April 23-30, 2019
November 18-25, 2019

An 8-day cultural journey into the beauty that is Havana, Trinidad and Viñales, Cuba

We’ve partnered with Coast to Costa to peek behind the curtain on this eye-opening, beautiful exploration of the magical culture of the long-prohibited island of Cuba. We will be spending our time between the bustling capital of Havana, the well-preserved colorful colonial town of Trinidad and the lush tobacco and farm region of Viñales. Come see what's in this time capsule filled with beautiful art, food, culture and music.

Starting at $2,545 per person


  • Accommodations

    • 7 nights in charming Cuban B&Bs in Havana and Trinidad.

  • Transportation

    • Dedicated personal driver

  • Activities

    • Locally guided architecture tours

    • Havana and Trinidad city tours

    • Tobacco farm tour and cigar rolling lesson

    • Organic farm visit

    • Personal translator

    • An authentic look into the lives and culture of Cuba

  • Meals

    • Daily breakfast

    • Welcome and farewell lunch/dinner

  • Additional

    • Travel Visas (required to visit the country)

    • Local guide + Traverse representative 24/7

    • Small group experience, max 14 people


Day 1: Arrival & Welcome Dinner

Arrive in Havana and be picked up by our private driver to check in at our central B&B. Rest up or take some time to explore the city before our Welcome Dinner together.

Meals: D

Day 2: Explore Havana

Wake up to a delicious breakfast at our central Havana B&B before our architecture, history and art walking tour with our local expert. Enjoy lunch from a variety of local options before our van tour of outer Havana in the afternoon. The evening is yours to enjoy in Old Havana for drinks, dinner and music. 

Meals: B

Day 3: Bay of Pigs & Trinidad

After breakfast & coffee, we’ll head out on the ocean route toward the center of Cuba to Trinidad, one of Cuba’s best-preserved colonial towns and a UNESCO world heritage site. We’ll stop at the Bay of Pigs and brush up some history before time for rest and a swim at a secluded beach. We’ll have a fantastic lunch at our secret seaside spot before heading to our boutique B&B. The afternoon & evening is yours to explore or get out for some live salsa and dancing! 

Meals: B, L

Day 4: Trinidad Art & pottery 

Enjoy breakfast & coffee at our Trinidad B&B before we explore the thriving art scene of this gorgeous city. We’ll visit a 6th generation pottery studio and do a walking tour to take in the town’s brightly colored buildings and cobblestone streets. Enjoy evening for some local dinner specialties and more music out on the town.

Meals: B

Day 5: Trinidad to Havana via Cienfuegos

Today we’ll make our way back to Havana through the southern city of Cienfuegos. The picturesque bayside city is known as the “Pearl of the South,” and its French influence can be seen in its food, architecture and elegance. We’ll explore the historical center, then after lunch we’ll continue on our way back to Havana. We’ll stop for snacks, mojitos, and an opportunity to purchase high quality Cuban cigars. Back in Havana, continue exploring the city and enjoy music and dinner in the evening.

Meals: B

Day 6: Havana – Art walk + Fishing at the beach

After breakfast you’ll have free time in the morning with the option to join on an art walk to numerous galleries, studios and a fabulous art market where we’ll meet with local artists. In the afternoon, we’ll take a van to the beach. Enjoy some fresh caught sea fare such as dorado or lobster and enjoy some sun & waves before heading back to Havana for dinner and an evening concert.

Meals: B, D

Day 7: Viñales – Horseride & cigar rolling

After breakfast & coffee this morning we’ll head to another UNESCO world heritage site, Viñales, in the Cuban countryside in the north-central Pinar del Rio province. We’ll jump on horses to ride through tobacco fields followed by a cigar rolling demonstration. Then, we’ll head to a local fincafor a huge farm-to-table farewell lunch. Back in Havana for the evening, we’ll end our time together in a converted factory known for its live music and art.

Meals: B

Day 8: departure

After breakfast & coffee, squeeze in any last minute photo ops, museums or shopping before heading to the airport any time that works for you today.

Meals: B

Trip Price:

$2545 per person, double occupancy

+$350 single supplement

Trip Does Not Include:

  • International airfare

  • Additional meals, excursions and activities

  • Required travel insurance


Heck yes it is! According to the US Department of Treasury, you are still allowed to travel to Cuba with American tour operators (us) with proper licensing (also us) on group educational tours. We pepper in the required educational aspects of the tour, a walking tour of Old Havana, a horse ride through a tobacco plantation with cigar rolling lessons and meetings with local artists. We like to keep it smart AND super entertaining! We are very happy to keep providing legal, culturally immersive trips to the island!

 about Your Traverse Representative:

Andrew Coast to Costa.jpg

While living in Spain for four years, Andrew developed fluency for the language and fell in love with the culture. His time there gave him the ability to create a local's experience, highlighting some of the best-kept secrets that cannot be found in a guidebook.

After moving back to San Francisco, Andrew continued to work in the Spanish food and wine industry. In this role he was able to build relationships with the best restaurants, wineries, and Mezcal producers in Northern Spain and Mexico.

From there, he developed a totally unique, “insider's” trip to Cuba that is easily accessible for the common traveler. With plenty of opportunity to explore the areas on your own, Andrew offers both the expertise of an experienced guide and the tools you need to discover and learn on your own.

Terms & Conditions

Please refer to registration for complete terms.

$1,000 non-refundable deposit due on booking. Balance due 60 days prior to start date.

Payment is made directly through Coast to Costa through payment link provided on registration.

Cancellation Policy
60 days or more prior to your trip: 75% of trip costs are refunded. 30 to 60 days prior to your trip: 50% of trip costs are refunded. 0 to 30 days prior to your trip: No refund is available.

Travel Insurance
Travel insurance is required for all trips with Traverse, and must cover injury, medical, evacuation, and repatriation as well as trip cancellation and trip interruption. Most insurance companies require purchase to be made within 2-3 weeks of booking for full benefits (in particular, trip cancellation). Once insurance is obtained, a copy must be sent to Traverse. Failure to provide proof of insurance within 30 days of booking will result in trip booking suspension until proof of insurance has been provided. We suggest using Wanderwell, a B-Corp Certified provider, or you can choose from any carrier that meets our requirements.

Documents, Personal Identification, Vaccinations
Traveler is responsible for all required travel documents including passport, visas, entry or exit fees, and vaccinations. Traverse does not cover the cost or assist in obtaining any of the above, and reserves the right to collect information on all.