The Thrill of Cuba: Havana, Tobacco Countryside, & Varadero Beach
11 Days
11 days/10 nights—$9,880/person (single add $1910)
Couples, Friends, and Solos
March 14-24, 2025
All Breakfasts, 8 Lunches, 7 Dinners
Premier Hotels & Meals
Cuba’s most thrilling locations: Glorious Havana, The Robust Tobacco Countryside, and the White Beaches and Markets of Varadero
Hemingway loved this electrifying land of pastel buildings, vivid coastline and emotional music. The warm Cuban culture and its classic fare and mojitos & daquiris at sunset captured his soul and inspired him to write The Old Man and the Sea. 75 years into the future, vintage cars, robust cigars, art & music fill the streets that are remarkably frozen in time from before Castro. Experience the unique vibrance of Havana’s promenading & nightlife before it disappears for good. Travel into the lush interior where very few Americans have stepped for undiscovered caves and unique karstic mini mountains; stay in a classic Cuban Casa Particular where you’ll be treated like visiting family. Visit world famous tobacco farms and sample the finest freshly rolled cigars in the world. Then, possibly the world’s most beautiful beach awaits you in Varadero. Along with markets, pickleball, seafood, and street art—you’ll be the judge! Tell your friends all about your lifetime trip to Cuba when you return.
Highlights
Taste, touch, and see the spectacle of historic Havana. Arrive from Miami with an Army Ranger & author whose care for people earned him the Bronze Star in Iraq, with all arrival documents needed.
Marvel at the spectacle of Old Havana for 4 nights. Feel the grandeur of fort El Morro on the Malecon waterfront; sample rum and cigars and the fashion of Cuban nightlife at Havana’s iconic Parisien Cabaret at the Nacional Hotel.
Stroll colorful Obispo Street and the birthplace of 2 cocktails—the Mojito and the Daquiri. Sample each from Hemingway’s 2 favorite pubs.
Drive in vintage style in a classic car as we tour Havana’s noted sites, the Cathedral, Colombus’s gravesite, Fusterlandia, and Finca Vigia. Get your first of many tastes of Cuban street art to bring home.
Immerse yourself in the hilly green interior of the Viñales region for 3 nights, home to tobacco plantations we’ll visit and find unlimited freshly rolled cigars for you to enjoy.
Stay in a Cuban Casa Particular—a regional family farmhouse noted for its hospitality. You’ll feel like you’ve gained a Cuban Aunt & Uncle.
Experience unexpected karstic limestone “mountains” the locals call Mogotes. The hidden Rainbow Falls and the Cave of Silence both await on a short drive and easy hike.
View Vinales famous mural and dip into a swimming hole, all the while enjoying rustic regional dishes and hospitality.
Cross the island and reach the enchanting white sand beaches of Varadero, Cuba’s #1 destination for international beach lovers.
Stroll through the many markets for crafts & street art. Join in for Pickleball on the courts at Parque Josone, or just relax with your toes in the sand.
Sail on a catamaran to Cayo Blanco and find its pristine beach. Enjoy a seafaring lunch of lobster & local delights. Let loose a little on the sail back with cocktails and a Cuban cigar.
Enjoy a sunny walk through Parque Central, Varadero Street markets and ArteCru; or maybe catch a dolphin show!
Who’s Your Host?
Captain Joe Sacchetti is a U.S. Army Ranger-qualified paratrooper in the 82nd Airborne and author of Guts, Smarts & Love, who served 2 tours in Iraq and was awarded the Bronze Star for actions in combat.
A Track & Field All-American and Welterweight Boxing Champ in the 82nd Airborne, Joe escorted the Olympic torch through his Pennsylvania hometown in 1980 on the way to Lake Placid as a kid, and from that moment knew he wanted to see the world!
After MIT’s Business Exec Ed program, Joe started Highroads Traveler to make sophisticated global travel easily accessible to small groups of 20 by “hosting” them, now via Legacy Collectibles.
It’s rare to mesh the world of combat vet and sophisticated traveler, yet Joe is on a journey to be the world’s first Army Ranger to visit every country on the globe. 160 out of 227 so far, and it’s much more than stamping a passport.
Connecting with people around the globe in their language makes every trip more fun. From European roots, Joe is comfortable in half a dozen or so, and always learning more.
Playing music is another fantastic people connector so he & his wife Domenica always keep an eye out for a piano to gather round at happy hour. It doesn’t take much nudging from her to get Joe to play either!
Why “Hosted?”
Go with a Pro.
You’ve saved up and are ready to take the trip of a lifetime. Do you really have time to plan all the details and get it all perfect? If yes, great! Yet for most, pretty much no way. And how about when you get there making your way to the best hotels, sites and restaurants? Most say… daunting. Our solution – let’s go together and make your greatest trip ever.
“Taste, touch and see what the world has to offer” is Joe & Domenica’s mantra, and now you’re invited to come share the journey to the best places in the world with their small-group hosted tours.
Day by Day
Day 1
Havana — Meet Joe in Miami Airport with the documents he’s collected for everyone, and fly together on American Airlines nonstop to Cuba.
Arrive in Havana, the magical Cuban city of thrills, and check into the 5-star Iberostar Grand Packard, situated on the Malecon waterfront, the primest real estate on the entire island overlooking El Morro Fort and the Caribbean Sea.
Gather for your first taste of Havana as the late afternoon sun slowly fades into evening. Open the doors of the hotel and off we go into Old Havana to stroll down the world famous Obispo Street to find El Floridita, the original home of the Daquiri and Hemingway’s favorite bar. Back out to Obispo Street for dinner in Old Havana.
Try the first of many Cuban cigars and learn the varietals and their history back at the hotel as you take in the scenes of the Havana Malecon at night.
Day 2
Havana — Hemingway traveled the same path as we will via the very same Classic Cars though Old Havana’s sights and beyond. The Malecon, El Morro, Columbus’ grave and the history-making sites of Castro and Che Guevara. Then out past the city limits to Fusterlandia for lunch and shopping in a concept town made entirely of mosaic tile.
Return to the city in the afternoon for our first taste of Rum and Cuban Salsa dancing out on the terrace. Sample the history of both and then learn your basic steps. Yes! After all this is Havana and the night is young.
Enjoy a little free time and then get dressed up for a night at the famous Le Parisien nightclub show at the Nacional Hotel, Havana’s most historic hotel where countless stars of old have stayed, and where the Godfather was filmed.
Day 3
Havana — After a night at Le Parisien, wake up leisurely to a lovely breakfast and the sunny Malecon waterfront. Remember the music and dancers from the night before over your coffee and chat.
Enjoy a walking tour of Plaza Cathedral and Old Havana, or carve out some time on your own for exploring.
Meet back on the terrace for Happy Hour, as we’ll be walking over to Hemingway’s other favorite bar in Old Havana, La Bodeguita del Medio, where the Mojito was born. Sample your first mojito of the trip along with a Cuban cigar at the bar that spills half in and half out onto Empedrado Street. Mix in and meet other travelers and Havanese, and take in the moment.
Then enjoy dinner on your own in Old Havana and a pleasant walk back to the Malecon.
Day 4
Havana — Enjoy a leisurely morning at the hotel and enjoy the fitness center and spa at the Grand Packard.
Take a lovely 20 minute drive to Hemingway House at Finca Vigia, Papa Hemingway’s home estate which was donated and now converted to a museum. Feel the serenity where Papa penned some of his greatest novels. Enjoy lunch and a stroll nearby before returning to Havana.
Gather for our last night in the city, starting with one more fantastic dinner at sunset followed by a taste of nightlife at the Cuban Art Factory, a mucho-hip urban hotspot full of art, music, and festivity.
Day 5
Viñales — Get ready to experience a taste of the Cuban tobacco countryside that few outsiders will ever get to see. The hospitality of small farm towns and their Casa Particular guesthouses, countryside beauty & geologic wonders, and the peace from a lifestyle of a time that has passed for most of the world.
Leave the bustle of Havana and head west 2 hours into the fresh farm air. Be amazed at how quickly the landscape changes. First stop on the road to Viñales will be Soroa, home to Rainbow Falls and a swimming hole where we’ll have a chance to eat lunch and go for a dip.
After Soroa, we’ll continue on to Viñales till we reach a little town with a famous rock mural. A great time for a photo and refreshment in the small town. Just a few more minutes and we’ll reach our rustic accommodations at a Cuban Casa Particular. Experience firsthand the hospitality of small family-run casa hotels who will welcome you like a member of the family.
Enjoy a hearty dinner at the Casa Particular and enjoy a quiet night with a drink and cigar looking out at nature.
Day 6
Viñales — Wake up in the nature of the countryside and take a brisk walk in the warm morning air. Eat a great breakfast with fresh fruit, baked goods and strong Cuban coffee.
Hop a van to the neighboring tobacco farm to see where the world’s most famous cigars are grown. Learn from the grower just how important the soil, type of tobacco and curing process are; see a master roll the cigars and best of all, sample the finished product. You’ll be able to stock up for the rest of the trip if you like.
Continue through the country to the Cave of Silence where you’ll find a subterranean lake to cool off in, and a chance to relax with refreshments at a cave pub.
Back to your casa in the afternoon in time for happy hour and dinner in the town.
Day 7
Viñales — No trip to the region is complete without seeing its unique geography.
After breakfast, vintage cars will pick us up to see the geologic oddity of the karstic mound-shaped green-covered mountains that locals call “Mogotes.” Along the way we’ll stop at a couple of the most famous local caves and tour inside one by boat.
We’ll stop for lunch and save some nature time to slow down.
Then we’ll head back to the village until it’s time for a spectacular happy hour at Balcon Del Valle to enjoy a drink & cigar, and a legendary view of the Viñales valley at sunset. Enjoy dinner and evening time on your own.
Day 8
Varadero Beach — Enjoy a final breakfast at your Casa Particular and say goodbye to tranquil Viñales and your gracious hosts.
Board comfy vehicles and watch the tobacco farms turn to banana and coffee plantations.
Stop for lunch and a stretch along the way as we head east along the coast to Varadero Beach, renowned by global travelers as the poshest beach community on the island.
Arrive to Varadero’s white sand beach in the early afternoon and check into a beachfront luxury hotel.
Pull out your pickleball paddle as we head to nearby Josone Park courts to play pickleball for a little exercise, or stay at the hotel and relax at the beach until the dinner bell rings.
Meet back for happy hour and a well deserved dinner at the resort.
Day 9
Varadero Beach — Enjoy breakfast and a leisurely beach chair morning outside, or inside at the resort and soak up relaxing vibes.
Board a catamaran for a daytrip to Cayo Blanco, a nearby island known for its pristine beach and excellent snorkeling. Sway to the music onboard and enjoy an early cocktail or cold drink on the way to the island. Spend a few glorious hours swimming & snorkeling, and enjoy a lunch buffet of lobster and island delights.
Sail back to Varadero and enjoy the rest of the afternoon playing Pickle in the park, shopping, or at the resort. Enjoy dinner on your own.
Day 10
Varadero Beach — After breakfast, get ready to check out the local shopping scene.
Varadero has a rich mix of markets selling all kinds of jewelry, clothing, cigars, spirits, and art — lots of art.
Take your time to shop leisurely as we check out the Parque Central Mercado. Then we’ll head over to Varadero Street, and finally a stop down the road about a mile to ArteCru, a haven for all types of artists and their works.
If shopping is not your thing, sign up for Varadero Beach’s Dolphin show for a couple hours of sea-life fun. It’s close to the resort and you can be back in time for a few hours in the baking sun to work on your tan.
Whichever way you choose to spend your last full day in paradise, we’ll meet for happy hour to exchange notes on your great day, and have a lively send-off dinner.
Will Cuba be your most exotic vacation ever? Vamos a encontrar!
Day 11
Varadero Beach — If the spirit moves you, rise early with the tide and get an invigorating swim or beach walk before breakfast.
Board your comfy van for an easy ride to Havana airport.
Return home victorious from a lovely island country that none of your friends at home have yet visited.
Say goodbye with a hug till next time.
You’re now an official Highroads Traveler!
What's Included
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All Breakfasts, Selected Lunches, Selected Dinners
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Bon Voyage gift(s) for your International Tour
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Expertise and service from your Highroads Traveler Host, Joe
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Additional regional guides and experts on several trips
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Comprehensive Trip Detailer with all-you-need-to-know info
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Guided tours at historic sites and select attractions as noted in the Trip Detailer
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All gratuities at hotels and restaurants
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Special events, including wine tastings and select attractions as mentioned in the Trip Detailer
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Park and other entry fees
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Fares for trains, ferries and other modes of travel as listed in the Trip Detailer
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Select coach transfers
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Baggage transfers
Not Included:
Leader gratuities, transportation to and from your Highroads Traveler trip start & end locations, and on-your-own meals & activities.
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Gallery & Testimonials
As an Army Ranger for 25 years, I served as Joe Sacchetti‘s 2nd-in- command during Desert Storm, and there is nowhere in the world that I wouldn’t follow him, He cares about people. If I had the money, I would go on every trip he takes.
Master Sergeant Al A. , 45th anniversary D-Day (1994) Jump Team, Army Ranger, Green Beret, Bronze Star, Master Parachutist
We first met Joe on the island of Martinique while he was leading his group on a New Year’s trip. Ooh la la, he lives life like a true Frenchman! C’est Bon, such joeux de vie!
Christian C. , Sergeant, French Maritime Marines
