23 days in Caribbean Itinerary

23 days in Caribbean Itinerary

Created using Inspirock itinerary maker

Plan created by another user. Make it yours
Fly to Punta Cana, Shuttle to Santo Domingo
1
Santo Domingo, Dominican Republic
— 2 nights
Drive
2
Barahona, Dominican Republic
— 2 nights
Drive
3
Puerto Plata, Dominican Republic
— 1 night
Drive
4
Las Terrenas, Dominican Republic
— 3 nights
Drive to Santo Domingo, Fly to San Juan
5
San Juan, Puerto Rico
— 2 nights
Fly
6
Isla de Vieques, Puerto Rico
— 2 nights
Fly
7
Montego Bay, Jamaica
— 2 nights
Drive
8
Port Antonio, Jamaica
— 3 nights
Drive to Norman Manley International Airport, Fly to José Martí International Airport
9
Havana, Cuba
— 3 nights
Fly

S M T W T F S
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
2
3
4
5
6
7
8

2
nights
Santo Domingo, Dominican Republic

Santo Domingo, the capital of the Dominican Republic, remains the oldest continuously inhabited settlement in the New World.
Your cultural itinerary includes sights like Alcazar de Colon and Palacio Consistorial. Discover out-of-the-way places like Kahkow Experience and Fortaleza Ozama. Next up on the itinerary: examine the collection at Museo De Las Casas Reales, get engrossed in the history at Museo Memorial de la Resistencia, and don't miss a visit to Reloj de Sol.

To find ratings, photos, other places to visit, and tourist information, use the Santo Domingo trip itinerary planning site.

London, UK to Santo Domingo is an approximately 13-hour combination of flight and shuttle. You can also fly. Traveling from London to Santo Domingo, you'll gain 4 hours due to the time zone difference. You'll have a few hours on the 16th (Thu) to wrap things up before traveling to Barahona.

Things to do in Santo Domingo

Museums · Historic Sites
Find places to stay Mar 14 — 16:

2
nights
Barahona, Dominican Republic

The port city of Barahona provides a convenient base for explorations of the region, while itself possessing an air of simplicity and a welcoming atmosphere.
On the 17th (Fri), see the interesting displays at Escuela Taller y Museo Larimar, then kick back and relax at Playa De Los Patos, then kick back and relax at Playa San Rafael, and finally kick back and relax at El Quemaito. Get ready for a full day of sightseeing on the 18th (Sat): kick back and relax at Playa Tortuguero and then tour the pleasant surroundings at La Caobita Beach.

To see more things to do, photos, traveler tips, and tourist information, refer to the Barahona online journey maker.

Traveling by car from Santo Domingo to Barahona takes 3 hours. Alternatively, you can take a bus. In March, daytime highs in Barahona are 36°C, while nighttime lows are 25°C. Finish your sightseeing early on the 19th (Sun) so you can drive to Puerto Plata.

Things to do in Barahona

Parks · Outdoors · Beaches · Museums

Side Trips

Find places to stay Mar 16 — 19:

1
night
Puerto Plata, Dominican Republic

Although out of fashion in the past decades, major revitalization efforts have made a trip to Puerto Plata a growingly popular option for the adventurous travelers.
On the 19th (Sun), steep yourself in history at Fortaleza San Felipe and then pause for some serene contemplation at Catedral San Felipe. Here are some ideas for day two: get engrossed in the history at Museum of Jewish Heritage, stroll through Encuentro Beach, then relax and rejuvenate at some of the best spas, and finally find your balance on the water with some of the best stand-up paddleboarding in the area.

For traveler tips, reviews, more things to do, and more tourist information, read Puerto Plata trip planner.

Getting from Barahona to Puerto Plata by car takes about 5.5 hours. Other options: take a shuttle; or take a bus. In March in Puerto Plata, expect temperatures between 34°C during the day and 22°C at night. Cap off your sightseeing on the 20th (Mon) early enough to go by car to Las Terrenas.

Things to do in Puerto Plata

Outdoors · Historic Sites · Parks · Beaches

Side Trips

Find places to stay Mar 19 — 20:

3
nights
Las Terrenas, Dominican Republic

Las Terrenas is a town on the northeast coast of the Dominican Republic, located in the province of Samaná. Get ready for a full day of sightseeing on the next day: stroll through Playa Coson and then wander the streets of Pueblo de Los Pescadores.

To see where to stay, other places to visit, maps, and other tourist information, read our Las Terrenas trip planner.

Traveling by car from Puerto Plata to Las Terrenas takes 3 hours. Alternatively, you can take a bus. In March, plan for daily highs up to 35°C, and evening lows to 26°C. You will have some time to spend on the 23rd (Thu) before leaving for San Juan.

Things to do in Las Terrenas

Outdoors · Parks · Beaches · Neighborhoods

Side Trip

Find places to stay Mar 20 — 23:

2
nights
San Juan, Puerto Rico

Walled City

Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Kick off your visit on the 23rd (Thu): pause for some serene contemplation at Catedral Metropolitana Basilica de San Juan Bautista, then explore the world behind art at Fundacion Casa Cortes, and then walk around Parque de las Palomas. On the 24th (Fri), you'll have a packed day of sightseeing: explore the world behind art at Museo de Las Americas, appreciate the extensive heritage of Sitio Histórico de San Juan, and then explore the different monuments and memorials at Santa Maria Magdalena de Pazzis Cemetery.

For maps, reviews, and tourist information, go to the San Juan travel planner.

Traveling by combination of car and flight from Las Terrenas to San Juan takes 4.5 hours. Alternatively, you can do a combination of car and ferry; or do a combination of bus and ferry. March in San Juan sees daily highs of 34°C and lows of 26°C at night. You will have some time to spend on the 25th (Sat) before leaving for Isla de Vieques.

Things to do in San Juan

Historic Sites · Museums · Parks
Find places to stay Mar 23 — 25:

2
nights
Isla de Vieques, Puerto Rico

Isla Nena

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.
Start off your visit on the 25th (Sat): take a leisurely stroll along Mosquito Pier.

To see reviews, where to stay, and tourist information, you can read our Isla de Vieques trip planner.

You can fly from San Juan to Isla de Vieques in 2 hours. Other options are to do a combination of car and ferry; or do a combination of shuttle and ferry. In March in Isla de Vieques, expect temperatures between 34°C during the day and 26°C at night. Wrap up your sightseeing on the 27th (Mon) to allow time to travel to Montego Bay.

Things to do in Isla de Vieques

Outdoors · Parks · Beaches · Wildlife
Find places to stay Mar 25 — 27:

2
nights
Montego Bay, Jamaica

The second largest city in Jamaica, Montego Bay boasts an international airport and a major cruise-line terminal, so it regularly receives a big influx of visitors to the island.
Explore hidden gems such as Parasailing & Paragliding and Rocklands Bird Sanctuary. The adventure continues: head outdoors with Outdoor Activities and contemplate the long history of Rose Hall Great House.

To find traveler tips, reviews, more things to do, and more tourist information, read Montego Bay trip itinerary maker.

You can fly from Isla de Vieques to Montego Bay in 11.5 hours. The time zone changes from Atlantic Standard Time (AST) to Eastern Standard Time (EST), which is usually a -1 hour difference. In March, daily temperatures in Montego Bay can reach 36°C, while at night they dip to 26°C. On the 29th (Wed), you'll have the morning to explore before heading off to Port Antonio.

Things to do in Montego Bay

Adventure · Outdoors · Tours · Wildlife

Side Trip

Find places to stay Mar 27 — 29:

3
nights
Port Antonio, Jamaica

A coastal getaway from coastal getaways, Port Antonio offers a break from the more touristy retreats in the west of the island.
On the 30th (Thu), you'll have a packed day of sightseeing: contemplate in the serene atmosphere at Portland Parish Church and then don't miss a visit to Folly Great House.

For where to stay, more things to do, photos, and tourist information, refer to the Port Antonio trip planning site.

Traveling by car from Montego Bay to Port Antonio takes 4 hours. Alternatively, you can take a bus. March in Port Antonio sees daily highs of 36°C and lows of 27°C at night. You'll have a few hours on the 1st (Sat) to wrap things up before traveling to Havana.

Things to do in Port Antonio

Historic Sites · Parks · Outdoors · Beaches
Find places to stay Mar 29 — Apr 1:

3
nights
Havana, Cuba

Rome of the Caribbean

Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Your cultural itinerary includes sights like Malecón of Havana and Fortaleza de San Carlos de la Cabana. Popular historic sites such as Palacio De Los Capitanes Generales and Fort San Salvador (Castillo De San Salvador De La Punta) are in your itinerary. There's much more to do: see the interesting displays at Museo Napoleonico, wander the streets of Vedado, make a trip to Plaza de Armas, and contemplate the long history of Castillo de la Real Fuerza.

For reviews, photos, other places to visit, and tourist information, go to the Havana trip site.

Use the Route module to find suitable travel options from Port Antonio to Havana. Traveling from Port Antonio in April, plan for little chillier nights in Havana, with lows around 22°C. You will have some time to spend on the 4th (Tue) before leaving for home.

Things to do in Havana

Historic Sites · Museums · Neighborhoods
Find places to stay Apr 1 — 4:

Dominican Republic travel guide

4
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.

Puerto Rico travel guide

4.5
Historic Walking Areas · Beaches · Forests
A U.S. territory encompassing one big island and several smaller ones, Puerto Rico appeals to visitors from around the globe with its rich history, pleasant climate, natural beauty, and renowned local cuisine. Most tourists take a vacation in Puerto Rico for that classic seaside experience, though the island offers much more than just sun and sand. Tours of Puerto Rico usually start in the city of San Juan, which boasts a trendy bar scene and plenty of art museums for visitors looking to add a bit of culture to their vacation. A short drive from the island's urban centers, pristine rainforests serve as peaceful retreats from the city bustle and ensure plenty of chances to spot wildlife and take exhilarating nature walks.

Jamaica travel guide

4
Waterfalls · Beaches · Nightlife
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.