Jamaica / Island Hopping

The islands around Jamaica in the north-western Caribbean are culturally very different from Jamaica, so they make an excellent combination if you visit them together on a trip. The problem is that they are also quite large, meaning that you will want to spend time in both, spending the time to travel around and explore the islands. They are also a relatively long way away, which can make transfers expensive. Don’t forget, though, that Jamaica itself is also large and varied enough for you to create an itinerary around it. Please see below for a sample itinerary.

Cuba obviously holds enormous fascination for many people and as a Latin island with an extraordinary political history, it makes a very good two-centre trip with Jamaica, say for a week. There are day and weekend trips to Santiago de Cuba, Havana and to the beach at Varadero, but you can also fix a week’s return flights, so you might consider travelling around it.

The Cayman Islands are extremely developed by comparison with Jamaica and much more modern and “American” in style. It can be something of a relief after the excitement and bustle of the bigger island. The Caymans have excellent diving, particularly Little Cayman, which is delightfully slow and gentle. There are also regional flights to The Bahamas and Turks and Caicos Islands. Finally, there is also Miami, so you can make a two-centre holiday with Florida.

Regional and local airlines that serve Jamaica include:
Most of the tour connections fly in and out of Montego Bay, but there are some scheduled services which also touch Kingston on the way in or out.

Caribbean Airlines-Air Jamaica - shared BW flight code (former BWIA) with services to Antigua, St Maarten, The Bahamas and Barbados. 

Air Turks and Caicos - three time a week from Providenciales to Kingston.

Cayman Airways - Connections three times a week to Montego Bay.

Jamaica Air Shuttle - Services from Kingston to Haiti and Montego Bay to Cuba.

REDjet - Services from Barbados and Trinidad into Kingston. STOP PRESS: As of 16 March 2012 REDjet has suspended all flights until further notice. 

Local Jamaican charter airlines include: 

Tim Air, Skylan Airways and Jamaica Air Shuttle are small airlines that offer scheduled flights within Jamaica from Montego Bay to Negril and to Kingston (local airport), Kingston to Montego Bay, Tinson Pen to Montego Bay as well as air charter services to any airport in Jamaica.

Day trips to other islands:

Tropical Tours Ltd - Offers overnight packages to Cuba from Montego Bay and day trips on request.  Also Cuban Visa Card. Passports are compulsory, but will not be stamped in Cuba. They also offer 7-night cultural packages.

Island Itinerary of Jamaica

You can make this tour of Jamaica, following the coastline clockwise, within a couple of weeks. It will give you some time in the major resorts if you want, but also the opportunity to see something a little more Jamaican, including the magnificent interior and possibly Kingston. It will also give you a chance to get the best of the island’s “chilled” atmosphere at the same time. There are places to stay to suit almost every budget.

Assuming you fly into Montego Bay, you will probably want to get beyond the main tourist towns on the north coast between Montego Bay and Ocho Rios in order to relax for a while. This is where many of the best beaches and the main facilities are, along with the liveliest crowds and you can return to them later if you want something a little lively. So instead, head for Port Antonio in the east, Treasure Beach on the south coast, or Negril, which although it has some large hotels, also has some of the coolest and calmest places to stay in the whole of the Caribbean.

Port Antonio is a charming and laid-back town set in the most strikingly fertile part of the island. It seems fairly undeveloped at first sight, but tucked into the hills and very pretty coves beyond the town there are actually quite a lot of places to stay – small hotels, guest-houses and plenty of villas. It is a lovely place to slow down and relax.

After three or four days you will be ready to move on. The trip to Kingston across the Blue Mountains (on the Section road, when open) or via Annotto Bay is absolutely stunning, but the east of Jamaica might also be worth considering. Beyond Boston Bay (itself worth a stop as the “Home of Jerk”) around Long Bay and Manchioneal it is extremely low key, much as the Caribbean was 20 or 30 years ago. When you get there, Kingston is busy and hectic and while it is not necessarily that relaxing, unlike most Caribbean islands, it has some “city” interest in the major monuments, shopping centres and restaurants and lively bars, as well as a park and a zoo. It also has the extraordinary history of Port Royal nearby. All of this is almost diametrically opposed to the atmosphere in the Blue Mountains, where you can escape for a bit more calm and quiet. The mountains are particularly good for nature too.

Many of the most interesting “sights” are around the tourist areas, so there is reason to dip into the humdrum of the North Coast (stay in one of the smaller, more charming hideouts), but if this doesn’t sound like you then head straight for Treasure Beach, a lovely sleepy village with just a few bars and hotels. If you didn’t stop in Negril on arrival, then you should definitely do so before leaving. It is just the right mix of tranquil cool and lively bars and beach activity to suit your mood before you leave. From Negril it is an hour’s drive to the airport at Montego Bay.