Full Itinerary: 24 Days, 13 cities, 4 Countries: USA, Cuba, Bahamas, UK

24 Days, 8 Flights, 13 Cities, 4 Countries
Our 24-day honeymoon took us across the USA, Cuba, the Bahamas and the United Kingdom. This itinerary combines iconic sights, local experiences, and very little downtime for relaxation. If you’re planning a similar trip, feel free to save these locations and adapt the schedule to your liking!
You can bookmark/save those locations on Google Maps and you can have a more flexible schedule.
Mobile Data: You may use the app Nomad and download an “eSim” to your phone to have mobile data in the USA, Cuba (in Cuba only GigSky app works) & Bahamas.
Transportation: Download Uber & Lyft and you can compare prices on your trips. In New York Uber was cheaper, in Washington D.C., Orlando & Miami, Lyft was cheaper.
United States (Part 1) – New York City, New Jersey, Philadelphia, Washington D.C., Orlando
We began our adventure in the USA, exploring the fast-paced cities of New York, New Jersey and Washington D.C. before heading south for some fun at Disney World in Orlando.
Day 1: Traveling to New York City
- Flight Tips:
- Flying through London is more comfortable because you split the trip in almost half.
- British Airways has better seats and entertainment than American Airlines.
- Aim to arrive late in the evening to help with jet lag.
Days 2-5: Exploring New York City
Day 2 – East Side NYC Highlights:
- Pier 57 & Little Island
- High Line
- Starbucks Reserve Roastery
- Chelsea Market (snack at Takumi Taco – Japanese fusion with Mexican)
- Edge Roof Garden
- Lunch at Sushi 35 West
- Grand Central Station
- Broadway Show (we saw Moulin Rouge – 2:30 hours)
- Times Square and drinks
Day 3 – A Relaxed NYC Day:
- Brunch in Central Park
- Bryant Park
- Washington Square Park
- Shopping on 5th Avenue
- Friends Experience
Day 4 – Free Day to Explore NYC:
Options:
- Boat ride to the Statue of Liberty
- Visit a local suburb
- Shop at an outlet or mall
- Visit State Liberty Park
- Catch an NBA or NFL game
Day 5 – Lower Manhattan & Brooklyn:
- 9/11 Memorial
- Oculus
- Wall Street & New York Stock Exchange
- Trinity Church
- Stone Street
- Brooklyn Bridge (walk across for photos)
- DUMBO iconic photo spot
- Coffee at %Arabica in Brooklyn
- Grimaldi’s Pizza in Brooklyn
- Walk through Williamsburg
More Tips for New York: https://www.youtube.com/@HereBeBarr/
Shortlisted restaurants: Xi’an Famous Foods, Au Cheval, Bubby’s, Dominique Ansel Bakery, Carbone New York, Joe’s Pizza, Lombardi’s Pizza, Skirt Steak, Soju Haus, I love Korean BBQ, Bubba Gump Shrimp Co., Little Italy Pizza, Sushi 35 West.
Day 6: Road Trip to Washington D.C. through Philadelphia
Pickup rental car (one-way rental) – Priceline.com has the best prices. Download SpotHero to book parking spaces easily.
- Drive to Philadelphia (1.5 hours)
- Independence Hall & Liberty Bell
- Lunch at Reading Terminal Market (best Philly Cheesesteak!)
- Philadelphia Museum of Art (Rocky Steps)
- Continue to Washington D.C. (2.5 hours)
- Dinner at The Wharf or Georgetown in Washington D.C.
Day 7: Washington D.C. & Flight to Orlando
- Bike Tour of the National Mall (10:00 – 13:00). You will visit all the important landmarks.
- Visit a Smithsonian Museum (we recommend the Museum of American History).
- Drop off the rental car to Avis next to the Airport with a free shuttle bus to the airport.
- Flight to Orlando (JetBlue is comfortable and punctual).
Days 8-10: Disney World, Orlando
Day 8 – Magic Kingdom
Day 9 – Animal Kingdom & EPCOT
Day 10 – Typhoon Lagoon & Hollywood Studios
Disney World Tips:
- If you’re between 25 and 40 (without kids), focus on Animal Kingdom and Hollywood Studios. You can do both in one day and save time to use on other locations. Disney Land in Paris is much cleaner, more organised and less crowded than the Magic Kingdom in Orlando.
Cuba – Havana, Varadero, Vinales
From the fast-paced city life in the U.S., we moved to Cuba, where time felt like it had stood still (since the 1950’s). Havana’s classic cars, Varadero’s stunning beaches, and the rustic charm of Vinales gave us a mix of culture and nature that felt both raw and authentic.
Day 11 & 12: Arrival in Havana & Exploring Havana
- Flight from Orlando to Havana (via Miami)
- Purchase a Cuban Visa for $100 at the Miami airport.
- Bring at least $100 cash per person per day, as credit cards are not accepted, and ATMs have unfavourable exchange rates.
- 09:30 Walking Tour of Havana: A great way to understand the city and its history.
- Lunch at Los Mercaderes: One of our best meals in Cuba.
- 16:00 Havana Photography Tour: Ride in a classic car and capture incredible photos of Havana’s landmarks. You may contact the photographer directly on WhatsApp here: +53 53 7 30135
Day 13: Varadero
- Full day at Varadero Beach (plus the travelling – about 2 hours from Havana)
- Stop for a Pina Colada at Bacunayagua Bridge (Cuba’s highest bridge).
- Book this day trip through Airbnb or Civitatis for beach activities.
Day 14: Vinales Day Trip
- Mural of Prehistory
- Horseback Riding in the Valley of Silence
- Lunch at a local restaurant (Creole cuisine)
- Cigar Factory Tour
- Learn to roll your own cigars.
- Cave Tour with stalagmites and stalactites.
- The trip to Vinales is 3 hours each way, so consider staying overnight. There are lots of more activities to do.
Day 15: Strolling Havana
- Wander through Havana’s local markets and streets.
- Evening at the Cuban Art Factory (highly recommended): A vibrant venue with art, music, and nightlife all under one roof.
Restaurants we visited in Havana: Antojos (9/10), Al Carbon (8/10), ChaChaCha (9/10), Floridita (great for drinks, average food), El Cafe (8/10 Brunch). Lobster & Pork is local speciality.
Contact my friend Reider who owns a classic car to take you or pick you up from the airport: +5353678689 (WhatsApp).
Day 16: Havana to Miami & Bahamas Cruise
- Early flight from Havana to Miami.
- 20-minute Uber from Miami Airport to Miami Port.
- Board Royal Caribbean’s Allure of the Seas.
- Departure for the Bahamas at 16:00.
Bahamas – Nassau & CocoCay
The next part of our trip took us to the Bahamas, where we enjoyed the pristine beaches, adrenaline-pumping waterparks, and serene adults-only retreats. It was the perfect way to wind down after two weeks of city and cultural exploration.
Day 17: Nassau, Bahamas
- Pearl Island + Pigs’ Island Experience.
Activities on the boat: Mamma Mia, Zipline, Floatrider, Rock the Wall, Ice Skating Show, Pools, Live Bands, Casino and more.
Day 18: CocoCay, Bahamas
- Thrill Waterpark in the morning: We spent 4–5 hours here and loved every minute of the thrilling rides.
- Adults’ Hideaway Beach in the afternoon: Relax with cocktails and enjoy live music while soaking up the ocean views.
This is a “Top 5” lifetime experience for myself.
United States (Part 2) – Miami & Key West
Wrapping up our honeymoon, we returned to Miami for some urban exploration before renting a Ford Mustang to drive to Key West. The scenic drive was filled with unique stops, incredible views, and a sense of freedom on the open road.
Day 19: Arrival in Miami
- 09:00 – Arrival at Miami Port
- Visit Domino Park in Little Havana.
- Shop at Little Havana Cigar Factory.
- Azucar Ice Cream for a sweet treat.
- Shopping at Bayside Marketplace.
- Ride the Skyviews Miami Observation Wheel.
Day 20: Road Trip to Key West
- Rent a Ford Mustang for the drive from MiamiConvertibles.com
- Stop at Robbie’s of Islamorada (feed fish and pelicans).
- What the Fish? Rolls & More for a seafood snack.
- Visit DJ Clam Shack in Key West for a lobster roll.
- Take a photo at the Southernmost Point of the Continental USA.
- Walk down Duval Street and explore the nightlife.
- We recommend staying overnight in Key West to experience the nightlife on Duval Street if you can.
Days 21-23: Miami
Day 21 – Beach Day:
- Relax at Misi Beach (the cleanest beach and best sand in South Beach) and visit South Point.
- Lunch at Espanola Way.
- Afternoon walks at the Miami Design District and Wynwood Walls.
- Dinner at KYU Wynwood.
- Walk Ocean Drive at night.
Day 22 – Relaxing Miami:
- Morning run along Ocean Drive.
- Brunch at Blue Lavender.
- Spend time at the pool with cocktails
- Lincoln Road Mall for some shopping
- Lunch at Five Guys
- Departure 21:05 from Miami
Other restaurants we visited or have as shortlist: Taco Taco, Cafe Americano, Mango’s Tropical Cafe, Joe’s Stone Crab, La Mulata (great Cuban Sandwich), Komodo Miami, Cipriani Downtown Miami.
Day 23: London Layover
With a 7-hour layover in London, we took the Heathrow Express into the city for a quick stop:
- Arrival 10:50
- Oxford Street for shopping
- Lunch at Kingly Court in Soho
- Walk to Piccadilly Circus, Leicester Square, Trafalgar Square, and Big Ben.
- Uber or Underground to Heathrow
- Departure 18:35
Day 24: Arrival in Cyprus
Arrival at 01:30 in Cyprus – tired but full of incredible memories from an unforgettable honeymoon.
This itinerary gave us the perfect balance between adventure, relaxation, and cultural immersion. We hope it inspires your own journey! Safe travels!
Sidenotes:
Disney World (Orlando):
If we could plan it again, we would visit only Animal Kingdom and Hollywood Studios in one day, as these parks were the most enjoyable for us. This would have freed up two more days to either explore more of Orlando or split that time between other destinations on our trip.
Cuba:
We wish we had stayed in Cuba for 2-3 more days. Here’s what we’d add:
- Vinales: Spend at least one night, and make sure to try a zipline and horseback riding.
- Varadero: We’d dedicate a full extra day here to fully enjoy the beaches, plus do a catamaran tour and scuba diving.
- Trinidad: We’ve heard amazing things about this place and would love to spend one night there as well, as it’s a fantastic location with a unique vibe.