NauticEd has teamed up with affiliate sailing school Sailors NYC to bring you a once-in-a lifetime opportunity! Celebrate Havana’s 500th anniversary with an amazing vacation to Cuba exploring by land and sea.

cuba sailing

Inquiries or Reservations: Contact Lauren at lauren@nauticed.org

Dates: November 7-19, 2019.

Why Cuba? Time-capsule culture, unique history, beautiful landscapes and beaches, fantastic food, rum, and cigars, arts and music, and fantastic sailing with cays and islets aplenty

Sailors NYC and Sailors Around the World. Experts in Cuba land-and-sea vacations with an experienced team of American and Cuban leaders and sailors. They take care of all the details including legal regulations, transfers, accommodations, and provisioning.

Highlights of the Land and Sea Vacation:

  • Accommodations at Casas Particulares (local B&B’s hosted by Cuban Families)
  • Delicious Paladars (Cuban home-style cooking restaurants)
  • Visits to live Cuban music venues
  • Tours of the historic districts of Havana, Trinidad, and Cienfuegos
  • Visits to Hemingway house and tobacco plantation

Tentative Itinerary:

  • November 7—9: Land tour
  • Havana, Trinidad, Cienfuegos
  • November 9-16: Sea tour
  • Cienfuegos, Cayo Guano del Este, Playa Sierna, Cayo Largo, Cayo Cantiles, Estopa Canal, Cayo Rico, Ballanetos, Cayo Sal
  • November 16—19: Land tour
  • Havana, Vinales, Pinar Del Rio


  • Land Tour: $1,550/person (double occupancy)
  • Sea Tour: Book a berth or Book a boat
  • Berths: $2,054-$2,389 per person depending on boat type.
  • Boats** Book an entire boat and fill it with friends and family; captained or bareboat. Some available boats include:
    • Oceanis 41.1 (2018)–$ 5,966
    • Sun Odyssey 449 (2018)–$6,584
    • Lagoon 380 (2017)–$7544
    • Lagoon 39 (2016(–$7,736
    • Bali 4.0 (2017)–$7,736
    • Lagoon 450 (2017)(with AC)–$10,406


** Boat prices include boat charter, damage waiver insurance, end cleaning, provisioning, starter kit, cruising tax, and flotilla fee. It does not include fuel (refill at end of charter), tourist tax (84 EUR per person) or security deposit (refundable with no damage) (price depends on the boat but ranged between 500-650 EUR). If you need a captain, there is an additional 95 EUR per day fee.

Inquiries or Reservations: Contact Lauren at lauren@nauticed.org



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My vision for NauticEd is to provide the highest quality sailing and boating education available - and deliver competence wherever sailors live and go.
Grant Headifen
Last updated on July 6th, 2022