One of the benefits of the easing travel restrictions between the United States and Cuba is that a (long) weekend in Cuba is becoming increasingly simpler to organize.
Of course, all the important caveats for Americans planning a Cuban excursion still apply: Make sure your trip falls under all State Department guidelines, and there must be some cultural elements. For peace of mind, it’s best to work through these with a travel guide experienced in working with these regulations and arranging flights to Havana, although there are more options for self-guided travel likely to emerge in the coming months. And remember — you’ll need lots of cash!
As for what to do? Here’s a suggested itinerary to get you started.
Day 1
In the morning, visit Partagas Cigar Factory. Enjoy a welcome mojito in the Hotel Nacional’s Hall of Fame. For lunch, either La Barraca (beautiful grounds at the hotel set along the water) or Cuban at Hotel Nacional, before an afternoon rum tasting. For dinner, visit La Guarida and jazz at Cuervo y Zorro or dinner at Café Madrigal, also with a musical performance. In the evening, make sure to talk to your Cuban guide or get suggestions from the hotel — they’ll know what places are open on a given day. Some highlights include Don Cangrejo (outdoor club with local music) and La Discoteca in the Hotel Florida.
Day 2
In the morning, walk Old City. Then try the great mojitos at lunch at Dona Eutimia Palador. In the afternoon/ evening, visit La Factoria, an art gallery with tons of bars. Go out afterward!
Day 3
Start with a Vintage Car Tour of Old Havana before lunch at El Divino. In the afternoon, take a trip to La Finca Yoandra (garden), Hemingway’s home and/or Callejon de Hamel (cool funky street with murals and music). Have dinner at 304 Orielly.
Day 4
Back to reality – flights back!
Read This Next
How to Have Fun in Havana
Destination
Aug 21, 2015#TrazeeTravel
Insta FeedDestinations / North America
Nov 4, 2026Where Can You Find the Mai Tai Mile?
Stay at Kona Village on the Big Island of Hawai’i and you may think your experience consists solely of private, residential-style luxury and perhaps the occasional fresh pineapple, but Rosewood Resort has something else a little special. More specifically, Kona Village has its very own Mai Tai Mile, where guests can find four unique and different takes on the Mai Tai. Each distinct drink is inspired by its setting and comes with its own story.
Sponsored Content
Taiwan: Whatever Your Pleasure
Taiwan’s wealth of offerings ensures travelers find destinations, activities and amenities to suit all interests.
Destinations / North America
Nov 4, 20266 Hotels Making a Splash with Holiday Décor
If your holiday travel bucket list includes seeing over-the-top holiday decorations at your hotel, this list of six hotels around the globe should be your guide.
Destinations / Europe
Nov 3, 2026Plan to Attend These 4 Zürich Christmas Markets
Zürich’s Christmas markets will welcome merrymakers in the very near future — some as soon as this weekend.
Sponsored Content
An Adults-Only Resort for All the Milestone Moments
On Saturday, Feb.14, Devossion by Live Aqua celebrated its grand opening, marking a significant milestone for Grupo Posadas and the Live Aqua brand. This adults-only resort focuses on celebration, authentic Mexican experiences and elevated hospitality — perfectly situated in the heart of the Riviera Maya.
Destinations
Nov 3, 202611 Must-Visit Bridges Around the World
It’s time to start dreaming of your next trip. Here are 11 must-visit bridges around the world.
ShareThis