A Guide To Chartering In The Caribbean & The Bahamas

The Caribbean and the Bahamas shimmer with turquoise waters, white-sand beaches, and countless secrets waiting beyond the postcard views.

In the Bahamas, beneath the sands of Lucayan National Park lies one of the world’s largest underwater cave systems, while Dean’s Blue Hole plunges 202 meters into the deep. In the Exumas, Big Major Cay—better known as Pig Beach—delights with its famous swimming pigs, paddling out to greet passing boats.

Across the Caribbean, each island reveals its own wonders. In Montserrat, emerald hills resound with the music of St. Patrick’s Day, blending Irish and African traditions. St. Lucia’s Sulphur Springs invites you into the world’s only drive-in volcano for mineral-rich mud baths. Hike Pico Duarte in the Dominican Republic, the Caribbean’s highest peak, or watch flamingos sweep across Bonaire’s pink salt flats. In Puerto Rico, nightfall transforms bioluminescent bays into glowing ribbons of light across the water.

Where are the must-see destinations in the Caribbean & the Bahamas?

The Bahamas

• Tourist hotspots: Nassau, Exumas, Eleuthera, Abaco
• Marinas and ports: Nassau Yacht Haven, Albany Marina, Bay Street Marina, Staniel Cay Yacht Club, Abaco Beach Resort & Marina
• Popular beaches: Pink Sands Beach (Harbour Island), Tropic of Cancer Beach (Exuma), Treasure Cay Beach (Abaco)
• Historic sites: Nassau’s colonial core (Queen’s Staircase, Fort Charlotte), Dunmore Town (Harbour Island)

The Bahamas offers some of the world’s clearest waters and hundreds of yacht‑friendly anchorages, making it a quintessential cruising ground. From bustling Nassau to the pristine Exumas, every stop offers a mix of luxury marinas, white‑sand beaches, and charming settlements. Pink Sands Beach and Tropic of Cancer Beach are postcard‑perfect, while Abaco’s Treasure Cay offers a serene escape. Historic Nassau, with its forts and colonial architecture, adds a cultural touch to an otherwise water‑focused paradise.

Turks and Caicos Islands

• Tourist hotspots: Providenciales, Grand Turk, Salt Cay
• Marinas and ports: Blue Haven Marina, Turtle Cove Marina
• Popular beaches: Grace Bay Beach, Long Bay Beach, Governor’s Beach (Grand Turk)
• Historic sites: Grand Turk Lighthouse, Salt Cay’s salt industry ruins

Known for silky‑white beaches and vibrant reefs, Turks and Caicos blends low‑key luxury with exceptional diving and snorkeling. Grace Bay and Long Bay are ideal for watersports, while Governor’s Beach on Grand Turk offers picture‑perfect calm. Grand Turk’s lighthouse and Salt Cay’s historic ruins add heritage to a largely nature‑driven destination.

British Virgin Islands (BVI)

• Tourist hotspots: Tortola, Virgin Gorda, Jost Van Dyke, Anegada
• Marinas and ports: Nanny Cay Marina, Soper’s Hole Wharf & Marina, Virgin Gorda Yacht Harbour
• Popular beaches: White Bay (Jost Van Dyke), The Baths (Virgin Gorda), Cow Wreck Beach (Anegada)
• Historic sites: Callwood Rum Distillery, Copper Mine Ruins (Virgin Gorda)

The BVI is a sailor’s paradise—calm waters, short island hops, and countless anchorages. White Bay is legendary for its barefoot beach bars, The Baths astonish with granite boulders and hidden pools, and Cow Wreck Beach offers Anegada’s endless white sands. Copper Mine Ruins and Callwood Distillery hint at the islands’ layered history.

U.S. Virgin Islands (USVI)

• Tourist hotspots: St. Thomas, St. John, St. Croix
• Marinas and ports: Yacht Haven Grande, Crown Bay Marina, American Yacht Harbor
• Popular beaches: Magens Bay (St. Thomas), Trunk Bay (St. John), Sandy Point (St. Croix)
• Historic sites: Fort Christian (St. Thomas), Estate Whim Plantation (St. Croix)

USVI combines U.S. convenience with Caribbean charm. Yacht Haven Grande in St. Thomas is a luxury hub, while nearby Trunk Bay and Magens Bay rank among the Caribbean’s most beautiful beaches. History buffs can explore Fort Christian’s colonial past and plantation estates on St. Croix.

Puerto Rico

• Tourist hotspots: San Juan, Culebra, Vieques
• Marinas and ports: Puerto del Rey Marina, San Juan Bay Marina, Puerto Real Marina
• Popular beaches: Flamenco Beach (Culebra), Sun Bay (Vieques), Condado Beach (San Juan)
• Historic sites: Old San Juan (El Morro, San Cristóbal), Ponce’s historic district

Puerto Rico blends Spanish colonial heritage with tropical beauty. Old San Juan’s cobblestone streets and colorful facades lead to centuries‑old forts, while Culebra’s Flamenco Beach and Vieques’ Sun Bay invite laid‑back barefoot days. Large marinas like Puerto del Rey provide prime yacht facilities and access to both offshore islands and mainland attractions.

Saint Lucia

• Tourist hotspots: Rodney Bay, Soufrière, Marigot Bay
• Marinas and ports: Rodney Bay Marina, Marigot Bay Marina
• Popular beaches: Reduit Beach, Anse Chastanet, Sugar Beach
• Historic sites: Morne Coubaril Estate, Fort Rodney (Pigeon Island)

Saint Lucia is famed for its twin Pitons, lush rainforest, and volcanic beaches. Yachts drop anchor in Marigot Bay, one of the Caribbean’s most beautiful harbors, before exploring Sugar Beach’s white sands or diving into Anse Chastanet’s reefs. Pigeon Island and Morne Coubaril Estate add a historical dimension to the island’s natural appeal.

Antigua & Barbuda

• Tourist hotspots: English Harbour, Jolly Harbour, Barbuda
• Marinas and ports: Nelson’s Dockyard Marina, Jolly Harbour Marina, Antigua Yacht Club Marina
• Popular beaches: Half Moon Bay, Darkwood Beach, Pink Sand Beach (Barbuda)
• Historic sites: Nelson’s Dockyard, Shirley Heights Lookout

Antigua boasts 365 beaches—one for every day of the year—and a yachting scene anchored in historic English Harbour. Nelson’s Dockyard offers a blend of maritime heritage and modern marina facilities. Barbuda’s Pink Sand Beach is a tranquil retreat, while Shirley Heights offers panoramic views and lively Sunday gatherings.

Grenada

• Tourist hotspots: St. George’s, Grand Anse, Carriacou
• Marinas and ports: Port Louis Marina, Clarkes Court Bay Marina
• Popular beaches: Grand Anse Beach, Sandy Island (Carriacou), Levera Beach
• Historic sites: Fort George, Fort Frederick

Grenada, the “Spice Island,” offers fragrant markets, lush landscapes, and superb sailing to nearby Carriacou and Petite Martinique. Grand Anse Beach is a signature stretch of white sand, while Sandy Island in Carriacou is an unspoiled anchorage. Fort George and Fort Frederick reveal the island’s strategic maritime history.

What are some cultural highlights, festivals, and events awaiting you?

February kicks off with the lively Trinidad Carnival, known for its costumes and soca music, alongside the Caribbean Multihull Challenge in St. Maarten—a major sailing event. In March, luxury yachting takes center stage with the St. Barts Bucket Regatta and the St. Thomas International Regatta in the USVI. April hosts the BVI Spring Regatta, a favorite among competitive sailors. In May, Saint Lucia Jazz & Arts Festival blends international jazz acts with Caribbean rhythm and local art. June brings spiritual and cultural energy with Barbados Gospelfest, a Christian music celebration, and Inti Raymi in Peru, an ancient Incan festival honoring the sun. July showcases Caribbean music at its best with Reggae Sumfest in Jamaica and the Saint Kitts Music Festival, both featuring top regional and international artists. In August, the festive Crop Over Festival in Barbados and the Anguilla Summer Festival celebrate island heritage with calypso, boat races, and carnival parades. September turns up the cultural heat with Grenada’s SpiceMas, a masquerade-filled carnival, and the Curaçao North Sea Jazz Festival, known for its global jazz and soul acts. October highlights sailing and culture with the Monohull Regatta in Antigua and the World Creole Music Festival in Dominica, which showcases Creole heritage through music and food. In November, the Pirates Week Festival in the Cayman Islands features mock pirate landings, fireworks, and street parties, while the Bahamas Restaurant Week offers a chance to sample top local cuisine. Finally, December ends the year with New Year’s Regattas in Antigua and St. Barts, and the final day of Junkanoo on January 1.

What local dishes should you try in the Caribbean & the Bahamas?

When sailing through the Bahamas and the Caribbean, some of the region’s most beloved local dishes can be found just steps from the marina or served fresh at dockside beach bars. In the Bahamas, cracked conch is the undeniable star—tenderized, deep-fried, and served with a squeeze of lime, it’s a must-try that’s easy to find near any harbor, along with the refreshing and citrusy conch salad, often prepared to order right at waterfront conch shacks. In Jamaica, jerk chicken and pork are staples near popular ports like Montego Bay and Ocho Rios, cooked low and slow over pimento wood and served with sides like festival or rice and peas. These smoky, spicy flavors define the island’s food culture and are readily available at beach grills and roadside spots near yacht anchorages. In Barbados, flying fish and cou-cou is the national dish and a common offering in Bridgetown’s harborfront restaurants, while in Trinidad, doubles—soft, curried chickpea-filled flatbreads—are a favorite grab-and-go bite just minutes from the docks. Whether you’re anchored off St. Lucia, the Virgin Islands, or the Exumas, these flavorful dishes reflect the islands’ rich heritage and are always within easy reach for charter guests wanting a true taste of the Caribbean.

What’s next? 

From the pink sands of Harbour Island to the volcanic views of St. Lucia, our Caribbean and Bahamas itineraries highlight some of the region’s best destinations. Check our itineraries to start planning your island journey.

Find your ideal yacht from our curated collection and experience these waters in true luxury.