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Inspiration and Advice from Cuba Travel Agents

Inspiration and Advice from Cuba Travel Agents

Cuba’s untouched ambiance, varied landscape, and emphasis on people-to-people connections make it an ideal destination for adventurous, experienced travelers.

“I like to think of it as Hawaii meets Art Deco Miami Beach,” says Florida-based travel agent Elsa Duarte. “Havana is like going into a time machine, with all the cars from the 40s and 50s.”

According to Massachusetts-based travel agent Lesley Hock, “I always tell people, if you want to really experience Cuba, go now. Don't wait 10 years from now when there's a McDonald’s and a Starbucks like on every other Caribbean island.”

Why book your Cuba trip through a travel agent? They can customize a travel plan to suit your interests and style. And, as Cuba cruise specialist Amy Stambaugh explains, “We may have a special that you can’t find online. Plus, I help you digest and figure out all that information.”

Considering a trip to Cuba? Let our Cuba experts provide ideas, tips, and guidance to make your trip unforgettable


Timing Your Trip to Cuba

What are the best times of year to visit Cuba?

Spring and late fall are the best times to visit Cuba, advises Cuba specialist Elsa Duarte. Those times give you a combination of good weather and fewer tourists.

“Like south Florida, the summer is hot and humid, with thunderstorms and chances of hurricanes,” says Duarte.

Winter has great weather but it’s the high season so expect more people visiting and less availability.”

How long should I stay in Cuba?

That depends on how much of the island you’d like to see. 4 or 5 days is usually enough to get to know Havana and venture outside of the city for day trip.

If you’d like to travel outside of Havana and stay in another city or two, agents recommend 10 to 14 days.

Accommodations in Cuba

You have 2 main options when staying in Cuba:

  • Approved hotels – As Elsa Duarte explains, “There are several hotels that we [Americans] can’t use, but there are a few that we can.” Your travel agent can help you book at a property that’s approved for Americans.

  • Private home bed & breakfasts – Staying in a private home open to guests (a casa particular) gives you more of a chance to see how locals live. These options are usually less expensive than hotels.

However, beware of booking on your own, particularly if you plan on renting. Travel agent Lesley Hock notes, “I've heard stories about people who booked Airbnb apartments, but when they got there and when turned on the faucet the water is brown from the old pipes.”

Travel agents can help you have  an authentic experience while ensuring all the conveniences you’d expect.

Safety and Logistics of Traveling to Cuba

Is Cuba safe to visit?

Yes, generally. Travel agent Elsa Duarte tells her clients not to be concerned: “People ask me, ‘is it safe to go to Cuba?’ Cuba is like the safest country in the world that you can visit. No one has a gun. It’s illegal. They have very strict and severe jail punishment for even misdemeanors.”

Like Paris, New York, and many tourist destinations, Cuba has occasional non-violent thefts, like purse snatching and pickpocketing. Just keep track of your belongings and avoid flashy jewelry. Your travel agent can provide more tips.

Where can I access the internet?

Your hotel is your best bet. According to Duarte, “The hotels do offer internet, but I tell clients to expect very, very slow internet.” Check in with your travel agent about your hotel’s internet availability.

Is there cell service in Cuba?

“AT&T T-Mobile has service. It’s very expensive if you're going to be calling the states, but you can stay connected,” says Duarte.

However, cell service is not dependable in all of Cuba. We recommend checking that your hotel has internet access. Plan your communications around that connection. Consult a travel professional about your options.

Can I use my credit cards in Cuba?

American credit cards are not accepted in Cuba. Make sure you bring enough cash. A travel agent can help you budget and plan as needed.

Can I bring cigars and/or rum back to the United States?

Yes, you can. Ask your travel agent about specific amounts you can take back home, since the regulations may change over time.

What are the restrictions and regulations for Americans who visit Cuba?

  • You’ll need a visa and an affidavit. Our agents recommend ordering a visa in advance. An affidavit confirms that you’re visiting Cuba to learn about the culture and meet people and that you agree to follow government restrictions. Your travel agent can work with you to handle the paperwork.

  • You must travel as part of a “group” of at least 2 people. A travel agent can plan an intimate trip that passes government regulations.

  • You’ll need to declare a general itinerary ahead of time. American visitors have to show that they’ll be mixing with Cuban people and visiting cultural sites. There’s plenty of flexibility, but planning is key.

  • No U.S. credit cards are accepted. There are no ATMs either. Go with all the cash you need.

  • Your choice of hotels is limited. Americans are only allowed to stay in certain hotels.

Restrictions may change. Consult a Cuba travel agent to plan a satisfying trip that follows the rules for Americans.

In and Around Havana: A 5-Day Itinerary from Lesley Hock

Hock was one of the first American travel agents to visit Cuba in 2014. She has booked custom trips to the island since then. Here’s one possibility she’d suggest for a couples Cuban getaway.

Day 1:

  • Morning: A driver, arranged by your agent, meets you the airport in a classic car from the 1950s. According to government restrictions, Americans must not wander around unaccompanied; your driver helps you follow the requirements.

  • Afternoon: Check in at your Havana hotel, where your agent has reserved your accommodations. Unpack, then explore the area.

  • Evening: Dinner, then visit the Buena Vista Social Club.

Day 2:

  • Morning: Breakfast, then a 3-hour walking tour of old Havana.

  • Afternoon: Visit the National Fine Arts Museum, the Museum of Decorative Arts, or the Revolutionary Museum. Take a dance class or a cooking class. Your agent can book one for you.

  • Evening: Dinner, then go to Morro Castle, the city’s old fortress, for a historic ceremony. “For over a hundred years at nine o'clock, they shoot the cannons and close the gates of the city.”

Day 3:

  • Morning: See famous artist José Fuster’s studio and his whimsical, tile-covered and sculpture-filled neighborhood, Fusterlandia.

  • Afternoon: “Visit a cigar factory, then go to a larger dock warehouse that’s now an enormous flea market. All the local Cubans sell their wares. It's great to get to know these people. Everything that's handmade down there is fabulous.”

  • Evening: After dinner, “I might send them to a show like the Tropicana,” for a vintage Vegas-style review.

Day 4:

  • Morning and afternoon: For glamour and literary history, visit Cojímar, just a short drive from Havana “It’s a fishing port with a lot of small art shops.” Tour Ernest Hemingway’s home, and see where he was inspired to write The Old Man and the Sea.

  • Evening: Eat in Cojímar before returning to your hotel, or dine in Havana. Your agent will reserve a table for you ahead of time.

Day 5:

  • Morning and afternoon: Make the most of your last day in Havana. Visit museums or the Palace Theater. Have a drink at the Hotel Nacional, once the headquarters of American gangsters in Havana. Or walk along the imposing Malecon sea wall.

  • Evening: Your driver takes you to the airport for your flight home.

Lesley Hayden-Hock

Framingham, MA
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Beyond Havana: Recommendations from Elsa Duarte

Elsa Duarte

Doral, FL
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Cuban-American travel agent Elsa Duarte leads tour groups to the island and creates custom trips for couples and smaller parties.

Xanadu Mansion and Varadero beach: Beaches are largely forbidden to Americans… but there are some loopholes. “Only 2 hours from Havana to the East, the DuPonts had a huge mansion there in Varadero, which they called Xanadu. It's spectacular and it's on the beach which is one of the best beaches in the world.” By visiting the mansion, you’re fulfilling the Cuban government’s cultural requirement, so you can relax on the beach afterwards.

Tobacco farms and caves near Viñales: “The drive is about almost 3 hours from Havana, but it can be done in a day trip. I've done that on my own and with small groups. You'll visit these caves, la Cueva del Indio. They're glistening and lit up inside.” Your agent can arrange a tour one of the valley’s many tobacco farms. Stay for a sumptuous lunch with all fresh local ingredients.

Bacardi Mansion: Near Santiago, you can visit another imposing vestige of Cuba’s former affluent leading families: the Bacardi rum dynasty. “You can see their mansion or palace, whatever you want to call it.” Although Bacardi no longer produces rum in Cuba, you’ll find delicious rum in the area around Santiago. “They have amazing rum in Cuba.”

Cienfuegos: “For those that have a week or more to spend in Cuba, you can stay in the city of Cienfuegos, which is probably the prettiest and best maintained for historic spots in Cuba.” Visit the restored 19th-century Tomas Terry Theater. Take a day trip out to El Nicho, a spectacular waterfall. “You can go swimming in there, and it’s all very clean river water.”

The colonial city of Trinidad, a UNESCO heritage site: “It's over 500 years old” with cobblestone streets and historic Spanish-style buildings. Keep an eye out for fun displays of “Cuban cowboys” in the area. “There will be horses being herded through the streets and cows. It’s really cool.”

Cuba Cruises: A Simpler Way to See the Island, According to Amy Stambaugh

Based in Pennsylvania, Stambaugh is an Accredited Cruise Counselor who specializes in Cuba.

Intimidated by the complications of Cuba travel? “I would recommend a cruise to someone who’s more nervous about the destination,” says Stambaugh.

Discover some of the benefits of cruising to Cuba:

  • All-inclusive cruises to Cuba are more budget-friendly than custom or group tours. “It’s a cost factor. A lot of the guided tours are pretty expensive,” notes Stambaugh.

  • An air-conditioned cabin serves as your home base for the whole trip. “You have more of a comfort level going into it” than if you stay at one of the few hotel choices for Americans.

  • The cruise line streamlines your paperwork. “They help you with the visa. They can add it to the package cost. Whereas if you book a flight and piece everything together, there’s a lot more paperwork.”

  • You can use American credit cards and ATMs on the ship, so you don’t have to worry about bringing enough cash.

  • Excursion options include many of the same highlights as private land tours. “It isn’t your typical cruise-line excursion where you go ziplining or hang out on the beach.” Visit San Juan Hill, tour cigar factories, follow Ernest Hemingway’s footsteps, and dine in private restaurants.

A travel agent can find you the best Cuba cruise deals, customize your trip, and offer travel-tested advice and impressions. As Stambaugh notes, “With Cuba being a relatively new destination [for Americans], it helps to have someone who’s been there, who can tell you, ‘Yes, I can tell you what I thought and felt.’”

Amy Stambaugh

Lancaster, PA
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Dining and Food in Cuba

Lesley Hayden-Hock

Framingham, MA
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“The food is just fabulous,” says Lesley Hock. She laughs to remember that, when she first visited Cuba, she was expecting to dine on only rice and beans. “I had lobster 3 times in a week!”

Ask your travel agent for the best Cuba restaurant recommendations. Your agent can help you plan your meals ahead of time and make reservations, since many well-known and/or small restaurants fill up. Some foodie highlights in Cuba:

  • Up-and-coming international culinary scene: “It's quickly becoming a place that chefs are exploring from all over the world and opening restaurants,” explains Hock.

  • Unexpectedly opulent Havana restaurants: “A lot of restaurants are located in these huge houses. When you walk up the front stairs, you think you're in a tenement, but there's this beautiful restaurant in there.”

  • Farm-to-table feasts in the country: No visit to tobacco farming country in the west of the island is complete without a big meal using fresh local meat and vegetables. According to Duarte, “The highlight is going to a farm for lunch. They'll have a whole pig roast. Everything is grown there. It's probably the best meal you're going to have in Cuba. Americans just rave about it.”

  • Restaurants in private homes: Private restaurants give owners more flexibility than public, government-run restaurants. You’ll eat a delicious meal in a welcoming space set up within someone’s residence. As a bonus, you’ll get to know your host and support their small business.

How can a travel agent help with a trip to Cuba?

A travel agent can work with you to navigate the many travel restrictions for Americans so that you don’t run into problems once you arrive. A travel consultant can help with:

  • Preparing the required paperwork, including a visa and an affidavit.

  • Creating a custom itinerary with cultural activities that fulfill government requirements.

  • Calculating the amount of cash you’ll need since American credit cards are not accepted in Cuba.

  • Finding the best accommodations from a limited list available to American tourists.

  • Figuring out communications logistics, like where you can access the internet.

  • Providing a lifeline in case something goes wrong. The American Embassy is often busy. A travel agent can often help more quickly in case of emergency.

Agents near you who may be able to help you

These agents near you can help answer any questions you have, or help you book the perfect trip. Don't see someone in the right neighborhood? Search our site to find the right agent for you.

Sarah Kelly

10 Reviews

Sarah Kelly

Manassas, VA
Caribbean and Mexico Travel Specialist
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Tamara Sivers

10 Reviews

Tamara Sivers

Potomac, MD
My passion is planning tropical vacations
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Katelyn Hirmer

5 Reviews

Katelyn Hirmer

Manassas, VA
All-Inclusive Resort & River Cruise Specialist
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Elaine Upton

11 Reviews

Elaine Upton

Bethesda, MD
Disney Specialist & Leisure Travel Consultant
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