Antigua, Miami, New Orleans and Chicago holiday

Tailor-made holidays
Duration (in days): 24

From: UK

To: Antigua | USA



Inc. International flights (per person, based on 2 sharing) 
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Combine the beaches of the Caribbean with the fascinating cities of the USA. Begin on the paradise island of Antigua, spending two days exploring and relaxing. Kayak between uninhabited islands, stroll along the perfect beaches and enjoy the spectacular views over English Harbour. Next, you’ll fly to Miami, for a few days of mojitos and Cuban culture. After this, you’ll taste fresh coffee and beignets in New Orleans, learn about the spooky voodoo history of the city and take a boat trip through the misty bayou wetlands. Finish your holiday in Chicago, where you can admire the spectacular architecture, laugh yourself silly at a comedy show and gaze out at the view over Lake Michigan. This is a diverse and exciting holiday for anyone looking for a city and beach adventure!

This itinerary can be tailored to suit your requirements; please contact one of our consultants to start planning your dream trip.

This holiday includes

  • International flights
  • All transfers
  • All accommodation in Antigua & the USA             
  • Excursions as mentioned in the itinerary
  • Meals as mentioned in the itinerary        


You’ll remember…

  • Strolling along the beautiful beaches of Antigua
  • Snorkelling with colourful fish in the warm waters                            
  • Learning about Cuban culture in Miami 
  • Tasting fresh gumbo and beignets in New Orleans            
  • Admiring the striking architecture of Chicago      



Itinerary in brief:

  • 13 nights Antigua
  • 3 nights Miami
  • 3 nights New Orleans
  • 3 nights Chicago

Day 1: UK to Antigua

Depart the UK from your chosen airport. On arrival in Antigua, you’ll be met and driven to your hotel, checking in for thirteen nights.

Included: International flights, transfers, 4* hotel

Days 2 - 13: Antigua

You have two weeks to relax and enjoy the spectacular island of Antigua. Stroll along perfect beaches, snorkel with colourful fish in the turquoise water and watch the sunset over the curved bays. Enjoy your relaxing hotel on an all-inclusive meal plan.

Included: All-inclusive meal plan, 4* hotel

Day 14: Fly to Miami

After breakfast, you will be driven back to the airport for the short flight over to Miami. On arrival, you’ll make your own way to your hotel, checking in for three nights.

Included: Breakfast, transfers, international flights, 4* hotel      

Days 15 & 16: Miami

Spend a few days relaxing on this famous stretch of sand and swimming in the turquoise waves. If you’re in the market for retail therapy, Miami Beach has some of the best shopping in the country, housed in huge modern malls or tiny art deco buildings like The Webster, brimming with boutique designers and cafes. Take a wander through Wynwood, packed with galleries, clubs and street art, before finishing your day with a Cuban sandwich and a few mojitos in one of the beachfront bars.

Included: 4* hotel           

Day 17: Fly to New Orleans

This morning, you will make your own way back to the airport for your flight to New Orleans. On arrival, you’ll head into the city and check into your hotel for three nights.  

Included: Internal flights, 3* hotel          

Day 18 & 19: New Orleans

Spend a couple of days exploring the eccentric city of New Orleans. We’d recommend you start with a stop at Café du Monde, where you’ll have to queue to get your hands on a bag of the famous beignets which will give you the energy you need to explore the city ( - for more ideas see our 3 days in New Orleans for foodies). Wander through the French Quarter past pretty balconies and colonial architecture and into one of the ornate cemeteries – “Cities of the Dead”, where huge carved angels look down on you from their plinths. New Orleans certainly has a spooky side to it – make sure you explore the voodoo history of the city and look out for ghosts that supposedly lurk around every corner. Finish up by enjoying a bowl of gumbo or a plate of ruby red crawfish served with buttery sweetcorn and andouille sausage for dinner.

On your second day, we’ve included a day tour to the bayou (wetlands), where you’ll drive alongside the Mississippi river and hop on a cruise through the swamp on the lookout for alligators, snakes and birds who make their home in the wetlands. Finish your time in New Orleans by dropping into one of the many jazz bars the city has to offer, settling in with a beer in hand to listen to some of the best musicians in America.

Included: Bayou tour, 3* hotel 

Day 20: Fly to Chicago

This morning, you’ll head to the airport for your flight to Chicago. On arrival in the Windy City, you’ll make your own way to the airport and check into your hotel for three nights.      

Included: Internal flights, 3* hotel          

Day 21 & 22: Chicago

Two days is enough time to enjoy the highlights of Chicago. Start with a trip to the Cloud Gate, more popularly known as “The Bean” where you can snap a photo in its distorted reflection, before heading to Intelligentsia Coffee for a latte. We’ve included the Chicago City Pass so you can use it to explore two of America’s best museums. The Art Institute of Chicago holds paintings by Picasso and O’Keefe, as well as the famous American gothic portrait by Grant Wood, while at the Field Museum you can visit Sue, the most complete T-Rex skeleton ever found.

Enjoy a slice of Chicago deep-dish pizza at Giordano’s before a night of comedy at Second City, where many famous comedians made their debuts. Don’t leave before heading to the top of the Willis Tower SkyDeck, where you can stand in a glass box high above the city and admire endless views of the city and Lake Michigan below.   

Included: Chicago City Pass, 3* hotel 

Day 23: Depart Chicago

Your time in Chicago has come to an end today so make your own way to the airport in time for your flight home.                               

Included: International flights 

Day 24: Arrive UK


Antigua & Barbuda have a tropical climate in line with their neighbouring islands. While the temperature doesn’t vary much throughout the year, the humidity changes hugely between the seasons. December to April is the coolest and driest time, perfect if you’re looking for some winter sun. The hurricane season looms between June and November, with spells of intense rainfall and thunderstorms. There is still plenty of sunshine, but chances of rain are high. Hurricanes are most likely between August and October.

Think of Florida, and you’ll picture clear skies and sunny days. The Sunshine State is well known for its warm weather but the hurricane season takes over between June and November, meaning sunny days will be peppered with rainy downpours and any hurricanes that venture north from the Caribbean. Winter is ideal if you are visiting Orlando as the parks are usually quiet with kids at school but December doesn’t bring beach weather, so if you’re looking to relax on the sand, March to May is the best time of year.        

The Deep South has cool winters and springs whilst the summer months are hot, with high humidity and sunny days. Afternoon showers can occur throughout but generally the weather down here is warm with long Indian summers keeping it hot often until late October.

Chicago has four distinct seasons – hot summers, mild autumns, snowy winters and wet springs. It’s often cloudy and a bit windy thanks to the city’s location on the shores of Lake Michigan. 

This itinerary is purely a suggestion and can be tailor-made to your requirements, so please contact us with your dates and requests, and we’ll put together a bespoke quotation for you.           

What's included: 

  • International flights
  • Return airport transfers
  • Accommodation as mentioned in the itinerary   
  • Meals as mentioned in the itinerary
  • Excursions as mentioned in the itinerary

Not included: 

  • Any meals not mentioned
  • Personal expenses
  • Tips & gratuities
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