Taking you from Boston’s bustle to Barbados’ palm-fringed beaches and quaint fishing bays, this 14-night itinerary pairs New England’s most-inviting city with one of the Caribbean’s most famous and exclusive islands.

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Itinerary
04 Nights – Boston
10 Nights – Barbados
✈ UK – Boston (4 Nights): You’ll fly from the UK to Boston, where we’ll transfer you to your hotel for 4 nights. Compact and easy to navigate on foot, the New England city of Boston is known for its distinctly European feel, wide open greenery, signature cuisine and charming architecture. Sharp skyscrapers Downtown contrast quaint cobbles over in Quincy Market, while sites like Faneuil Hall and the Paul Revere House offer a wealth of cultural significance along the Freedom Trail.
There’s a real fusion feel to Boston. Beacon Hill’s gas lanterns and red-brick rows add quaint charm to prestige over in neighbouring Cambridge, where Harvard University has churned out some of the greatest minds in history. Snaking its way through classy waterfront dining spots, the River Charles and 1,100-acre Emerald Necklace also give Boston a carefree feel. It carries over into Back Bay’s boutiques, Boston Common’s hot dog stands and the trendy South End. Wander the picturesque Copley Square, explore the towering Prudential Center, pop into Fenway’s museums and sample the region’s New England clam chowder. Whether you’re grabbing gourmet ice-cream at Cambridge’s famed Toscanini or retracing the American Revolution at the Waterfront, you’ll be in a city that’s bustling, beautiful and on the map for a reason. You can walk, take public transport, or hop into cabs to get around, although we can always arrange private transfers for you.
✈ Boston – Barbados (10 Nights): Leaving the USA for the Calypso lifestyle, you’ll now fly to the Caribbean island of Barbados for 10 nights of uninterrupted bliss. With its secluded beaches, palms, clear waters and white or pink sands, Barbados has been topping traveller wishlists for decades.
Dotted among sugar cane plantations and inland hills, the coast’s reefs and shipwrecks give way to a world of local culture, foods, sights and scents. From the Bridgetown capital’s Malibu Rum Factory and sophisticated dining scenes to the happening Oistin Bay, this island is just bursting with colourful architecture, friendly locals and the biggest draw of all. Windswept or blissfully calm beaches here are uncrowded, unspoiled, sun-drenched and just waiting for those morning footprints. With 10 nights, you’ll have all the time in the world to explore the island, top up the tan and fully recharge those batteries. We’ll happily arrange transfers for whichever part of Barbados you want to visit.
✈ Barbados – UK: We’ll be at your hotel on your departure day to meet and escort you to the airport for your flight back to the UK.
Why choose eShores?

One to One Service
Our experienced personal travel consultants will ensure you find the most suitable holiday, whilst taking care of every last detail. Everything from start to finish will be effortless.

100% Tailor Made
We can use any hotel, in any destination, so we will craft an itinerary to suit your exact needs. Also, as we can provide any itinerary, the only holiday we'll offer, is the one that's right for you.

Fully Protected
Our ATOL bonding provides you with the financial protection you need and as a member of the Travel Trust Association, you'll have 100% financial protection. Covering you for any eventuality.

Competitive Pricing
As a tour operator & travel agent, we'll search the market to ensure that we find you the best price. Also as an online business, we can ensure our prices are as competitive as possible.






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Anonymous
We were looking for a two island holiday at Rhodes and Kos. Emily provided us with a number of options and recommendations for flights and hotels which enabled us to make a final choice. She was extremely helpful in dealing with our requests and room preferences and the whole process was handled very efficiently.
Posted 1 day ago -
Julia
So impressed with Eshores. Chris Eaves handles our arrangements and we have just booked our fifth holiday with him. Nothing is too much trouble and as we are two mature ladies his patience is much appreciated. We always feel confident in his advice and suggestions. Over the years he has arranged some complex itineraries for us including a three stop holiday with all flights, hotels and transfers organised - bliss. This time were off to Turkey and Chris has organised everything for us. Another worry free holiday sorted in 2026! Thanks Chris to you and everyone at Eshores.
Posted 1 day ago -
LukeRoger
Rob was very helpful and attentive and responded to my emails quickly and I was very impressed with the service provided. I have no hesitation in recommending eShores and I will certainly be using them again for future holidays.
Posted 2 days ago -
Keith
Excellent service
Posted 3 days ago -
Kaye
Leanne was a delight to work with, proactively suggesting options, whilst remembering they had to be practical. What I appreciated most was how responsive and efficient Leanne was. Everything was handled promptly. Even though we haven’t taken the trip yet, I already feel confident that things will run smoothly thanks to the excellent groundwork that Leanne put in place.
Posted 3 days ago -
Sally
I’ve now lost count of the trips I’ve booked with Gavin at e-shores and how he always manages to know exactly what we like and gets a great price - always the same or less than I research myself. Our latest was Greek island hopping to Mykonos, Paros, Naxos and Santorini and the hotels Gavin booked were all outstanding and the typically small, boutique hotels with less crowds. We went out of season (1st - 13th Sept) and everything went smoothly from the airport transfers, the welcome we had at each hotel and the beauty of each island having its own magic. Looking forward to the next trip already booked through Gavin in November! Thank you everyone-shores - the Napiers!
Posted 4 days ago -
Anonymous
I found your representative very informatative. She listened carefully to our requests and completed every thing we asked for, including changing flight times that were better suited to us.Many thanks. I have already recommended the company already.
Posted 6 days ago -
Alaine
Great care is given to assist with what your looking for in a holiday.
Posted 6 days ago -
Robert
Always get great service from EShores (thank you, Emma). Nothing is ever too much trouble no matter how many times I change my mind! Would not consider using anyone else
Posted 1 week ago -
Christopher
Laura was fanastic, knew just what we needed and found it hassle fre when other agents had struggled :-)
Posted 1 week ago



Talk To The Experts
Your personal travel consultant will get to know your needs, ensuring they find you the most suitable holiday, at the best price!