Caribbean Countries – Sixteen Days Itinerary

Caribbean Countries - Sixteen Days Itinerary

December brings cold weather across North America and Europe, so we were ready for some sun, beach and some visa-free countries. There are over 7,000 islands in the Caribbean surrounded by blue waters and pristine white beaches. It was the peak season to travel there in December, but it was the prefect way to enjoy the holidays!

Most visitors to the Caribbean arrive on a pre-arranged packages – all-inclusive resort or cruise ships. Independent and budget travelers are rare and mostly avoid this time of the year for everything expensive.

With a bit of planning and knowledge, island hopping across all 13 independent countries is possible. And depending on your itinerary, you might visit a few overseas territories as well. And every island offers much more than just a beach.

Countries in the Caribbean

There are 13 sovereign countries in the Caribbean and it is possible to visit them all in just one trip.

  1. Antigua and Barbuda
  2. Bahamas
  3. Barbados
  4. Cuba
  5. Dominica
  6. Dominican Republic
  7. Grenada
  8. Haiti
  9. Jamaica
  10. Saint Kitts and Nevis
  11. Saint Lucia
  12. Saint Vincent and the Grenadines
  13. Trinidad and Tobago

And these are the overseas territories in the Caribbean:

  • British overseas territories: Anguilla, British Virgin Islands (Tortola, Virgin Gorda, Anegada, Jost Van Dyke), Cayman Islands, Montserrat, Turks and Caicos Islands
  • France overseas territories: Guadeloupe, Martinique, Saint Barthélemy, Saint Martin
  • U.S.A. overseas territories: Puerto Rico, United States Virgin Islands (Saint Croix, Saint John, Saint Thomas)
  • Netherlands overseas territories: Bonaire, Sint Eustatius, Saba, Aruba, Curaçao, Sint Maarten


With a lot of direct flights from Europe and North America, it is easy to get to the Caribbean. If you are traveling on a budget, then the best option is to search for European charter flights to Barbados, Guadeloupe or Martinique and start your travels from there. Remember that although you may not need a visa to the independent Caribbean nations, you might need visas to territories. Make sure to read visa requirements before traveling.

Arriving from Canada or the USA gives you a choice of flights to either the northern island (Bahamas) or the southern one (Trinidad).

If you are aiming to visit all of them, then it’s a good idea to start either in the south (Trinidad or Barbados) and go your way north (Bahamas or Cuba). Or vice versa.

The options to hopping islands are either fly between them or take ferries. Note that there are not many ferries, but you can catch a private boat as a helper. Flying is the best and fastest option but there are simply no cheap flights (minimum of $100-$150).

These are the islands we visited in this trip for Sixteen days (in order of visit):

  1. Antigua and Barbuda
  2. St. Kitts and Nevis
  3. Dominica
  4. St. Lucia
  5. St. Vincent and The Grenadines
  6. Grenada
  7. Barbados
  8. Trinidad & Tobago

Some tips and pointers:

  • Flight between the countries on Liat Airlines which are the de facto taxi service across the tiny island nations. Book in advance to get special ‘web’ prices on Liat. Also check prices on Inter Caribbean Airways and other airlines that matches your frequent flyer alliance.
  • Spent 1.5 to 2 days in each country. You can spend a lot more in each country if you plan to visit every island and every place. We visited some highlighted destinations and made the best off of the trip!
  • Stayed at Airbnb or hotels in all the countries. With a lot of resorts on each island, you have options to go luxury or check out Airbnb for cheaper in-town places. We compared the prices of rooms on Airbnb and hotels (as opposed to resorts) and found Airbnb and hotels to be cheaper.
  • US Dollars or EC Dollars. Both USD and XCD (East Caribbean Dollars; referred to as ‘EC’ across the islands) are accepted everywhere. Although the official exchange rate is pegged to 2.7 XCD to 1 USD, the reality will vary anything from XCD 2.5 to XCD 2.67 to a USD.
  • SIM Card – There are two companies across all the island nations we were visiting – Flow and Digicell. Although the costs of prepaid plans are quite similar, Flow seems to have the best network coverage across each nation. Even though both companies have a presence across all island, they do not offer a single SIM card that works in all countries, but you have to buy individual SIM cards in each country! And the rates are quite expensive – example, USD 30 for 3GB data to be used in 30-days! So we chose to use the AT&T’s ‘International Day Pass’ that offers unlimited data, text and calls for USD 10.

Initial Costs


City Cost/night Notes
St. John’s, Antigua $145.00 Two nights. Double bed with ensuite bathroom. Air condition, linen.
Basseterre, St. Kitts $180.66 Two nights. Double bed with ensuite bathroom. Air condition, linen.
Roseau, Dominica $130.32 Two nights. Double bed with shared bathroom. Fan, linen.
Castries, St. Lucia $128.00 Two nights. Apartment with double bed & ensuite bathroom. Fan, linen.
Kingstown, St. Vincent $87.00 Two nights. Double bed with ensuite bathroom. Air condition, linen.
St. George’s, Grenada $83.55 Two nights. Double bed with shared bathroom. Fan, linen.
Pirate’s Inn, Barbados $243 Two nights. Double bed with ensuite bathroom. AC.
Inn at 87, Trinidad $297 Two nights. Double bed with ensuite bathroom. AC, breakfast included.



This list does not include the international flights from anywhere to the Caribbean. These are just the ones between the island nations.

From-to Airline Cost Notes
Antigua (ANU) to St. Kitts (SKB) Liat 312 $113.25 One-way flight. Economy.
St. Kitts (SKB) to Antigua (ANU) to Dominica (DOM) Liat 313 and Liat 323 $160.05 One-way flight. Economy.
Dominica (DOM) to Antigua (ANU) to St. Lucia (SLU) Liat 364 and Liat 309 $135.37 One-way flight. Economy.
St. Lucia (SLU) to St. Vincent (SVD) Liat 371 $140.57 One-way flight. Economy.
St. Vincent (SVD) to Trinidad (POS) to Grenada (GND) Liat 771 and Liat 772 $117.18 One-way flight. Economy.
Grenada (GND) to Barbados (BGI) Caribbean Airlines 441 $115.20 One-way flight. Economy.
Barbados (BGI) to Trinidad (POS) Caribbean Airlines 441 $97.50 One-way flight. Economy.



Note: All values in USD, unless otherwise mentioned, are approximate and based on the exchange rate at the time of publishing. Each cost is for one adult. The exchange rate at the time of publishing is assumed to be USD 1 = XCD 2.60.

What Cost Notes
All flights $879.12 See details above
Accommodation for all days $647.26 Total was $1,294.53 for two persons. Per person. See the list and costs above.
SIM Card $120 AT&T International Day Pass for $10 a day.
Total Costs $1,646.38 Per person
Overall Costs $1,646.38 Per person

To give you a better insight, here what we did on each island…

Days 1 & 2

Antigua and Barbuda

First country in the trip.

Days 3 & 4

St. Kitts and Nevis

Second country in the trip.

Days 5 & 6


Third country in the trip.


Days 7 & 8

St. Lucia

Fourth country in the trip.

Days 9 & 10

St. Vincent and the Grenadines

Fifth country in the trip.

Days 11 & 12


Sixth country in the trip.


Days 13 & 14


Seventh country in the trip.

Day 15

Trinidad & Tobago (North)

Eighth country in the trip.

Day 16

Trinidad & Tobago (South)

Eighth country in the trip.

#AntiguaandBarbuda #Barbados #Caribbean #Dominica #Grenada #Itinerary #StKittsandNevis #StLucia #StVincentandGrenadines #Travel #TrinidadandTobago

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