Have questions? We're here.
Vivid blue waters of the Caribbean

Windward Islands Small Ship Cruises

Travel made your way
Talk with an expert
Customize any aspect of your Caribbean trip. 1.406.541.2677
Help Me Plan My Trip
 Choose from one of these sailing cruises or small ship cruises that will let you access the best of the Windward Islands' culture, wildlife, and isolated beaches. Additionally, on many of Adventure Life's cruises, you'll have the opportunity to swim, snorkel, eat traditional cuisines, and explore the underwater reefs. Consider taking a small ship cruise on your Caribbean trip in order to be able to access smaller reefs, beaches, and coves.  Contact one of Adventure Life's Caribbean experts if you have any questions about traveling to the Windward Islands or anywhere else in the Caribbean.

10 Best Windward Islands Small Ship Cruises & Tours for 2021

Top Windward Islands Small Ship Cruises & Tours for 2021

Top-Rated Windward Islands Small Ship Cruises

Best Windward Island Cruise Deals for 2021

Trip NameSaveFromDaysNext DepartureSummary
Leeward IslandsSavings$23208Nov 27, 2021The Star Flyer authentic clipper hosts this 8-day cruise of the Caribbean, departing on a roundtrip from St. Maarten and sailing Nevis, Dominica, …
GrenadinesSavings$21608Jan 2, 2022Departing from Barbados on this 8-day roundtrip Caribbean cruise aboard the Royal Clipper luxury sailing ship, this relaxing trip through the …
Windward IslandsSavings$23808Dec 11, 2021Board the luxurious Royal Clipper sailing ship for this 8-day roundtrip cruise of the Caribbean, departing from Bridgetown, Barbados to St. Lucia, …
Transatlantic: Lisbon to BarbadosSavings$261017Oct 21, 2022Join the Royal Clipper on a fantastic adventure across the Atlantic Ocean from the capital city of Lisbon, Portugal to Barbados, a heaven on Earth. …
Transatlantic Voyage from Miami to LisbonSavings$488015Apr 20, 2021During your 15-day cruise, board your luxurious ship in Miami and stop in the stunning Bahamas, then sail across the tropical Caribbean waters on …
Panama Canal: Barbados to PanamaSavings$423015Nov 6, 2021Starting at the Caribbean port of Bridgetown, this 15-day cruise aboard the Royal Clipper sails through the turquoise Caribbean waters en route to …
Antigua to BarbadosSavings$23808Dec 4, 2021Royal Clipper offers the ultimate sea-going experience as you travel to the beautiful beaches and landscapes of the Caribbean. This 8-day sailing …
Fort Lauderdale to BridgetownSavings$470011Dec 17, 2021Discover the Caribbean on this 11-day sailing adventure. Visit the colorful small cities and the exceptional beaches this archipelago is famous for …

Windward Islands Travel Guide

All Windward Islands Articles
Windward Islands Wildlife

The 750 sq km Dominica has been called the “Nature Isle of the Caribbean,” home to the rain forest as well as xeric areas on the coast, the world’s second largest boiling lake which results from the geothermal-volcanic activity on the island. Rare plants and animals and bird species. It makes sense that the economy here is dominated by agriculture and tourism. Over 160 avian species exist on the island including nesting of endangered parrot species.

The mountains and forests of the Windward island group facilitate diversity and abundance of flora and fauna. Animals such as crocodiles, iguanas (including the endangered blue iguana), monkeys and ocelot can be seen in parks and on wildlife tours. The warm waters of the Caribbean provide an ideal environment for coral, sea turtles and dolphins. Saint Lucia is known for its rain forest walks which expose visitors to a combination of tropical plants, rare birds and exotic animals.
Best time to visit the Windward Islands

St. Lucia:
St. Lucia's best weather comes between December and April but there will be large crowds and rooms can be extremely expensive. Between May and June is the best time to visit as there is still excellent weather, but the crowds and prices will have dropped vastly. Between July and November is hurricane season but there will be lower prices and this is the peak of the festival season.

Grenada: The best time to visit Grenada is between mid-December and April. Although the prices and crowds will be at their high point, you can rely on solid weather. Between May and November prices will drop a ton but during the summer it's extremely rainy in Grenada.
Dominica: Between February and May is widely considered the best time to visit Dominica because the crowds aren't extremely large and the weather is perfect but the hotel rates will be high. Between June and September is the peak of the hurricane season in Dominica and it's highly recommended that you avoid these months because it will be extremely rainy day in and day out; but there will be amazing hotel deals if you can find one that's open. Between October and January lodgings will be cheaper and although there may be some infrequent rain, it shouldn't ruin your trip.

Trinidad & Tobago: Between January and May is widely considered the best time to visit Trinidad and Tobago this is because the Trinidad Carnival is during this time and the weather is ideal but during this time. The only problem with visiting during this time is room rates will be higher, especially between February and March when the Trinidad Carnival begins. Between June and December is also a good time to visit, it's extremely unlikely that a hurricane will appear but the season is still relatively wet. A lot of European travelers come to Tobago during this time for the deals on lodgings so be sure to book something in advance, regardless of what season you're planning on visiting.

Martinique: Between December and April is the best time to visit because, although lodging and activity prices are extremely high, the Martinique Carnival happens annually in this season and the temperatures are perfect, generally in the low 80's degrees Fahrenheit (26.7 degrees Celsius). Between May and early June are also good months to visit Martinique because hotels will have discounted prices and there will be fewer crowds but these months will still have around the same temperatures and little rain. Between June and November is the rainy and hurricane season and Martinique gets very wet. Additionally, lodging rates do get lower (for the few hotels that are still open) but may not be as low as you'd expect.

St. Vincent & the Grenadines: The most popular time to visit St. Vincent and the Grenadines is between mid-November and April as the temperatures are ideal and there are a ton of festivals during this time but you'll have to book your accommodations at least 3 months in advance and the hotel prices will be extremely high. Between May and June is a sweet spot between high tourism season and hurricane season where you can get great deals on hotels and the temperatures are still fantastic, with little rain. Between July and October is hurricane season with the most rain being in July but the threat of tropical storms throughout the season. The benefit of visiting St. Vincent and the Grenadines during this time is you can observe St. Vincent's lush landscape in its prime.
Windward Islands Geography

The Caribbean island chain is over two thousand miles long. To the east of the islands is the Atlantic Ocean, to the south is the Caribbean Sea and the north of South America, to the right in the Gulf of Mexico and to the north is mainland America. The Caribbean Islands became known as the West Indies when Columbus arrive there and thought he was seeing the west of the Indian subcontinent.

The Windward Islands are located in the foot of the Caribbean Sea. The islands form part of the easternmost boundary of the Caribbean Sea.
Since there are over seven thousands Caribbean islands islets reefs and cays the diversity among them is pronounced. The Windward Islands are generally mountainous and volcanic in origin. Some islands have active volcanoes such as Mount Pelee on Martinique where gray and black sand beaches are the result of volcanic ash. Saint Lucia actually has a drive in volcano. Saint Vincent is one of the few places which has both white and black sand beaches.

Grenada, sometimes called “Island of Spice” due to being a major exporter of nutmeg and mace is an island country to the southwest of Saint Vincent is the largest island of the Grenadines which are six hundred plus in number.

Windward Islands FAQs

What islands make up the Windward Islands?
The Windward Islands are made up of the larger islands of the Lesser Antilles. These include Dominica, Martinique, Saint Lucia, Saint Vincent & the Grenadines, Grenada, and Trinidad and Tobago.

Is Barbados a Windward Island?
Although it may seem like it due to its proximity to the other Windward Islands, it is not. 

Is Dominica a Leeward Island?
No, originally Dominica was a Leeward Island but in the 1940's for political reasons the British changed it to a Windward Island.

Why are the Windward Islands called such?
The Windward Islands are called this because they faced the wind for ships heading to the New World: making it easier to dock.

Which side of the road do they drive on in the Windward Islands?
On the left side of the road. 

Do you need a visa to visit the Windward Islands?
A visa isn't required for citizens of the US, Canada, the EU, and many of the Commonwealth countries.

Should I purchase travel insurance when visiting the Windward Islands?
You should definitely purchase travel insurance, and Adventure Life makes it easy through Travel Guard on our Once You've Booked page.

Caribbean Travel Guide

Favorite Caribbean Tours & Cruises

Top Windward Islands Travel Destinations

Windward Islands Trips by Departure Date

Windward Islands Trips by Duration

Why Travel With Adventure Life

More Reasons

Recognized By

All News