31 days in Caribbean Itinerary

31 days in Caribbean Itinerary

Created using Inspirock Caribbean visit planner

Plan created by another user. Make it yours
1
Punta Cana, Dominican Republic
— 4 nights
2
San Juan, Puerto Rico
— 3 nights
3
Culebra, Puerto Rico
— 2 nights
4
Philipsburg, St. Maarten-St. Martin
— 3 nights
5
English Harbour, Antigua and Barbuda
— 3 nights
6
Bridgetown, Barbados
— 3 nights
7
Willemstad, Curacao
— 3 nights
8
Oranjestad, Aruba
— 4 nights
9
Havana, Cuba
— 3 nights

S M T W T F S
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28
29
30
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13
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26

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.
Change things up with these side-trips from Punta Cana: La Romana (Altos de Chavon & Teeth Of The Dog). Spend a day of island exploring on the 23rd (Mon) at Saona Island. Next up on the itinerary: look for all kinds of wild species at Aqua Track Private Day Trips, play a few rounds at Punta Espada Golf Course, kick back and relax at Bavaro Beach, and look for gifts at La Perla Dominicana.

To see more things to do, photos, other places to visit, and more tourist information, read our Punta Cana driving holiday planner.

Manila, Philippines to Punta Cana is an approximately 26-hour flight. You'll gain 12 hours traveling from Manila to Punta Cana due to the time zone difference. Expect a daytime high around 34°C in November, and nighttime lows around 27°C. Finish your sightseeing early on the 26th (Thu) to allow enough time to travel to San Juan.

Things to do in Punta Cana

Outdoors · Parks · Golf · Nature

Side Trips

Find places to stay Nov 22 — 26:
Highlights from your plan
Saona Island ©
Saona Island
Altos de Chavon ©
Altos de Chavon
Bavaro Beach ©
Bavaro Beach

3
nights
San Juan, Puerto Rico

San Juan ©

Walled City

Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Go for a jaunt from San Juan to El Yunque National Forest to see El Yunque Rain Forest about 1h 10 min away. There's still lots to do: contemplate the long history of Old San Juan, indulge in some culinary diversions at a local gastronomic tour, admire the masterpieces at Museo de Las Americas, and pause for some serene contemplation at Catedral Metropolitana Basilica de San Juan Bautista.

To find ratings, traveler tips, maps, and more tourist information, read our San Juan tour itinerary planner.

Traveling by flight from Punta Cana to San Juan takes 2.5 hours. Alternatively, you can do a combination of bus and ferry. In November in San Juan, expect temperatures between 36°C during the day and 28°C at night. Wrap up your sightseeing on the 29th (Sun) early enough to travel to Culebra.

Things to do in San Juan

Parks · Historic Sites · Wildlife · Nature

Side Trip

Find places to stay Nov 26 — 29:
Highlights from your plan
Old San Juan ©
Old San Juan
El Yunque Rain Forest ©
El Yunque Rain Forest
Condado Beach ©
Condado Beach

2
nights
Culebra, Puerto Rico

Culebra ©

Little Island

With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
Kick off your visit on the 30th (Mon): see Jerry’s Jeep Rental and then tour the pleasant surroundings at Flamenco Beach. Get ready for a full day of sightseeing on the 1st (Tue): enjoy the sand and surf at Playa Punta Soldado Beach, enjoy the sand and surf at Zoni Beach, and then head off the coast to Culebrita Island.

To see photos, traveler tips, more things to do, and other tourist information, read Culebra online travel route planner.

You can fly from San Juan to Culebra in 2 hours. Other options are to do a combination of car and ferry; or do a combination of shuttle and ferry. In November, daily temperatures in Culebra can reach 35°C, while at night they dip to 28°C. Wrap up your sightseeing on the 1st (Tue) to allow time to travel to Philipsburg.

Things to do in Culebra

Parks · Outdoors · Beaches · Nature
Find places to stay Nov 29 — Dec 1:
Highlights from your plan
Culebrita Island ©
Culebrita Island
Flamenco Beach ©
Flamenco Beach
Zoni Beach ©
Zoni Beach

3
nights

Philipsburg ©
Take a trip to Philipsburg, the capital of Sint Maarten, and enjoy dynamic nightlife and great shopping.
Philipsburg is known for shopping, beaches, and wildlife. Your plan includes some of its best attractions: tour the pleasant surroundings at Maho Beach, enjoy the sand and surf at Orient Bay Beach, explore the activities along Mullet Bay Beach, and race across the water with Captain Alan's Boat Charters.

For more things to do, where to stay, maps, and other tourist information, go to the Philipsburg trip builder.

You can fly from Culebra to Philipsburg in 5.5 hours. In December, plan for daily highs up to 34°C, and evening lows to 28°C. Finish your sightseeing early on the 4th (Fri) to allow enough time to travel to English Harbour.

Things to do in Philipsburg

Outdoors · Parks · Beaches · Wildlife

Side Trips

Find places to stay Dec 1 — 4:
Highlights from your plan
Maho Beach ©
Maho Beach
Captain Alan's Boat Charters ©
Captain Alan's Boat Charters
Mullet Bay Beach ©
Mullet Bay Beach

3
nights

English Harbour ©
Take a break from English Harbour with a short trip to Silver Chelles in St. John's, about 36 minutes away. Spend the 5th (Sat) exploring nature at Nelson's Dockyard.

To find more things to do, where to stay, maps, and other tourist information, refer to the English Harbour online holiday planner.

You can fly from Philipsburg to English Harbour in 3.5 hours. Expect a daytime high around 33°C in December, and nighttime lows around 27°C. Finish up your sightseeing early on the 7th (Mon) so you can travel to Bridgetown.

Things to do in English Harbour

Parks · Nature · Outdoors · Tours

Side Trips

Find places to stay Dec 4 — 7:
Highlights from your plan
Nelson's Dockyard ©
Nelson's Dockyard
Dickenson Bay ©
Dickenson Bay
Shirley Heights ©
Shirley Heights

3
nights
Bridgetown, Barbados

Bridgetown is the capital and largest city of Barbados. Change things up with a short trip to Bottom Bay in Saint Philip Parish (about 36 minutes away). Next up on the itinerary: take a tour by water with Boat Tours & Water Sports, admire the natural beauty at Welchman Hall Gully, kick back and relax at Browne's Beach, and stroll through Soup Bowl.

For where to stay, traveler tips, and more tourist information, read Bridgetown trip itinerary tool.

You can fly from English Harbour to Bridgetown in 6 hours. In December, daytime highs in Bridgetown are 34°C, while nighttime lows are 28°C. Wrap up your sightseeing on the 10th (Thu) early enough to travel to Willemstad.

Things to do in Bridgetown

Parks · Outdoors · Beaches · Tours

Side Trips

Find places to stay Dec 7 — 10:
Highlights from your plan
Boat Tours & Water Sports
Bottom Bay ©
Bottom Bay
Harrison's Cave. ©
Harrison's Cave.

3
nights
Willemstad, Curacao

Willemstad is the capital city of Curaçao, an island in the southern Caribbean Sea that forms a constituent country of the Kingdom of the Netherlands. Willemstad is known for wildlife, nature, and adventure. Your plan includes some of its best attractions: snap pictures at Queen Emma Pontoon Bridge, enjoy the sand and surf at Cas Abao Beach, stroll through Mambo Beach, and take a tour by water with Boat Tours & Water Sports.

To find more things to do, ratings, photos, and other tourist information, go to the Willemstad holiday builder site.

You can fly from Bridgetown to Willemstad in 8 hours. In December, plan for daily highs up to 35°C, and evening lows to 29°C. Finish your sightseeing early on the 13th (Sun) so you can travel to Oranjestad.

Things to do in Willemstad

Outdoors · Parks · Beaches · Tours

Side Trip

Find places to stay Dec 10 — 13:
Highlights from your plan
Scuba & Snorkeling
Queen Emma Pontoon Bridge ©
Queen Emma Pontoon Bridge
Cas Abao Beach ©
Cas Abao Beach

4
nights
Oranjestad, Aruba

Oranjestad ©
When vacationing on Aruba, don't miss taking a tour of Oranjestad, the capital of the small Caribbean island.
Change things up with a short trip to Baby Beach in San Nicolas (about 32 minutes away). There's much more to do: stroll through Eagle Beach, enjoy the sea views from California Lighthouse, explore the striking landscape of Arikok National Park, and discover the deep blue sea with Aruba Bob Snorkeling.

To find photos, maps, ratings, and more tourist information, you can read our Oranjestad road trip planning tool.

Traveling by flight from Willemstad to Oranjestad takes 4.5 hours. In December in Oranjestad, expect temperatures between 36°C during the day and 30°C at night. Finish your sightseeing early on the 17th (Thu) so you can travel to Havana.

Things to do in Oranjestad

Parks · Outdoors · Beaches · Nature

Side Trips

Find places to stay Dec 13 — 17:
Highlights from your plan
Eagle Beach ©
Eagle Beach
Palm Beach ©
Palm Beach
Arikok National Park ©
Arikok National Park

3
nights
Havana, Cuba

Havana ©

Rome of the Caribbean

Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Havana is known for historic sites, nightlife, and museums. Your plan includes some of its best attractions: make a trip to Malecón of Havana, contemplate the long history of Fortaleza de San Carlos de la Cabana, explore the world behind art at Museu Nacional de Belas Artes de Cuba, and get to know the fascinating history of Old Havana.

For where to stay, reviews, other places to visit, and tourist information, read Havana vacation builder app.

Traveling by flight from Oranjestad to Havana takes 9 hours. The time zone changes from Atlantic Standard Time (AST) to Cuba Standard Time (CST), which is usually a -1 hour difference. Traveling from Oranjestad in December, expect Havana to be a bit cooler, temps between 32°C and 20°C. Finish up your sightseeing early on the 20th (Sun) so you can travel back home.

Things to do in Havana

Find places to stay Dec 17 — 20:
Highlights from your plan
Old Havana ©
Old Havana
Malecón of Havana ©
Malecón of Havana
Plaza de la Catedral ©
Plaza de la Catedral

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