Insider’s Cuba

WAIT LIST ask to join by calling 843-279-0310; waitlists do clear quite regularly and if you don’t sign up you’ll never know! Hosted by M&K.

May 8, 2024 for 10 Days

Kelly and Michael were honored to visit Cuba in 2019 and it a magical place seemingly lost in time. Now accessible to US travelers through the “support of the Cuban people” permission, next May will be a perfect time to visit this beautiful country. Will visit 4 major regions/cities, and have a guide that we know personally (that speaks excellent English). This trip is limited to 12 guests plus your hosts, Michael & Kelly.

The journey cost is $5499 per person nonrefundable, based on double occupancy. You can secure your spot with a $1200 per person deposit.

Optional group priced insurance will be quoted as all aspects are non refundable. Airfare is not included but we would likely fly on American Airlines into Havana and out of Santiago. We will help you book the air.

Full Itinerary

Wednesday May 8

VIP Arrival

Upon leaving the plane at the top of the ramp you will be meet by an airport rep that will guide you through customs into the VIP lounge to wait for your luggage to come out.

Private transfer from Jose Marti airport to your hotel in Havana

See all photos from Michael & Kelly’s time in Havana (2019)

Check in at Loma del Angel

  • B&B

Loma del Ángel is an amazing private property located at one of the more famous and beautiful places in Old Havana. From the hotel, you can easily reach the Revolution Museum, the Museum of Modern Art, the Tobacco Museum, the Rum Museum, the National Theater of Havana “Alicia Alonso”, the Central Park La Habana Vieja and the Malecón in front of Havana Bay.

The hotel has a total of seven rooms in two adjacent buildings. You can enjoy complementary WiFi or relax with traditional cocktails on the rooftop. Rooms are serviced daily.

Calle Cuarteles 104. Loma del angel. La habana, Cuba

Meet our Representative in Havana – Andy Escandell

Your private concierge/contact person on land will welcome you at your accommodation to go through your itinerary with you and answer any questions you may have.  She will also make suggestions for evening entertainment during your stay and places to visit for your afternoons at leisure.

Outlander Welcome Dinner at Paladar Los Mercaderes (Included)

Romantic and refined, this place serves great Cuban and international food with charming service in a luxurious first floor dining room. 

Calle Mercaderes #207 e/ Lamparilla y Amargura, old Havana
+53 7 8012437

Thursday May 9

City Tour Colonial Havana

This a walking tour, so please wear comfortable shoes 

Walk in the footsteps of Havanas colonial past visiting the four key squares of Old Havana, a UNESCO World Heritage site. Visit Plaza de Armas, Plaza San Francisco de Asis, Plaza Vieja, and the Plaza de la Cathedral with our expert guide offering insights into history along the way. 

Walk by Castillo De Los Tres Reyes Del Morro

Casa del Lombillo was built in 1741 and once served as a post office.

Palacio de los Marqueses de Aguas Claras, completed in 1760 and widely lauded for the beauty of its shady Andalusian patio (today it houses the Restaurante Paris)

Palacio de los Condes de Casa Bayona, built in 1720, which today hosts the Museo de Arte Colonial

Hotel Ambos Mundos (it is closed at the moment)

Central Park

Walk by National Capitol and Grand Theater of Havana

Lunch at Chef Ivan Justo/Carbon food (Included)

The style of the place is thoroughly Mediterranean, located in a building that must be 200 years old. There is a comfortable, airy feel to the restaurant which serves Spanish influenced Cuban cuisine. The meat dishes are hearty and flavoursome and the fish sourced fresh everyday. Leave room for the gorgeous Cuatro Leches dessert! Aguacate 9, Esquina Chacon. Havana Vieja. Telf.: +(53) 78639697

Free afternoon

Sunset at Malecón with the local guide

El Malecón, a 8 kilometres driveway and sidewalk connecting the old 16th century fortresses with the moderns neighborhoods of the 20th century, is the place were most Habaneros meet at evenings. It is been considered, humoredly, the longest couch of the world. To much of Habaneros life happens here, from sports and line fishing  to romantics first dates, B Day celebration or serenades and late Saturday parties. Take a walk with your guide and enjoy  the shifting colors of the facades as the sun fades away at sunset. 

Dinner at Cinco Sentidos (Included)

Pick up time: 7:45 pm

Departure point: hotel lobby

From the quality of the food to the exceptional service … one of the best new restaurants in town. Spectacular seafood dishes and great wine list.

San Juan de Dios #67 entre Compostela y Habana 

Friday May 10

9:00 am

Cigar Factory Tour in Havana

Pick up time: 09:00

Departure point: hotel lobby

Approx duration: 45 min

Admire the skill with which the experts torcedores hand-roll famous Montecristos and Cohiba cigars at one of Havanas oldest cigar factories. Open hours: 9:00am-1:00pm from Monday to Friday only. The tour takes approximately 45 minutes. Note that this is not a private tour.

10:30 am

Art Tour 2 studios and Bellas Artes

Pick up time: 10:20 am

Departure point: Cigar factory

Aprox time: 3h

Departure point: Susette, our curator, will meet you at hotel lobby. You will have a taxi at disposal for this experience and the tour will end at Costa Vino restaurant

Accompanied by our expert guide you will visit 2 Cuban artist’s studios. Get behind the facade and interact with this thriving artistic community according to your interests, Photography, Sculpture or Painting? Specify whether you would like to see well known or up and coming artists. After you will visit the Museo de Bellas Artes.

Lunch at La Vitrola (Included)

Considered one of the most typical of bars/restaurants in Old Havana, this retro´s 50s restaurant has lively live music in the afternoons and evenings.

Muralla No.151 e/ San Ignacio y Cuba

2:00 pm – 4 hours

Panoramic City Tour in open top vintage Cars (4 hours)

Our Panoramic Tours of Havana City are completely bespoke and tailormade.

We take you on a whirlwind journey in an open top vintage are (original engines) from Historic Old Havana to take in the Morro Cabana Fortress and El Cristo for spectacular views of the city. Zooming along the Malecon we take in The Hotels National and Riviera where we take a look at the spectacular interiors and have a refreshing mojito. By request we can show you the room used by the Mob in their pre revolution New Years Eve Meeting as seen in the Godfather 2. It’s a real surprise to many to see the Rio Almendares and the Havana Forest before doubling back via Cementerio Colon. There are many stops on the way and we can organize at anytime during the day or cooler evening.

Dinner at Costa Vino (included)

At the entrance of the tunnel dividing the Vedado and Miramar neighborhoods just where the Malecón begins, you’ll find one of Havana’s newest wine restaurants. Its owner, a renowned Cuban sommelier, pays special attention to his wine selection, which although expensive is really diverse, especially by Cuban standards. The list offers a wide variety of reds, whites and sparkling wines from all over the world. The stylised cuisine by Cuban chef Boris Prieto is a masterclass in fusion and pairing and focuses on seafood dishes. Don’t miss the rice balls with chicken a la chorrera and the pork loin with chicharrones (pork rind) served with tamarind sauce.

Calle Calzada #1209 e/ 18 y 20, Vedado   +53 5290 7255

Music suggestion by your concierge

Your concierge will make suggestions of places to listen to music according to events taking place locally during your stay

Cigar and Rum pairing (included but optional)

Our cigar expert will join you for a pre-paid rum and cigar pairing. The tour will be 1.5 to 2 hours and he or she will pair your cigar with a good rum and explain how cigars are made and smoked. Includes two aged rums, and one cigar.

Saturday May 11

Your driver will collect you at Havana and transfer you to Viñales for a day trip

Tobacco tour with our expert in Viñales with lunch included.

Note that the tour will be adapt to your needs, please request a shorter walk if you prefer.

Aprox time: 2.3h experience

Inclusion: lunch

Note: Comfortable shoes for walking are advised!

From growing it to drying it, rolling it and smoking it, this is the in-depth tour of tobacco from seedling to cigar. Walk into the lush, stunning countryside with the natural karst rock formations that are dotted across the landscape known as mogotes.  Viñales was designated a UNESCO World Heritage site not just because of the uniqueness of the landscape but also due to the very traditional farming methods from times past which have been praised for being eco-friendly.

You’ll visit the tobacco plantations where they still plough with oxen, see how they dry the leaves in the famous drying houses and watch a tobacco farmer show you how to roll a cigar. If you fancy it you can also smoke one! 

Please be advised that we will not be there during planting or harvest season (January to March).

Return to Havana

Dinner at El Cocinero (Included)

Dine in a high-ceilinged room inside, or al fresco under the canopy beneath the 80ft chimney stack. Great seafood and delicious, modern Cuban cuisine with a twist. Reservations are recommended as the place is often fully booked. A slightly different menu on the rooftop bar to the restaurant downstairs. For Cuban standards, the food is excellent, especially in the downstairs restaurant. Very nicely designed space, both inside and outside. All in all probably one of the best restaurant experiences you can find in Havana.

Address Calle 26 # 57 between 11 st y 13 st, Vedado. 

Sunday May 12

Your driver will collect you at Habana and transfer you to Trinidad via Cienfuegos

See all photos from Michael & Kelly’s time in Cienfuegos (2019)

Cienfuegos city tour

Approx duration: 1.30h

This city tour includes a walk by Jose Marti Park with an explanation of the history and architectural style, Tomas Terry Theatre, to local markets around the Boulevard and Palacio del Valle.

– Jose Marti Park

 -Arch of Triumph

 – Museo de las Artes Palacio Ferrer

 – Paseo del Prado

–  Statua de Benny More

Lunch at Finca del Mar (Included)

A fine restaurant by any yardstick in terms of service and food – seafood, including lobster and octopus. Calle 35 Entre 18 et 20 | Punta Gorda, Cienfuegos, Cuba
Phone: 043-526598

Continue to Trinidad

Check in at La Casona

  • B&B

Built in the second half of the nineteenth century on the edge of Santa Rosa Valley, it is one of the oldest houses in Trinidad. Situated in a middle class residential area. It has 8 spacious Bed & Breakfast rooms with a stylish, modern design within a natural and rustic setting. The large garden and back yard looks out on the ruins of a colonial fort. Each room is air conditioned and is en-suite and has a pretty private sitting area outside the front of the room with table, chairs, rocking chairs and sometimes even a hammock. Please note that the private bathrooms are designed to be open airflow and are not air conditioned.

Though it boasts a large swimming pool, it is closed due to local water conservancy regulations that have banned private swimming pools. Rooms are serviced daily.

Address: 759 Frank País, Trinidad 62600

Dinner at La Casona (Included)

Exquisite natural food from the house. A variety of dishes and tasty homemade sweets that you will never forget.

Address:  759 Frank Pais, Trinidad , 62600

Monday May 13

Trinidad City Tour

A walking tour which introduces you to this UNESCO World Heritage Site. An expert guide will explain the history of the town, while visiting its architecture highlights, and give you insight into its fascinating history in the colonial era, and during the years after the Revolution. Wear comfortable shoes for the cobblestone city center streets.

– Museo Nacional de lucha contra bandidos

– Museo Histórico Municipal

– Casa del Alfarero

– Galería de Arte Benito

 – Palacio Iznaga

 – Church of the Holy Trinity

 – Casa Templo de Santeria Yemallà

Restaurant reservation at Adita Cafe (Included)

Enjoy surprisingly good food and great service in a relaxed atmosphere at Adita Cafe. Great for tapas, pizza and drinks and provides a break from the enormous portions served in most restaurants in Trinidad.

Antonio Maceo Nro 452-B, Trinidad, Cuba

Afternoon at Leisure at Trinidad

Dinner at La Esquina 373 (Included)

In this downtown restaurant you can taste traditional Cuban food and a combination of international dishes, thanks to its varied menu that recreates a world of flavors.

Dancing at Casa de la Musica and Casa de la Trova (optional)

Two great locations for music in Trinidad. Casa de la Trova is a good venue earlier in the evening around 9pm with a mix of Trova and traditional Son music. Later from 10 pm the Casa de la Musica is a lively place for dancing to contemporary salsa.

Tuesday May 14

9:00 am

Your driver will collect you at Trinidad and transfer you to Camaguey

Lunch at el Anden Camaguey (Included)

Enjoy a light lunch at a local place. You can try Pan con Lechón and fresh juice, beer or frapuchino.

Van Horne esquina C. Padre Olallo, Camaguey Cuba 70100

3:00 pm

Check in at San Rafael Hotel

  • B&B

Located in San Juan de Dios Square, San Rafael is a great hotel in a building from XVIII century. This place also has a restaurant with  International and creole cuisine offers. With 9 rooms this place offers the opportunity of enjoying a comfortable stay: all of them have minibar, private bathroom, air conditioning, TV, daily cleaning service and 24 hr reception.

Address:  San Rafael #191, e/ Rito Arencibia y Ramon Pinto,  Camagüey, Cuba ( Plaza San Juan de Dios)

4:00 pm

City tour Colonial Camaguey with the local guide

Camagueys historic centre is considered the largest as well as the best preserved on the island has been designated a UNESCO World Heritage Site. Visitors delight in, or are intrigued by, the citys many lavish churches and the twisted maze of streets, formerly designed to confound marauding pirates.

Camaguey is the birthplace of former Cuban National Port Nicolas Guillen and the home of the world-renowned Ballet de Camaguey. It is full of charming cobblestone plazas, historic statues and intriguing museums. You will find plenty of tinajones [earthenwarejars] decorating the streets. The people of Camaguey originally produced the jars to collect rainwater during a drought. Today, they are one of the citys decorative hallmarks.

 – Pl. de los trabajadores

 – Museo Casa Natal de Ignacio Agramonte

 – Ignacio Agramonte. Park

 – Our Lady of Candelaria Cathedral

 – Plaza de San Juan de Dios

– Martha Jimenez Perez Workshop Gallery

–  Teatro “Principal”

Dinner at Melange (Included)

Enjoy nice cocktails and delicious dishes at this new restaurant in town.

Address: Cisneros 126 entre San Clemente y Pobre, Camaguey, Cuba 10400. 

Wednesday May 15

9:00 am

Your driver will collect you at Camaguey and transfer you to Santiago de Cuba

See all photos from Michael & Kelly’s time in Santiago de Cuba (2019)

Lunch at local paladar (Included) 12:30pm

5:00 pm

Check in at Heredia Place

  • B&B

Modern but warm furnishings and all mod cons await you in this centrally located B&B in Santiago de Cuba.

Photo URL:

Heredia # 564 % Barnada y Paraíso 90100 Santiago de Cuba, Santiago de Cuba, Cuba.

Visit to El Morro fortress to enjoy the sunset in Santiago de Cuba by the guide

The Morro Castle or the San Pedro de la Roca Castle is a fortress declared World Heritage by UNESCO in 1997 for being the most complete and the most preserved example of Spanish-American military architecture, based on the principles of Italian and Renaissance styles. It constituted the defensive system of the eastern part of the country against corsairs and pirates. Visit of this historical site with a panoramic view of the Bay of Santiago. The Museum is open from Monday to Sunday, 8:00am – 7:30pm

Restaurant reservation at Palenquito (Included)

Barbecue is the specialty of this casual backyard restaurant on the outskirts of Santiago. Grilled pork and chicken are served with the typical sides, but the real star is dessert. Try rich zapote or coconut ice cream in the shells of the original fruit. Portions are huge, but you suddenly might not want to share. 

Avenida de Rio #28 | Calle 6 y Carretera del Caney, Santiago de Cuba 20400, Cuba


Thursday May 16

9:00 am

City tour Santiago de Cuba

Visit the main historical and cultural places of the urban historic center of the city, which was declared National Monument on October 10, 1978, religious and cultural sites and enjoy a sit in the Cespedes Park.

 – Casa de Diego Velazquez

Lunch to go, TikTok Bar (Included)

Among locals favorites, this is a place for kids and young visitors or adults looking for a to-go lunch while touring Santiago de Cuba. The house has a variety of fast food, juices, milkshakes, and drinks.

Free afternoon

Dinner Bar Setien (Included)

Speakeasy with the best food and drinks in Santiago. Lobster, langoustines, and cocktails are incredible. You can find this secret place behind a marked door on a quiet street

San Felix No 309 entre Habana y Trinidad, Santiago de Cuba 

Service can be a little slow so perhaps ask your guide to order in advance for you.

Tropicana Santiago de Cuba (included but optional) 10pm

Tropicana Santiago de Cuba 

TROPICANA CABARET opened in 1931 the Tropicana has played host to Benny More, Nat King Cole, Jack Nicholson and Lucky Luciano and many, many more. This is a Vegas-style extravaganza with seating for 1400 people and 10 performers going through the full range of popular Cuban dance. The dancers are beautiful and the costumes, choreography and routines are excellent, but the food is poor, the show lasts forever and it is seething with tourists. A recent revamp seems to have changed everything and nothing with the basic formula remaining as it has been for years.

Friday May 17


Your driver will collect you at Santiago de Cuba and transfer you Santiago de Cuba airport for your flight home

How to Join the Waitlist

Just email or call 843-279-0310 and we will add your name. If a spot opens up we will reach out to you and see if you still want to go. At that time, you can follow the below procedures:

How to sign up

Lodging, activities and land itineraries are subject to change at any time. This itinerary is not finalized and pricing may be adjusted for fuel or inflation. IMPORTANT: Please note that this is an Outlander Society trip and The Outlander Society Travel Club requires invitation but you may request to apply with Michael Graham or ask another member to stand for you.

The deposit is $1200 per person and is non-refundable.

Prices are Per Person, estimated and subject to change prior to deposit, based on availability and double-occupancy. They include tour, land, host, Outlander amenities, taxes and fees. Does not include Airfare. Optional insurance is available and will be quoted for you. Prices and fares are non-refundable so you will need the insurance to cancel. It is not cancel-for-any-reason insurance so it will need to be for a covered reason.

Call for limited Solo Traveler Pricing if available. The Deposit amount (and total price shown) already includes a $200 per person non refundable Outlander Add-on and a $200 per person nonrefundable professional fee paid to MGA Travel, which includes a special dinner and other amenities, planning, and our time. Please note that until deposited, pricing is subject to change and based on availability.

Want to go? Simply complete this Secure Payment Form to authorize nonrefundable deposit (as shown above). For the name of the trip put “Cuba 2024″ Unless we already have it, please complete this Secure Passport Form for each passenge. Questions simply call us 843-279-0310 or email .

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