23 days in Caribbean Itinerary

23 days in Caribbean Itinerary

Created using Inspirock Caribbean trip itinerary planner

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Route & dates

23 days in Caribbean Itinerary

Start: Athens, Greece
Fly:  14​h 30​min
1
Havana, Cuba
— 3 nights
Fly:  2​h
2
Seven Mile Beach, Cayman Islands
— 2 nights
Fly:  7​h 45​min
3
Culebra, Puerto Rico
— 3 nights
Fly:  30​min
4
San Juan, Puerto Rico
— 4 nights
Fly:  2​h
5
Isla de Vieques, Puerto Rico
— 5 nights
Fly + bus:  10​h
6
Saint Joseph Parish, Barbados
— 3 nights
Drive + Fly:  17​h 30​min
End: Athens, Greece

3
nights
Havana, Cuba

Havana ©
Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Havana is known for historic sites, museums, nightlife, beaches, and classes. Your plan includes some of its best attractions: get to know the fascinating history of El Malecon, contemplate the long history of Fortaleza de San Carlos de la Cabana, don't miss a visit to Plaza de la Catedral, and wander the streets of Christopher Columbus Cemetery (Cemetario de Colon).

To see reviews, photos, other places to visit, and other tourist information, refer to the Havana trip planner .

Athens, Greece to Havana is an approximately 14.5-hour flight. You can also do a combination of bus and flight. Traveling from Athens to Havana, you'll gain 7 hours due to the time zone difference. While traveling from Athens, expect much warmer days and a bit warmer nights in Havana, ranging from highs of 32°C to lows of 20°C. Wrap up your sightseeing on the 29th (Sun) to allow time to travel to Seven Mile Beach.

Things to do in Havana

Historic Sites Museums Neighborhoods
Find places to stay Dec 26 — 29:
Highlights from your plan
Old Havana ©
Old Havana
Malecón of Havana ©
Malecón of Havana
Plaza de la Catedral ©
Plaza de la Catedral

2
nights
Seven Mile Beach, Cayman Islands

Seven Mile Beach ©
Kick off your visit on the 30th (Mon): stroll through Seven Mile Beach, brush up on your knowledge of spirits at Cayman Spirits Co. Distillery, and then look for all kinds of wild species at Stingray City Grand Cayman. Here are some ideas for day two: discover the deep blue sea with a scuba or snorkeling tour, then identify plant and animal life at Cayman Turtle Centre: Island Wildlife Encounter, and then take in the dramatic natural features at Hell Gift Store.

To find traveler tips, other places to visit, photos, and other tourist information, go to the Seven Mile Beach road trip tool .

Traveling by flight from Havana to Seven Mile Beach takes 2 hours. Traveling from Havana in December, Seven Mile Beach is somewhat warmer at night with lows of 28°C. Cap off your sightseeing on the 31st (Tue) early enough to travel to Culebra.

Things to do in Seven Mile Beach

Parks Wildlife Outdoors

Side Trips

Grand Cayman, Cayman Spirits Co. Distillery, Cayman Turtle Centre: Island Wildlife Encounter
Find places to stay Dec 29 — 31:
Highlights from your plan
Stingray City Grand Cayman ©
Stingray City Grand Cayman
Seven Mile Beach ©
Seven Mile Beach

3
nights
Culebra, Puerto Rico

Culebra ©
With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
Culebra is known for beaches, wildlife, nature, outdoors, and adventure. Your plan includes some of its best attractions: tour the pleasant surroundings at Flamenco Beach, look for all kinds of wild species at Culebra National Wildlife Refuge, enjoy the sand and surf at Zoni Beach, and get lost in a book at Culebra Public Library.

To see reviews, photos, traveler tips, and tourist information, read Culebra travel itinerary planner.

Traveling by flight from Seven Mile Beach to Culebra takes 8 hours. Alternatively, you can do a combination of flight, shuttle, and ferry. Traveling from Seven Mile Beach to Culebra, you'll lose 1 hour due to the time zone difference. In January, daytime highs in Culebra are 34°C, while nighttime lows are 26°C. Finish your sightseeing early on the 4th (Sat) so you can fly to San Juan.

Things to do in Culebra

Parks Beaches Outdoors
Find places to stay Dec 31 — Jan 4:
Highlights from your plan
Flamenco Beach ©
Flamenco Beach
Culebrita Island ©
Culebrita Island
Zoni Beach ©
Zoni Beach

4
nights
San Juan, Puerto Rico

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Venture out of the city with trips to El Yunque Rain Forest (in El Yunque National Forest) and Ponce (Cathedral of our Lady of Guadaloupe & Museo de Arte de Ponce). The adventure continues: take a stroll through Old San Juan, let your taste buds guide you at a local gastronomic tour, look for gifts at Coqui el Original, and pause for some serene contemplation at Catedral Metropolitana Basilica de San Juan Bautista.

Before you visit San Juan, use our trip planner to discover what you can do and see there.

San Juan is just a short distance from Culebra. In January, plan for daily highs up to 34°C, and evening lows to 26°C. Wrap up your sightseeing on the 8th (Wed) to allow time to travel to Isla de Vieques.

Things to do in San Juan

Parks Outdoors Historic Sites

Side Trips

Ponce, El Yunque Rain Forest
Find places to stay Jan 4 — 8:
Highlights from your plan
Old San Juan ©
Old San Juan
El Yunque Rain Forest ©
El Yunque Rain Forest
Sitio Histórico de San Juan ©
Sitio Histórico de San Juan

5
nights
Isla de Vieques, Puerto Rico

Isla de Vieques ©
For sixty years until 2003, most of the Isla de Vieques was closed off to the public, with the US Navy using the island's beaches and surrounding waters for drills and testing of new military machinery, such as bombs.
Isla de Vieques is known for nature, beaches, wildlife, adventure, and nightlife. Your plan includes some of its best attractions: explore the activities along Sun Bay Beach, enjoy the sand and surf at La Chiva, tour the pleasant surroundings at La Plata Beach, and expand your understanding of the military at Camp Garcia.

For maps, more things to do, other places to visit, and tourist information, use the Isla de Vieques online trip itinerary maker .

Getting from San Juan to Isla de Vieques by flight takes about 2 hours. Other options: do a combination of car and ferry; or do a combination of shuttle and ferry. In January, daytime highs in Isla de Vieques are 32°C, while nighttime lows are 26°C. Wrap up your sightseeing on the 13th (Mon) early enough to travel to Saint Joseph Parish.

Things to do in Isla de Vieques

Parks Outdoors Beaches
Find places to stay Jan 8 — 13:
Highlights from your plan
Sun Bay Beach ©
Sun Bay Beach
Vieques National Wildlife Refuge ©
Vieques National Wildlife Refuge
La Chiva ©
La Chiva

3
nights
Saint Joseph Parish, Barbados

Saint Joseph Parish ©
Lush Saint Joseph Parish has a particularly rugged aspect to it down by the sea, so much so that it has gained the nickname 'Scotland District'.
Explore Saint Joseph Parish's surroundings by going to Bridgetown (Carlisle Bay & Scuba & Snorkeling) and Saint Philip Parish (Bottom Bay & Sunbury Plantation House). Next up on the itinerary: Head underground at Harrison's Cave., enjoy breathtaking views from Gun Hill Signal Station, explore the activities along Foul Bay, and take in nature's colorful creations at Hunte's Gardens.

To see traveler tips, more things to do, other places to visit, and more tourist information, you can read our Saint Joseph Parish travel route planning app .

You can do a combination of flight and bus from Isla de Vieques to Saint Joseph Parish in 10 hours. In January, daytime highs in Saint Joseph Parish are 34°C, while nighttime lows are 27°C. Finish up your sightseeing early on the 17th (Fri) so you can travel back home.

Things to do in Saint Joseph Parish

Parks Outdoors Beaches

Side Trips

Saint Philip Parish, Bridgetown, St. Nicholas Abbey, Harrison's Cave., Gun Hill Signal Station
Find places to stay Jan 13 — 17:
Highlights from your plan
Hunte's Gardens ©
Hunte's Gardens
Harrison's Cave. ©
Harrison's Cave.
Bottom Bay ©
Bottom Bay

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