50 days in Havana, Caribbean & Peru Itinerary

50 days in Havana, Caribbean & Peru Itinerary

Make it your trip
Fly to Tallahassee Regional Airport, Drive to Havana
1
Havana, United States
— 1 night
+2
Drive to Tallahassee Regional Airport, Fly to Owen Roberts International Airport, Drive to Seven Mile Beach
2
Seven Mile Beach, Cayman Islands
— 2 nights
Fly
3
Ocho Rios, Jamaica
— 6 nights
Fly
4
Machu Picchu, Peru
— 4 nights
+2
Drive to Alejandro Velasco Astete International Airport, Fly to Queen Beatrix International Airport, Drive to Palm - Eagle Beach
5
Palm - Eagle Beach, Aruba
— 2 nights
Fly
6
Santo Domingo, Dominican Republic
— 4 nights
Fly
7
Providenciales, Turks and Caicos
— 4 nights
Fly
8
Punta Cana, Dominican Republic
— 6 nights
Fly
9
San Juan, Puerto Rico
— 4 nights
Fly
10
Culebra, Puerto Rico
— 5 nights
Fly
11
Shoal Bay Village, Anguilla
— 2 nights
Ferry to Sint Maarten, Fly to St. John's
12
St. John's, Antigua and Barbuda
— 5 nights
Fly
13
Saint James Parish, Barbados
— 4 nights
Drive to Grantley Adams International Airport, Fly to Copenhagen

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Havana, United States — 1 night

Havana is a town in Gadsden County, Florida, United States, and a suburb of Tallahassee. Kick off your visit on the 11th (Wed): don't miss a visit to The Planters Exchange.

To find reviews, ratings, more things to do, and tourist information, use the Havana day trip planner.

Copenhagen, Denmark to Havana is an approximately 18-hour combination of flight and car. The time zone changes from Central European Standard Time to Eastern Standard Time, which is usually a -6 hour difference. Wrap up your sightseeing by early afternoon on the 11th (Wed) to allow time for travel to Seven Mile Beach.
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Find places to stay Jan 10 — 11:
Highlights from your trip

Seven Mile Beach, Cayman Islands — 2 nights

Seven Mile Beach is a long crescent of coral-sand beach on the western end of Grand Cayman island. Kick off your visit on the 12th (Thu): get engrossed in the history at Cayman Islands National Museum, then stroll through Stingray City Grand Cayman, and then kick back and relax at Seven Mile Beach. On the 13th (Fri), you'll have a packed day of sightseeing: try out the rides at Cayman Turtle Centre: Island Wildlife Encounter, then discover the deep blue sea with a scuba or snorkeling tour, and then sample the fine beverages at Cayman Spirits Co. Distillery.

To find traveler tips, photos, reviews, and more tourist information, read our Seven Mile Beach trip itinerary website.

Explore your travel options from Havana to Seven Mile Beach with the Route module. In January, daytime highs in Seven Mile Beach are 33°C, while nighttime lows are 27°C. Finish your sightseeing early on the 13th (Fri) so you can fly to Ocho Rios.
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Parks · Outdoors · Wildlife · Zoos & Aquariums
Side Trips
Find places to stay Jan 11 — 13:

Ocho Rios, Jamaica — 6 nights

A trip to Ocho Rios, the tourist hub of Saint Ann Parish, offers travelers a staggering amount of activities and cultural attractions.
Explore the numerous day-trip ideas around Ocho Rios: Blue Mountain Peak (in Blue Mountains National Park), Bob Marley Museum (in St. Ann's Bay) and Rose Hall (Rose Hall Great House & White Witch Golf Course). The adventure continues: take in the dramatic scenery at Dunn's River Falls and Park, get close to the beloved marine mammals with a swim-with-the-dolphins experience, take a pleasant ride with a tour on horseback, and explore the fascinating underground world of Green Grotto Caves.

To see more things to do, traveler tips, where to stay, and tourist information, go to the Ocho Rios attractions planning tool.

You can fly from Seven Mile Beach to Ocho Rios in 4.5 hours. In January, daytime highs in Ocho Rios are 36°C, while nighttime lows are 27°C. Wrap up your sightseeing by early afternoon on the 19th (Thu) to allow time for the flight to Machu Picchu.
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Parks · Nature · Outdoors · Historic Sites
Side Trips
Find places to stay Jan 13 — 19:

Machu Picchu, Peru — 4 nights

A symbol of the Incan civilization, the abandoned city of Machu Picchu represents a must-see on a Peru vacation.
Step out of Machu Picchu with an excursion to Ruinas de Choquequirao in Cachora--about 1h 30 min away. There's still lots to do: contemplate the long history of Santuario Historico de Machu Picchu, take some stellar pictures from Intipuncu, and delve into the distant past at Winay Wayna.

To find where to stay, other places to visit, ratings, and tourist information, read our Machu Picchu trip planner.

Getting from Ocho Rios to Machu Picchu by flight takes about 10.5 hours. Finish your sightseeing early on the 23rd (Mon) to allow enough time to travel to Palm - Eagle Beach.
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Side Trip
Find places to stay Jan 19 — 23:

Palm - Eagle Beach, Aruba — 2 nights

A long stretch of powdery white sand and aquamarine waters, Palm - Eagle Beach remains one of Aruba's most visited vacation spots.
Kick off your visit on the 24th (Tue): tour the pleasant surroundings at Eagle Beach and then take in the dramatic natural features at Ayo Rock Formations. On your second day here, visit a coastal fixture at California Lighthouse and Sasariwichi Dunes and then stroll through Palm Beach.

For maps, traveler tips, other places to visit, and tourist information, read our Palm - Eagle Beach day trip planner.

Explore your travel options from Machu Picchu to Palm - Eagle Beach with the Route module. The time zone difference moving from Peru Standard Time (PET) to Atlantic Standard Time (AST) is 1 hour. In January in Palm - Eagle Beach, expect temperatures between 35°C during the day and 28°C at night. Wrap up your sightseeing on the 25th (Wed) to allow time to fly to Santo Domingo.
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Parks · Beaches · Outdoors · Nature
Side Trips
Find places to stay Jan 23 — 25:

Santo Domingo, Dominican Republic — 4 nights

Santo Domingo, the capital of the Dominican Republic, remains the oldest continuously inhabited settlement in the New World.
Santo Domingo is known for historic sites, sightseeing, and nature. Your trip includes some of its best attractions: take in the architecture and atmosphere at Basilica Cathedral of Santa Maria la Menor, contemplate the long history of Fortaleza Ozama, appreciate the history behind Columbus Lighthouse (Faro A Colon), and make a trip to Plaza de la Cultura.

To find photos, ratings, more things to do, and more tourist information, refer to the Santo Domingo vacation planner.

You can fly from Palm - Eagle Beach to Santo Domingo in 5.5 hours. Wrap up your sightseeing on the 29th (Sun) early enough to fly to Providenciales.
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Neighborhoods · Historic Sites · Museums · Zoos & Aquariums
Find places to stay Jan 25 — 29:

Providenciales, Turks and Caicos — 4 nights

The most commercialized part of the Turks and Caicos, Providenciales remains the islands' tourism heaven, boasting many resorts, hotel chains, and condominiums.
Providenciales is known for beaches, wildlife, and sightseeing. Your trip includes some of its best attractions: kick back and relax at Grace Bay Beach, take in the dramatic natural features at Smith's Reef, get interesting insight from Tours, and tee off at Royal Turks and Caicos Golf Club.

For where to stay, photos, reviews, and more tourist information, you can read our Providenciales road trip planning app.

Fly from Santo Domingo to Providenciales in 5 hours. The time zone difference moving from Atlantic Standard Time to Eastern Standard Time is minus 1 hour. In January, daytime highs in Providenciales are 32°C, while nighttime lows are 27°C. Finish up your sightseeing early on the 2nd (Thu) so you can catch the flight to Punta Cana.
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Outdoors · Parks · Beaches · Wildlife
Side Trip
Find places to stay Jan 29 — Feb 2:

Punta Cana, Dominican Republic — 6 nights

In an area boasting beaches that face both the Atlantic Ocean and the Caribbean Sea, vacations in Punta Cana have been popular with tourists since the early 1970s.
Change things up with a short trip to Altos de Chavon in La Romana (about 1h 20 min away). Spend a day of island exploring on the 6th (Mon) at Saona Island. Next up on the itinerary: enjoy the sand and surf at Bavaro Beach, tee off at Punta Espada Golf Course, don't miss a visit to Jesus Maestro Parish, and find something for the whole family at Manati Park Bavaro.

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

You can fly from Providenciales to Punta Cana in 5 hours. The time zone difference when traveling from Providenciales to Punta Cana is 1 hour. In February, daytime highs in Punta Cana are 33°C, while nighttime lows are 25°C. Finish your sightseeing early on the 8th (Wed) to allow enough time to fly to San Juan.
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Outdoors · Parks · Beaches · Tours
Side Trips
Find places to stay Feb 2 — 8:

San Juan, Puerto Rico — 4 nights

Walled City

Founded by the Spanish in 1521, San Juan is the oldest city under U.S. jurisdiction and one of the oldest in the Americas.
You'll find plenty of places to visit near San Juan: Ponce (Parque de Bombas & Museo de Arte de Ponce) and El Yunque National Forest (in El Yunque National Forest). There's still lots to do: kick back and relax at Condado Beach, admire the masterpieces at Museo de Arte de Puerto Rico, get to know the fascinating history of Old San Juan, and tour the pleasant surroundings at Pine Grove Beach.

For ratings, photos, reviews, and tourist information, refer to the San Juan trip itinerary app.

Traveling by flight from Punta Cana to San Juan takes 3 hours. Alternatively, you can do a combination of bus and ferry. February in San Juan sees daily highs of 34°C and lows of 26°C at night. Finish up your sightseeing early on the 12th (Sun) so you can catch the flight to Culebra.
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Parks · Museums · Nature · Beaches
Side Trips
Find places to stay Feb 8 — 12:

Culebra, Puerto Rico — 5 nights

Little Island

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, and outdoors. Your trip includes some of its best attractions: kick back and relax at Flamenco Beach, visit a coastal fixture at Culebrita Lighthouse, tour the pleasant surroundings at Playa Tamarindo, and examine the collection at Museo Historico de Culebra.

To find where to stay, reviews, maps, and more tourist information, go to the Culebra trip planner.

You can fly from San Juan to Culebra in 2 hours. Alternatively, you can do a combination of car and ferry; or do a combination of shuttle, taxi, and ferry. In February, daytime highs in Culebra are 34°C, while nighttime lows are 26°C. Cap off your sightseeing on the 17th (Fri) early enough to catch the flight to Shoal Bay Village.
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Parks · Outdoors · Beaches · Nature
Find places to stay Feb 12 — 17:

Shoal Bay Village, Anguilla — 2 nights

Kick off your visit on the 18th (Sat): tour the pleasant surroundings at Sandy Ground, then get a taste of the local shopping with Limin' Boutique, and then tour the pleasant surroundings at Shoal Bay. On the next day, enjoy the sand and surf at Meads Bay, explore the activities along Maundays Bay, and then enjoy the sand and surf at Rendezvous Bay Beach.

For traveler tips, maps, where to stay, and tourist information, refer to the Shoal Bay Village route website.

Traveling by flight from Culebra to Shoal Bay Village takes 7.5 hours. February in Shoal Bay Village sees daily highs of 33°C and lows of 26°C at night. Finish your sightseeing early on the 19th (Sun) so you can travel to St. John's.
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Parks · Beaches · Outdoors · Nature
Side Trips
Find places to stay Feb 17 — 19:

St. John's, Antigua and Barbuda — 5 nights

The capital and largest city of Antigua and Barbuda, St John's represents the commercial and touristic center of the twin-island country.
Get out of town with these interesting St. John's side-trips: English Harbour (Nelson's Dockyard & Shirley Heights) and Half Moon Bay (in Saint Philip Parish). The adventure continues: stroll through Dickenson Bay, buy something for everyone on your list at Heritage Quay, get outside with jetovator Antigua, and take in the exciting artwork at Fig Tree Studio Art Gallery.

To see other places to visit, ratings, maps, and tourist information, use the St. John's trip itinerary builder app.

Traveling by combination of ferry and flight from Shoal Bay Village to St. John's takes 4.5 hours. In February, daytime highs in St. John's are 32°C, while nighttime lows are 26°C. Finish up your sightseeing early on the 24th (Fri) so you can catch the flight to Saint James Parish.
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Parks · Outdoors · Beaches · Nature
Side Trips
Find places to stay Feb 19 — 24:

Saint James Parish, Barbados — 4 nights

Saint James Parish, with its white sand coastline and modern coastal developments, has gained a reputation as a favorite haunt of the rich and famous.
Get out of town with these interesting Saint James Parish side-trips: Saint Philip Parish (Bottom Bay & Foul Bay) and Andromeda Botanic Gardens (in Bathsheba). The adventure continues: Head underground at Harrison's Cave., take in nature's colorful creations at Hunte's Gardens, steep yourself in history at Gun Hill Signal Station, and admire the landmark architecture of St. Nicholas Abbey.

For photos, other places to visit, ratings, and other tourist information, go to the Saint James Parish trip maker website.

You can fly from St. John's to Saint James Parish in 4.5 hours. In February, plan for daily highs up to 34°C, and evening lows to 27°C. Finish your sightseeing early on the 28th (Tue) so you can travel back home.
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Parks · Outdoors · Beaches · Historic Sites
Side Trips
Find places to stay Feb 24 — 28:

Jamaica travel guide

4.1
The third most populous English-speaking country in the Americas, Jamaica remains a member of the Commonwealth of Nations, with the British monarch its official head of state. Jamaica tourism thrives thanks to the island nation's reputation for natural beauty, outstanding cuisine, and lively music scene. The country's landscape is as diverse as its population, its tropical climate supporting varied ecosystems that include everything from savannahs to rugged mountain slopes. For most visitors, a holiday in Jamaica is a largely outdoor affair, with hiking, fishing, golfing, camping, snorkeling, horseback riding, and kite surfing among the most popular things to do.
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Peru travel guide

4.6
Historic Sites · Parks · Landmarks
Land of the Incas
In a country renowned for its pre-Columbian archeological sites, no Peru vacation would be complete without an adrenaline-inducing hike to Machu Picchu, World Heritage-listed symbol of the once-mighty Incan Empire. Aside from visiting these spectacular ruins set against the backdrop of photogenic mountain peaks, most holidays in Peru also include an exploration of the country's pretty cities, boasting well-preserved colonial architecture and a slew of modern buildings housing fine museums, galleries, shops, and restaurants. Ideal for active vacationers, Peru trips are also tailor-made for gourmands, as the country's eclectic cuisine blends tasty influences from Africa, Asia, and Europe.
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Dominican Republic travel guide

4.2
Beaches · Islands · Zipline
Sharing the island of Hispaniola with Haiti, friendly Dominican Republic offers two distinct coastlines, one bathed by the Caribbean Sea and the other by the Atlantic Ocean. Nearly 1,600 km (1,000 mi) of palm-shaded beaches figure highly on most Dominican Republic itineraries, allowing visitors to design their vacation around a range of water-based activities. The sun-kissed country benefits from pleasant temperatures throughout the year, so it's no surprise that holidays in Dominican Republic remain a popular choice for visitors from distant and colder corners of the world. A big producer of coffee, cocoa, rum, sugarcane, and tobacco, the country provides a vibrant cultural experience in multicultural cities and quaint countryside.
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