What does the New York, Toronto and Jamaica trip include, and what does it cost?
Fourteen nights. Four nights in New York at a 4★, three in Toronto at a 4★ with breakfast, and seven in Jamaica at Sandals Montego Bay or similar 5★ on an all-inclusive basis. Return UK flights and the internal flights from New York to Toronto to Montego Bay are included. ATOL protection under licence 10713 applies and a £99 per person deposit holds it. Meals in New York, attraction tickets, the ESTA, the Canadian eTA and travel insurance are not included. It suits couples and honeymooners who want a week of two cities followed by a week of nothing at all.
Why does half the trip happen in Jamaica?
Because seven nights on a beach, all inclusive, is a holiday in its own right — and the seven nights before it are not restful.
New York and Toronto are cities you walk. Four nights and three nights of that, back to back, with a flight between them, is a week of being on your feet and spending money. The Jamaica half exists to balance it, and at seven nights it is long enough to properly stop rather than just pause.
Four nights in New York is what the city actually needs — enough for two or three museums, a viewpoint, Central Park and a neighbourhood beyond midtown. Three in Toronto is right for a city whose main draw beyond itself is Niagara Falls, ninety minutes away.
How does this compare with our Orlando and Jamaica trip?
Both end in Montego Bay all inclusive, and they are aimed at different people.
The Orlando trip looks cheaper on the headline, but it needs park tickets on top and this one does not — so the real difference between them is narrower than the two lead-in prices suggest. Which you should take depends on one question: theme parks, or two cities?
What you will actually do
In New York, four nights is three full days. Enough for the Met or MoMA, one viewpoint, Central Park properly, and a neighbourhood beyond midtown — Brooklyn, the Village or Harlem. Four nights is where New York stops being a checklist and starts being a place you have spent time in.
In Toronto, breakfast is included, which on a trip this long is a small relief. The CN Tower, the waterfront, Kensington Market and St Lawrence Market fill two days comfortably, and Niagara Falls is around ninety minutes away as the obvious third. Toronto is a large city that asks considerably less of you than New York does, which is the right shape for the middle of a fortnight.
In Jamaica, Sandals Montego Bay or similar, all inclusive for seven nights. The island rewards leaving the resort — Dunn’s River Falls, the Blue Mountains, rafting on the Martha Brae — but seven nights is also long enough that doing none of it is a legitimate choice.
When is the best time to go?
January is the cheapest month, and the trade is real: New York and Toronto in January are genuinely cold, while Jamaica is in its dry season and at its best. If you do not mind the cities cold and quiet, it is the strongest value on this itinerary.
December is the most expensive — the festive fortnight in the Caribbean drives that, and New York at Christmas adds to it.
Atlantic hurricane season runs 1 June to 30 November, with September and October the most active for Jamaica. September is higher again here, close to the January low, which tells you how the risk is priced.
What changes your price?
- The month. January at its cheapest against December at its dearest across the same fourteen nights.
- How the nights split. Four, three and seven is standard; shifting a city night to Jamaica is priced on request and usually costs less.
- Departure airport. Priced from the UK, with the routing and any regional supplement confirmed at enquiry.
- Room grade. All three are as stated or similar; ocean-view and suite categories in Montego Bay are quoted individually.
- What you spend in New York. Four nights of eating out in Manhattan is the largest uncontrolled cost on the trip.
Who this holiday suits
- Couples and honeymooners who want a week of cities and a week of nothing.
- Anyone who wants New York for long enough to do it properly rather than sprint it.
- Travellers who want half the holiday paid for up front.
- People who would rather have two cities than theme parks.
- Anyone with a full fortnight who does not want to spend it in one place.
Who might prefer something else
- If you are travelling with children, our Orlando, Miami and Jamaica trip is the family version of this shape, per person.
- Prefer everything included? Seven of the fourteen nights are not, and New York is expensive.
- If you have ten nights or fewer, three stops at this distance does not compress. New York and Barbados does city-and-beach in two.
- If Toronto does not appeal, it is three of your fourteen nights and there is no version of this without it.
- For guaranteed city warmth, the cheapest months are cheap because New York and Toronto in January are cold.
- Not sure this is the one? Browse our other all-inclusive holidays and tell us what appeals.
- Worth comparing against our 10 Nights USA & Canada Explorer – New York, Toronto & Niagara Falls, which covers similar ground.
Ways to upgrade
All quoted at enquiry against your dates.
- A more central or higher-category New York hotel
- Ocean-view, swim-up or suite categories in Montego Bay
- An alternative Jamaican resort, in Montego Bay or Negril
- A Niagara Falls day trip arranged rather than self-organised
- Broadway tickets, observation decks or museum passes booked in advance
- Extra nights in Jamaica, or a shorter Toronto leg in exchange
What is not included?
- Meals and drinks in New York, which is four nights in one of the world’s most expensive cities.
- Lunch and dinner in Toronto — breakfast is included there, the rest is not.
- The ESTA, $40.27 per person including children.
- The Canadian eTA, required because you arrive in Toronto by air. GOV.UK does not publish the fee, so we confirm it at booking rather than quote one.
- Attraction tickets in both cities, and the Niagara Falls day trip.
- Excursions in Jamaica and anything outside the all-inclusive list.
- Travel insurance, which matters both for US healthcare costs and for hurricane season.
Getting there and getting between
Return UK flights and the internal flights from New York to Toronto to Montego Bay are all on the same booking. New York is around eight hours westbound from the UK, New York to Toronto roughly ninety minutes, and Toronto to Montego Bay about four hours. New York and Toronto run five hours behind the UK, Jamaica six.
In New York the subway is faster than anything on the roads. Toronto is walkable in its core with a decent transit system. Montego Bay’s airport transfer is short, which is welcome after two flights and a fortnight of moving.
Entry requirements for UK travellers
Checked against GOV.UK foreign travel advice on 17 September 2026. Three countries, three sets of rules.
United States: an ESTA is required before you fly, $40.27, valid two years. Every traveller needs their own including children, and it applies to transit as well as entry.
Canada: an eTA is required for air arrivals, and on this itinerary you fly from New York to Toronto — so the exemption for arriving by land or sea from the USA does not apply to you. GOV.UK does not state the fee or validity, so we confirm the current position when you book rather than quote figures.
Jamaica: no visa, usually 90 days. Your passport must be valid for the duration of your stay with two blank pages. The Immigration and Customs Form C5 must be completed online before arrival, and it is mandatory. Arrival and departure taxes are normally included in the ticket.
Booking and protection
Your booking is covered by our ATOL licence 10713 and we hold IATA accreditation 91285611. It is held with a deposit of £99 per person, with the balance due before travel.
Prices are per person, based on two people sharing. Four flight sectors have to align, so availability tightens sooner than on a single-destination holiday, and January is both the cheapest month and the driest in Jamaica — those dates move first.
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