Caribbean Vacations

Everyone has heard of a horror story where someone they know went to an Island only to have chair wars on the beach, or very little breathing room to take in the culture, sights, and beauty of the island they are on. Touristy Islands tend to be where Spring Breakers flock in droves and high school kids barely 18 are ecstatic they can drink. If you prefer crowds and lively night life our Island suggestions would be different than if you wanted space to explore on your own and even different islands still if you want to feel as though you are marooned in paradise all by yourselves. There are exceptions to the rules when you have an Island, like Jamaica, which has 3 distinctly separate vibes. That is why you will find some Islands in multiple categories below.

Touristy: Mexico, Dominican Republic, Aruba, Costa Rica, Panama, Trinidad, Hawaii Big Island), Puerto Rico, Jamaica, Turks & Caicos, Bahamas, Florida Keys

Semi-Touristy: Jamaica, Curacao, Barbados, Saint Lucia, Martinique, Saint Martin, US & British Virgin Islands, Jamaica, Cayman Islands, Bahamas, Hawaii (except big island)

Non-Touristy: Belize, Bonaire, Grenada, St Vincent, Antigua, Dominiqua, Guadalupe, St Kitts & Nevis, Anguilla, Jamaica, Bahamas, Hawaii (except big island)

Most vacation packages we can book can include flights at a highly discounted rate. Do you prefer direct flights? While not available to every island, there are a ton of options depending on which major international airport you're closest to and if you're willing to drive to get there. 

Generally, the further away from the United States you get, the less likely you are to get a direct flight, but there are exceptions to the rule. 

November to April is peak season for travel to the Caribbean and airlines typically offer more direct flights for peak season than they do for the slow season. Once you get into hurricane season (June to October) there's even less availability for flights with fewer airlines and airports. Have a question on flight availability in your area? Reach out and we're happy to talk about all of your options. 

Direct Flights to Caribbean: Altana, Boston, Charlotte, Chicago, Dallas, Denver, Detroit, Houston, Los Angeles, Minneapolis, New York, Newark, Orlando, Philidelphia, Seattle & Washington D.C.

There are over 7000 islands, and they all have different characteristics. While some islands are flat, others have lush jungles and steep cliffs.  You can find volcanos, waterfalls, deserts, tropical forests, and uninhabited islands. There are soft white sand beaches, black sand beaches, pebble beaches and steep cliff drop offs. The larger the island, the more likely they are to have a variety of regions offering your choice of habitat to play in. We separate activities on Islands into three main categories. We take into consideration if there are a variety of land sports, watersports, or a combination of the two. Your love of being IN the ocean will give us a better idea of which island is right for you. Here are some examples:

A little bit of both: Antigua, Saint Martin, Guadalupe, St Vincent & the Grenadines, Cayman Islands, Bermuda & Grenada

A lot of both: Jamaica, Saint Lucia, Hawaii, Trinidad, Costa Rica, Curacao, Mexico, Puerto Rico, & Barbados

Mainly land sports: Saba, Dominique, Panama & Montserrat

Mainly water sports: Turks & Caicos, US & British Virgin Islands, Guadalupe, Fiji, Bali, Belize, Dominican Republic, Aruba, Bahamas, Maldives & Bonaire

In the United States we have private and public beaches. While different islands have different regulations on their beaches, some islands are more private than others. Antigua, for example, declares that all of its 365 beaches are public, but you can find areas of beach that FEEL Secluded from the world around you. Here is a list of some islands with different beach regulations. 

Public: Antigua, Barbados, Grenada, Anguilla, Costa Rica, Belize, Puerto Rico, Turks & Caicos, Mexico, Cayman Islands, Bahamas, Bonaire, Saint Lucia, Puerto Rico, Hawaii, Panama, St Kitts & Nevis

Technically public: Aruba, Dominican Republic, Saint Vincent

Public & Private: Jamaica, Bermuda, Florida Keys, Bali, Fiji

Private only: Maldives 

The Caribbean Islands offer many cultural experiences. Whether you prefer wine tasting or rum tasting, we have an Island just for you. The fun doesn't stop there. Some islands offer cooking classes in their local cuisine, have historical buildings and ruins to tour, or put on a display of color you will never forget in something called a "Carnival". No two Carnivals are alike, so it's not a one and done celebration. While Trinidad is the birthplace of the carnival, nearly every Caribbean Island now hosts their own Carnival celebrating freedom from colonial rule, enslavement, and in honor of their culture and ancestorial roots.  Carnival goers don masks and costumes and walk in parades so bright with color that you'll need to wear your best pair of sunglasses just to watch it all. Carnivals are held ahead of religious holidays or fasts and allow attendees to break from religious rules they typically follow. Some islands celebrate for so long it stretches into months instead of days. Below is a list of Carnivals typically held each month. Contact us to book your cultural island experience today!

We hope that any trip you take with us is one you want to call home and tell everyone about. We understand that budgets can be tight and that vacations can be once in a lifetime. That's all the more reason to let us work for you to get you the best deal for your unforgettable vacation.   

No island is off limits no matter what price range you are in.  It just means that if you choose a higher priced island in general, we will need to get creative with your hotel accommodations. That may mean you could go for 4 days versus 7, your hotel would be further from the beach, or you'd stay in a rental home and need to rent a car and cook your own food. No matter the location, we have tons of options. Below you will find a list of where each island generally sits on the cost scale.