Guide to Traveling to Cuba from the US: Flights, Vacation Packages & Cruises

Diplomatic relations between the U.S. and Cuba have warmed significantly since restrictions eased in December 2014 after 54 years. Travel companies now offer more accessible trips, with tourism surging 15% year-over-year as of a July 2015 Bloomberg Business report, driven largely by Americans eager to visit before crowds grow.

U.S. travelers cannot yet jet off for a simple beach vacation like in the Bahamas or Jamaica, but Cuba remains a top Caribbean draw for Canadians and Europeans—and that could change soon.

Here are reliable options for direct U.S.-to-Cuba travel:

Airfare

• JetBlue: Charter flights from JFK and MIA via Cuba Travel Services since July 2015. Book exclusively at cubatravelservices.com; weekly Friday service.
• American Airlines: ABC Charters operates AA flights from Miami and Tampa to Havana, Cienfuegos, and Santiago de Cuba.
• Sun Country: Nonstop charters from Miami and JFK.
• Fly via a third country like Canada, Mexico, or the Bahamas (book legs separately).

Note: Book hotels early as they fill fast for independent itineraries.

Vacation Packages

Packages handle paperwork—visas, insurance, compliance—often included in pricing for hassle-free trips under authorized categories.

• smarTours: 10-night people-to-people itinerary across Havana, Cienfuegos, Camagüey (UNESCO site), and Holguín (Columbus landing spot). Highlights: cigar factories, vintage car rides.
• Discovery Tours by Gate 1: Small groups (max 22) with 10+ years' expertise. Features cooking classes, jazz, Trinidad tours.
• Friendly Planet: Three options (5-8 nights)—Havana intros, Varadero beaches, or in-depth multi-destination tours.
• Apple Vacations: Affordable, shorter people-to-people tours launching fall 2015.
• Cultural Contrast: 25 years' experience; unique trips like culinary tours, yoga, Havana Marathon.
• Globus Journeys: Varied itineraries (8-16 nights), including eastern Cuba and coast-to-coast epics.

Cruises

• Carnival: People-to-people cruises from Miami starting May 2016, with cultural activities included.
• MSC Cruises: First to Cuba (Dec 2015); 2.5 days in Havana plus Jamaica/Caymans.
• Group IST: Intimate mega-yacht from Havana to Cienfuegos; daily tours (national parks, beaches, Trinidad).

Essential Travel Tips

Key advice for smooth U.S.-Cuba trips:

• Bring euros/CAD cash to exchange (U.S. dollars face 10% penalty; cards limited).
• Import limit: $400 goods; $100 max alcohol/tobacco.
• Wi-Fi/Internet scarce—research access points beforehand.
• Travel under 12 OFAC categories (no license needed): family visits, journalism, education, research, humanitarian, etc. Tourist visa + medical insurance required (often covered by operators).
  • Visiting family
  • Official business
  • Journalistic activity
  • Professional research/meetings
  • Educational activities
  • Religious activities
  • Public performances/competitions/exhibitions
  • Support for Cuban people
  • Humanitarian projects
  • Private foundations/research institutes
  • Information export/import
  • Authorized exports

Cuba costs more than typical Caribbean spots due to regs, but offers authentic experiences—book now.

Facts accurate as of July 20, 2015. Verify current U.S. State Department/OFAC rules before travel, as policies evolve.