36 days in Puerto Rico & Florida Itinerary

36 days in Puerto Rico & Florida Itinerary

Make it your trip
Fly
1
Isla de Vieques, Puerto Rico
— 3 nights
Fly
2
Culebra, Puerto Rico
— 4 nights
Fly
3
San Juan, Puerto Rico
— 4 nights
Fly
4
Key Largo, United States
— 4 nights
Drive
5
Islamorada, United States
— 4 nights
Drive
6
Key West, United States
— 5 nights
Fly
7
Orlando, United States
— 5 nights
Fly
8
Fort Walton Beach, United States
— 4 nights
Drive
9
Panama City Beach, United States
— 2 nights
Fly

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Isla de Vieques, Puerto Rico — 3 nights

Isla Nena

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.
Isla de Vieques is known for beaches, nature, and adventure. Your trip includes some of its best attractions: tour the pleasant surroundings at Balneario Sun Bay, take in the waterfront at Mosquito Pier, kick back and relax at Playa La Chiva, and add some adventure to your tour with a kayaking and canoeing tour.

To see other places to visit, where to stay, maps, and more tourist information, read our Isla de Vieques holiday maker app.

New York City, USA to Isla de Vieques is an approximately 8-hour flight. The time zone difference moving from Eastern Standard Time to Atlantic Standard Time is 1 hour. Traveling from New York City in July, Isla de Vieques is somewhat warmer at night with lows of 79°F. Finish your sightseeing early on the 23rd (Sat) to allow enough time to fly to Culebra.
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Parks · Outdoors · Beaches · Wildlife
Find places to stay Jul 20 — 23:

Culebra, Puerto Rico — 4 nights

Little Island

With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
Culebra is known for beaches, wildlife, and outdoors. Your trip includes some of its best attractions: stroll through Flamenco Beach, kick back and relax at Playa Punta Soldado Beach, visit a coastal fixture at Culebrita Lighthouse, and head off the coast to Culebra National Wildlife.

To see maps, where to stay, reviews, and other tourist information, read Culebra trip planner.

Traveling by flight from Isla de Vieques to Culebra takes 3.5 hours. Alternatively, you can ride a ferry. July in Culebra sees daily highs of 90°F and lows of 80°F at night. Wrap up your sightseeing on the 27th (Wed) to allow time to fly to San Juan.
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Parks · Outdoors · Beaches · Nature
Find places to stay Jul 23 — 27:

San Juan, Puerto Rico — 4 nights

Walled City

Founded by the Spanish in 1521, San Juan is the oldest city under U.S. jurisdiction and one of the oldest in the Americas.
Venture out of the city with trips to Playa Luquillo (in Luquillo) and El Yunque National Forest (in El Yunque National Forest). There's still lots to do: tour the pleasant surroundings at Condado Beach, scramble along the landscape with a canyoning and rapelling tour, enjoy the sand and surf at Pine Grove Beach, and pause for some serene contemplation at Our Lady of Sorrows Catholic Church.

To see ratings, other places to visit, maps, and other tourist information, read San Juan vacation builder app.

Getting from Culebra to San Juan by flight takes about 2 hours. Other options: do a combination of ferry and car; or do a combination of ferry, taxi, and shuttle. In July in San Juan, expect temperatures between 89°F during the day and 78°F at night. Wrap up your sightseeing on the 31st (Sun) early enough to fly to Key Largo.
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Parks · Outdoors · Beaches · Nature
Side Trips
Find places to stay Jul 27 — 31:

Key Largo, United States — 4 nights

Diving Capital of the World

The northernmost island of the Florida Keys, Key Largo provides stunning scenery, a number of watersports opportunities, and plenty of areas to relax on vacation.
Go for a jaunt from Key Largo to Everglades National Park to see Anhinga Trail about 56 minutes away. There's much more to do: take a memorable tour with Tours, immerse yourself in nature at John Pennekamp Coral Reef State Park, explore the gorgeous colors at Spiegel Grove, and identify plant and animal life at North Dry Rocks.

To see reviews, other places to visit, maps, and tourist information, you can read our Key Largo tour itinerary site.

Getting from San Juan to Key Largo by flight takes about 6 hours. You'll gain 1 hour traveling from San Juan to Key Largo due to the time zone difference. Expect a daytime high around 89°F in July, and nighttime lows around 76°F. Finish your sightseeing early on the 4th (Thu) to allow enough time to drive to Islamorada.
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Parks · Wildlife · Outdoors · Tours
Side Trip
Find places to stay Jul 31 — Aug 4:

Islamorada, United States — 4 nights

The Village of Islands

Islamorada, long recognized as one of the world's top spots for sport fishing, encompasses six islands in the Florida Keys.
Change things up with these side-trips from Islamorada: Marathon (Sombrero Beach, The Turtle Hospital, &more). There's lots more to do: get close to the beloved marine mammals with Theater of the Sea, take a memorable tour with Contagious Charters, step off the mainland to explore Windley Key, and explore the gorgeous colors at Alligator Reef Light House.

To see reviews, more things to do, maps, and tourist information, you can read our Islamorada road trip site.

Islamorada is very close to Key Largo. Expect a daytime high around 92°F in August, and nighttime lows around 80°F. Cap off your sightseeing on the 8th (Mon) early enough to go by car to Key West.
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Wildlife · Parks · Outdoors · Tours
Side Trip
Find places to stay Aug 4 — 8:

Key West, United States — 5 nights

Conch Republic

Located just 140 km (90 mi) from Cuba, Key West is an island only about 6.4 km (4 mi) long and 1.6 km (1 mi) wide.
Key West is known for sightseeing, wildlife, and adventure. Your trip includes some of its best attractions: see the interesting displays at The Ernest Hemingway Home and Museum, make a trip to Southernmost Point, take a leisurely stroll along Mallory Square, and explore the gorgeous colors at Vandenberg Wreck.

For ratings, photos, reviews, and more tourist information, go to the Key West day trip app.

You can drive from Islamorada to Key West in 2 hours. Another option is to take a bus. In August, plan for daily highs up to 90°F, and evening lows to 81°F. Wrap up your sightseeing on the 13th (Sat) early enough to fly to Orlando.
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Museums · Parks · Wildlife · Shopping
Find places to stay Aug 8 — 13:

Orlando, United States — 5 nights

Theme Park Capital of the World

For most people, any mention of Orlando immediately conjures up images of sprawling theme parks filled with characters plucked right out of popular animated movies.
Have a day of magic on the 14th (Sun) at Walt Disney World Resort. Plan for a day of cool, family-friendly fun on the 15th (Mon) at Discovery Cove. Next up on the itinerary: find something for the whole family at SeaWorld, make an unforgettable trip to Disney's Animal Kingdom Theme Park, and test your team's savvy at popular escape rooms.

To find photos, ratings, reviews, and tourist information, read Orlando online driving holiday planner.

Traveling by flight from Key West to Orlando takes 3.5 hours. Alternatively, you can drive; or take a bus. Traveling from Key West in August, Orlando is a bit cooler at night with lows of 76°F. Finish your sightseeing early on the 18th (Thu) to allow enough time to fly to Fort Walton Beach.
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Find places to stay Aug 13 — 18:

Fort Walton Beach, United States — 4 nights

Fort Walton Beach is a city in southern Okaloosa County, Florida, United States. Venture out of the city with trips to Yellow River Marsh Aquatic Preserve (in Milton), Pensacola (National Naval Aviation Museum & Gulf Islands) and Pensacola Beach (Innerlight Surf Shop, Fort Pickens Area, &more). There's lots more to do: discover the deep blue sea with ScubaTech, head outdoors with Sunshine Water Sports, head off the coast to Santa Rosa Island, and stroll around Destin Dog Park.

For maps, ratings, more things to do, and more tourist information, read Fort Walton Beach online journey planner.

Traveling by flight from Orlando to Fort Walton Beach takes 3 hours. Alternatively, you can drive; or do a combination of bus, car, and taxi. The time zone difference moving from Eastern Standard Time to Central Standard Time is minus 1 hour. In August, plan for daily highs up to 89°F, and evening lows to 74°F. Finish your sightseeing early on the 22nd (Mon) to allow enough time to drive to Panama City Beach.
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Parks · Outdoors · Beaches · Nature
Side Trips
Find places to stay Aug 18 — 22:

Panama City Beach, United States — 2 nights

World's Most Beautiful Beaches

Boasting 43 km (27 mi) of white sandy beaches and plenty of sunshine, Panama City Beach is an ideal choice for a relaxing holiday.
Start off your visit on the 23rd (Tue): test your team's savvy at popular escape rooms, do a tasting at Panama City Beach Winery, then identify plant and animal life at Panama City Beach Dolphin Tours & More, and finally take an unforgettable tour with a helicopter tour. On your second day here, enjoy the sand and surf at Panama City Beach, enjoy the sand and surf at Santa Rosa Beach, and then look for gifts at Emerald Coast Olive Oil.

To see maps, reviews, more things to do, and tourist information, you can read our Panama City Beach trip itinerary builder website.

You can drive from Fort Walton Beach to Panama City Beach in 1.5 hours. The time zone changes from Central Standard Time to Eastern Standard Time, which is usually a 1 hour difference. In August, daily temperatures in Panama City Beach can reach 91°F, while at night they dip to 74°F. Cap off your sightseeing on the 24th (Wed) early enough to catch the flight back home.
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Outdoors · Parks · Beaches · Tours
Side Trips
Find places to stay Aug 22 — 24:

Puerto Rico travel guide

4.5
Historic Walking Areas · Beaches · Kayaking & Canoeing
A U.S. territory encompassing one big island and several smaller ones, Puerto Rico appeals to visitors from around the globe with its rich history, pleasant climate, natural beauty, and renowned local cuisine. Most tourists take a vacation in Puerto Rico for that classic seaside experience, though the island offers much more than just sun and sand. Tours of Puerto Rico usually start in the city of San Juan, which boasts a trendy bar scene and plenty of art museums for visitors looking to add a bit of culture to their vacation. A short drive from the island's urban centers, pristine rainforests serve as peaceful retreats from the city bustle and ensure plenty of chances to spot wildlife and take exhilarating nature walks.
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Florida travel guide

4.3
Disney Parks & Activities · Beaches · Theme Parks
The Sunshine State
The “Sunshine State,” Florida became a favorite winter destination for the affluent crowd over a century ago. Today, the state attracts visitors from around the world with its golden beaches and modern theme parks. You can spend your entire vacation enjoying the state's highly developed seaside areas, but remember that some of Florida's best-kept secrets are in secluded locations. Visit the big cities and their comfortable resorts offering top-notch dining and nightlife, but leave some time to see the peninsula's swampy landscape, filled with wild creatures and native plants. Farther away from the tourist-packed urban areas, the untamed wetlands of Florida offer a selection of things to do, such as kayaking, boat rides, and numerous other outdoor activities.
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