Best Road Trip Planner For 3 Beautiful Tropical Destinations

If you’ve been cooped up and craving a new adventure, sometimes a road trip is just what you need. Many take road trips as a means of getting to their destination, but imagine if you integrated a road trip as part of your adventure? Better yet, what if you hit the open road in a place splashed with sunshine and views of the palm trees and an ocean in your rear-view mirror?

The first step is deciding where, then choose how long you’d like your road trip to be — and if you’d like it to be the main focus of your vacation, or simply a part of it. We’ve gathered itineraries to create the best road trip planner for some of the most beautiful tropical places to visit for three-, five-, and seven-day road trips. Experience everything from all-inclusive resorts in Mexico to pristine beaches in the Caribbean to unforgettable views of Hawaii’s rugged landscape. So, pick your region, select your timeline, and put a pin in the others so that you can revisit on your next great escape.

1. Mexico Road Trip Planners

3-Day Cancun Road Trip Itinerary

  • Day 1: Settle into the Mexican salt life in Cancun, fronting the Caribbean Sea.
  • Day 2: Drive south just over 1 hour to Playa del Carmen for top-notch golf or an unforgettable day at Xcaret Park.
  • Day 3: Drive 1 hour south to swim in the crystal-clear cenotes or visit the Mayan ruins around Tulum.


5-Day Mexico City Road Trip Itinerary

  • Day 1: Dive into delicious street food and world-class museums in Mexico City, one of Latin America’s most culturally vibrant capitals.
  • Day 2: Day trip 1 hour northeast to walk the Avenue of the Dead and other archeological wonders at Teotihuacan then return to Mexico City.
  • Day 3: Drive 2 2/3 hours southwest to Taxco, Mexico’s famous center of silversmithing, and shop for beautiful handmade accessories.
  • Day 4: Drive 3 ½ hours south to Acapulco in time to feast on ceviche and fish tacos with sunset ocean views.
  • Day 5: Flop down on an epic Acapulco beach with your favorite frosty drink and bask in the Mexican good life.


7-Day Baja California Sur Road Trip Itinerary

  • Day 1: Start your adventure in La Paz, the capital of Baja California Sur, that fronts the Sea of Cortez.
  • Day 2: Head out on a snorkeling adventure in the Sea of Cortez, which Jacques Cousteau called the Aquarium of the World.
  • Day 3: Drive south 1 hour to San Ignacio to go whale watching and spot migrating gray whales just offshore.
  • Day 4: Drive 20 minutes south from San Ignacio to Cerritos Beach before continuing south 1 hour to Cabo San Lucas.
  • Day 5: Take a boat trip to visit El Arco, a natural arch in the sea cliffs, or spend the day golfing one of the area’s many excellent courses.
  • Day 6: Continue around the coastal road 30 minutes to San Jose del Cabo to explore the historic district and relax on the beautiful beaches.
  • Day 7: Spend the day exploring San Jose del Cabo’s historical center, packed with galleries and restaurants.


2. Caribbean Road Trip Planners

3-Day Old San Juan and Rio Grande Road Trip Itinerary

  • Day 1: Explore El Morro, the San Juan citadel that dates to the 16th century. Then dine al fresco along the atmospheric streets of Old San Juan in Puerto Rico.
  • Day 2: Marvel at the verdant views and spot endemic birds within El Yunque National Forest, 45 minutes from San Juan. Then continue 20 minutes to Rio Grande.
  • Day 3: Spend the day enjoying golf or beach time in the exceptional resort areas of Rio Grande.


5-Day Dominican Republic Road Trip Itinerary

  • Day 1: Kick off your Dominican Republic adventure along the legendary beaches of Punta Cana, where sailing, snorkeling, and bachata music await.
  • Day 2: Spend another day taking in Punta Cana, with time for a zip lining adventure through the rainforest canopy or a sunset cruise.
  • Day 3: Drive 50 minutes to Bayahibe, known for excellent diving and snorkeling, with more than 20 sites spread across coral reefs and wrecks just offshore.
  • Day 4: Drive 30 minutes west to the resort town of La Romana, known for its white sand beaches and world-class golfing.
  • Day 5: Spend another day taking in all La Romana has to offer.


7-Day Jamaica Road Trip Itinerary

  • Day 1: Kick things off in Jamaica’s gorgeous western beaches, where Negril’s bohemian lifestyle and stunning Seven Mile Beach await.
  • Day 2: Explore Negril’s laid-back West End and take in the sunset cliff-diving spectacle at Rick’s Cafe.
  • Day 3: Drive 1 2/3 hours to Montego Bay, where you can go horseback riding on the beach at Sandy Bay along the way.
  • Day 4: Drive 40 minutes east to Falmouth for a nighttime boat adventure at Glistening Waters Restaurant & Marina’s Luminous Lagoon.
  • Day 5: Continue 45 minutes east to Runaway Bay to explore the Green Grotto Caves.
  • Day 6: On your way east 30 minutes to Ocho Rios, stop in St. Ann’s and Nine Mile for the Bob Marley Museum.
  • Day 7: Spend the day frolicking in the famous cascades at Dunn’s River Falls before a lobster dinner with ocean views in Ocho Rios.


3. Hawaii Road Trip Planners

3-Day Kauai Road Trip Itinerary

  • Day 1: On Kauai, explore quirky Hanalei Town’s historic church and art galleries, drink a mai tai, seek out South Pacific locales, then relax at Hanalei Bay or Tunnels Beach.
  • Day 2: Drive an all-day loop through the ever-changing landscapes from Princeville, stopping at the Wailua Falls, then to Waimea Canyon State Park.
  • Day 3: Explore the green, rugged, and remote Nāpali Coast by air or boat. Then steer east to The Sunny South Side’s Poipu. Continue 40 minutes to Old Kapaa Town to see ukeles, boutiques, and shave ice.


5-Day Maui Road Trip Itinerary

  • Day 1: On Maui, immerse yourselves in the past in the Lahaina Historic District. Drive 30 minutes to Kihei for karaoke or dancing.
  • Day 2: Drive inland an hour to see the sunrise from the Haleakala Crater. Go another 30 minutes to tour the Ali’i Kula Lavender Farm.
  • Day 3: Drive a couple hours clockwise toward the quiet outpost, stopping at Twin Falls, the Garden of Eden Arboretum, Lava Tube, and Wai’anapanapa State Park. Lunch in Hana Town and continue to Seven Scared Pools.
  • Day 4: From Kihei, drive 10 minutes to the Maui Ocean Center to see underwater life. Continue 25 minutes to Lahaina for a whale-watching tour.
  • Day 5: Drive 40 minutes to Maui Pineapple Tours. Proceed 10 minutes to Makawai to zip line, then head 45 minutes to the Iao Needle in a lush state park.


7-Day Honolulu Road Trip Itinerary

  • Day 1: See the sites of Waikiki, including the 2-mile beach, Chinatown, Iolani Palace, the Diamond Head volcanic cone and Shangri La, heiress Doris Duke’s 1937 home.
  • Day 2: Take a surfing lesson, lunch along the Waikiki Beach Walk, then drive 25 minutes east to snorkel among 300 species of marine life in Hanauma Bay.
  • Day 3: Drive 35 minutes north to the Dole Plantation with the world’s largest maze. Continue to Haleiwa Town for a surf museum and art galleries, then Waimea Falls for a hike, and Sunset Beach for sundown.
  • Day 4: Head west 20 minutes to Pearl Harbor for World War II and Naval history including a battleship, submarine, museums, and memorials. Swing back via the Honolulu Zoo just outside Waikiki.
  • Day 5: Steer north 40 minutes to Kualoa Ranch for a Hollywood movie site, ATV, mountain bike, and horseback tours. Continue 20 minutes to the Polynesian Cultural Center.
  • Day 6: Fly an hour from Honolulu to The Big Island. Drive 10 minutes south to the Ocean Rider Seahorse Farm tour, then 30 minutes to Kailua-Kona for a manta ray snorkel. Then 22 minutes south is the Kona Coffee Living History Farm.
  • Day 7: Venture two hours to Hawaii Volcanoes National Park for live volcanoes, a lava tube, rain forest hiking and exhibits. Steer north to Hilo and the Rainbow Falls.

NOTE: Information may have changed since publication. Please confirm key details before planning your trip.

*These vacations are limited and subject to availability.

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