39 days in United States Itinerary

39 days in United States Itinerary

Created using Inspirock United States holiday planner

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Route & dates

39 days in United States Itinerary

Start: Thiruvananthapuram (Trivandrum)
Fly + bus:  27​h
1
Haleiwa, Oahu
— 2 nights
+2
bus + foot + Fly:  4​h 30​min
2
Lahaina, Maui
— 3 nights
Fly:  4​h
3
Kailua-Kona, Island of Hawaii
— 3 nights
+2
Fly + tram + bus:  10​h 45​min
4
Cannon Beach
— 2 nights
+2
bus + tram + Fly:  11​h 15​min
5
Panama City Beach
— 2 nights
Fly + bus:  6​h 15​min
6
Marathon
— 1 night
bus:  1​h 15​min
7
Key West
— 3 nights
Fly + Drive:  5​h 45​min
8
St. Augustine
— 2 nights
Drive:  4​h
9
Hilton Head
— 3 nights
Drive:  4​h 45​min
10
Myrtle Beach
— 2 nights
Fly + bus:  3​h 45​min
11
New York City
— 9 nights
bus + Fly:  20​h 15​min
End: Thiruvananthapuram (Trivandrum)

2
nights
Haleiwa, Oahu

Haleiwa ©
Haleiwa is a North Shore community and census-designated place (CDP) in the Waialua District of the island of Oahu, City and County of Honolulu. You'll enjoy a bit of beach vacationing at Ko Olina Lagoons and Waiale'e Beach. Explore hidden gems such as Polynesian Cultural Center and Sharks Cove. Change things up with these side-trips from Haleiwa: Kawela Bay Beach (in Kahuku) and Keawaula (Yokohama Beach) (in Makaha). There's still lots to do: kick back and relax at Ehukai Beach Park, stroll through Sunset Beach Park, and explore the gorgeous colors at Banzai Pipeline.

Plan trip to Haleiwa with our itinerary maker to find out where to go and what to do.

Thiruvananthapuram (Trivandrum), India to Haleiwa is an approximately 27-hour flight. You'll gain 15 hours traveling from Thiruvananthapuram (Trivandrum) to Haleiwa due to the time zone difference. Plan for slightly colder temperatures traveling from Thiruvananthapuram (Trivandrum) in May, with highs in Haleiwa at 30°C and lows at 21°C. Cap off your sightseeing on the 13th (Mon) early enough to travel to Lahaina.

Things to do in Haleiwa

Outdoors Beaches Parks

Side Trips

Pupukea, Polynesian Cultural Center, Aweoweo Beach Park, Waiale'e Beach, Ko Olina Lagoons
Highlights from your plan
Ko Olina Lagoons ©
Ko Olina Lagoons
Polynesian Cultural Center ©
Polynesian Cultural Center
Sunset Beach Park ©
Sunset Beach Park

3
nights
Lahaina, Maui

Lahaina ©
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.
Bring the kids along to Wailea Beach and Kapalua Beach. Eschew the tourist crowds and head to Napili Beach and Lahaina Banyan Court. You'll find plenty of places to visit near Lahaina: Kalepolepo Beach Park (in Kihei) and Wailea (Keawakapu Beach, Wailea Beach Path, & more). The adventure continues: admire nature's wide array of creatures at Maui Ocean Center, see majestic marine mammals with a dolphin and whale watching tour, stop by Sand People, and take a stroll through Lahaina Front Street.

Take the guesswork out of planning a Lahaina vacation by using our trip itinerary maker.

Traveling by combination of bus and flight from Haleiwa to Lahaina takes 4.5 hours. Alternatively, you can do a combination of bus and flight; or do a combination of bus, flight, and ferry. In May, daytime highs in Lahaina are 32°C, while nighttime lows are 24°C. Finish up your sightseeing early on the 16th (Thu) so you can travel to Kailua-Kona.

Things to do in Lahaina

Outdoors Parks Beaches

Side Trips

Wailea, Kalepolepo Beach Park, Kapalua Beach, Maui Ocean Center
Highlights from your plan
Wailea Beach ©
Wailea Beach
Kapalua Beach ©
Kapalua Beach
Napili Beach ©
Napili Beach

3
nights
Kailua-Kona, Island of Hawaii

Kailua-Kona ©
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.
Explore hidden gems such as Hapuna Beach State Recreation Area and Mauna Kea. Family-friendly places like Manini'owali Beach (Kua Bay) and Makalawena/Pu'u Ali'i will thrill your kids. Explore Kailua-Kona's surroundings by going to Pu'uhonua O Honaunau National Historical Park (in Honaunau) and Swim with Dolphins (in Waikoloa). There's still lots to do: see some colorful creatures with a scuba or snorkeling tour, kick back and relax at Kahaluu Beach, stop by 2nd Wave Beach and Boat, and get interesting insight from Tours.

For photos, where to stay, reviews, and tourist information, you can read our Kailua-Kona trip maker website .

Traveling by flight from Lahaina to Kailua-Kona takes 4 hours. Alternatively, you can do a combination of bus, flight, and taxi; or do a combination of bus and flight. In May, plan for daily highs up to 33°C, and evening lows to 26°C. Finish up your sightseeing early on the 19th (Sun) so you can travel to Cannon Beach.

Things to do in Kailua-Kona

Outdoors Parks Tours

Side Trips

Pu'uhonua O Honaunau National Historical Park, Hapuna Beach State Recreation Area, Kahaluu Beach, Swim with Dolphins
Highlights from your plan
Hapuna Beach State Recreation Area ©
Manini'owali Beach (Kua Bay) ©
Manini'owali Beach (Kua Bay)

2
nights
Cannon Beach

Cannon Beach ©
Cannon Beach is a city in Clatsop County, Oregon, United States. Attractions like Cannon Beach and Hug Point State Recreation Site make great kid-friendly stops. You'll discover tucked-away gems like Haystack Rock and Rockaway Beach Wayside. Change things up with these side-trips from Cannon Beach: Long Beach (in Long Beach), Adelaide's Coffee and Sweet Shoppe (in Ocean Park) and Astoria Column (in Astoria). There's still lots to do: enjoy the sand and surf at Manzanita Beach, tour the pleasant surroundings at Short Sands Beach, and play a few rounds at Manzanita Golf Course.

To find more things to do, photos, maps, and more tourist information, read Cannon Beach day trip planning site .

Getting from Kailua-Kona to Cannon Beach by combination of flight and bus takes about 11 hours. Other options: do a combination of bus and flight. You'll lose 2 hours traveling from Kailua-Kona to Cannon Beach due to the time zone difference. Prepare for much colder weather when traveling from Kailua-Kona in May: high temperatures in Cannon Beach hover around 19°C and lows are around 10°C. Cap off your sightseeing on the 22nd (Wed) early enough to travel to Panama City Beach.

Things to do in Cannon Beach

Outdoors Parks Beaches

Side Trips

Manzanita, Astoria Column, Rockaway Beach Wayside, Hug Point State Recreation Site, Adelaide's Coffee and Sweet Shoppe
Highlights from your plan
Haystack Rock ©
Haystack Rock
Cannon Beach ©
Cannon Beach
Hug Point State Recreation Site ©
Hug Point State Recreation Site

2
nights
Panama City Beach

Panama City Beach ©
Boasting 43 km (27 mi) of white sandy beaches and plenty of sunshine, Panama City Beach is an ideal choice for a relaxing holiday.
You'll visit kid-friendly attractions like Panama City Beach and St. Andrews State Park. You'll get in some beach time at Henderson Beach State Park and Santa Rosa Beach. Step out of Panama City Beach with an excursion to Mexico Beach in Mexico Beach--about 54 minutes away. There's much more to do: identify plant and animal life at Wildlife Areas, stroll through Blue Mountain Beach, buy something for everyone on your list at Pier Park, and take a memorable tour with Tours.

To see more things to do, photos, where to stay, and more tourist information, read Panama City Beach itinerary planner.

Traveling by combination of bus and flight from Cannon Beach to Panama City Beach takes 11.5 hours. Alternatively, you can drive. The time zone difference moving from Pacific Standard Time to Eastern Standard Time is 3 hours. Traveling from Cannon Beach in May, expect nights in Panama City Beach to be somewhat warmer, around 19°C, while days are warmer, around 34°C. Wrap up your sightseeing on the 25th (Sat) early enough to travel to Marathon.

Things to do in Panama City Beach

Outdoors Beaches Parks

Side Trips

Santa Rosa Beach, Henderson Beach State Park, Mexico Beach
Highlights from your plan
St. Andrews State Park ©
St. Andrews State Park
Panama City Beach ©
Panama City Beach
Henderson Beach State Park ©
Henderson Beach State Park

1
night
Marathon

Marathon ©
A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
On the 26th (Sun), enjoy the sand and surf at Sunset Park Beach, view the masterpieces at Shady Palm Art Gallery & Photography, then identify plant and animal life at The Turtle Hospital, then snap pictures at Seven Mile Bridge, and finally immerse yourself in nature at Bahia Honda State Park. Keep things going the next day: kick back and relax at Sombrero Beach, then stop by Bayshore Clothing, then look for all kinds of wild species at Dolphin Research Center, and finally see what you can catch with a fishing tour.

For more things to do, maps, ratings, and tourist information, read Marathon trip planner.

Getting from Panama City Beach to Marathon by combination of flight and bus takes about 6.5 hours. Other options: do a combination of car, flight, and shuttle; or drive. Traveling from Panama City Beach in May, Marathon is a bit warmer at night with lows of 29°C. Wrap up your sightseeing on the 27th (Mon) to allow time to take a bus to Key West.

Things to do in Marathon

Outdoors Parks Wildlife

Side Trips

Sunset Park Beach, Fishing Charters & Tours, Bahia Honda State Park
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
Dolphin Research Center ©
Dolphin Research Center
Sunset Park Beach ©
Sunset Park Beach

3
nights
Key West

Key West ©
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.
You'll explore the less-touristy side of things at Fort Zachary Taylor and The Overseas Highway. Spend the 29th (Wed) exploring nature at Dry Tortugas National Park. There's lots more to do: see what you can catch with a fishing tour, take a tour by water with Boat Tours & Water Sports, get up close and personal with brilliant marine life at Florida Keys Eco-Discovery Center, and take a memorable tour with Tours.

Plan my trip to Key West with suggested itineraries provided by Inspirock.

You can take a bus from Marathon to Key West in 1.5 hours. Alternatively, you can drive. In May, plan for daily highs up to 34°C, and evening lows to 29°C. Cap off your sightseeing on the 30th (Thu) early enough to travel to St. Augustine.

Things to do in Key West

Outdoors Parks Tours
Highlights from your plan
Fort Zachary Taylor ©
Fort Zachary Taylor
Florida Keys Eco-Discovery Center ©
Florida Keys Eco-Discovery Center
Key West Local Luxe ©
Key West Local Luxe

2
nights
St. Augustine

St. Augustine ©
SAINT AUGUSTINE | PONTE VEDRA on Florida's Historic Coast The Nation's oldest city (est. We've included these beaches for you: St. Augustine Beach and Beach at Daytona Beach. Bring the kids along to Frank Butler County Park West and Crescent Beach Public Beach. Explore St. Augustine's surroundings by going to Ormond Beach (Andy Romano Beachfront Park & Ormond Beach). There's much more to do: brush up on your knowledge of spirits at St. Augustine Distillery, enjoy the sand and surf at Vilano Beach, enjoy the sea views from St. Augustine Lighthouse & Maritime Museum, Inc., and don't miss a visit to St. George Street.

To find ratings, where to stay, traveler tips, and tourist information, read our St. Augustine trip itinerary maker app .

Traveling by combination of flight and car from Key West to St. Augustine takes 6 hours. Alternatively, you can do a combination of flight and bus; or drive. Plan for slightly colder nights when traveling from Key West in May since evenings lows in St. Augustine dip to 22°C. Cap off your sightseeing on the 2nd (Sun) early enough to go by car to Hilton Head.

Things to do in St. Augustine

Outdoors Beaches Parks

Side Trips

Ormond Beach, Crescent Beach Public Beach, Beach at Daytona Beach
Highlights from your plan
Ormond Beach ©
Ormond Beach
St. Augustine Beach ©
St. Augustine Beach
Beach at Daytona Beach ©
Beach at Daytona Beach

3
nights
Hilton Head

A Hilton Head vacation may be heaven for a golfer, but the area also offers all kinds of other options for sports fans.
Bring the kids along to Coligny Beach and Singleton Beach. You'll discover tucked-away gems like Dolphin & Whale Watching and Burkes Beach. And it doesn't end there: kick back and relax at Alder Lane Beach Access, race across the water with a speed boat tour, walk around Folly Field Beach Park, and tour the pleasant surroundings at Driessen Beach Park.

For where to stay, photos, and tourist information, you can read our Hilton Head online tour planner .

Traveling by car from St. Augustine to Hilton Head takes 4 hours. Alternatively, you can do a combination of train and taxi; or take a bus. June in Hilton Head sees daily highs of 36°C and lows of 26°C at night. Finish your sightseeing early on the 5th (Wed) to allow enough time to drive to Myrtle Beach.

Things to do in Hilton Head

Outdoors Parks Beaches
Highlights from your plan
Waterskiing & Jetskiing
Coligny Beach ©
Coligny Beach
Dolphin & Whale Watching

2
nights
Myrtle Beach

Myrtle Beach ©
Myrtle Beach is a coastal city on the east coast of the United States in Horry County, South Carolina. Start off your visit on the 6th (Thu): tour the pleasant surroundings at Myrtle Beach, shop like a local with Broadway at the Beach, and then stroll through Litchfield Beach. Keep things going the next day: explore the world behind art at Brookgreen Gardens, then make a trip to Barefoot Landing, and then kick back and relax at Cherry Grove Beach.

To see where to stay, ratings, photos, and tourist information, use the Myrtle Beach vacation maker site .

Traveling by car from Hilton Head to Myrtle Beach takes 5 hours. Alternatively, you can do a combination of car and bus; or fly. June in Myrtle Beach sees daily highs of 35°C and lows of 26°C at night. Finish your sightseeing early on the 7th (Fri) to allow enough time to travel to New York City.

Things to do in Myrtle Beach

Parks Outdoors Beaches

Side Trips

North Myrtle Beach, Litchfield Beach, Brookgreen Gardens
Highlights from your plan
Myrtle Beach ©
Myrtle Beach
Broadway at the Beach ©
Broadway at the Beach
Litchfield Beach ©
Litchfield Beach

9
nights
New York City

New York City ©
Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
Attractions like Central Park and The Metropolitan Museum of Art make great kid-friendly stops. Discover out-of-the-way places like Ocean Grove Beach and The Music Man Singing Ice Cream Shoppe. Venture out of the city with trips to Bronx Zoo (in Bronx), Woodbury Common Premium Outlets (in Central Valley) and Seaside Park Beach (in Seaside Park). There's lots more to do: enjoy breathtaking views from Empire State Building, admire the striking features of Grand Central Terminal, learn more about the world around you at American Museum of Natural History, and don't miss a visit to Rockefeller Center.

To find more things to do, where to stay, maps, and other tourist information, go to the New York City journey planner.

Do a combination of flight and bus from Myrtle Beach to New York City in 4 hours. Alternatively, you can fly; or drive. Plan for slightly colder temperatures traveling from Myrtle Beach in June, with highs in New York City at 31°C and lows at 21°C. You will have some time to spend on the 16th (Sun) before leaving for home.

Things to do in New York City

Parks Museums Shopping

Side Trips

Bronx Zoo, Ocean Grove Beach, Seaside Park Beach, Brooklyn Botanic Garden, Woodbury Common Premium Outlets
Highlights from your plan
Central Park ©
Central Park
Woodbury Common Premium Outlets ©
Woodbury Common Premium Outlets
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art

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