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Cuba Land and Sea!

January 7 - 21, 2025


Cuba Land and Sea

November 1-14, 2023

   What better way to experience Cuba than by Land AND Sea!

You will experience the true essence of Cuba as you travel under the “Support of the Cuban People” category, forging meaningful connections with the local community through our collaboration with authentic Cuban operators and entrepreneurs.  By the end of our time together, you will better understand this dynamic place and what makes it so special.

   We've partnered with a well-established agency that specializes in educational Cuba.
Explore history, art walks and private city tours. Sample some of the best food on the island such as authentic farm-to-table lunch and dinner with spectacular views. We will stay at the cutest Casa Particulares in Havana and Trinidad and enjoy full breakfasts each day made with love, by your casa hosts.

   After a few days of exploring by land, we find our sea legs, for a spectacular week of sailing! The multiple tiny islands we will visit are part of the Canarreos Archipelago. Coral reefs, pristine beaches, and awesome snorkeling and diving that attract enthusiasts from all over the world. Fish and lobster in abundance, prepared by our Cuban chefs, aboard for the week.

   Get ready to be captivated by the sheer fascination of this extraordinary nation, where time seems to stand still, and every moment is filled with vivid hues and vibrant energy. From the rhythmic beats of salsa echoing through the cobblestone streets of Havana to the colonial architecture adorned with vibrant pastel shades in Trinidad, Cuba casts an

irresistible spell on all who visit.

Land AND Sea portion 12 day $4150  ($2150 sea $2000 land)
Land AND Sea portion 13 day $4400 ($2150 sea $2250 land)
Land AND Sea portion 14 day $4600 ($2150 sea $2450 land)
Single supplement entire land portion

(I want my own room on land) add $475

Included In Land Package:

  • Visas and all paperwork handled by our affiliate partner and mailed to you directly.

  • 6 nights at casas, tours, some meals, admissions etc

  • Private bus and driver

Included In Land Package:

  • 7 nights aboard luxury catamaran

  • Captain and cook

  • Galley Equipment

  • Bed Linens and towels

  • Basic Paper Products and Essentials

  • Snorkel gear

  • End Cleaning

  • Dock and Port Fees and boat Taxes

  • Vessel insurance

  • Damage Waiver Insurance

NOT Included Overall:

  • Airfare and baggage fees

  • Personal Travel Insurance (mandatory)

  • Two lunches and two dinners

  • Alcohol

  • Personal specialty foods

  • Tips for the Cuban ground team

Daily Itinerary



Tuesday, Jan 7th

Arrival to Cuba

Check into Havana Casas


Welcome dinner at 7pm Location TBD



Wednesday Jan 8th

Walking tour: 4 plazas

Tour of Museo de Bellas


Artes with private docent guide if time allows

Dinner on your own

Classic Car Cruise (included)



Thursday, Jan 9th

Visit Cuba Libro or other donation place

Depart towards Trinidad

Lunch on the road

Upon arrival: Walking Tour around the city of Trinidad


Check in to Casas

Dinner in Trinidad, night cap at Disco Ayala, set inside a natural cave

Depart for Cienfuegos

Lunch in Cienfuegos

Tour in town



Friday, Jan 10th


Walking tour of Trinidad – history, Santeria religion, architecture

Depart for Cienfuegos

Walking tour Punta Gorda and Main Plaza of Cienfuegos

Lunch on rooftop with views of the harbor.


Pelicano in Cienfuegos.

Drop off at the boats by 4pm.



Jan 11-18 SAILING

Check into our boats


Debriefing with your captain

Cienfuegos – Cayo Guano del Este

Cayo Guano del Este to Playa Sirena/Cayo Largo

Cayo Largo – Cayo Cantiles

Cayo Cantiles – Estopa

Canal – Cayo Rico – Cayo Largo

Cayo Largo – Cayo Sal

Cayo Sal –Cienfuegos

Stay aboard at the dock in Cienfuegos



Saturday | Jan 18th

Pick up at Cienfuegos and transfer to Havana

On the way to Havana,


Visit Bay of Pigs, stellar views and lunch beachside swim, mojitos. Hang at the beach. Remember to bring your own towel.

Arrival to Havana. Check into Casas.


Walk to Art factory for private tour of original Cuban artists, with the curators


Dinner at one of the 3 restaurants in the Art Factory (dinner not included).



Sunday | Jan 19th


Visit art collective, meet Cuban artists, if there’s time, a rooftop viewpoint for pictures

Drive to Hemingway’s Havana home Finca Vigia for a tour


Drive to Cojimar (where Old Man and the Sea was inspired) back to Havana for walking tours of Hemingway’s favorite watering holes.

Dinner in Havana (not included)



Monday | Jan 20th


Alternate day of touring or they depart for US

Excursion day to Vinales. (Includes bfst lunch and dinner)

Visit a tobacco farm, purchase directly from the farmers


Lunch organic farm/restaurant Finca Paraiso

Walking tour of the center of Vinales

Dinner at restaurant Las Terrazas, a coffee plantation and beautiful farm for dinner

Return to Havana



Tuesday | Jan 21st


Departure day for everyone else.
Final Adios! Shuttles will take guests back for flights all day 

Please Note:

We MUST speak on the phone and your forms must be returned with deposit to hold your spot. Email me here -

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