Barbados, Miami, San Francisco and Boston holiday

Tailor-made holidays
Duration (in days): 24

From: UK

To: Barbados | USA



Inc. International flights (per person, based on 2 sharing) 
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Enjoy a relaxing beach break with exciting city hopping on this unique holiday to Barbados and the USA. Start with a stay on the exotic island of Barbados, where you’ll find white-sand beaches to sink your toes into, as well as fascinating history and rum cocktails a-plenty! After two weeks of chilling, you’ll head to Miami, taking in the vibrant Cuban culture and art deco history of the city. Fly to the west coast to soak up the best of San Francisco – dumplings in Chinatown, cycling across the Golden Gate Bridge and strolling through the famous City Lights bookstore. Finish your trip in Boston, where you can catch a baseball game at Fenway Park, learn about the history of New England and look for whales off Cape Cod. This unique holiday is a brilliant combination of cool cities and beautiful beaches.  

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 Barbados and the USA      
  • Excursions as mentioned in the itinerary
  • Meals as mentioned in the itinerary        


You’ll remember…

  • Strolling along the beautiful beaches of Barbados
  • Tasting local rum in the island’s distilleries
  • Admiring the pastel-hued Art Deco architecture in Miami
  • Cycling over the Golden Gate Bridge in San Francisco      
  • Looking for whales off Cape Cod



Itinerary in brief:

  • 13 nights Barbados
  • 3 nights Miami
  • 3 nights San Francisco
  • 3 nights Boston

Day 1: UK to Barbados

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

Included: International flights, transfers, 4* hotel  

Day 2 - 13: Barbados

Barbados has long been known as an island paradise, with white-sand beaches, swaying palm trees and a fantastic restaurant scene. You’ve got two weeks to enjoy the best the island has to offer.

During your time in Barbados, we’ve included a day tour of the island. You’ll be picked up in the morning and head off with a guide to explore. Take the tramway through Harrison’s Cave, a magnificent cavern made of crystallised limestone, passing cascading waterfalls and towering stalagmites. Next, you’ll visit Welchman Hall Gully and enjoy a tour of the rainforest, looking for wild green monkeys in the natural habitat. Relax on the beach at Carlisle Bay before tucking into a delicious Caribbean lunch at the Copacabana Beach Club. In the afternoon, you’ll board a glass-bottom boat and search for sea turtles, snorkelling with these beautiful creatures in the clear waters.

Included: Breakfast, 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 San Francisco

Today you’ll make your way to the airport for the flight across to San Francisco. On arrival, you will make your own way to the hotel, checking in for three nights.

Included: Internal flights, 4* hotel          

Day 18 & 19: San Francisco

Hop on the bus and start your day at Fisherman’s Wharf, where you can watch sea lions laze in the sun before tucking into a clam chowder bread bowl for lunch. We’ve included a hop on hop off bus pass so you can easily navigate the city, whether you want to grab dim sum in Chinatown, window shop in Union Square or take the ferry over to Alcatraz to explore the famous prison on the rock.

Another great idea is to hire a bike and cycle over the Golden Gate Bridge – not only an exciting way to experience this iconic landmark but you’ll be able to visit the Marin Headlands with beautiful views back over the bridge towards the city. You’ll find history and culture here round every corner, whether you’re browsing through the shelves of City Lights Booksellers or trying to find the best burrito in the Mission district – 2 days in San Francisco will fly by!

Included: Hop on Hop off bus tour, 4* hotel         

Day 20: Fly to Boston

This morning, you’ll make your way back to the airport for your flight to Boston. On arrival, you’ll make your own way to the hotel, checking in for three nights.  

Included: Internal flights, 4* hotel     

Day 21 & 22: Boston

You have two days to explore the city of Boston, and there’s so much to see! We recommend that you start by following the Freedom Trail, which will guide you around the historical highlights of the city, including Old North Church and Boston Common. Grab a lobster roll or a bowl of New England clam chowder for lunch before wandering the pretty streets of Beacon Hill and heading over the river to Cambridge, home to Harvard University and MIT. Try and catch a baseball game at Fenway Park – the field is iconic, as well as the hot dogs!

On your second day we’ve included a whale watching tour to lovely Cape Cod. You’ll head out to the Stellwagen Bank, where humpback, finback and minke whales are found in their natural habitat. Hopefully, you’ll spot some of these beautiful creatures in the waves. Whether it’s a tail splash, a fin slap or a full breach – any glimpse will be a thrill!                               

Included: Whale watching tour, 4* hotel              

Day 23: Depart Boston

This morning, you’ll make your way to the airport in time for your flight back to the UK.

Included: International flights

Day 24: Arrive UK


Barbados is a good destination for year-round sunshine, with the driest part of the year falling between December and April. Wet season arrives between June and November, with sporadic rainfall and bright but rarer sunshine. This time is very humid and although Barbados’ position as one of the easternmost Caribbean islands means it doesn’t often experience hurricanes, it is still a possibility.

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 coastal cities of central California sit on the edge of the Pacific Ocean giving them a changeable climate, where you can experience summer and winter in the same day. Coastal breezes keep the cities cool and huge fog drifts can sweep over the San Francisco during the summer meaning winter is usually more reliable with clear days and moderate temperatures. Cooler than most areas of California – you are more likely to be too cold than too hot, so bring a jacket!

New England enjoys glorious summers and cold winters. If you want to visit the Cape to enjoy the pretty beaches then it’s best to arrive between May and October, and while Boston is definitely a year-round destination, you’ll need a very warm coat and hat in preparation for some snowy days

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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