31 days in Hawaii & Puerto Rico Itinerary

31 days in Hawaii & Puerto Rico Itinerary

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1
Lihue, United States
— 2 nights
Fly
2
Honolulu, United States
— 5 nights
Fly
3
Lahaina, United States
— 4 nights
Fly
4
Hilo, United States
— 3 nights
Drive
5
Kailua-Kona, United States
— 1 night
Fly
6
San Juan, Puerto Rico
— 4 nights
Drive
7
El Yunque National Forest, Puerto Rico
— 1 night
Fly
8
Culebra, Puerto Rico
— 4 nights
Fly to Vieques, Taxi to Isla de Vieques
9
Isla de Vieques, Puerto Rico
— 5 nights
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Lihue, United States

— 2 nights
Lihue or Līhue is an unincorporated census-designated place (CDP) and the county seat of Kauai County, Hawaii. Explore Lihue's surroundings by going to Boat Tours & Water Sports (in Kekaha), Waimea Canyon State Park (in Waimea) and Na Pali Coast State Park (in Wainiha). There's still lots to do: hit the best photo ops around with an inspiring photography tour, enjoy the sand and surf at Hanalei Beach, don't miss a visit to Kalalau Lookout, and see the world from above with a helicopter tour.

To see where to stay, more things to do, and other tourist information, refer to the Lihue online trip itinerary maker.

Los Angeles to Lihue is an approximately 7.5-hour flight. Traveling from Los Angeles to Lihue, you'll gain 2 hours due to the time zone difference. Expect somewhat warmer evenings in Lihue when traveling from Los Angeles in June, with lows around 73°F. Wrap up your sightseeing on the 3rd (Sat) to allow time to fly to Honolulu.

Things to do in Lihue

Parks · Tours · Outdoors · Nature

Side Trips

Honolulu, United States

— 5 nights

Big Pineapple

In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.
Get out of town with these interesting Honolulu side-trips: Pu’u O Mahuka Heiau State Monument (in Pupukea) and Haleiwa (Waimea Bay, Sunset Beach Park, &more). And it doesn't end there: tour the pleasant surroundings at Diamond Head State Monument, admire the sheer force of Manoa Falls, explore the different monuments and memorials at USS Arizona Memorial, and contemplate the long history of Battleship Missouri Memorial.

For more things to do, photos, and tourist information, read Honolulu online vacation planner.

Fly from Lihue to Honolulu in 2.5 hours. In June, plan for daily highs up to 86°F, and evening lows to 74°F. Finish your sightseeing early on the 8th (Thu) to allow enough time to fly to Lahaina.

Things to do in Honolulu

Parks · Outdoors · Beaches · Museums

Side Trips

Lahaina, United States

— 4 nights

Crown Jewel of Maui

Once the booming capital of the Hawaiian Kingdom, the tropical paradise of Lahaina still remains one of Maui's top vacation attractions, providing both culture and recreation.
Step out of Lahaina to go to Wailuku and see Iao Valley, which is approximately 44 minutes away. Spend the 11th (Sun) exploring the striking scenery along Hana Highway - Road to Hana. Next up on the itinerary: see some colorful creatures with a scuba or snorkeling tour, kick your exploration up a notch at some of the top local zipline courses and adventure parks, tour the pleasant surroundings at Kapalua Beach, and meet the residents at Maui Ocean Center.

To find photos, ratings, more things to do, and more tourist information, you can read our Lahaina holiday maker website.

You can fly from Honolulu to Lahaina in 2.5 hours. In June, plan for daily highs up to 84°F, and evening lows to 72°F. Wrap up your sightseeing on the 12th (Mon) early enough to fly to Hilo.

Things to do in Lahaina

Outdoors · Parks · Beaches · Scenic Drive

Side Trips

Hilo, United States

— 3 nights

America's Wettest City

One of the island of Hawaii's major towns, Hilo contains a mix of Asian and Polynesian cultures and is known for its proximity to a national park encompassing two active volcanoes.
Change things up with these side-trips from Hilo: Hawaii Volcanoes National Park (Keanakakoi Crater Overlook, Kilauea Iki Trailhead, &more), Jagger Museum (in Volcano) and Laupahoehoe Beach Park (in Laupahoehoe). And it doesn't end there: take in the dramatic scenery at Akaka Falls State Park, get up close and personal with brilliant marine life at Mokupapapa Discovery Center, take in nature's colorful creations at Liliuokalani Gardens, and pick up some local products at Hilo Farmers Market.

To find maps, other places to visit, photos, and tourist information, read Hilo online road trip planner.

Fly from Lahaina to Hilo in 2.5 hours. In June in Hilo, expect temperatures between 83°F during the day and 69°F at night. Cap off your sightseeing on the 15th (Thu) early enough to go by car to Kailua-Kona.

Things to do in Hilo

Parks · Outdoors · Trails · Nature

Side Trips

Kailua-Kona, United States

— 1 night

Heart of the Kona Coast

Thanks to its favorable location near a mountain range blocking the northeasterly trade winds, Kailua-Kona gets little rainfall, allowing adventure seekers and nature lovers a chance to enjoy over 300 days of sunshine each year.
Kick off your visit on the 16th (Fri): look for all kinds of wild species at Kona Cloud Forest and then fulfill a lifelong dream with a swim-with-the-dolphins experience.

To find photos, more things to do, reviews, and more tourist information, go to the Kailua-Kona trip itinerary tool.

You can drive from Hilo to Kailua-Kona in 2 hours. Alternatively, you can take a bus. Expect a daytime high around 85°F in June, and nighttime lows around 74°F. Finish your sightseeing early on the 16th (Fri) so you can fly to San Juan.

Things to do in Kailua-Kona

Wildlife · Parks · Tours · Outdoors

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.
Get out of town with these interesting San Juan side-trips: Zipline (in Rio Grande) and Luquillo Beach (in Luquillo). Next up on the itinerary: get to know the fascinating history of Old San Juan, kick back and relax at Pine Grove Beach, indulge your taste buds at Food & Drink, and tour the pleasant surroundings at Condado Beach.

To see other places to visit, photos, where to stay, and tourist information, use the San Juan attractions planner.

Traveling by flight from Kailua-Kona to San Juan takes 18.5 hours. The time zone changes from Hawaii-Aleutian Standard Time to Atlantic Standard Time, which is usually a 6 hour difference. In June, daytime highs in San Juan are 89°F, while nighttime lows are 78°F. Finish your sightseeing early on the 21st (Wed) to allow enough time to drive to El Yunque National Forest.

Things to do in San Juan

Outdoors · Parks · Beaches · Historic Sites

Side Trips

El Yunque National Forest, Puerto Rico

— 1 night
On the 22nd (Thu), delve into the lush surroundings at El Yunque Rain Forest.

For reviews, where to stay, ratings, and tourist information, use the El Yunque National Forest online trip maker.

Drive from San Juan to El Yunque National Forest in 1.5 hours. Alternatively, you can take a shuttle. In June, plan for daily highs up to 89°F, and evening lows to 78°F. Finish up your sightseeing early on the 22nd (Thu) so you can catch the flight to Culebra.

Things to do in El Yunque National Forest

Parks · Wildlife · Nature
Highlights from your trip

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 nature. Your plan includes some of its best attractions: stroll through Flamenco Beach, kick back and relax at Melones Beach, get a new perspective on things with Boat Tours & Water Sports, and step off the mainland to explore Culebrita.

To see where to stay, traveler tips, more things to do, and more tourist information, read our Culebra online road trip planner.

Traveling by flight from El Yunque National Forest to Culebra takes 2 hours. Alternatively, you can do a combination of car and ferry. June in Culebra sees daily highs of 89°F and lows of 79°F at night. Finish your sightseeing early on the 26th (Mon) to allow enough time to travel to Isla de Vieques.

Things to do in Culebra

Parks · Outdoors · Beaches · Historic Sites

Isla de Vieques, Puerto Rico

— 5 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 wildlife. Your plan includes some of its best attractions: kick back and relax at Balneario Sun Bay, tour the pleasant surroundings at Caracas Beach, take a pleasant ride with a tour on horseback, and take in the waterfront at Mosquito Pier.

To see where to stay, more things to do, other places to visit, and tourist information, you can read our Isla de Vieques trip tool.

Getting from Culebra to Isla de Vieques by combination of flight and taxi takes about 3.5 hours. Other options: do a combination of flight, car, and ferry; or ride a ferry. In June, daily temperatures in Isla de Vieques can reach 87°F, while at night they dip to 78°F. Wrap up your sightseeing by early afternoon on the 1st (Sat) to allow enough time to fly back home.

Things to do in Isla de Vieques

Outdoors · Parks · Beaches · Tours

Hawaii travel guide

4.4
Scuba & Snorkeling · Beaches · Zipline
The Aloha State
An archipelago of hundreds of volcanic islands located in a geological hot spot in the middle of Pacific, Hawaii offers diverse natural scenery and a warm tropical climate. The six major islands open to tourism draw visitors with their sun-drenched public beaches and craggy natural trails. Thanks to their mid-Pacific location, the islands boast a vibrant native culture influenced by both North America and Asia. You can spend your vacation basking in the modern comforts of the big hotels, but to experience the true spirit of these islands, remember that real Hawaiians live outdoors. Encounter nature by surfing, swimming, fishing, and picnicking, or join a guided tour across the ancient lava flows to the top of Hawaii's rugged volcanic peaks.

Puerto Rico travel guide

4.5
Historic Walking Areas · Beaches · Forests
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.