23 days in Puerto Rico, Dominican Republic & Cuba Itinerary

23 days in Puerto Rico, Dominican Republic & Cuba Itinerary

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Route & dates

23 days in Puerto Rico, Dominican Republic & Cuba Itinerary

Start: Tel Aviv, Israel
Fly:  17​h 30​min
1
San Juan, Puerto Rico
— 3 nights
Fly:  30​min
2
Culebra, Puerto Rico
— 4 nights
Fly:  3​h 30​min
3
Punta Cana, Dominican Republic
— 4 nights
4
Santo Domingo, Dominican Republic
— 3 nights
Fly:  4​h 30​min
5
Havana, Cuba
— 3 nights
Drive:  2​h
6
Varadero, Cuba
— 4 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.
Deepen your sense of the past at sights like Old San Juan and Paseo de la Princesa. Escape the urban bustle at El Yunque Rain Forest and Condado Beach. There's still lots to do: appreciate the extensive heritage of Sitio Histórico de San Juan, get interesting insight from Tours, and pause for some serene contemplation at Catedral Metropolitana Basilica de San Juan Bautista.

To see traveler tips, other places to visit, more things to do, and more tourist information, read our San Juan trip itinerary planning app .

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. In September, daytime highs in San Juan are 38°C, while nighttime lows are 30°C. Cap off your sightseeing on the 30th (Mon) early enough to catch the flight to Culebra.

Things to do in San Juan

Parks Outdoors Historic Sites

Side Trip

El Yunque Rain Forest
Find places to stay Sep 27 — 30:
Highlights from your plan
Old San Juan ©
Old San Juan
El Yunque Rain Forest ©
El Yunque Rain Forest
Condado Beach ©
Condado Beach

4
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.
Visit Flamenco Beach and Tamarindo Beach for some beach relaxation. Take a break from the city and head to Zoni Beach and Scuba & Snorkeling. There's still lots to do: visit a coastal fixture at Culebrita Lighthouse.

For where to stay, traveler tips, maps, and more tourist information, use the Culebra trip maker app .

Culebra is very close to San Juan. Expect a daytime high around 37°C in September, and nighttime lows around 30°C. Wrap up your sightseeing by early afternoon on the 3rd (Thu) to allow enough time to travel to Punta Cana.

Things to do in Culebra

Outdoors Parks Beaches
Find places to stay Sep 30 — Oct 4:
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.
Take a break from the city and head to Bavaro Beach and Swim with Dolphins. There's lots more to do: take an exotic tour of a safari tour, kick back and relax at Macao Beach, and examine the collection at Aromas Museum.

To see other places to visit, reviews, maps, and tourist information, read our Punta Cana day trip tool .

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 in Punta Cana, expect temperatures between 36°C during the day and 28°C at night. You will have some time to spend on the 7th (Mon) before leaving for Santo Domingo.

Things to do in Punta Cana

Outdoors Wildlife Tours
Find places to stay Oct 4 — 8:
Highlights from your plan
Bavaro Beach ©
Bavaro Beach
Swim with Dolphins
Safaris

3
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.
Alcazar de Colon and Fortaleza Ozama will appeal to history buffs. Catedral Primada de America and Basilica Cathedral of Santa Maria la Menor are good opportunities to explore the local culture. The adventure continues: don't miss a visit to Zona Colonial, wander the streets of Malecon, and take in the dramatic natural features at The 3 Eyes National Park.

To see photos, reviews, maps, and other tourist information, use the Santo Domingo trip maker app .

You can take a shuttle from Punta Cana to Santo Domingo in 2 hours. Alternatively, you can drive; or take a bus. Finish your sightseeing early on the 11th (Fri) so you can travel to Havana.

Things to do in Santo Domingo

Neighborhoods Nature Parks
Find places to stay Oct 8 — 11:
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.
Popular historic sites such as El Malecon and Fortaleza de San Carlos de la Cabana are in your itinerary. Get some cultural insight at Old Havana and Old Square (Plaza Vieja). Take a break from Havana with a short trip to Las Terrazas Complex in Las Terrazas, about 56 minutes away. The adventure continues: take a stroll through Christopher Columbus Cemetery (Cemetario de Colon), make a trip to Plaza de la Catedral, steep yourself in history at Revolution Plaza, and pause for some photo ops at Neptune Statue.

To find maps, more things to do, traveler tips, and more tourist information, go to the Havana online tour planner .

You can fly from Santo Domingo to Havana in 3 hours. You'll gain 1 hour traveling from Santo Domingo to Havana due to the time zone difference. In October, daily temperatures in Havana can reach 35°C, while at night they dip to 24°C. Cap off your sightseeing on the 14th (Mon) early enough to go by car to Varadero.

Things to do in Havana

Historic Sites Wildlife Parks

Side Trip

Las Terrazas Complex
Find places to stay Oct 11 — 14:
Highlights from your plan
El Malecon ©
El Malecon
Old Havana ©
Old Havana
Fortaleza de San Carlos de la Cabana ©

4
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.
You'll enjoy a bit of beach vacationing at Varadero Beach and Coral Beach - Playa Coral. Cueva de Ambrosio and House of Rum are good opportunities to explore the local culture. Take a break from Varadero with a short trip to Zapata Swamp in Playa Larga, about 2 hours away. There's still lots to do: kick back and relax at Cayos Blancos, admire nature's wide array of creatures at Delfinario, stroll around Josone Park, and Head underground at Cueva de Saturno.

To see maps, ratings, photos, and more tourist information, read Varadero trip planner .

You can drive from Havana to Varadero in 2 hours. Alternatively, you can take a shuttle; or do a combination of train and taxi. In October, daily temperatures in Varadero can reach 35°C, while at night they dip to 24°C. Wrap up your sightseeing on the 17th (Thu) to allow time to travel back home.

Things to do in Varadero

Parks Outdoors Wildlife

Side Trips

Zapata Swamp, Cayos Blancos
Find places to stay Oct 14 — 18:
Highlights from your plan
Varadero Beach ©
Varadero Beach
Cayos Blancos ©
Cayos Blancos
Cueva de Saturno ©
Cueva de Saturno

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