41 days in Caribbean & Cancun Itinerary

41 days in Caribbean & Cancun Itinerary

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Route & dates

41 days in Caribbean & Cancun Itinerary

Start: Auckland, New Zealand
+2
Fly + Shuttle + Taxi:  27 h
1
Punta Cana, Dominican Republic
— 6 nights
Fly:  4 h 30 min
2
San Juan, Puerto Rico
— 6 nights
Fly:  3 h 45 min
3
Shoal Bay Village, Anguilla
— 3 nights
+2
Drive + Fly + Drive:  4 h
4
Grand Case, St. Maarten-St. Martin
— 4 nights
+2
Drive + Fly + Drive:  8 h 15 min
5
Saint Joseph Parish, Barbados
— 3 nights
+2
Bus + Fly + Bus:  5 h 15 min
6
Port of Spain, Trinidad and Tobago
— 5 nights
Bus + Fly:  5 h 15 min
7
Havana, Cuba
— 5 nights
Fly:  4 h
8
Cancun, Mexico
— 5 nights
Fly:  22 h 15 min
End: Auckland, New Zealand

6
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.
Explore Punta Cana's surroundings by going to Teeth Of The Dog (in La Romana) and Bayahibe (Museo y Fabrica de Puras & Scuba & Snorkeling). Spend a day of island exploring on the 5th (Mon) at Saona Island. There's lots more to do: enjoy the sand and surf at Bavaro Beach, tour the pleasant surroundings at Playa La Vacama, tee off at Punta Espada Golf Course, and get close to the beloved marine mammals with a swim-with-the-dolphins experience.

To see maps, traveler tips, more things to do, and tourist information, use the Punta Cana trip planner.

Auckland, New Zealand to Punta Cana is an approximately 27-hour combination of flight, shuttle, and taxi. You can also fly. Due to the time zone difference, you'll gain 16 hours traveling from Auckland to Punta Cana. Traveling from Auckland in April, expect Punta Cana to be somewhat warmer, temps between 35°C and 27°C. Cap off your sightseeing on the 10th (Sat) early enough to travel to San Juan.

Things to do in Punta Cana

Outdoors Parks Golf

Side Trips

Bayahibe, Teeth Of The Dog
Find places to stay Apr 4 — 10:
Highlights from your plan
Saona Island ©
Saona Island
Bavaro Beach ©
Bavaro Beach
Punta Espada Golf Course ©
Punta Espada Golf Course

6
nights
San Juan, Puerto Rico

Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Explore San Juan's surroundings by going to Luquillo (Monkey Threads & Luquillo Beach), El Yunque Rain Forest (in El Yunque National Forest) and Ponce (Museo de Arte de Ponce & Casa Wiechers-Villaronga). There's much more to do: contemplate the long history of Old San Juan, stroll through Condado Beach, get to know the fascinating history of Sitio Histórico de San Juan, and delve into the lush surroundings at Bosque Nacional El Yunque.

To see traveler tips, maps, more things to do, and tourist information, read San Juan attractions planning tool .

You can fly from Punta Cana to San Juan in 4.5 hours. Alternatively, you can do a combination of shuttle and flight; or do a combination of bus and ferry. In April in San Juan, expect temperatures between 36°C during the day and 28°C at night. Finish your sightseeing early on the 16th (Fri) to allow enough time to travel to Shoal Bay Village.

Things to do in San Juan

Outdoors Parks Tours

Side Trips

Luquillo, Ponce, El Yunque Rain Forest, Bosque Nacional El Yunque
Find places to stay Apr 10 — 16:
Highlights from your plan
Climbing Tours
El Yunque Rain Forest ©
El Yunque Rain Forest
Old San Juan ©
Old San Juan

3
nights
Shoal Bay Village, Anguilla

Shoal Bay Village ©
Change things up with a short trip to Limin' Boutique in West End Village (about 38 minutes away).

To see topicsMoreInfo.option.ratings, more things to do, traveler tips, and tourist information, read our Shoal Bay Village travel planning tool .

You can fly from San Juan to Shoal Bay Village in 4 hours. Alternatively, you can do a combination of flight and ferry. In April, plan for daily highs up to 34°C, and evening lows to 28°C. Finish your sightseeing early on the 19th (Mon) so you can travel to Grand Case.

Things to do in Shoal Bay Village

Parks Outdoors Beaches

Side Trips

Sandy Ground, West End Village, Anguilla
Find places to stay Apr 16 — 19:
Highlights from your plan
Maundays Bay ©
Maundays Bay
Shoal Bay ©
Shoal Bay
Rendezvous Bay Beach ©
Rendezvous Bay Beach

4
nights
Grand Case, St. Maarten-St. Martin

Grand Case is known for wildlife, classes, and beaches. Your plan includes some of its best attractions: kick back and relax at Orient Bay Beach, contemplate the waterfront views at Mullet Bay Beach, tour the pleasant surroundings at Cupecoy Bay Beach, and take your sightseeing to a higher altitude at Paradise Peak.

To find topicsMoreInfo.option.ratings, reviews, and tourist information, go to the Grand Case trip builder site .

Use the Route module to find suitable travel options from Shoal Bay Village to Grand Case. Expect a daytime high around 34°C in April, and nighttime lows around 28°C. Wrap up your sightseeing on the 23rd (Fri) to allow time to travel to Saint Joseph Parish.

Things to do in Grand Case

Outdoors Parks Beaches

Side Trips

Philipsburg, Sint Maarten, Parotte Ville Bird Sanctuary, Casino Royale, Paradise Peak
Find places to stay Apr 19 — 23:
Highlights from your plan
Speed Boats Tours
Dawn Beach ©
Dawn Beach
Orient Bay Beach ©
Orient Bay Beach

3
nights
Saint Joseph Parish, Barbados

Saint Joseph Parish ©
Lush Saint Joseph Parish has a particularly rugged aspect to it down by the sea, so much so that it has gained the nickname 'Scotland District'.
Explore Saint Joseph Parish's surroundings by going to Saint Philip Parish (Sunbury Plantation House & Bottom Bay) and Bridgetown (Carlisle Bay, Scuba & Snorkeling, &more). There's still lots to do: Head underground at Harrison's Cave., steep yourself in history at Andromeda Botanic Gardens, take in nature's colorful creations at Welchman Hall Gully, and examine the collection at Mallalieu Motor Collection & Car Museum.

Plan my Saint Joseph Parish trip by asking Inpirock to come up with tips and suggestions.

Explore your travel options from Grand Case to Saint Joseph Parish with the Route module. In April, plan for daily highs up to 35°C, and evening lows to 28°C. Wrap up your sightseeing on the 27th (Tue) early enough to travel to Port of Spain.

Things to do in Saint Joseph Parish

Parks Historic Sites Outdoors

Side Trips

Bridgetown, Saint Philip Parish, Saint Thomas Parish, Gun Hill Signal Station, Mallalieu Motor Collection & Car Museum
Find places to stay Apr 23 — 27:
Highlights from your plan
Hunte's Gardens ©
Hunte's Gardens
Harrison's Cave. ©
Harrison's Cave.
Andromeda Botanic Gardens ©
Andromeda Botanic Gardens

5
nights
Port of Spain, Trinidad and Tobago

Port of Spain ©
Port of Spain, the country's capital, sits between the sea and a scenic green mountain range, and acts as a gateway for eclectic adventures on land and sea.
Change things up with these side-trips from Port of Spain: Arima Dial (in Arima) and Yerette (in Maracas Bay). The adventure continues: stroll through Asa Wright Nature Centre, take in the architecture and atmosphere at Holy Trinity Cathedral, steep yourself in history at Fort George, and explore the fascinating underground world of Gasparee Caves.

To see topicsMoreInfo.option.ratings, reviews, photos, and other tourist information, you can read our Port of Spain day trip planning website .

Traveling by combination of bus and flight from Saint Joseph Parish to Port of Spain takes 5.5 hours. In April in Port of Spain, expect temperatures between 38°C during the day and 28°C at night. Wrap up your sightseeing on the 2nd (Sun) early enough to travel to Havana.

Things to do in Port of Spain

Parks Wildlife Historic Sites

Side Trips

Trinidad, Arima Dial, Yerette
Find places to stay Apr 27 — May 2:
Highlights from your plan
Asa Wright Nature Centre ©
Asa Wright Nature Centre
Queen's Park Savannah ©
Queen's Park Savannah
Maracas Beach
Maracas Beach

5
nights
Havana, Cuba

Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Change things up with these side-trips from Havana: Cayo Largo (Playa Paraiso, Playa Mal Tiempo, &more). Next up on the itinerary: get to know the fascinating history of Malecón of Havana, make a trip to Plaza de Armas, steep yourself in history at El Morro, and get the lay of the land with Walking tours.

For where to stay, reviews, photos, and other tourist information, read Havana itinerary maker.

Traveling by flight from Port of Spain to Havana takes 5.5 hours. The time zone changes from Atlantic Standard Time (AST) to Cuba Standard Time (CST), which is usually a -1 hour difference. Expect a bit cooler evenings in Havana when traveling from Port of Spain in May, with lows around 24°C. Finish your sightseeing early on the 7th (Fri) so you can travel to Cancun.

Things to do in Havana

Historic Sites Parks Outdoors

Side Trip

Cayo Largo
Find places to stay May 2 — 7:
Highlights from your plan
Walking tours
Malecón of Havana ©
Malecón of Havana
Old Havana ©
Old Havana

5
nights
Cancun, Mexico

Few destinations in Mexico dazzle visitors quite like Cancun, a modern resort town filled with glitzy hotels sitting on picturesque and well-developed Caribbean beaches.
Venture out of the city with trips to Cobá Zona Arqueológica Cobá (in Coba) and Playa del Carmen (Scuba & Snorkeling, Zipline, &more). Next up on the itinerary: fulfill a lifelong dream with a swim-with-the-dolphins experience, tour the pleasant surroundings at Playa Delfines, explore the ancient world of El Rey Archaeological Zone, and browse the eclectic array of goods at Mercado 28.

To see maps, reviews, photos, and tourist information, go to the Cancun trip itinerary builder.

You can fly from Havana to Cancun in 4 hours. Traveling from Havana in May, expect a bit warmer with lows of 28°C in Cancun. Wrap up your sightseeing on the 12th (Wed) to allow time to travel back home.

Things to do in Cancun

Outdoors Tours Wildlife

Side Trips

Playa del Carmen, Cobá Zona Arqueológica Cobá
Find places to stay May 7 — 12:
Highlights from your plan
Zipline
Scuba & Snorkeling
Cobá Zona Arqueológica Cobá ©
Cobá Zona Arqueológica Cobá

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