60 days in United States Itinerary

60 days in United States Itinerary

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60 days in United States Itinerary

New York City
bus + Fly + bus:  12​h 15​min
Healdsburg
— 7 nights
bus + Fly + taxi:  9​h 45​min
Poipu, Kauai
— 6 nights
taxi + Fly + taxi:  2​h
Wailea, Maui
— 7 nights
taxi + Fly:  1​h 30​min
Hilo, Island of Hawaii
— 6 nights
Fly:  2​h 45​min
Honolulu, Oahu
— 7 nights
Fly:  14​h 15​min
Key West
— 8 nights
Fly + taxi + bus:  5​h 30​min
Sarasota
— 7 nights
Drive:  4​h 15​min
St. Augustine
— 5 nights
Drive:  3​h 15​min
Savannah
— 6 nights
Fly:  5​h
New York City

6
days
Healdsburg

Healdsburg
The quaint city of Healdsburg is one of northern California's wine capitals, serving as the meeting point for three of Sonoma's most important wine-producing regions.
Explore hidden gems such as Highlight Gallery and Brassfield Estate Winery. Your cultural itinerary includes sights like Navarro Vineyards & Winery and Saracina Vineyards. Explore the numerous day-trip ideas around Healdsburg: Historic Courthouse Museum (in Lakeport), Barra of Mendocino (in Redwood Valley) and Philo (Toulouse Vineyards & Winery, Handley Cellars Winery, & more). And it doesn't end there: learn about winemaking at BobDog Winery, steep yourself in history at Ford House Visitor Center & Museum, and step into the grandiose world of Castello di Amorosa.

To find where to stay, photos, reviews, and tourist information, use the Healdsburg trip planner .

New York City to Healdsburg is an approximately 12.5-hour combination of bus and flight. You can also do a combination of train, flight, and bus; or drive. You'll gain 3 hours traveling from New York City to Healdsburg due to the time zone difference. Traveling from New York City in February, expect Healdsburg to be somewhat warmer, temps between 61°F and 39°F. Wrap up your sightseeing on the 8th (Thu) to allow time to travel to Poipu.

Things to do in Healdsburg

Wineries Museums Historic Sites

Side Trips

Philo, Geyserville, Mendocino, Hopland, BobDog Winery
Accommodations
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Navarro Vineyards & Winery
Navarro Vineyards & Winery
Brassfield Estate Winery
Brassfield Estate Winery
Saracina Vineyards ©
Saracina Vineyards

6
days
Poipu, Kauai

Poipu ©
Poipū is a census-designated place in Kauai County on the southern side of the island of Kauai in the U.S. Do your shopping at The Wine Shop and Aunty Lilikoi Passion Fruit Products. Visit Hanalei Beach and Makawehi Bluff for some beach relaxation. Get out of town with these interesting Poipu side-trips: Kayaking & Canoeing (in Kapaa) and Waimea Canyon State Park (in Waimea). Spend the 10th (Sat) observing fascinating marine mammals with a dolphin and whale watching tour. Next up on the itinerary: enjoy the sand and surf at Shipwreck Beach, take an unforgettable tour with a helicopter tour, examine the collection at Waioli Mission House, and take in the dramatic natural features at Spouting Horn.

To find other places to visit, more things to do, and tourist information, refer to the Poipu tour itinerary planner .

You can do a combination of bus, flight, and taxi from Healdsburg to Poipu in 10 hours. Another option is to do a combination of bus, flight, and taxi. The time zone difference when traveling from Healdsburg to Poipu is minus 2 hours. When traveling from Healdsburg in February, plan for a bit warmer days and much hotter nights in Poipu: temperatures range from 77°F by day to 66°F at night. Wrap up your sightseeing on the 14th (Wed) early enough to travel to Wailea.

Things to do in Poipu

Outdoors Parks Beaches

Side Trips

Kauai, Waimea, Helicopter Tours, Kayaking & Canoeing, The Wine Shop
Accommodations
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Poipu Beach Park ©
Poipu Beach Park
Hanalei Beach ©
Hanalei Beach
Shipwreck Beach ©
Shipwreck Beach

6
days
Wailea, Maui

Wailea ©
Wailea is a census-designated place (CDP) in Maui County, Hawaii, United States. You'll explore the less-touristy side of things at Ho'okipa Beach Park and Napili Beach. You'll enjoy a bit of beach vacationing at Wailea Beach and Mokapu Beach Park. You'll find plenty of places to visit near Wailea: Lahaina (Ka'anapali Beach, Lahaina Front Street, & more), Sherri Reeve Gallery & Gifts (in Makawao) and Haleakala Crater (in Haleakala National Park). The adventure continues: stroll through Ulua Beach, see majestic marine mammals with a dolphin and whale watching tour, enjoy the sand and surf at Keawakapu Beach, and get some jogging in at Wailea Beach Path.

For reviews, other places to visit, photos, and more tourist information, go to the Wailea road trip planner .

Traveling by combination of taxi and flight from Poipu to Wailea takes 2 hours. Alternatively, you can do a combination of taxi and flight. In February, plan for daily highs up to 82°F, and evening lows to 64°F. Wrap up your sightseeing on the 21st (Wed) early enough to travel to Hilo.

Things to do in Wailea

Parks Outdoors Beaches

Side Trips

Lahaina, Haleakala Crater, Ho'okipa Beach Park, La Perouse Bay, Dolphin & Whale Watching
Accommodations
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Ka'anapali Beach ©
Ka'anapali Beach
Wailea Beach ©
Wailea Beach
Napili Beach ©
Napili Beach

6
days
Hilo, Island of Hawaii

Hilo ©
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.
Eschew the tourist crowds and head to Jagger Museum and Original Donkey Balls Factory and Store.. Satisfy your inner culture vulture at Pu'uhonua O Honaunau National Historical Park and Mauna Kea Observatories. Venture out of the city with trips to Mauna Kea (in Kailua-Kona), Hapuna Beach State Recreation Area (in Puako) and Laupahoehoe Beach Park (in Laupahoehoe). The adventure continues: look for gifts at Hilo Coffee Mill, stroll through Mauna Kea Beach, kick back and relax at Waialea Beach, and see the world from above with a helicopter tour.

To find reviews, ratings, where to stay, and more tourist information, you can read our Hilo trip itinerary planning website .

You can do a combination of taxi and flight from Wailea to Hilo in 1.5 hours. In February, daily temperatures in Hilo can reach 79°F, while at night they dip to 64°F. Wrap up your sightseeing on the 27th (Tue) early enough to travel to Honolulu.

Things to do in Hilo

Parks Outdoors Beaches

Side Trips

Island of Hawaii, Honaunau, Waialea Beach, Hapuna Beach State Recreation Area, Original Donkey Balls Factory and Store.
Accommodations
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Hapuna Beach State Recreation Area ©
Hapuna Beach State Recreation Area
Jagger Museum ©
Jagger Museum
Mauna Kea Beach ©
Mauna Kea Beach

7
days
Honolulu, Oahu

Honolulu ©
In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.
Explore hidden gems such as Ko Olina Lagoons and Sunset Beach Park. Satisfy your inner culture vulture at Bishop Museum and USS Bowfin Submarine Museum & Park. Get out of town with these interesting Honolulu side-trips: Polynesian Cultural Center (in Laie), Kailua (Lanikai Beach & Kailua Beach Park) and Pupukea (Ehukai Beach Park & Banzai Pipeline). And it doesn't end there: enjoy the sand and surf at Waimea Bay, take an in-depth tour of Iolani Palace, stroll through Kapiolani Regional Park, and contemplate the long history of Battleship Missouri Memorial.

For reviews, traveler tips, photos, and tourist information, read Honolulu day trip tool .

Fly from Hilo to Honolulu in 3 hours. In February, daily temperatures in Honolulu can reach 81°F, while at night they dip to 68°F. Finish your sightseeing early on the 6th (Tue) to allow enough time to travel to Key West.

Things to do in Honolulu

Outdoors Beaches Parks

Side Trips

Kailua, Pupukea, Haleiwa, Kokololio Beach Park, Keawaula (Yokohama Beach)
Accommodations
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Kailua Beach Park ©
Kailua Beach Park
Lanikai Beach ©
Lanikai Beach
Waimea Bay ©
Waimea Bay

7
days
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.
Museum-lovers will get to explore Mel Fisher Maritime Museum and Florida Keys Eco-Discovery Center. Give yourself a bit of retail therapy at Alan S Maltz Gallery and Rodriguez Cigar Factory. Spend the 8th (Thu) exploring nature at Dry Tortugas National Park. Next up on the itinerary: enjoy the sea views from Key West Lighthouse and Keeper's Quarters Museum, go for a walk through Key West Garden Club, admire the natural beauty at West Martello Tower, and relax and rejuvenate at some of the top local wellness centers.

To see reviews, photos, and more tourist information, go to the Key West trip planner .

Fly from Honolulu to Key West in 14.5 hours. Alternatively, you can do a combination of flight and shuttle; or do a combination of flight, taxi, and ferry. The time zone difference when traveling from Honolulu to Key West is 5 hours. In March, plan for daily highs up to 79°F, and evening lows to 70°F. Finish up your sightseeing early on the 14th (Wed) so you can travel to Sarasota.

Things to do in Key West

Parks Outdoors Museums
Accommodations
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6
days
Sarasota

Sarasota ©
Sarasota is a city located in Sarasota County on the southwestern coast of the U.S. You'll explore and learn at Tour Lake Placid and The Dalí Museum. Step off the beaten path and head to Bean Point and Bradenton Beach. Explore Sarasota's surroundings by going to Clearwater Beach (in Clearwater), Venice Beach (in Venice) and Englewood Beach (in Englewood). The adventure continues: enjoy the sand and surf at Crescent Beach, do a tasting at Bunker Hill Vineyard & Winery, stroll through Nokomis Beach, and buy something for everyone on your list at St. Armands Circle Association.

For ratings, maps, traveler tips, and more tourist information, refer to the Sarasota online road trip planner .

Traveling by combination of flight and bus from Key West to Sarasota takes 5.5 hours. Alternatively, you can drive; or do a combination of ferry, taxi, and bus. Expect little chillier evenings in Sarasota when traveling from Key West in March, with lows around 58°F. Cap off your sightseeing on the 21st (Wed) early enough to go by car to St. Augustine.

Things to do in Sarasota

Outdoors Beaches Parks

Side Trips

Siesta Key, The Dalí Museum, Clearwater Beach, Bunker Hill Vineyard & Winery, Englewood Beach
Accommodations
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Siesta Beach ©
Siesta Beach
Bean Point ©
Bean Point
Bradenton Beach ©
Bradenton Beach

5
days
St. Augustine

St. Augustine ©
St. Relax by the water at Vilano Beach and St. Augustine Beach. Discover out-of-the-way places like Lightner Museum and St. Augustine Pirate & Treasure Museum. Get out of town with these interesting St. Augustine side-trips: Beach at Daytona Beach (in Daytona Beach) and Sawgrass Country Club (in Ponte Vedra Beach). There's lots more to do: do a tasting at San Sebastian Winery, appreciate the history behind Castillo de San Marcos, get engrossed in the history at St. Augustine Lighthouse & Maritime Museum, and admire all the interesting features of Flagler College.

To find other places to visit, more things to do, where to stay, and more tourist information, refer to the St. Augustine attractions planner.

Traveling by car from Sarasota to St. Augustine takes 4.5 hours. Alternatively, you can do a combination of bus and flight; or do a combination of bus and flight. Expect little chillier weather when traveling from Sarasota in March: highs in St. Augustine hover around 72°F, while lows dip to 54°F. Finish your sightseeing early on the 26th (Mon) to allow enough time to drive to Savannah.

Things to do in St. Augustine

Outdoors Beaches Parks

Side Trips

Beach at Daytona Beach, Sawgrass Country Club
Accommodations
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Beach at Daytona Beach ©
Beach at Daytona Beach
Lightner Museum
Lightner Museum
St. Augustine Pirate & Treasure Museum ©

7
days
Savannah

Savannah ©
Savannah is the oldest city in the U.S.
Get a sense of the local culture at Tybee Island Lighthouse Museum and The Olde Pink House. We've included these beaches for you: Tybee Island Beach and Coligny Beach. Explore the numerous day-trip ideas around Savannah: Watermelon Creek Vineyard (in Glennville), September Oaks Winery (in Ridgeland) and Old Sheldon Church Ruins (in Yemassee). There's lots more to do: get to know the fascinating history of Fort Pulaski National Monument, relax and rejuvenate at some of the top local wellness centers, contemplate in the serene atmosphere at The Cathedral of St. John the Baptist, and admire the striking features of Historic Savannah Theatre.

To see where to stay, other places to visit, maps, and tourist information, use the Savannah tour itinerary tool .

Getting from St. Augustine to Savannah by car takes about 3.5 hours. Other options: take a bus; or do a combination of bus and train. In March, daytime highs in Savannah are 71°F, while nighttime lows are 50°F. Cap off your sightseeing on the 1st (Sun) early enough to travel back home.

Things to do in Savannah

Historic Sites Parks Outdoors

Side Trips

Tybee Island, Hilton Head, Watermelon Creek Vineyard, Fort Morris Historic Site, September Oaks Winery
Accommodations
Get expert advice on where to stay in Savannah.
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Savannah Historic District ©
Savannah Historic District
Tybee Island Beach ©
Tybee Island Beach
Tybee Island Lighthouse Museum
Tybee Island Lighthouse Museum

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