seaside town and Unesco World Heritage site).

The islands of the Caribbean are quintessential cruise destinations. There are a lot of them, they have deep ports for ships, and their beaches and laid-back lifestyle are very attractive to passengers.

2018

14-day cruise to Cuba on Holland America Line. Round-trip from Boston to Key West (Florida), Havana (Cuba), Cienfuegos (Cuba), Grand Cayman (Cayman Islands), Ocho Rios (Jamaica) and Half Moon Cay (Bahamas).
• 2018 departure: June 23.

14-day cruise to Cuba on Holland America Line. Round-trip from Boston to Key West (Florida), Havana (Cuba), Cienfuegos (Cuba), Grand Cayman (Cayman Islands), Ocho Rios (Jamaica) and Half Moon Cay (Bahamas).
• 2018 departure: August 4.

14-day cruise to the Caribbean on Norwegian Cruise Line. Round-trip from Boston to St Thomas (US Virgin Islands), St Maarten, Martinique, Antigua, St Kitts, Tortola (British Virgin Islands) and San Juan (Puerto Rico).
• 2018 departure: October 26.

12-night cruise to the Caribbean on Royal Caribbean. One-way from Boston to Fort Lauderdale (Florida). Visit St Maarten, Antigua, Barbados, Curacao and Aruba.
• 2018 departure: October 28.

9-day cruise to the Caribbean on Norwegian Cruise Line. One-way from Boston to San Juan (Puerto Rico). Visit St Thomas, St Maarten, St Kitts, Antigua and Tortola.
• 2018 departure: November 9.

2019

14-day cruise to the Caribbean on Norwegian Cruise Line. Round-trip from Boston to St Thomas (US Virgin Islands), St Maarten, Antigua, Barbados, St Lucia, St Kitts and Tortola (British Virgin Islands).
• 2019 departure: March 29.

14-day cruise to the Caribbean on Norwegian Cruise Line. Round-trip from Boston to St Thomas (US Virgin Islands), St Maarten, Antigua, Barbados, St Lucia, St Kitts and Tortola (British Virgin Islands).
• 2019 departure: October 25.

12-night cruise to the Caribbean on Royal Caribbean. One-way from Boston to Fort Lauderdale (Florida). Visit St Maarten, Antigua, Barbados, Aruba and Curacao.
• 2019 departure: October 27.

13-day cruise to the Caribbean on Norwegian Cruise Line. Round-trip from Boston to St Thomas (US Virgin Islands), Antigua, Barbados, St Lucia, St Kitts and Tortola (British Virgin Islands).
• 2019 departure: November 8.

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