14 days in Caribbean Itinerary

14 days in Caribbean Itinerary

Created using Inspirock Caribbean trip planner

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Route & dates

14 days in Caribbean Itinerary

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 El Malecon and Christopher Columbus Cemetery (Cemetario de Colon). Old Havana and Castillo de la Real Fuerza will appeal to history buffs. Next up on the itinerary: contemplate the long history of Fortaleza de San Carlos de la Cabana, admire the masterpieces at Museu Nacional de Belas Artes de Cuba, get engrossed in the history at Museum of the Revolution (Museo de la Revolucion), and don't miss a visit to Old Square (Plaza Vieja).

Plan a trip to Havana easily and quickly by telling Inspirock to suggest an itinerary.

Portland, USA to Havana is an approximately 10.5-hour flight. You can also do a combination of train and flight. Due to the time zone difference, you'll lose 3 hours traveling from Portland to Havana. In November, Havana is much warmer than Portland - with highs of 83°F and lows of 65°F. Finish your sightseeing early on the 27th (Wed) so you can 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 ©
Kick off your visit on the 28th (Thu): enjoy the sand and surf at Seven Mile Beach, then brush up on your knowledge of spirits at Cayman Spirits Co. Distillery, and then look for all kinds of wild species at Stingray City Grand Cayman. On the next day, discover the deep blue sea with a scuba or snorkeling tour, cool off at Cayman Turtle Centre: Island Wildlife Encounter, and then explore the striking landscape at Hell Gift Store.

To find reviews, traveler tips, more things to do, and other tourist information, you can read our Seven Mile Beach route planner .

Fly from Havana to Seven Mile Beach in 2 hours. Traveling from Havana in November, Seven Mile Beach is a bit warmer at night 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.
Relax by the water at Eagle Beach and Baby Beach. Step out of the city life by going to Palm Beach and Arikok National Park. There's still lots to do: visit a coastal fixture at California Lighthouse.

To find more things to do, reviews, and tourist information, read Palm - Eagle Beach vacation maker .

Traveling by flight from Seven Mile Beach to Palm - Eagle Beach takes 6.5 hours. The time zone difference moving from Eastern Standard Time (EST) to Atlantic Standard Time (AST) is 1 hour. In November, daytime highs in Palm - Eagle Beach are 89°F, while nighttime lows are 79°F. Wrap up your sightseeing on the 2nd (Mon) to allow time to travel to Santo Domingo.

Things to do in Palm - Eagle Beach

Parks Beaches Outdoors

Side Trips

Baby Beach, California Lighthouse, Arikok National Park
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.
Start off your visit on the 3rd (Tue): pause for some serene contemplation at Basilica Cathedral of Santa Maria la Menor, take in the spiritual surroundings of Catedral Primada de America, then contemplate the long history of Alcazar de Colon, then steep yourself in history at Fortaleza Ozama, and finally explore the ancient world of Monasterio de San Francisco. Get ready for a full day of sightseeing on the next day: pause for some photo ops at Columbus Lighthouse (Faro A Colon) and then don't miss a visit to Zona Colonial.

You can plan Santo Domingo trip in no time by asking Inspirock to help create your itinerary.

Traveling by flight from Palm - Eagle Beach to Santo Domingo takes 2.5 hours. Wrap up your sightseeing on the 4th (Wed) early enough to 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.
You've now added Paddle Yoga Puerto Rico to your itinerary. Get some cultural insight at Old San Juan and Paseo de la Princesa. Get outdoors at El Yunque Rain Forest and Condado Beach. Next up on the itinerary: get to know the fascinating history of Sitio Histórico de San Juan and pause for some serene contemplation at Catedral Metropolitana Basilica de San Juan Bautista.

To find other places to visit, more things to do, maps, and more tourist information, read our San Juan vacation builder app .

You can fly from Santo Domingo to San Juan in 3 hours. Alternatively, you can do a combination of shuttle and flight; or ride a ferry. In December, daytime highs in San Juan are 85°F, while nighttime lows are 75°F. Wrap up your sightseeing by early afternoon on the 7th (Sat) to allow enough time to 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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