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Ultimate 2-Month Caribbean Adventure: Explore Tropical Paradises from the Bahamas to Grenada

Viewed by 67 travelers

Day 1: Arrival Bahamas

Nassau, Bahamas on May 16, 2025

9:00am

Breakfast at The Poop Deck

Start your Caribbean journey with a breakfast at The Poop Deck, known for its fresh seafood and tropical vibes, open from 8:00am to 10:30pm.
USD25, 1h

10:30am

Explore Nassau Downtown

Stroll around historic Nassau to see Straw Market, Queen's Staircase, and colorful colonial architecture, ideal for cultural immersion and shopping local crafts.
Free, 2h30m

1:00pm

Lunch at Arawak Cay

Enjoy authentic Bahamian cuisine like conch salad and fried fish at the popular Arawak Cay Food Truck Park, open until 9:00pm.
USD15, 1h

2:30pm

Relax at Cable Beach

Spend a peaceful afternoon soaking up the sun on the white sands of Cable Beach, one of Nassau's best-known beaches.
Free, 3h

6:00pm

Dinner at Graycliff Restaurant

Have an elegant dinner at Graycliff, renowned for its fine dining and extensive wine cellar, open from 6:00pm.
USD60, 2h
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Day 2: Bahamas to Cuba

Havana, Cuba on May 17, 2025

7:00am

Early Breakfast at your hotel

Fuel up with a light Caribbean-style breakfast before your morning flight to Havana.
Included in accommodation, 1h

9:00am

Flight to Havana

Catch a direct flight from Nassau to Havana, approx. 1.5 hours, arriving ready to explore Cuban culture.
USD150, 1.5h

11:00am

Visit Old Havana (Habana Vieja)

Explore the UNESCO World Heritage streets of Old Havana, including Plaza Vieja and the Cathedral of Havana, open all day.
Free, 3h

2:00pm

Lunch at La Guarida

Dine at one of Havana’s most famous paladares (private restaurants), offering traditional Cuban dishes in an atmospheric setting.
USD25, 1.5h

4:00pm

Visit the Museum of the Revolution

Learn about Cuban history and the revolution at this well-curated museum with extensive exhibits, open until 5:30pm.
USD8, 1.5h

6:00pm

Dinner at San Cristobal Paladar

Enjoy dinner where President Obama once dined, with authentic Cuban cuisine and live music, open from 6:00pm.
USD30, 2h
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Day 3: Cuba Cultural Day

Havana, Cuba on May 18, 2025

8:30am

Breakfast at Café El Escorial

Enjoy Cuban coffee and pastries in this popular café in Obispo Street, open from 8:00am.
USD8, 1h

9:30am

Ride Classic Cars Tour

Take a 2-hour classic convertible car tour of Havana’s highlights including Malecón and Vedado district.
USD50, 2h

12:00pm

Visit the Fine Arts Museum

Explore Cuban and international art collections in a stunning colonial building, open 10:00am to 6:00pm.
USD10, 1.5h

1:30pm

Lunch at Doña Eutimia

Taste traditional Cuban fare in an intimate, local eatery located near the cathedral.
USD15, 1h

3:00pm

Walk along the Malecón

Take a stroll along Havana’s famous seaside promenade for beautiful views and local culture, free access and always open.
Free, 2h

6:30pm

Dinner and live music at La Zorra y El Cuervo

Enjoy an evening of Cuban jazz in this intimate club, ordering dinner from their bar menu, open from 6:00pm.
USD20, 2h
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Day 4: Cuba to Jamaica

Montego Bay, Jamaica on May 19, 2025

7:00am

Early Breakfast at hotel

Have a nourishing breakfast before your flight to Jamaica.
Included in accommodation, 1h

9:30am

Flight to Montego Bay

Fly from Havana to Montego Bay, Jamaica, approximately 1.5-hour flight.
USD120, 1.5h

11:30am

Explore Doctor’s Cave Beach

Relax and swim at this iconic beach famous for its crystal clear waters and white sand, open all day.
USD6 entrance fee, 3h

2:30pm

Lunch at The Pork Pit

Sample authentic Jamaican jerk pork and other grilled delights at this local favourite spot, open 11:00am to 9:00pm.
USD15, 1h

4:00pm

Visit Rose Hall Great House

Take a guided tour of this restored plantation house with fascinating history and ghost stories, open until 5:00pm.
USD25, 1.5h

6:30pm

Dinner at HouseBoat Grill

Dine on a floating restaurant serving fresh seafood with lovely waterfront views, open from 6:00pm.
USD40, 2h
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Day 5: Jamaica Excursion

Montego Bay, Jamaica on May 20, 2025

7:30am

Breakfast at Sugar Mill Restaurant

Enjoy breakfast with picturesque views inside the Half Moon Resort, open from 7:00am.
USD20, 1h

9:00am

Day trip to Dunn’s River Falls

Climb the famous terraced waterfalls located near Ocho Rios with a guide, open 8:00am to 5:00pm.
USD25, 5h

3:00pm

Return and relax at the hotel

Rest and refresh after an adventurous day before evening plans.
Free, 2h

6:00pm

Dinner at Scotchies Jerk Centre

For a casual and authentic Jamaican dinner, enjoy jerk chicken and festival in a lively atmosphere.
USD15, 1.5h
Find Hotels in Montego Bay
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