37 days in Caribbean Itinerary

37 days in Caribbean Itinerary

Created using Inspirock Caribbean trip planner

Make it your trip
Fly
1
San Juan, Puerto Rico
— 5 nights
Fly
2
Punta Cana, Dominican Republic
— 4 nights
Drive
3
Puerto Plata, Dominican Republic
— 5 nights
Fly
4
Montego Bay, Jamaica
— 5 nights
Drive
5
Kingston, Jamaica
— 5 nights
Fly
6
Nassau, Bahamas
— 4 nights
Ferry
7
Harbour Island, Bahamas
— 5 nights
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San Juan, Puerto Rico

— 5 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.
Take a break from San Juan with a short trip to Museo de Arte de Ponce in Ponce, about 1h 35 min away. Make the 6th (Sat) a memorable day with a climbing tour. Next up on the itinerary: get to know the fascinating history of Old San Juan, kick back and relax at Condado Beach, admire the masterpieces at Museum of History, Anthropology and Art, and contemplate the long history of Sitio Histórico de San Juan.

To find where to stay and other tourist information, use the San Juan attractions planning site.

Orlando, USA to San Juan is an approximately 6-hour flight. The time zone difference moving from Eastern Standard Time to Atlantic Standard Time is 1 hour. Traveling from Orlando in November, expect San Juan to be somewhat warmer, temps between 87°F and 76°F. Finish up your sightseeing early on the 6th (Sat) so you can catch the flight to Punta Cana.

Things to do in San Juan

Outdoors · Tours · Historic Sites · Parks

Side Trips

Find places to stay Nov 1 — 6:

Punta Cana, Dominican Republic

— 4 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.
Explore the numerous day-trip ideas around Punta Cana: Altos de Chavon (in La Romana) and Speed Boats Tours (in Bayahibe). Spend the 9th (Tue) spotting exotic species with a safari tour. Next up on the itinerary: stroll through Bavaro Beach, tee off at Punta Espada Golf Course, contemplate the waterfront views at Hoyo Azul, and try to win big at Hard Rock Casino Punta Cana.

To find ratings, more things to do, photos, and other tourist information, go to the Punta Cana travel app.

You can fly from San Juan to Punta Cana in 3 hours. Alternatively, you can do a combination of ferry and bus. In November in Punta Cana, expect temperatures between 85°F during the day and 74°F at night. Finish your sightseeing early on the 11th (Thu) so you can drive to Puerto Plata.

Things to do in Punta Cana

Outdoors · Tours · Wildlife · Parks

Side Trips

Find places to stay Nov 6 — 11:

Puerto Plata, Dominican Republic

— 5 nights
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.
When in Puerto Plata, make a side trip to see Scuba & Snorkeling in Sosua, approximately Sosua away. Spend the 12th (Fri) exploring the fascinating underwater world at Ocean World Adventure Park, Puerto Plata. There's still lots to do: take in the dramatic scenery at 27 Charcos, see the interesting displays at Dominican Amber Museum, take in the awesome beauty at Pico Isabel de Torres, and steep yourself in history at Fortaleza San Felipe.

To see other places to visit, maps, more things to do, and more tourist information, go to the Puerto Plata driving holiday planner.

You can drive from Punta Cana to Puerto Plata in 5 hours. Alternatively, you can take a shuttle; or do a combination of flight and shuttle. Expect a daytime high around 87°F in November, and nighttime lows around 71°F. Cap off your sightseeing on the 16th (Tue) early enough to catch the flight to Montego Bay.

Things to do in Puerto Plata

Parks · Outdoors · Beaches · Zoos & Aquariums

Side Trip

Find places to stay Nov 11 — 16:

Montego Bay, Jamaica

— 5 nights
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.
You'll find plenty of places to visit near Montego Bay: Original Mayfield Falls Jamaica (in Pennycooke) and Negril (Seven Mile Beach & Spas & Wellness). Spend the 19th (Fri) wandering through the wild on a nature and wildlife tour. There's still lots to do: steep yourself in history at Rose Hall Great House, browse the different shops at Main Street Jamaica (formerly The Shoppes at Rose Hall), stroll through Rocklands Bird Sanctuary, and take an in-depth tour of Greenwood Great House.

Inspirock's itinerary builder makes planning a Montego Bay trip simple and quick.

Getting from Puerto Plata to Montego Bay by flight takes about 8.5 hours. You'll gain 1 hour traveling from Puerto Plata to Montego Bay due to the time zone difference. November in Montego Bay sees daily highs of 88°F and lows of 76°F at night. Wrap up your sightseeing on the 21st (Sun) to allow time to drive to Kingston.

Things to do in Montego Bay

Outdoors · Wildlife · Parks · Tours

Side Trips

Find places to stay Nov 16 — 21:

Kingston, Jamaica

— 5 nights
The country's capital, Kingston offers all the excitement of a lively and storied city, while also housing the services and facilities travelers need to get around and see the rest of the island.
Step out of Kingston to go to Blue Mountains National Park and see Blue Mountain Peak, which is approximately 1h 55 min away. On the 26th (Fri), dedicate a day to the elevated beauty of Blue Mountains. The adventure continues: browse the exhibits of Bob Marley Museum, don't miss a visit to 41 Fleet Street, admire the masterpieces at Jamaica National Gallery, and stroll around Emancipation Park.

To find more things to do, photos, reviews, and tourist information, go to the Kingston travel route planning tool.

You can drive from Montego Bay to Kingston in 3 hours. Another option is to take a bus. In November in Kingston, expect temperatures between 89°F during the day and 76°F at night. Cap off your sightseeing on the 26th (Fri) early enough to catch the flight to Nassau.

Things to do in Kingston

Parks · Historic Sites · Nature · Museums

Side Trip

Find places to stay Nov 21 — 26:

Nassau, Bahamas

— 4 nights
On a trip to Nassau you can immerse yourself in a dynamic city atmosphere or spend your days lazing on the soft golden sands.
Nassau is known for theme parks, beaches, and shopping. Your trip includes some of its best attractions: kick back and relax at Cable Beach, admire the masterpieces at The National Art Gallery of The Bahamas, contemplate the long history of Queen's Staircase, and take an in-depth tour of Pirates of Nassau Museum.

To see traveler tips, maps, where to stay, and more tourist information, refer to the Nassau day trip planning app.

Traveling by flight from Kingston to Nassau takes 5 hours. Plan for slightly colder temperatures traveling from Kingston in November, with highs in Nassau at 83°F and lows at 71°F. Finish your sightseeing early on the 30th (Tue) so you can ride a ferry to Harbour Island.

Things to do in Nassau

Parks · Outdoors · Museums · Wildlife

Side Trip

Find places to stay Nov 26 — 30:

Harbour Island, Bahamas

— 5 nights
The casual Bahamian vibee of Harbour Island comes through in its atmospheric seaside eateries, the colonial English architecture of its main urban zones, and its wealth of attractive coastal areas.
Harbour Island is known for beaches, wildlife, and spas. Your trip includes some of its best attractions: kick back and relax at Pink Sands Beach, discover the deep blue sea with a scuba or snorkeling tour, view the masterpieces at Princess Street Gallery, and steep yourself in history at Dunmore Town.

To see other places to visit, reviews, photos, and more tourist information, refer to the Harbour Island day trip planning website.

Traveling by ferry from Nassau to Harbour Island takes 3.5 hours. On the 5th (Sun), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Harbour Island

Outdoors · Shopping · Historic Sites · Spas
Find places to stay Nov 30 — Dec 5:

Puerto Rico travel guide

4.5
Historic Walking Areas · Beaches · Surfing, Windsurfing & Kitesurfing
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.

Dominican Republic travel guide

4.1
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.

Jamaica travel guide

4.1
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.

Bahamas travel guide

3.8
Beaches · Islands · Water & Amusement Parks
Part of an archipelago encompassing hundreds of islets and cays, Bahamas boast many pink beaches, which get their vibrant color from fractured seashells mixed with ordinary sand. For most pleasure seekers an ideal holiday in Bahamas consists of various sea activities, occasionally interrupted by tours of several cities, offering an eclectic music scene dominated by calypso, soca, and junkanoo genres. Romantic enough to attract newlyweds from around the globe, the islands are also a major center of eco-tourism, with visits to national parks and diving tours in colorful reefs among the most popular things to do in Bahamas.