Which Caribbean Island Has the Best.....

This is my notebook to help figure out which Caribbean island to visit for vacation. First, we divide it up to give ideas of which islands to concentrate on. For instance, if you want to go shopping in the Caribbean, you can see which Caribbean island has the best shopping. In due time, there will be a listing with a summary about each island. This is a work in progress but I figured I might as well share it as it develops. Enjoy!

Which Caribbean Island has the Best Beaches

Caribbean Islands with the best beaches would be Anguilla, Antigua, Aruba, the Bahamas, the British Virgin Islands, the Cayman Islands, Curacao, the Dominican Republic, Grenada, Guadeloupe, Martinique, St Barts, St Maarten, Saint Vincent and the Grenadines (specifically the Grenadines), Trinidad & Tobago (specifically Tobago), Turks & Caicos and the US Virgin Islands (specifically St John).

Beach + Diving = Grenadines, Turks & Caicos, British Virgin Islands, the Cayman Islands, Guadeloupe.

Which Caribbean Island has the Best Diving and/or Snorkeling

I believe the best Caribbean snorkeling and diving islands are Bonaire, Dominica, Saba, Sint Eustatius, Saint Vincent and the Grenadines (specifically St Vincents) and Turks & Caicos. Also islands to consider would be Antigua, Aruba, the British Virgin Islands, Cayman Islands, Montserrat, St John and St Maarten. St Lucia many times doesn’t make these lists but there are a couple great snorkeling spots accessible from shore such as at Anse Chastenet Resort (all beaches open to public) and a little further up the west coast at Anse la Raye.

If you want to swim with humpback whales, you can look into the Dominican Republic if you are going in February or March.

Diving + Beach = Grenadines, Turks & Caicos, British Virgin Islands, the Cayman Islands, Guadeloupe.

Which Caribbean Island has the Best Interior Exploration

You might want an island with a rainforest, or something different to explore on the interior. For those kinds, look into Dominica, Grenada, Guadeloupe, Jamaica, Saba (very small and easily accessed via St Maarten), Sint Eustatius, Saint Kitts and Nevis, Saint Vincent and the Grenadines (specifically St Vincents), Trinidad & Tobago, US Virgin Islands (specifically St. John). Barbados is a large enough island to explore and although the interior isn’t immensely dynamic, it does make a good day trip or two via car.

Some say Puerto Rico is a great place to explore. I was underwhelmed by Puerto Rico’s El Yunque. If you are interested in Puerto Rico, check out the islands–Isla Culebra and Isla de Vieques–off the coast. St Lucia has a lot of mountainous terrain (waterfalls, hiking) on the southwestern corner and rainforest in the central region.

Which Caribbean Island has the Best Shopping

For shopping, great choices would be the Bahamas, Cayman Islands (specifically Grand Cayman), St Barts, St Maarten and St Thomas in the US Virgin Islands. However, many allures of duty free don’t help the US traveler much where prices are often cheaper.

Which Caribbean Island has the Best Nightlife

Generally, the following are good islands for Caribbean nightlife: Aruba, Bahamas, Cuba, Curacao, Dominican Republic, Puerto Rico, St Lucia (Castries/Rodney Bay), St Maarten and Trinidad. Aruba will be more of the touristy type nightlife.

Which Caribbean Islands are Affordable?

Excluding flight costs, if you are looking for bang for the buck, look into the Bahamas, Curacao, Dominica, the Dominican Republic, Grenada, Guadeloupe, Puerto Rico, Jamaica and US Virgin Islands.

Which Caribbean Island has the Best All Inclusive Resorts

In general, look at Antigua, Jamaica or the Dominican Republic. If money is an issue, and you want the cheapest all inclusive resorts in the Caribbean, then the Dominican Republic and Jamaica should probably be your primary focus. Antigua has some very nice all inclusives (according to people who like these things) for a higher budget. In Saint Lucia, I thought Sugar Resort was much more peaceful and non-touristy than the Sandals property I passed through.

Quick Caribbean Island Hit List

Anguilla

Great beaches. Great weather due to its flat landscape. Very easy to get to St Maarten & St Martin via a quick ferry. English speaking.

Antigua

Can be crazy in April if you go during Sailing Week. Great weather December through April with good temps and low rainfall. English speaking.
Check out Barbuda – frigate bird. You can get to Montserrat via ferry.

Aruba

Very nice beaches (all public). Desert ecosystem. Exploration throughout island easy with rental car. Some hiking and remote scenery on the eastern half of island. Much of western half feels very Americanized (Kitschy tourist nightlife, middling overpriced tourist-centric restaurants, etc). Steady trade breeze provides comfort to heat. Some beaches have palapas (aka tiki-huts) which are free for public use (legally) but some hotels try to make you think otherwise. These provide much needed shade but there has been government action to remove all palapas from beaches. Dutch speaking with widespread English & Spanish.

Bahamas

English speaking.

Barbados

Very friendly and helpful locals. Nice beaches. Driving around the island makes for a great day trip. Excellent Friday fish fry in Oistins. Can get around by shared van. English speaking.

Bonaire

Dutch/English speaking.

The British Virgin Islands:

You can travel to the US Virgin Islands via ferry. English speaking.

Cayman Islands

Great beaches, swimming, snorkeling, diving. Pretty much no panhandling and beach touts which is very nice. You get left alone. English-speaking, driving on the left. Not much land exploration – can drive island in day. Can also get around by bus service. Much closed Sunday. Prices are on higher side. English speaking.

Curacao

Dutch/English speaking.

Cuba

Rich sights in a poor economical backdrop. Great beaches, tobaccos plantations, etc. but expensive to rent a car amongst other things. Havana has great colour and texture but felt over-rated with all the media attention lately (and with its infrastructure overmatched by the tourist throngs). Definitely an interesting feel. Spanish speaking.

Dominica

English-speaking. A nature island with rainforests, waterfalls, etc. You can get to Guadeloupe (2 hours 15 minutes), Martinique (2 hours) and St Lucia (4 hours 30 minutes) by ferry. Diving/Snorkeling is excellent. You come here to hike & find adventure. Drive on the left. Driving in Roseau can be challenging at first due to crazy unposted one-way roads. English speaking.

Dominican Republic

Spanish speaking.

Grenada

English speaking.

Guadeloupe

Consists of several islands. Nice beaches generally on both sides of the main islands. Some hiking on the western side. Part of France so great bread, cheese, etc. French-speaking but entirely feasible in English. You can get to Dominica (2 hours 15 minutes), Martinique (4 hours 30 minutes) and St Lucia (7 hours) by ferry. French speaking.

Haiti

French speaking.

Jamaica

English speaking.

Martinique

You can get to Dominica (2 hours), Guadeloupe (4 hours 30 minutes) and St Lucia (1 hour 30 minutes) by ferry. Similar to Guadeloupe as it is part of France. Nice beaches. French speaking.

Montserrat

English speaking.
Quiet beaches, hiking in interior rainforest (terrain steep). Southern portion is in an exclusionary zone due to volcanic aftermath. You can get here from Antigua via ferry. English speaking.

Puerto Rico

Mediocre beaches, casinos, hotel resorts. Rainforest on east coast. Coffee plantations and roasted pork in interior. History in Old San Juan. For more nature and a nicer experience, the islands of Culebra and Vieques. Spanish speaking.

Saba

Dutch/English Speaking.

Saint Kitts and Nevis

English speaking.

St Barts:

Can get to St Maarten via ferry (45 minutes) French speaking. Expensive. More European than Caribbean feeling.

St Maarten / St Martin:

Can get to St Barts via various ferry, to Anguilla via a quick public or more expensive private ferry, and to Saba via Ferry. St Maarten (English/Dutch speaking), St Martin (French speaking). Dutch side has a lot of traffic, cruise port, casino, etc. French side is quieter. I think Anguilla is better than both sides unless you want noise/activities/KFC.

St Lucia

Relative to the Caribbean, St Lucia’s beaches are middling with the best near Pigeon Island and on the southeast corner (all beaches public/accessible). Bus service allows for transit without rental car. Nice scenery. Mountainous terrain in the southwest contains many waterfalls to explore/find/swim under as well as hiking opportunity. Rain forest and banana plantations in the central region. Touristy area in the northern half, centered mostly around Rodney Bay. If you don’t want a tourist feel but want action and location, Castries might make a good choice as it has good food and nightlife options and is near Rodney Bay. Generally people are not very welcoming but typically helpful when needed.

If you are considering honeymoon in St Lucia, and want the cliche, go to Sandals. If you want a feeling of exclusivity and real luxury, look at Sugar Beach.

You can get to Martinique (1 hour 30 minutes), Dominica (4 hours 30 minutes) and Guadeloupe (7 hours) by ferry.

St Lucia is English speaking.

Saint Vincent and the Grenadines

English speaking.

Sint Eustatius

Dutch/English speaking.

Trinidad & Tobago:

Certain foods are offered in December such as Pastelles, Black Cake and Ponche de Creme. Tobago is the more natural of the two. Trinidad is the more lively. Good beaches, good nature. English speaking.

Turks and Caicos:

Great diving and beaches. Turks and Caicos is a place to go for relaxing, swimming, diving & snorkeling. At night, there are restaurants and casinos but nightlife is not the main draw. There isn’t much to explore here as far as wildlife or natural wonders (outside of what is found in the sea). English speaking.

The US Virgin Islands:

St Thomas (High Energy), St John (Sleepy/Nature), St Croix (Hybrid). You can travel to the British Virgin Islands via ferry. English speaking.

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Tak

New York, NY
Internationally-published photographer with a passion for creative food, fine products, unique cultures and underground music. Twitter / Instagram / takw at triphash dot com