22 days in Caribbean Itinerary

22 days in Caribbean Itinerary

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Route & dates

22 days in Caribbean Itinerary

Start: San Francisco, United States
Fly:  12​h 30​min
1
San Juan, Puerto Rico
— 5 nights
Fly:  30​min
2
Culebra, Puerto Rico
— 4 nights
Fly:  4​h 30​min
3
Santo Domingo, Dominican Republic
— 3 nights
Fly:  3​h
4
Palm - Eagle Beach, Aruba
— 3 nights
Fly:  5​h 45​min
5
Havana, Cuba
— 5 nights
Fly:  10​h 30​min
End: San Francisco, United States

5
nights
San Juan, Puerto Rico

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
You'll enjoy a bit of beach vacationing at Condado Beach and Pine Grove Beach. Satisfy your inner culture vulture at Old San Juan and Paseo de la Princesa. Venture out of the city with trips to Luquillo Beach (in Luquillo) and El Yunque Rain Forest (in El Yunque National Forest). There's lots more to do: appreciate the extensive heritage of San Juan National Historic Site, kick back and relax at Carolina Beach, get engrossed in the history at Catedral Metropolitana Basilica de San Juan Bautista, and steep yourself in history at 104 Calle La Fortaleza.

For ratings, more things to do, other places to visit, and tourist information, refer to the San Juan online trip maker .

San Francisco, USA to San Juan is an approximately 12.5-hour flight. You can also do a combination of flight and car; or do a combination of flight and shuttle. The time zone difference moving from Pacific Standard Time to Atlantic Standard Time is 4 hours. Plan for much warmer temperatures traveling from San Francisco in November, with highs in San Juan at 87°F and lows at 76°F. Finish your sightseeing early on the 25th (Mon) so you can fly to Culebra.

Things to do in San Juan

Parks Beaches Outdoors

Side Trips

Carolina, Bosque Nacional El Yunque, El Yunque Rain Forest, Luquillo Beach
Find places to stay Nov 20 — 25:
Highlights from your plan
Old San Juan ©
Old San Juan
El Yunque Rain Forest ©
El Yunque Rain Forest
Luquillo Beach ©
Luquillo Beach

4
nights
Culebra, Puerto Rico

Culebra ©
With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
Relax by the water at Flamenco Beach and Melones Beach. Do some cultural sightseeing at Culebrita Lighthouse and Museo Historico de Culebra. The adventure continues: kick back and relax at Zoni Beach, stroll through Brava Beach, step off the mainland to explore Culebrita Island, and browse the collection at Culebra Public Library.

To find reviews, other places to visit, maps, and more tourist information, use the Culebra trip planner.

Culebra is just a short distance from San Juan. November in Culebra sees daily highs of 86°F and lows of 76°F at night. Finish your sightseeing early on the 29th (Fri) so you can travel to Santo Domingo.

Things to do in Culebra

Parks Beaches Outdoors
Find places to stay Nov 25 — 29:
Highlights from your plan
Flamenco Beach ©
Flamenco Beach
Zoni Beach ©
Zoni Beach
Tamarindo Beach ©
Tamarindo Beach

3
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.
Your inner history buff will appreciate Alcazar de Colon and Fortaleza Ozama. Get in touch with nature at National Aquarium and National Botanical Garden. There's much more to do: contemplate in the serene atmosphere at Catedral Primada de America, pause for some serene contemplation at Basilica Cathedral of Santa Maria la Menor, explore the ancient world of Monasterio de San Francisco, and steep yourself in history at Palacio Consistorial.

To see where to stay, photos, other places to visit, and other tourist information, you can read our Santo Domingo route maker app .

Traveling by flight from Culebra to Santo Domingo takes 4.5 hours. Alternatively, you can do a combination of ferry, shuttle, and flight; or ride a ferry. Finish your sightseeing early on the 2nd (Mon) so you can travel to Palm - Eagle Beach.

Things to do in Santo Domingo

Historic Sites Parks Nature
Find places to stay Nov 29 — Dec 2:
Highlights from your plan
Alcazar de Colon ©
Alcazar de Colon
Catedral Primada de America
Catedral Primada de America
Zona Colonial ©
Zona Colonial

3
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.
Deepen your sense of the past at sights like California Lighthouse and Bushiribana Gold Mill Ruins. Your itinerary includes some good beach time at Palm Beach and Eagle Beach. When in Palm - Eagle Beach, make a side trip to see Baby Beach in San Nicolas, approximately 48 minutes away. There's lots more to do: kick back and relax at Arashi Beach, look for all kinds of wild species at Donkey Sanctuary Aruba, and tour the pleasant surroundings at Hadicurari Beach.

For traveler tips, maps, more things to do, and other tourist information, read Palm - Eagle Beach driving holiday app .

Fly from Santo Domingo to Palm - Eagle Beach in 3 hours. In December, plan for daily highs up to 88°F, and evening lows to 78°F. Wrap up your sightseeing on the 5th (Thu) to allow time to travel to Havana.

Things to do in Palm - Eagle Beach

Parks Beaches Outdoors

Side Trips

Noord, Baby Beach, Donkey Sanctuary Aruba, Arashi Beach, Bushiribana Gold Mill Ruins
Find places to stay Dec 2 — 5:
Highlights from your plan
Eagle Beach ©
Eagle Beach
Palm Beach ©
Palm Beach
Baby Beach ©
Baby Beach

5
nights
Havana, Cuba

Havana ©
Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
El Malecon and Old Square (Plaza Vieja) are good opportunities to explore the local culture. Your inner history buff will appreciate Old Havana and El Morro. There's still lots to do: steep yourself in history at Fortaleza de San Carlos de la Cabana, admire the striking features of Casa de la Amistad, admire the masterpieces at Museu Nacional de Belas Artes de Cuba, and contemplate in the serene atmosphere at Havana Cathedral.

For maps, traveler tips, where to stay, and more tourist information, read Havana journey planner.

Traveling by flight from Palm - Eagle Beach to Havana takes 6 hours. The time zone difference moving from Atlantic Standard Time to Cuba Standard Time is minus 1 hour. Plan for a bit cooler temperatures traveling from Palm - Eagle Beach in December, with highs in Havana at 82°F and lows at 64°F. Finish your sightseeing early on the 10th (Tue) so you can travel back home.

Things to do in Havana

Historic Sites Museums Neighborhoods

Side Trip

Espiritu Santo Church (Iglesia Del Espiritu Santo)
Find places to stay Dec 5 — 10:
Highlights from your plan
Old Havana ©
Old Havana
El Malecon ©
El Malecon
Fortaleza de San Carlos de la Cabana ©

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