14 days in Kissimmee & Puerto Rico Itinerary

14 days in Kissimmee & Puerto Rico Itinerary

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Route & dates

14 days in Kissimmee & Puerto Rico Itinerary

Start: Newark, United States
Fly:  8 h
1
Kissimmee, United States
— 3 nights
+2
Drive + Fly + Drive:  8 h 15 min
2
Ponce, Puerto Rico
— 2 nights
Shuttle + Fly:  1 h 45 min
3
Culebra, Puerto Rico
— 3 nights
Fly + Drive:  30 min
4
Isla de Vieques, Puerto Rico
— 3 nights
Fly:  30 min
5
San Juan, Puerto Rico
— 2 nights
Fly:  7 h 15 min
End: Newark, United States

3
nights
Kissimmee, United States

Kissimmee ©
A popular vacation destination in the central part of Florida, Kissimmee's major claim to fame remains its sunny weather and proximity to a large Disney entertainment complex.
On your second day here, examine the collection at Kennedy Space Center Visitor Complex and then stop by Ron Jon Surf Shop.

To find other places to visit, more things to do, ratings, and other tourist information, refer to the Kissimmee trip builder.

Newark to Kissimmee is an approximately 8-hour flight. You can also drive. In August, daytime highs in Kissimmee are 90°F, while nighttime lows are 74°F. You will leave for Ponce on the 9th (Wed).

Things to do in Kissimmee

Childrens Museums Museums Parks

Side Trips

NASA Kennedy Space Center Visitor Complex, Brevard Zoo, Ron Jon Surf Shop
Find places to stay Aug 6 — 9:
Highlights from your plan
Ron Jon Surf Shop ©
Ron Jon Surf Shop
Brevard Zoo ©
Brevard Zoo

2
nights
Ponce, Puerto Rico

Ponce ©
Ponce is both a city and a municipality in the southern part of Puerto Rico. Kick off your visit on the 10th (Thu): admire all the interesting features of La Guancha, admire the masterpieces at Museo de Arte de Ponce, then admire the landmark architecture of Casa Wiechers-Villaronga, and finally see the interesting displays at Parque de Bombas. Get ready for a full day of sightseeing on the 11th (Fri): see the interesting displays at El Museo Castillo Serralles and then head off the coast to Isla de Caja de Muertos.

To find more things to do, maps, and tourist information, use the Ponce trip builder.

Explore your travel options from Kissimmee to Ponce with the Route module. The time zone difference when traveling from Kissimmee to Ponce is 1 hour. In August, daytime highs in Ponce are 88°F, while nighttime lows are 76°F. Finish your sightseeing early on the 11th (Fri) to allow enough time to travel to Culebra.

Things to do in Ponce

Parks Museums Nature
Find places to stay Aug 9 — 11:
Highlights from your plan
La Guancha ©
La Guancha
Museo de Arte de Ponce ©
Museo de Arte de Ponce
El Museo Castillo Serralles ©
El Museo Castillo Serralles

3
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.
You'll discover tucked-away gems like Tamarindo Beach and Carlos Rosario Beach. Get a sense of the local culture at Museo Histotico de Culebra and Culebrita Lighthouse. There's more to do: tour the pleasant surroundings at Flamenco Beach and kick back and relax at Playa Punta Soldado Beach.

To find where to stay, other places to visit, traveler tips, and other tourist information, read our Culebra trip generator.

Getting from Ponce to Culebra by combination of car and flight takes about 2 hours. Other options: do a combination of taxi and flight. Expect a daytime high around 88°F in August, and nighttime lows around 78°F. Finish your sightseeing early on the 14th (Mon) to allow enough time to travel to Isla de Vieques.

Things to do in Culebra

Parks Outdoors Beaches
Find places to stay Aug 11 — 14:
Highlights from your plan
Flamenco Beach ©
Flamenco Beach
Tamarindo Beach ©
Tamarindo Beach
Zoni Beach ©
Zoni Beach

3
nights
Isla de Vieques, Puerto Rico

Isla de Vieques ©
For sixty years until 2003, most of the Isla de Vieques was closed off to the public, with the US Navy using the island's beaches and surrounding waters for drills and testing of new military machinery, such as bombs.
We've included these beaches for you: Blue Beach and Caracas Beach. Do some cultural sightseeing at Gallery Galleon and Puerto Ferro Lighthouse. Next up on the itinerary: enjoy the sand and surf at Sun Bay, stroll through Secret Beach, and discover the deep blue sea with a scuba or snorkeling tour.

To see traveler tips, ratings, photos, and tourist information, read our Isla de Vieques travel itinerary creator.

Isla de Vieques is very close to Culebra. August in Isla de Vieques sees daily highs of 88°F and lows of 79°F at night. Finish your sightseeing early on the 17th (Thu) to allow enough time to travel to San Juan.

Things to do in Isla de Vieques

Outdoors Parks Beaches
Find places to stay Aug 14 — 17:
Highlights from your plan
La Chiva ©
La Chiva
Caracas Beach ©
Caracas Beach
Sun Bay Beach ©
Sun Bay Beach

2
nights
San Juan, Puerto Rico

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Kick off your visit on the 18th (Fri): appreciate the extensive heritage of Old San Juan, then stop by Caribbean Trading Company Store, and then get engrossed in the history at Cathedral of San Juan Bautista.

To find more things to do, maps, ratings, and other tourist information, you can read our San Juan holiday planner.

San Juan is just a stone's throw from Isla de Vieques. In August, daily temperatures in San Juan can reach 89°F, while at night they dip to 78°F. Wrap up your sightseeing by early afternoon on the 19th (Sat) to allow enough time to travel back home.

Things to do in San Juan

Historic Sites Neighborhoods Shopping

Side Trip

Caribbean Trading Company Store
Find places to stay Aug 17 — 19:
Highlights from your plan
Old San Juan ©
Old San Juan
Paseo de la Princesa ©
Paseo de la Princesa

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