14 days in Caribbean Itinerary

14 days in Caribbean Itinerary

Created using Inspirock Caribbean trip planner

This plan was created by another user. Make it your plan

Route & dates

Start: Portland, United States
Fly:  10 h 30 min
1
Havana, Cuba
— 3 nights
Fly:  2 h
2
Seven Mile Beach, Cayman Islands
— 2 nights
Fly:  6 h 15 min
3
Palm - Eagle Beach, Aruba
— 2 nights
Fly:  2 h 15 min
4
Santo Domingo, Dominican Republic
— 2 nights
Fly:  2 h 45 min
5
San Juan, Puerto Rico
— 3 nights
Fly:  12 h 30 min
End: Portland, United States

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.
Get a sense of the local culture at Malecón of Havana and Christopher Columbus Cemetery (Cemetario de Colon). Old Havana and El Morro will appeal to history buffs. There's much more to do: steep yourself in history at Old Square (Plaza Vieja), don't miss a visit to Plaza de la Catedral, explore the world behind art at Museu Nacional de Belas Artes de Cuba, and take an in-depth tour of Museum of the Revolution (Museo de la Revolucion).

To see reviews, other places to visit, photos, and other tourist information, read Havana driving holiday planning site.

Portland, USA to Havana is an approximately 10.5- hour flight. You can also do a combination of train, bus, and flight. The time zone difference moving from Pacific Standard Time (PST) to Cuba Standard Time (CST) is 3 hours. Expect much hotter temperatures when traveling from Portland in November; daily highs in Havana reach 83°F and lows reach 65°F. Wrap up your sightseeing on the 27th (Wed) early enough to travel to Seven Mile Beach.

Things to do in Havana

Historic Sites Museums Neighborhoods
Find places to stay Nov 24 — 27:
Highlights from your plan
Old Havana ©
Old Havana
Malecón of Havana ©
Malecón of Havana
Old Square (Plaza Vieja) ©
Old Square (Plaza Vieja)

2
nights
Seven Mile Beach, Cayman Islands

Seven Mile Beach ©
Seven Mile Beach is a long crescent of coral-sand beach on the western end of Grand Cayman island. On the 28th (Thu), kick back and relax at Seven Mile Beach, sample the fine beverages at Cayman Spirits Co. Distillery, and then stroll through Stingray City Grand Cayman. On your second day here, discover the deep blue sea with a scuba or snorkeling tour, try out the rides at Cayman Turtle Centre: Island Wildlife Encounter, and then explore the striking landscape at Hell Gift Store.

To find where to stay, ratings, and more tourist information, refer to the Seven Mile Beach vacation planning site.

Getting from Havana to Seven Mile Beach by flight takes about 2 hours. Traveling from Havana in November, you can expect nighttime temperatures to be a bit warmer in Seven Mile Beach, with lows of 77°F. Wrap up your sightseeing on the 29th (Fri) early enough to travel to Palm - Eagle Beach.

Things to do in Seven Mile Beach

Parks Wildlife Outdoors

Side Trips

Grand Cayman, Cayman Turtle Centre: Island Wildlife Encounter, Cayman Spirits Co. Distillery
Find places to stay Nov 27 — 29:
Highlights from your plan
Seven Mile Beach ©
Seven Mile Beach
Stingray City Grand Cayman ©
Stingray City Grand Cayman
Scuba & Snorkeling

2
nights
Palm - Eagle Beach, Aruba

Palm - Eagle Beach ©
A long stretch of powdery white sand and aquamarine waters, Palm - Eagle Beach remains one of Aruba's most visited vacation spots.
You'll get in some beach time at Eagle Beach and Palm Beach. Get outdoors at Baby Beach and Arikok National Park. There's more to do: enjoy the sea views from California Lighthouse.

To see maps, other places to visit, ratings, and tourist information, read Palm - Eagle Beach trip itinerary builder tool.

Traveling by flight from Seven Mile Beach to Palm - Eagle Beach takes 6.5 hours. You'll lose 1 hour traveling from Seven Mile Beach to Palm - Eagle Beach due to the time zone difference. Expect a daytime high around 89°F in November, and nighttime lows around 79°F. Finish your sightseeing early on the 2nd (Mon) to allow enough time to travel to Santo Domingo.

Things to do in Palm - Eagle Beach

Parks Beaches Outdoors

Side Trips

California Lighthouse, Arikok National Park, Baby Beach
Find places to stay Nov 29 — Dec 2:
Highlights from your plan
Eagle Beach ©
Eagle Beach
Baby Beach ©
Baby Beach
Palm Beach ©
Palm Beach

2
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.
On the 3rd (Tue), take in the architecture and atmosphere at Basilica Cathedral of Santa Maria la Menor, contemplate in the serene atmosphere at Catedral Primada de America, then contemplate the long history of Alcazar de Colon, then contemplate the long history of Fortaleza Ozama, and finally explore the ancient world of Monasterio de San Francisco. Here are some ideas for day two: make a trip to Columbus Lighthouse (Faro A Colon) and then don't miss a visit to Zona Colonial.

For ratings, photos, traveler tips, and more tourist information, refer to the Santo Domingo trip itinerary app.

You can fly from Palm - Eagle Beach to Santo Domingo in 2.5 hours. Finish up your sightseeing early on the 4th (Wed) so you can travel to San Juan.

Things to do in Santo Domingo

Historic Sites Museums
Find places to stay Dec 2 — 4:
Highlights from your plan
Alcazar de Colon ©
Alcazar de Colon
Catedral Primada de America
Catedral Primada de America
Zona Colonial ©
Zona Colonial

3
nights
San Juan, Puerto Rico

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Paddle Yoga Puerto Rico has been added to your itinerary. Visiting El Yunque Rain Forest and Condado Beach will get you outdoors. Old San Juan and Sitio Histórico de San Juan will appeal to history buffs. Next up on the itinerary: appreciate the extensive heritage of Paseo de la Princesa and take in the architecture and atmosphere at Catedral Metropolitana Basilica de San Juan Bautista.

To see maps, reviews, photos, and more tourist information, use the San Juan trip itinerary planner.

Traveling by flight from Santo Domingo to San Juan takes 3 hours. Alternatively, you can do a combination of shuttle and flight; or ride a ferry. In December, daily temperatures in San Juan can reach 85°F, while at night they dip to 75°F. Wrap up your sightseeing by early afternoon on the 7th (Sat) to allow time for travel back home.

Things to do in San Juan

Parks Historic Sites Wildlife

Side Trip

El Yunque Rain Forest
Find places to stay Dec 4 — 7:
Highlights from your plan
Old San Juan ©
Old San Juan
El Yunque Rain Forest ©
El Yunque Rain Forest
Sitio Histórico de San Juan ©
Sitio Histórico de San Juan

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