Sailing in the Caribbean is a dream of many sailors. The beautiful sea, the trade wind and the pleasant waters are ideal for a sailing vacation, not to mention the fact that navigating amongst the many islands here is quite exciting. The ports and islands in the Caribbean are ideal for those who love adventures, beautiful sights, and hotness.
Read more information about crewed sailboat charter in the Caribbean on the following tabs: About Caribbean, Caribbean weather. Get some inspiration from the Caribbean itineraries tab and start planning your next sailing itinerary, read detailed descriptions of Caribbean sailing destinations, or read our Caribbean sailing article.
Location of the Caribbean
The phrase, Caribbean region, stands for the North and Central American groups of islands. In a broader sense, some Central and South American countries also belong here, such as Columbia or Venezuela. There are more than 700 islands in the region. We can divide the Caribbean Islands into three main parts. The Bahamas, the Greater Antilles, and the Lesser Antilles.
History of the Caribbean
Christopher Columbus discovered the vicinity of the Caribbean Sea. Spain and Portugal colonized the region. According to the Treaty of Tordesillas, both parties agreed on a peaceful subdivision of the area. Spanish and Portuguese influence decreased in the 1600s as the Dutch, French, and British expropriated the islands. The region engaged in the trade of sugar, coffee, tobacco, cotton, and rice thanks to the plantations on the Caribbean islands.
Beaches in the Caribbean
There are several gorgeous beaches, gulfs, and lagoons here. The crystal clear seawater and warm sunlight create a picturesque view. The beauty of the landscape will surely make your travel memorable. The white sandy shores of the Caribbean Sea are among the most astonishing swimming sites in the world. Here are some:
Gulf of Maundays, Anguilla
One of the most popular holiday resorts, Cap Julica is in this gulf. The amazing five-star resort provides full comfort and luxury. Thus, no wonder celebrities also like staying here. The beach has a private bar and other services as well.
Valley Church, Antigua
A cosy beach that enchants visitors with different shades of blue water. The water is calm and crystal clear, white sand carpet covers its shore. You can discover hundreds of other beaches between Antigua and Barbuda. They will certainly outshine your expectations. The secret gems of this area are its hidden gulfs, which you too can explore if you rent a boat.
Pink Sands beach
Many visit Harbour Island to view this famous section of the seaside. The coral is a unique mixture of broken shells, miniature stones, and calcium carbonate. It colours the sand with pink fragments. It’s a wide and long beach surrounded by calm water. It can be an ideal and beautiful venue for wedding ceremonies, sports, or yoga.
Treasure beach, Bahamas
It’s among the best beaches in the world. Treasure beach is a 3, 5-mile-long section of the shore with every service available to make a vacation incomparable and even more excellent. You can enjoy pleasant cafés and restaurants or try watersports.
Main attractions in the Caribbean
The picturesque scenery welcomes visitors with several colourful and unique programs. Besides beautiful beaches, you can take pleasure in viewing the exotic flora of the jungle or the underwater wildlife. Sea turtles are amazing residents of the Caribbean Sea. They are one of the endangered species, thus, numerous rescue and breeding programs started in the past few years to protect the animals. Many visitors come to Puerto Rico to see the turtles, while they’re laying their eggs in the sand. They also come to see the exciting moment, when the little turtles leave their nests and go into the water. Besides water and seaside sights the Caribbean region also has a rich cultural heritage. There are more than 40 museums in Cuba, that display art, music, the revolution, chocolate, or cigars.
The Caribbean weather
The Caribbean region has the traits of all year hot and humid tropical climate. The weather is somewhat cool and dry from the middle of January to the middle of April. From the middle of June to the middle of November it’s usually hot, wet, and rainy. Subtropical monsoon climate dominates in the region. The average yearly temperature is 28 °C.
Sailboat charter Caribbean with crew
A roundtrip on the Caribbean Sea could be a very exciting and memorable program for the whole family. Rent a small boat, a luxury yacht, or a sailboat. It’s important that you find out about landing places. The Caribbean region involves numerous ports, small and large. However, they might be very different. The most popular and high-standard ports are in the larger cities. These are the ports of for example Nassau, Falmouth, Puerto Rico, Philipsburg, or Mexico. They are well-equipped and provide all services inevitable for boating. The majority of sea centers and smaller islands are in daily connection.
The most popular ports in the Bahamas
Great Guana Cay
Great Guana Cay is located in the centre of the Exumas. It has two great anchorages: Black Point and Little Bay. Black Point is a true gem with a nice port and several moorings. People are very friendly and casual, and they find it important to help sailors in any way they can. Little Bay is a small bay at the southern end of Black Point. The sea bottom is sandy, making it ideal for securing our boat safely. The depth of water is app. 3-4 metres. There is a beautiful beach here, but there are no establishments, ports or shops. Information about Exumas sailing or boat rental in Exumas
Spanish Wells is located on St. Georges Cay, west of the northern corner of Eleuthera. Its port is constituted by a long channel bordered by two small islands. It is protected well and is only open for the winds coming from the eastern direction. There is a great port and a hurricane hole in the west where boats are tied to mangrove trees. There are six anchoring buoys on the eastern side. We can find Spanish Wells Yacht Haven & Marina here which is a full-service yacht marina with 40 berths; besides the basic services, they also have a bicycle rental.
The downtown is within walking distance. We can anchor at Royal Island Harbour in the west, which provides ideal anchorages for vessels with a larger draft. The only disadvantage is that they have no amenities or services. Information about Eleuthera sailing, or boat rental in EleutheraMore about Bahamas sailing tours, or Bahamas yacht rental
The most popular ports in the BVI
Nanny Cay is located on the southern coast of Tortola. It is located a little over 3 kilometres from Burt Point. At this port, we have the opportunity to pull our boat from the water, among other services. Nanny Cay Marina offers 320 berths; 120 on the outer parts and 200 in the inside. They provide access to fuel and electricity in both areas. We need to pass through a narrow route for entry.
Road Town is the capital of Tortola and the sailing centre of the British Virgin Islands. We can enter the port through the Sir Francis Drake Channel. Road Harbour has several yacht marinas providing full service and accommodation. We can find Road Reef Marina, Fort Burt and Wickham’s Cay I and II here; Road Reef Marina and Fort Burt are on the western side, while Wickham’s Cay is on the north. There are over 120 berths and downtown Road Town can be found nearby. Many sailors start their trip here when visiting the British Virgin Islands. Information about sailing in Tortola, or boat hire in Tortola
Virgin Gorda Yacht Harbor és St. Thomas Bay
The Virgin Gorda Yacht Harbor is in St. Thomas Bay. It is easy to approach it, we only have to sail the marked channel. The harbour is beautiful, offering great services and marine gas. There are 100 berths, and it is possible to stay for only a few hours, a day, or long-term as well. It is close to the centre of Spanish Town. It is a very peaceful town where you can find many shops, restaurants, and bars. One of the most famous attractions of the town, The Baths, is about 3 km from here. This is a collection of granite rocks on the beach that have become large rock formations. The rocks from tidal basins, channels, and spectacular caves open to the surrounding waters. Information about Virgin Gorda sailing, or Virgin Gorda boat chartersMore about BVI sailing routes, or BVI boat rental
The biggest ports in Puerto Rico
San Juan Cruise Port
With two terminals, San Cruise Port is one of the largest and busiest ports in the Caribbean. The two terminals can accommodate up to 9 cruise ships at the same time. Due to its geographical location, the port is safe even during hurricane season. The port offers several services like towing, drinking water access and electricity, telecommunication services and shops. The city’s tourist attractions are easily accessible by public transport.
Marina Puerto Chico ( Fajardo )
The marina of Fajardo is located on the east coast of Puerto Rico. It is a natural, quiet coast, the depth of the water is 5-6 m. Despite its small size, it has a great infrastructure: water, electricity and refuelling are available. You can easily visit Culebra, Vieques and the British Virgin Islands from here.
Port of Mayagüez
The third busiest port in Puerto Rico is northwest of downtown Mayagüez, stretching for 6 km along the coast. The depth of the water is 8-9 m. Despite being one of the smaller ports, it can accommodate boats up to 150 m in length. The communication infrastructure is also outstanding. More about Puerto Rico sailing, or boat rental in Puerto Rico
The most popular ports in Mexico
La Paz is the most city in southern Mexico on the Baja California Península. It has several ports.. One of the best-equipped ports is Marina Cortez, located in the heart of the bay. It offers a number of exclusive services for even the largest sea yachts.
The city’s port, called El Cid, is way more than a simple landing opportunity. There is a bustling market and several miles of nearby beaches with golden sand. The local dive shop is excellent, you can get all the necessary equipment here. In the port area, you will find plenty of high-quality accommodation opportunities. More about Mexico sailing, or boat rental in Mexico
The biggest ports in Cuba
Port of Cienfuegos
The main port in the southern part of the island is La Perla del Sur or the Pearl of the South. The port of Cienfuegos is considered a large port in Cuba. It can accommodate boats up to 150 m. The depth of the seabed is 12 m. While Christopher Columbus visited in 1494, it was formally founded in 1819.
Port of Santiago de Cuba
The second-largest port city of Cuba is located in the south-eastern part of the island, in Oriente Province. It is a major port for import and export in the region. The bay is quiet and protected against winds. The famous Casa del Habano is a few-minute walk from the port. Here, you can buy the best-quality Cuban cigars and you can visit the Bacardi Museum. More about Cuba sailing, or boat rental in CubaAnother option is to explore the sea by yourself on a deck of a yacht charter. If your only wish is an amazing sea vacation, or the presence of stunning natural wonders, visit the Caribbean Sea to find all of these.Find sailing routes in the Caribbean.
For more precise information about the Caribbean area, please narrow down your search. It is necessary in this case, because of geographic diversity and the large scope of the area. First, select a destination on the crewed sailboat charter in the Caribbean tab and choose the Weather tab of the selected area and read the related description.
Rent a sailboat in the Caribbean wit crew, and cruise around the Caribbean
Puerto Rico sailing itineraries
Day 1. San Juan – Loiza 30, 98 km (19, 25 mi), Day 2. Loiza – Fajardo (Isleta Marina) 53, 34 km (33, 15 mi), Day 3. Fajardo – St.Thomas (Yacht Haven Grande) 76, 68 km (47, 65 mi), Day 4. Yacht Haven Grande – Red Hook (St.Thomas) 15, 84 km (9, 84 mi), Day 5. Red Hook – Hull bay (St.Thomas) 15, 12 km (9, 40 mi), Day 6. Hull bay – Culebra (Dewey Harbor) 41, 04 km (25, 50 mi), Day 7. Culebra – Playa Fortuna – San Juan 94, 80 km (58, 91 mi).
Bahamas sailing itineraries
Day 1. Miami – Port Royal 82, 63 km (51, 34 mi), Day 2. Port Royal – Gun Cay (Honeymoon Harbour) 13, 86 km (8, 61 mi), Day 3. Gun Cay – Ocean Cay 21, 53 km (13, 38 mi), Day 4. Ocean Cay – North Cat Cay (Honeymoon Harbour), Day 5. North Cat Cay – Bailey Town 17, 74 km (11, 02 mi), Day 6. Bailey Town – Alice Town 2, 39 km (1, 48 mi), Day 7. Alice Town – Miami 82, 95 km (51, 54 mi).
Day 1. Marsh Harbour – Little Harbour 24, 55 km (15, 25 mi), Day 2. Little Harbour – Abaco National Park – Sandy Point 97, 10 km (60, 34 mi), Day 3. Sandy Point – Wood Cay – Great Abaco 47, 96 km (29, 80 mi), Day 4. Great Abaco – Big Joe Downer Cay -Little Joe Downer Cay – South Riding Point 96, 70 km (60, 09 mi), Day 5. South Riding Point – Nunjack Cay – Green Turtle Cay 103, 35 km (64, 22 mi), Day 6. Green Turtle Cay – Treasure Cay – Man-O-War Cay / Guana Cay 28, 44 km (17, 67 mi), Day 7. Guana Cay – Pelican Cay Land & Sea Park – Elbow Cay – Marsh Harbour 53, 60 km (33, 30 mi).
Day 1. Providenciales (Turks- és Caicos islands) Turtle Cove Marina – Mangrove Cay 10, 80 km (6, 71 mi) Day 2. Mangrove Cay – Cockburn Harbor 70, 10 km (43, 56 mi) Day 3. Cockburn Harbor – Big Sand Cay 45, 00 km (27, 96 mi) Day 4. Big Sand Cay – Luperón Harbor (Dominican Republic) 148, 30 km (92, 15 mi) Day 5. Luperón – Puerto Plata 30, 20 km (18, 77 mi) Day 6. Puerto Plata – Sosúa 20, 15 km (12, 52 mi) Day 7. Sosúa – Playa el Valle 142, 95 km (88, 82 mi) Day 8. Playa el Valle – Puerto Bahia Samaná 62, 70 km (38, 96 mi) Day 9. Samaná – Miches 35, 05 km (21, 78 mi) Day 10. Miches – Cap Cana (Punta Cana) 102, 30 km (63, 57 mi) Day 11. Cap Cana – Isla Mona (Puerto Rico) 65, 00 km (40, 39 mi) Day 12. Isla Mona – Mayagüez 71, 70 km (44, 55 mi) Day 13. Mayagüez – Boquerón 26, 90 km (16, 72 mi) Day 14. Boquerón – Isla Giligan – Guanica 48, 40 km (30, 07 mi)
Read more about Bahamas sailing trips
Antigua sailing itineraries
Day 1. English Harbour – Nonsuch Bay 18, 24 km (11, 33 mi), Day 2. Nonsuch Bay – Low Bay (Barbuda) 55, 26 km (34, 34 mi), Day 3. Low Bay – Coco Point (Barbuda)18, 41 km (11, 44 mi), Day 4. Coco Point – Dickenson Bay 52, 91 km (32, 88 mi), Day 5. Dickenson Bay – St.John’s 6, 34 km (3, 94 mi), Day 6. St.John’s – Jolly Harbour 13, 56 km (8, 42 mi), Day 7. Jolly Harbour – Carlisle Bay – English Harbour 20, 13 km (12, 51 mi).
Day 1. Antigua, English Harbour – Jolly Harbour 21, 00 km (13, 05 mi), Day 2. Jolly Harbour – St. Kitts, Cristophe Harbour 81, 60 km (50, 71 mi), Day 3. Christophe Harbour – Sint Eustatius, Oranjestad 49, 90 km (31, 01 mi), Day 4. Oranjestad – Saint Martin, Marigot, Marina Port Royal 76, 20 km (47, 35 mi), Day 5. Marigot – Anguilla, Sandy Ground 26, 80 km (16, 65 mi), Day 6. Sandy Ground – Virgin Gorda, Biras Creek 137, 60 km (85, 50 mi), Day 7. Biras Creek – Beef Island, Bluffy Bay 24, 00 km (14, 91 mi), Day 8. Bluffy Bay – Peter Island, Great Harbor 11, 20 km (6, 96 mi), Day 9. Great Harbor – Salt Island 7, 35 km (4, 57 mi), Day 10. Salt Island – Saint Barthelémy, Gustavia 182, 85 km (113, 62 mi), Day 11. Gustavia – St. Kitts Marine Works 64, 00 km (39, 77 mi), Day 12. St. Kitts Marine Works – Nevis, Tamarind Cove Marina 28, 60 km (17, 77 mi), Day 13. Tamarind Cove Marina – Montserrat, Little Bay 57, 10 km (35, 48 mi), Day 14. Little Bay – Antigua Nonsuch Bay – English Harbor 69, 10 km (42, 94 mi).Read more Antigua sailing itineraries
BVI sailing itineraries
Day 1. Road Town – Parham Town 9, 38 km (5, 83 mi), Day 2. Parham Town – Spanish Town (Virgine Gorda Island) 14, 02 km (8, 71 mi), Day 3. Spanish Town – Anegada 31, 11 km (19, 33 mi), Day 4. Anegada – Scrub Island 32, 34 km (20, 10 mi), Day 5. Scrub Island – Jost Van Dyke 25, 61 km (15, 91 mi), Day 6. Jost Van Dyke – Cruz Bay 13, 75 km (8, 54 mi), Day 7. Cruz Bay – Nanny Cay – Road Town 25, 25 km (15, 69 mi).
Cuba sailing itineraries
Day 1. Baracoa – Moa 62, 00 km (38, 53 mi), Day 2. Moa – Tanamo 47, 17 km (29, 31 mi), Day 3. Tanamo – Nicaro 29, 92 km (18, 59 mi), Day 4. Nicaro – Antilla 43, 58 km (27, 08 mi), Day 5. Antilla – Banes 49, 26 km (30, 61 mi), Day 6. Banes – Punta Gorda 96, 39 km (59, 89 mi), Day 7. Punta Gorda – Cayo Güín – Baracoa 54, 26 km (33, 71 mi).