22 days in Puerto Rico, Dominican Republic & Cuba Itinerary

22 days in Puerto Rico, Dominican Republic & Cuba Itinerary

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Route & dates

22 days in Puerto Rico, Dominican Republic & Cuba Itinerary

Start: Tel Aviv, Israel
Fly:  17​h 15​min
1
San Juan, Puerto Rico
— 3 nights
Fly:  30​min
2
Culebra, Puerto Rico
— 3 nights
Fly:  3​h 30​min
3
Punta Cana, Dominican Republic
— 4 nights
shuttle:  2​h 30​min
4
Santo Domingo, Dominican Republic
— 2 nights
Fly:  4​h 30​min
5
Havana, Cuba
— 3 nights
Drive:  2​h
6
Varadero, Cuba
— 5 nights
Fly:  18​h 30​min
End: Tel Aviv, Israel

3
nights
San Juan, Puerto Rico

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Popular historic sites such as Old San Juan and Paseo de la Princesa are in your itinerary. Get outdoors at El Yunque Rain Forest and Condado Beach. Next up on the itinerary: get to know the fascinating history of Sitio Histórico de San Juan, scramble along the landscape with a canyoning and rapelling tour, and take in the architecture and atmosphere at Catedral Metropolitana Basilica de San Juan Bautista.

To see photos, ratings, maps, and other tourist information, refer to the San Juan trip planner.

Tel Aviv, Israel to San Juan is an approximately 17.5-hour flight. You'll gain 6 hours traveling from Tel Aviv to San Juan due to the time zone difference. September in San Juan sees daily highs of 38°C and lows of 30°C at night. Wrap up your sightseeing on the 30th (Mon) early enough to fly to Culebra.

Things to do in San Juan

Parks Outdoors Historic Sites

Side Trip

El Yunque Rain Forest
Highlights from your plan
Old San Juan ©
Old San Juan
El Yunque Rain Forest ©
El Yunque Rain Forest
Condado Beach ©
Condado 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.
Step out of the city life by going to Flamenco Beach and Zoni Beach. Get a sense of the local culture at Culebrita Lighthouse and Museo Historico de Culebra. It doesn't end there: enjoy the sand and surf at Tamarindo Beach and see some colorful creatures with a scuba or snorkeling tour.

For reviews, other places to visit, ratings, and more tourist information, read Culebra trip planner.

Culebra is just a stone's throw from San Juan. In September in Culebra, expect temperatures between 37°C during the day and 30°C at night. Wrap up your sightseeing by early afternoon on the 3rd (Thu) to allow time for travel to Punta Cana.

Things to do in Culebra

Outdoors Parks Beaches
Highlights from your plan
Flamenco Beach ©
Flamenco Beach
Zoni Beach ©
Zoni Beach
Tamarindo Beach ©
Tamarindo Beach

4
nights
Punta Cana, Dominican Republic

Punta Cana ©
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.
Altos de Chavon and Aromas Museum are good opportunities to explore the local culture. We've included these beaches for you: Bavaro Beach and Macao Beach. There's still lots to do: get interesting insight from Tours, look for all kinds of wild species at Wildlife Areas, and look for gifts at HARRISON'S Fine Caribbean Jewelers.

To see reviews, other places to visit, where to stay, and other tourist information, read our Punta Cana attractions planner.

You can fly from Culebra to Punta Cana in 4 hours. Alternatively, you can do a combination of flight and shuttle; or do a combination of ferry, shuttle, and flight. In October, daily temperatures in Punta Cana can reach 36°C, while at night they dip to 28°C. Finish up your sightseeing early on the 7th (Mon) so you can catch the shuttle to Santo Domingo.

Things to do in Punta Cana

Outdoors Wildlife Tours

Side Trip

Altos de Chavon
Highlights from your plan
Bavaro Beach ©
Bavaro Beach
Swim with Dolphins
Safaris

2
nights
Santo Domingo, Dominican Republic

Santo Domingo ©
Santo Domingo, the capital of the Dominican Republic, remains the oldest continuously inhabited settlement in the New World.
Satisfy your inner culture vulture at Alcazar de Colon and Fortaleza Ozama. There's lots more to do: contemplate in the serene atmosphere at Catedral Primada de America, make a trip to Zona Colonial, wander the streets of Malecon, and admire the masterpieces at Amber Museum.

Quickly create a custom-made itinerary for Santo Domingo using our trip planner.

You can take a shuttle from Punta Cana to Santo Domingo in 2 hours. Other options are to drive; or take a bus. Finish your sightseeing early on the 9th (Wed) to allow enough time to travel to Havana.

Things to do in Santo Domingo

Neighborhoods Parks Nature
Highlights from your plan
Malecon ©
Malecon
Alcazar de Colon ©
Alcazar de Colon
Catedral Primada de America
Catedral Primada de America

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.
El Malecon and Fortaleza de San Carlos de la Cabana are good opportunities to explore the local culture. Old Havana and Christopher Columbus Cemetery (Cemetario de Colon) will appeal to history buffs. Step out of Havana to go to Las Terrazas and see Las Terrazas Complex, which is approximately 56 minutes away. The adventure continues: contemplate the long history of Old Square (Plaza Vieja), pause for some photo ops at Neptune Statue, and don't miss a visit to Plaza de la Catedral.

To see traveler tips, ratings, other places to visit, and other tourist information, read Havana online trip planner .

You can fly from Santo Domingo to Havana in 3 hours. The time zone difference moving from Atlantic Standard Time (AST) to Cuba Standard Time (CST) is minus 1 hour. In October, daytime highs in Havana are 35°C, while nighttime lows are 24°C. Finish your sightseeing early on the 12th (Sat) so you can drive to Varadero.

Things to do in Havana

Historic Sites Wildlife Parks

Side Trip

Las Terrazas Complex
Highlights from your plan
El Malecon ©
El Malecon
Old Havana ©
Old Havana
Fortaleza de San Carlos de la Cabana ©

5
nights
Varadero, Cuba

Varadero ©
One of the largest resort towns in the Caribbean, Varadero boasts a 20 km (12 mi) long stretch of sand, lined with hotels and all-inclusive resorts.
Get some cultural insight at Pharmaceutical Museum and Cueva de Ambrosio. Visit Cardenas Cathedral and Iglesia Santa Elvira for their historical value. You'll find plenty of places to visit near Varadero: Parque de la Libertad (in Matanzas) and Zapata Swamp (in Playa Larga). There's still lots to do: kick back and relax at Varadero Beach, identify plant and animal life at Varahicacos Ecological Reserve, see some colorful creatures with a scuba or snorkeling tour, and stroll through Cayos Blancos.

For photos, maps, and tourist information, go to the Varadero trip planner .

You can drive from Havana to Varadero in 2 hours. Other options are to take a shuttle; or do a combination of train and taxi. In October, plan for daily highs up to 35°C, and evening lows to 24°C. Finish your sightseeing early on the 17th (Thu) to allow enough time to travel back home.

Things to do in Varadero

Parks Outdoors Beaches

Side Trips

Matanzas, Zapata Swamp, Cardenas Cathedral
Highlights from your plan
Varadero Beach ©
Varadero Beach
Cayos Blancos ©
Cayos Blancos
Coral Beach - Playa Coral ©
Coral Beach - Playa Coral

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