29 days in United States Itinerary

29 days in United States Itinerary

Created using Inspirock United States itinerary planner

Make it your trip
Fly
1
New York City
— 4 nights
Fly
2
Key West
— 4 nights
Drive
3
Marathon
— 3 nights
Drive
4
Islamorada
— 2 nights
Fly
5
Hilo, Island of Hawaii
— 2 nights
Drive
6
Kailua-Kona, Island of Hawaii
— 5 nights
Fly
7
Poipu, Kauai
— 4 nights
Fly
8
Lahaina, Maui
— 4 nights
Fly

S M T W T F S
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15

New York City

— 4 nights

Big Apple

Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
Eschew the tourist crowds and head to Fifth Avenue and The Museum of Modern Art (MoMA). Do some cultural sightseeing at The Metropolitan Museum of Art and St. Patrick's Cathedral. Next up on the itinerary: don't miss a visit to Empire State Building, pause for some photo ops at Statue of Liberty National Monument, go for a walk through Times Square, and see the interesting displays at 9/11 Memorial.

To see reviews, traveler tips, other places to visit, and tourist information, you can read our New York City online trip maker.

Minneapolis to New York City is an approximately 4.5-hour flight. You can also drive; or take a bus. Traveling from Minneapolis to New York City, you'll lose 1 hour due to the time zone difference. Expect somewhat warmer temperatures when traveling from Minneapolis in December; daily highs in New York City reach 48°F and lows reach 36°F. Finish your sightseeing early on the 16th (Thu) to allow enough time to fly to Key West.

Things to do in New York City

Museums · Parks · Neighborhoods · Shopping

Key West

— 4 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.
You'll discover tucked-away gems like Fort Zachary Taylor and Key West Lighthouse and Keeper's Quarters Museum. Get a sense of the local culture at Truman Little White House and Key West Cemetery. Spend the 17th (Fri) exploring nature at Dry Tortugas National Park. There's still lots to do: take a memorable drive along The Overseas Highway, admire the striking features of Oldest House & Garden Museum, stroll through Key West Butterfly & Nature Conservatory, and cast your line with a fishing tour.

To find traveler tips, reviews, photos, and tourist information, you can read our Key West trip planner.

You can fly from New York City to Key West in 5 hours. Other options are to drive; or take a bus. Traveling from New York City in December, expect Key West to be warmer, temps between 79°F and 71°F. Finish your sightseeing early on the 20th (Mon) to allow enough time to drive to Marathon.

Things to do in Key West

Parks · Outdoors · Nature · Museums

Marathon

— 3 nights

Heart of the Florida Keys

A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
We've included these beaches for you: Bahia Honda State Park and Sombrero Beach. Get in touch with nature at The Turtle Hospital and Crane Point Museum & Nature Center. Step out of Marathon with an excursion to Florida Keys Wild Bird Rehabilitation Center in Tavernier--about 58 minutes away. It doesn't end there: cast your line with a fishing tour and stroll through Dolphin Research Center.

To see reviews, ratings, traveler tips, and other tourist information, go to the Marathon trip maker site.

Traveling by car from Key West to Marathon takes 1.5 hours. Alternatively, you can take a bus. In December in Marathon, expect temperatures between 80°F during the day and 71°F at night. Finish your sightseeing early on the 23rd (Thu) to allow enough time to drive to Islamorada.

Things to do in Marathon

Parks · Wildlife · Outdoors · Beaches

Side Trips

Islamorada

— 2 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.
On the 24th (Fri), take in the dramatic natural features at Windley Key Fossil Reef Geological State Park and then cast your line with a fishing tour. On the 25th (Sat), you'll have a packed day of sightseeing: get outside with Pelican Cove Resort.

To see photos, where to stay, maps, and tourist information, go to the Islamorada tour itinerary planner.

Traveling by car from Marathon to Islamorada takes an hour. Alternatively, you can take a bus. In December, daily temperatures in Islamorada can reach 80°F, while at night they dip to 71°F. On the 25th (Sat), wrap the sightseeing up by early afternoon so you can fly to Hilo.

Things to do in Islamorada

Wildlife · Outdoors · Tours · Parks

Hilo, Island of Hawaii

— 2 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.
Kick off your visit on the 26th (Sun): trek along Napau-Makaopuhi Crater Trail, see the interesting displays at Jagger Museum, then tour the pleasant surroundings at Kilauea Iki Trailhead, and finally cruise along Devastation Trail. Get ready for a full day of sightseeing on the next day: admire the sheer force of Rainbow Falls, browse the fresh offerings at Hilo Farmers Market, take in nature's colorful creations at Hawaii Tropical Bioreserve and Garden, then take in the dramatic scenery at Akaka Falls State Park, and finally take in nature's colorful creations at Liliuokalani Gardens.

To find traveler tips, more things to do, photos, and more tourist information, go to the Hilo driving holiday planning tool.

Traveling by flight from Islamorada to Hilo takes 13 hours. The time zone difference moving from Eastern Standard Time (EST) to Hawaii-Aleutian Standard Time (HST) is minus 5 hours. Traveling from Islamorada in December, expect slightly colder with lows of 65°F in Hilo. Finish up your sightseeing early on the 27th (Mon) so you can go by car to Kailua-Kona.

Things to do in Hilo

Parks · Outdoors · Trails · Wildlife

Side Trips

Kailua-Kona, Island of Hawaii

— 5 nights

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.
We've included these beaches for you: Papakōlea Green Sand Beach and Manini'owali Beach (Kua Bay). You'll discover tucked-away gems like Fishing Charters & Tours and Pu'uhonua O Honaunau National Historical Park. Get out of town with these interesting Kailua-Kona side-trips: Puukohola National Historic Park (in Kawaihae), Hapuna Beach State Recreation Area (in Puako) and Kula Kai Caverns (in Ocean View). There's lots more to do: kick back and relax at Punalu‘U Beach, cruise along Saddle Road, admire the verdant scenery at Pololu Valley Lookout, and take your sightseeing to a higher altitude at Mauna Kea.

To find more things to do, where to stay, maps, and tourist information, you can read our Kailua-Kona journey planner.

Traveling by car from Hilo to Kailua-Kona takes 2 hours. Alternatively, you can take a bus. In December in Kailua-Kona, expect temperatures between 82°F during the day and 70°F at night. Cap off your sightseeing on the 1st (Sat) early enough to catch the flight to Poipu.

Things to do in Kailua-Kona

Parks · Outdoors · Nature · Beaches

Side Trips

Poipu, Kauai

— 4 nights
Poipū is a census-designated place in Kauai County on the southern side of the island of Kauai in the U.S. state of Hawaii. We've included these beaches for you: Poipu Beach Park and Hanalei Beach. Visiting Waimea Canyon State Park and Maha'ulepu Heritage Trail will get you outdoors. Explore Poipu's surroundings by going to Polihale State Park (in Waimea) and Wailua Falls (in Lihue). Next up on the itinerary: hike along Kalalau Trail, kick back and relax at Shipwreck Beach, discover the deep blue sea with a scuba or snorkeling tour, and explore the striking landscape at Spouting Horn.

For traveler tips, where to stay, ratings, and tourist information, use the Poipu sightseeing site.

Traveling by flight from Kailua-Kona to Poipu takes 2.5 hours. January in Poipu sees daily highs of 79°F and lows of 65°F at night. Finish up your sightseeing early on the 5th (Wed) so you can catch the flight to Lahaina.

Things to do in Poipu

Parks · Outdoors · Beaches · Nature

Side Trips

Lahaina, Maui

— 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.
Discover out-of-the-way places like Lahaina Front Street and Zipline. Relax by the water at Napili Beach and Wailea Beach. Take a break from Lahaina with a short trip to Kamaole Beach Park III in Kihei, about 44 minutes away. There's more to do: get up close to creatures of the deep with a dolphin and whale watching tour and stroll around Lahaina Banyan Court.

For reviews, photos, and other tourist information, read Lahaina trip itinerary planner.

Getting from Poipu to Lahaina by flight takes about 2.5 hours. In January, daily temperatures in Lahaina can reach 78°F, while at night they dip to 67°F. Finish up your sightseeing early on the 9th (Sun) so you can catch the flight back home.

Things to do in Lahaina

Outdoors · Parks · Beaches · Tours

Side Trips

United States travel guide

4.5
Specialty Museums · Beaches · History Museums
More than the country of car-packed streets seen in TV shows and movies, the United States of America is a complex and diverse home to over 300 million people living in a wide range of landscapes and climates. From its big-city skyscrapers to its sprawling natural parks, the country's ''melting pot'' combines many ethnic groups that share a strong sense of national identity despite their cultural differences. A country of road trips and big blue skies, the United States harbors orderly cities filled with restaurants, parks, museums, and innumerable sightseeing opportunities, as well as pristine natural areas perfect for a holiday in the great outdoors. To see as much as you can of this diverse land quickly, drive over some of the more than 6 million km (4 million mi) of highways leading through deserts, mountain peaks, fertile fields, and giant urban centers.