A fun long weekend in Havana

Carry on Cuba

Get off the beaten track and escape to Cuba for a long weekend of amazing experiences. Three full days, of exploring the highlights and the hidden gems of Havana, will give you a great introduction to this seductive island. Interact with experts in all things Cuban, and have true "insider" experiences. Private tours and small groups available. 

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Start Date of the Trip
Start Date of the Trip

Carry on Cuba

  • Architectural tours

  • Art safari

  • Practice salsa dancing

  • Beach outing

  • Visit Hemingway's haunts


Day 1

  • Afternoon

    • Airport pick up by your Amigo – responsible for the coordination of all the activities while you are in the country - and proceed to your villa for check in

    • City orientation tour

    • Welcome cocktail on the grounds of the "legendary" Hotel Nacional

    • Ride one of Havana’s iconic vintage convertibles along the Malecón (Havana’s seawall) to experience the sunset over Havana

  • Evening

    • Welcome dinner at one of the top restaurants in Havana

    • Unscheduled - entertainment recommendations and reservations will be provided

Day 2

  • Morning

    • Breakfast at your B&B

    • Walking architectural tour of Old Havana (a UNESCO World Heritage site) accompanied by your knowledgeable guide

  • Afternoon­

    • Lunch in Old Havana

    • Travel outside of the city to visit Finca La Vigia - the legendary Hemingway estate from where he resided and wrote "The Old Man and the Sea"

  • Evening

    • Dine at a top paladar

    • Unscheduled - Experience the nightlife of contemporary Havana with an evening out in an up and coming neighborhood

Day 3

  • Morning & Afternoon

    • Breakfast at your B&B

    • Journey to Viñales valley – “The Garden of Cuba.”

      • Discover how the world famous Cuban cigar is made

      • Take a horseback ride through the Viñales Valley

    • Lunch at a traditional Cuban grill perched on a stunning hillside overlooking the Valley

  • Evening

    • Unscheduled - dining/entertainment recommendations and reservations will be provided

Day 4

  • Morning

    • Breakfast at your B&B

    • Guided bicycle tour of Havana

  • Afternoon

    • Lunch at a top paladar in Havana

    • Unscheduled afternoon to accommodate last minute requests

  • Evening

    • Wrap up dinner at a top restaurant in Havana

Day 5

  • Morning

    • Breakfast at your home away

    • At leisure, until it is time to travel to the airport


Starting at USD1,430 /pp


  1. Prices include: accommodation at one of our curated selection of private apartment and villas; all experiences; trip management fee; all internal transportation; staff and concierge services; and scheduled meals

  2. Airfare and drinks are not included

  3. Prices subject to change based on rates at the time of confirmation

Please let us know if you if you prefer alternate accommodations or if you require assistance securing your travel visa and airfare. We will be happy to assist you.