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21 Days Caribbean Pirate Adventure Itinerary

Last updated: 2024 Jun 29

Pirate Legends in Nassau

Morning

Start your adventure with a visit to the Pirates of Nassau Museum. This interactive museum brings the Golden Age of Piracy to life, offering a glimpse into the lives of infamous pirates like Blackbeard and Anne Bonny. The exhibits are immersive and educational, making it a perfect start to your pirate-themed journey. Enjoy breakfast at Café Matisse, known for its delightful pastries and coffee.

Afternoon

After the museum, head over to the Queen's Staircase, a historic site built by slaves in the late 18th century. The staircase offers stunning views and is steeped in history. For lunch, dine at Greycliff Restaurant, which offers a luxurious dining experience with Bahamian flavors.

Evening

In the evening, embark on Pirate Sunset Cruise. This tour takes you around Nassau's harbor as you enjoy tales of pirate lore while watching the sunset. End your day with dinner at The Poop Deck, famous for its seafood and waterfront views.

Bedtime

Find amazing hotels in Nassau, Bahamas.

Exploring Pirate Havens in Jamaica

Morning

Begin your day with a visit to Rose Hall Great House, rumored to be haunted by the White Witch of Rose Hall. This historic plantation house offers guided tours that delve into its eerie past. Have breakfast at The Pelican Grill, known for its hearty Jamaican breakfast options.

Afternoon

Next, head to Doctor's Cave Beach for some relaxation and snorkeling in crystal-clear waters. For lunch, try Margaritaville Montego Bay, which offers delicious food and fun beachside activities.

Evening

In the evening, join Luminous Lagoon Tour. This unique tour takes you to one of only four bioluminescent lagoons in the world where you can swim among glowing microorganisms. Conclude your day with dinner at Houseboat Grill, an iconic floating restaurant offering fresh seafood.

Bedtime

Find amazing hotels in Montego Bay, Jamaica.

Pirate Adventures in Puerto Rico

Morning

Start your day exploring Castillo San Felipe del Morro (El Morro), a 16th-century citadel that once protected San Juan from pirates and invaders. Enjoy breakfast at Caficultura, known for its artisanal coffee and local pastries.

Afternoon

After El Morro, wander through Old San Juan's cobblestone streets filled with colorful colonial buildings and shops. Have lunch at La Bombonera, a historic café famous for its mallorcas (sweet bread) sandwiches.

Evening

In the evening, take part in Night Kayak Tour in Bio Bay. Paddle through bioluminescent waters under the stars while learning about local marine life from expert guides. End your night with dinner at Raíces, celebrated for its authentic Puerto Rican cuisine.

Bedtime

Find amazing hotels in San Juan, Puerto Rico.

Treasure Hunting in the Cayman Islands

Morning

Begin your day with a visit to the Cayman Islands National Museum. This museum offers fascinating exhibits on the islands' natural and cultural history, including pirate artifacts. Enjoy breakfast at Café del Sol, known for its excellent coffee and pastries.

Afternoon

After the museum, head to Seven Mile Beach for some relaxation and water activities. This iconic beach is perfect for snorkeling, swimming, or simply lounging under the sun. For lunch, dine at Calypso Grill, which offers a delightful menu of fresh seafood and Caribbean flavors.

Evening

In the evening, embark on Pirate Adventure Cruise. This tour takes you on a pirate ship replica where you can enjoy live entertainment, treasure hunts, and stunning sunset views. End your day with dinner at The Wharf, famous for its waterfront dining and seafood specialties.

Bedtime

Find amazing hotels in Grand Cayman, Cayman Islands.

Pirate Legends in St. Thomas

Morning

Start your day with a visit to Blackbeard's Castle, one of five National Historic Landmarks in the U.S. Virgin Islands. The castle offers panoramic views of Charlotte Amalie and an intriguing history linked to the infamous pirate Blackbeard. Have breakfast at Hermitage Hill, known for its delicious breakfast options and scenic views.

Afternoon

St Thomas Island Tour will take you around key historical sites including Fort Christian and Emancipation Garden while narrating tales of pirate lore associated with these landmarks. For lunch, try Oceana Restaurant & Bistro, offering exquisite dishes with a Caribbean twist.

Evening

Sunset Sail & Pirate Stories is perfect for winding down your day as you sail around St. Thomas while listening to captivating pirate stories from expert guides. Conclude your evening with dinner at Havana Blue, celebrated for its fusion cuisine and stunning ocean views.

Bedtime

Find amazing hotels in Charlotte Amalie, St. Thomas.

Exploring Pirate Caves in Barbados

Morning

Harrison's Cave Tour will start your day by taking you through an underground wonderland filled with stalactites, stalagmites, streams, and waterfalls that were once rumored to hide pirate treasures. Enjoy breakfast at The Coffee Bean, known for its great coffee and pastries.

Afternoon

Barbados Island Tour will guide you through key historical sites such as St. Nicholas Abbey and Gun Hill Signal Station while narrating tales of pirates who once roamed these lands. For lunch, dine at Champers Restaurant, offering beautiful sea views and delicious Caribbean cuisine.

Evening

In the evening join Pirate Dinner Show, an interactive experience where you'll enjoy a feast while watching live performances that bring pirate legends to life! End your night with drinks at Tides Restaurant, known for its elegant setting and impressive cocktail menu.

Bedtime

Find amazing hotels in Bridgetown, Barbados.

Pirate Lore in the Dominican Republic

Morning

Begin your day with a visit to the Indigenous Eyes Ecological Park and Reserve. This natural reserve features twelve freshwater lagoons, some of which are swimmable. The park is a great place to learn about the local flora and fauna, as well as the history of the Taino people who once inhabited the island. Enjoy breakfast at Dalia's Cafe & Bakery, known for its fresh pastries and coffee.

Afternoon

After exploring the ecological park, head to Bavaro Beach for some relaxation and water activities. This beautiful beach is perfect for snorkeling, swimming, or simply lounging under the sun. For lunch, dine at Captain Cook Restaurant, which offers a delightful menu of fresh seafood and Caribbean flavors.

Evening

Pirate Ship Cruise will take you on an exciting evening adventure aboard a pirate ship replica. Enjoy live entertainment, treasure hunts, and stunning sunset views as you sail along the coast of Punta Cana. End your day with dinner at La Yola, famous for its waterfront dining and seafood specialties.

Bedtime

Find amazing hotels in Punta Cana, Dominican Republic.

Pirate Tales in Tortola

Morning

Sage Mountain National Park Hike will start your day with an invigorating hike through lush tropical forests. The park offers stunning views of Tortola and neighboring islands from its highest peak. Have breakfast at Dove Restaurant & Wine Bar, known for its delicious breakfast options and scenic views.

Afternoon

Tortola Island Tour will guide you through key historical sites such as Fort Burt and Callwood Rum Distillery while narrating tales of pirates who once roamed these lands. For lunch, try Pusser's Road Town Pub, offering exquisite dishes with a Caribbean twist.

Evening

Sunset Pirate Sail is perfect for winding down your day as you sail around Tortola while listening to captivating pirate stories from expert guides. Conclude your evening with dinner at Brandywine Estate Restaurant, celebrated for its fusion cuisine and stunning ocean views.

Bedtime

Find amazing hotels in Tortola, British Virgin Islands.

Pirate Legends in Antigua

Morning

Nelson's Dockyard Tour will start your day by taking you through this historic naval dockyard that was once a base for British naval operations in the Caribbean. Enjoy breakfast at Hemingway's Caribbean Cafe, known for its great coffee and pastries.

Afternoon

Antigua Island Tour will guide you through key historical sites such as Shirley Heights Lookout and Betty's Hope Plantation while narrating tales of pirates who once roamed these lands. For lunch, dine at Shear Rocks, offering beautiful sea views and delicious Caribbean cuisine.

Evening

Pirate Dinner Cruise, an interactive experience where you'll enjoy a feast while watching live performances that bring pirate legends to life! End your night with drinks at Catherine's Café Plage, known for its elegant setting and impressive cocktail menu.

Bedtime

Find amazing hotels in St. John's, Antigua.

Pirate Legends in Martinique

Morning

Start your day with a visit to the Schoelcher Library, an architectural marvel named after Victor Schoelcher, a French abolitionist. The library's design and historical significance make it a must-see. Enjoy breakfast at La Pâtisserie des Îles, known for its delicious pastries and coffee.

Afternoon

After the library, head to Fort Saint Louis, a historic fort that offers stunning views of the bay and a glimpse into Martinique's military past. For lunch, dine at Le Babaorum, which offers a delightful menu of French-Caribbean cuisine.

Evening

Pirate Night Tour will take you on an exciting evening adventure exploring Fort-de-France under the stars while listening to captivating pirate stories from expert guides. End your day with dinner at Le Cloud, famous for its rooftop dining and panoramic views.

Bedtime

Find amazing hotels in Fort-de-France, Martinique.

Pirate Adventures in St. Lucia

Morning

Soufrière Volcano Tour will start your day by taking you to the world's only drive-in volcano where you can learn about its geological history and enjoy a mud bath. Have breakfast at Jamie's Restaurant, known for its hearty breakfast options and scenic views.

Afternoon

St Lucia Island Tour will guide you through key historical sites such as Pigeon Island National Park and Morne Fortune while narrating tales of pirates who once roamed these lands. For lunch, try The Coal Pot Restaurant, offering exquisite dishes with a Caribbean twist.

Evening

Sunset Pirate Cruise is perfect for winding down your day as you sail around St. Lucia while listening to captivating pirate stories from expert guides. Conclude your evening with dinner at Bayside Restaurant, celebrated for its fusion cuisine and stunning ocean views.

Bedtime

Find amazing hotels in Castries, St. Lucia.

Pirate Tales in Grenada

Morning

Grand Etang National Park Tour will start your day with an invigorating hike through lush tropical forests filled with exotic wildlife and stunning waterfalls. Enjoy breakfast at Coconut Beach Restaurant, known for its great coffee and pastries.

Afternoon

Grenada Island Tour will guide you through key historical sites such as Fort George and Belmont Estate while narrating tales of pirates who once roamed these lands. For lunch, dine at BB's Crabback Caribbean Restaurant, offering beautiful sea views and delicious Caribbean cuisine.

Evening

Pirate Dinner Show, an interactive experience where you'll enjoy a feast while watching live performances that bring pirate legends to life! End your night with drinks at The Aquarium Restaurant, known for its elegant setting and impressive cocktail menu.

Bedtime

Find amazing hotels in St. George's, Grenada.

Pirate Myths in St. Kitts

Morning

Brimstone Hill Fortress Tour will start your day by taking you to this UNESCO World Heritage Site that offers panoramic views and a rich history of colonial battles and pirate raids. Enjoy breakfast at The Gallery Cafe, known for its delicious pastries and coffee.

Afternoon

St Kitts Island Tour will guide you through key historical sites such as Romney Manor and the Black Rocks while narrating tales of pirates who once roamed these lands. For lunch, dine at Marshall's Restaurant, offering beautiful sea views and delicious Caribbean cuisine.

Evening

Pirate Sunset Cruise, an interactive experience where you'll enjoy a feast while watching live performances that bring pirate legends to life! End your night with drinks at Salt Plage, known for its elegant setting and impressive cocktail menu.

Bedtime

Find amazing hotels in Basseterre, St. Kitts.

Pirate Legends in Dominica

Morning

Boiling Lake Hike will start your day with an invigorating hike to the world's second-largest boiling lake, surrounded by lush tropical forests filled with exotic wildlife. Enjoy breakfast at The Palisades Restaurant, known for its great coffee and pastries.

Afternoon

Dominica Island Tour will guide you through key historical sites such as Fort Shirley and Trafalgar Falls while narrating tales of pirates who once roamed these lands. For lunch, dine at Zam Zam Cafe, offering beautiful sea views and delicious Caribbean cuisine.

Evening

Pirate Dinner Show, an interactive experience where you'll enjoy a feast while watching live performances that bring pirate legends to life! End your night with drinks at The Great Old House, known for its elegant setting and impressive cocktail menu.

Bedtime

Find amazing hotels in Roseau, Dominica.

Pirate Adventures in Guadeloupe

Morning

La Soufrière Volcano Tour will start your day by taking you to this active volcano where you can learn about its geological history and enjoy stunning views from the summit. Have breakfast at Café de France, known for its hearty breakfast options and scenic views.

Afternoon

Guadeloupe Island Tour will guide you through key historical sites such as Fort Delgrès and Jardin Botanique de Deshaies while narrating tales of pirates who once roamed these lands. For lunch, try Le Poisson Rouge, offering exquisite dishes with a Caribbean twist.

Evening

Sunset Pirate Cruise is perfect for winding down your day as you sail around Guadeloupe while listening to captivating pirate stories from expert guides. Conclude your evening with dinner at Le Yacht Club, celebrated for its fusion cuisine and stunning ocean views.

Bedtime

Find amazing hotels in Pointe-à-Pitre, Guadeloupe.

Pirate Legends in Aruba

Morning

Arikok National Park Tour will start your day with an adventure through this expansive park filled with unique geological formations, caves, and indigenous flora and fauna. Enjoy breakfast at The Dutch Pancake House, known for its delicious pancakes and coffee.

Afternoon

Aruba Island Tour will guide you through key historical sites such as the California Lighthouse and Alto Vista Chapel while narrating tales of pirates who once roamed these lands. For lunch, dine at Papiamento Restaurant, offering beautiful garden views and delicious Caribbean cuisine.

Evening

Pirate Dinner Cruise, an interactive experience where you'll enjoy a feast while watching live performances that bring pirate legends to life! End your night with drinks at The West Deck, known for its elegant setting and impressive cocktail menu.

Bedtime

Find amazing hotels in Oranjestad, Aruba.

Pirate Adventures in Curaçao

Morning

Christoffel National Park Tour will start your day by taking you through this beautiful park filled with diverse wildlife and stunning landscapes. Enjoy breakfast at Bagels & Beans, known for its great coffee and pastries.

Afternoon

Curaçao Island Tour will guide you through key historical sites such as the Queen Emma Bridge and the Kura Hulanda Museum while narrating tales of pirates who once roamed these lands. For lunch, dine at Governor's Restaurant, offering beautiful sea views and delicious Caribbean cuisine.

Evening

Sunset Pirate Cruise is perfect for winding down your day as you sail around Curaçao while listening to captivating pirate stories from expert guides. Conclude your evening with dinner at Fort Nassau, celebrated for its fusion cuisine and stunning ocean views.

Bedtime

Find amazing hotels in Willemstad, Curaçao.

Pirate Tales in Trinidad & Tobago

Morning

Asa Wright Nature Centre Tour will start your day with an adventure through this renowned nature reserve filled with exotic birds, butterflies, and lush tropical forests. Enjoy breakfast at Chaud Cafe & Wine Bar, known for its delicious pastries and coffee.

Afternoon

Trinidad Island Tour will guide you through key historical sites such as Fort George and the Magnificent Seven while narrating tales of pirates who once roamed these lands. For lunch, dine at Buzo Osteria Italiana, offering exquisite dishes with a Caribbean twist.

Evening

Pirate Dinner Show, an interactive experience where you'll enjoy a feast while watching live performances that bring pirate legends to life! End your night with drinks at Roomor Lounge, known for its elegant setting and impressive cocktail menu.

Bedtime

Find amazing hotels in Port of Spain, Trinidad & Tobago.

Pirate Legends in the Bahamas

Morning

Start your day with a visit to the Pirates of Nassau Museum. This interactive museum brings the Golden Age of Piracy to life, offering a glimpse into the lives of infamous pirates like Blackbeard and Anne Bonny. The exhibits are immersive and educational, making it a perfect start to your pirate-themed journey. Enjoy breakfast at Café Matisse, known for its delightful pastries and coffee.

Afternoon

Evening

Bedtime

Find amazing hotels in Nassau, Bahamas.

Exploring Pirate Havens in Jamaica

Morning

Afternoon

Next, head to Doctor's Cave Beach for some relaxation and snorkeling in crystal-clear waters. For lunch, try Margaritaville Montego Bay, which offers delicious food and fun beachside activities.

Evening

Bedtime

Find amazing hotels in Montego Bay, Jamaica.