14 days in United States Itinerary

14 days in United States Itinerary

Created using Inspirock United States sightseeing planner

This plan was created by another user. Make it your plan

Route & dates

Start: Philadelphia
Fly:  4 h 45 min
1
Key West
— 3 nights
Bus:  1 h 15 min
2
Marathon, Florida Keys
— 2 nights
Shuttle + Fly:  6 h 15 min
3
St. Augustine, Florida
— 2 nights
Drive:  3 h 15 min
4
Savannah
— 2 nights
Fly:  16 h 45 min
5
Kailua-Kona, Island of Hawaii
— 2 nights
Fly:  15 h 30 min
End: Philadelphia

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.
Your cultural itinerary includes sights like The Ernest Hemingway Home and Museum and Saint Mary Star of the Sea. Escape the urban bustle at Key West Butterfly & Nature Conservatory and Dolphin & Whale Watching. Next up on the itinerary: take in the architecture and atmosphere at St. Paul's Episcopal Church, tour the pleasant surroundings at Key West Garden Club, enjoy the sand and surf at Smathers Beach, and enjoy the sea views from Key West Lighthouse and Keeper's Quarters Museum.

To see where to stay, photos, traveler tips, and tourist information, you can read our Key West trip itinerary maker site.

Philadelphia to Key West is an approximately 5- hour flight. You can also do a combination of train and flight; or drive. Traveling from Philadelphia in May, you will find days in Key West are a bit warmer (85°F), and nights are much warmer (77°F). Finish your sightseeing early on the 26th (Tue) so you can take a bus to Marathon.

Things to do in Key West

Historic Sites Outdoors Parks
Highlights from your plan
The Ernest Hemingway Home and Museum ©
The Ernest Hemingway Home and Museum
Dolphin & Whale Watching
Saint Mary Star of the Sea ©
Saint Mary Star of the Sea

2
nights
Marathon, Florida Keys

Marathon ©
A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
Kick off your visit on the 27th (Wed): see the interesting displays at Crane Point Museum & Nature Center, sample the tasty concoctions at Islamorada Brewery & Distillery, get engrossed in the history at History of Diving Museum, then view the masterpieces at Old Road Gallery, and finally look for all kinds of wild species at Florida Keys Wild Bird Rehabilitation Center. Keep things going the next day: explore the gorgeous colors at Sombrero Reef, identify plant and animal life at The Turtle Hospital, and then discover the deep blue sea with a scuba or snorkeling tour.

To find more things to do, other places to visit, reviews, and more tourist information, read Marathon tour planner.

You can take a bus from Key West to Marathon in 1.5 hours. Alternatively, you can drive. In May, daytime highs in Marathon are 88°F, while nighttime lows are 77°F. Wrap up your sightseeing on the 28th (Thu) early enough to travel to St. Augustine.

Things to do in Marathon

Wildlife Parks Museums

Side Trips

Islamorada, Florida Keys Wild Bird Rehabilitation Center
Highlights from your plan
History of Diving Museum ©
History of Diving Museum
Florida Keys Wild Bird Rehabilitation Center ©
Crane Point Museum & Nature Center ©
Crane Point Museum & Nature Center

2
nights
St. Augustine, Florida

St. Augustine ©
St. Start off your visit on the 29th (Fri): contemplate in the serene atmosphere at St. Photios Greek Orthodox National Shrine, then tour the pleasant surroundings at St. Augustine Beach, then get a taste of the local shopping with High Tide Gallery Art & Gifts, and finally contemplate the long history of Old St. Augustine Village. Get ready for a full day of sightseeing on the 30th (Sat): get engrossed in the history at The Oldest Store Museum, examine the collection at The Ximenez-Fatio House, take an in-depth tour of Government House Museum, then steep yourself in history at Villa Zorayda Museum, and finally take in the architecture and atmosphere at Memorial Presbyterian Church.

To see photos, where to stay, other places to visit, and other tourist information, you can read our St. Augustine vacation planner.

You can do a combination of shuttle and flight from Marathon to St. Augustine in 6.5 hours. Other options are to drive; or do a combination of shuttle, flight, and bus. Prepare for a bit cooler weather when traveling from Marathon in May: high temperatures in St. Augustine hover around 83°F and lows are around 67°F. Finish your sightseeing early on the 30th (Sat) so you can drive to Savannah.

Things to do in St. Augustine

Historic Sites Museums Outdoors
Highlights from your plan
The Ximenez-Fatio House ©
The Ximenez-Fatio House
Memorial Presbyterian Church ©
Memorial Presbyterian Church
St. Photios Greek Orthodox National Shrine ©
St. Photios Greek Orthodox National Shrine

2
nights
Savannah

Savannah ©
Georgia's oldest city, Savannah displays its colonial history proudly on every corner.
Start off your visit on the 31st (Sun): take in the spiritual surroundings of First African Baptist Church, examine the collection at Ships of the Sea Maritime Museum, then get to know the fascinating history of City Market, and finally appreciate the extensive heritage of Savannah Historic District. Get ready for a full day of sightseeing on the next day: contemplate the long history of Juliette Gordon Low's Birthplace, contemplate in the serene atmosphere at Mickve Israel Temple, stroll the grounds of Colonial Park Cemetery, brush up on your military savvy at Webb Military Museum, then examine the collection at American Prohibition Museum, and finally contemplate in the serene atmosphere at Cathedral of St. John the Baptist.

Use Inspirock's suggestions to plan your Savannah trip and find the best activities and attractions for your vacation.

Traveling by car from St. Augustine to Savannah takes 3.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. In May, daytime highs in Savannah are 83°F, while nighttime lows are 64°F. Wrap up your sightseeing on the 1st (Mon) early enough to travel to Kailua-Kona.

Things to do in Savannah

Historic Sites Museums Neighborhoods
Highlights from your plan
Ships of the Sea Maritime Museum ©
Ships of the Sea Maritime Museum
Webb Military Museum ©
Webb Military Museum
Mickve Israel Temple ©
Mickve Israel Temple

2
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.
Your inner history buff will appreciate Puukohola Heiau and St. Michael the Archangel Church. You'll discover tucked-away gems like Manini'owali Beach (Kua Bay) and Mahai'ula Beach. Explore Kailua-Kona's surroundings by going to Manini Kapahukapu Beach (in Honaunau) and Puukohola National Historic Park (in Kawaihae). Next up on the itinerary: enjoy the sand and surf at Kikaua Point Park, look for gifts at Mrs. Barry's Kona Cookies, get engrossed in the history at H.N. Greenwell Store Museum, and explore the striking landscape of Lapakahi State Historical Park.

To see reviews, more things to do, ratings, and more tourist information, go to the Kailua-Kona travel route builder.

Getting from Savannah to Kailua-Kona by flight takes about 17 hours. Other options: do a combination of bus and flight. Traveling from Savannah to Kailua-Kona, you'll gain 5 hours due to the time zone difference. June in Kailua-Kona sees daily highs of 85°F and lows of 74°F at night. Wrap up your sightseeing on the 4th (Thu) early enough to travel back home.

Things to do in Kailua-Kona

Parks Outdoors Beaches

Side Trips

Island of Hawaii, Kealakekua, Kawaihae, Manini Kapahukapu Beach
Highlights from your plan
Manini'owali Beach (Kua Bay) ©
Manini'owali Beach (Kua Bay)
Puukohola Heiau ©
Puukohola Heiau
Puukohola National Historic Park ©
Puukohola National Historic Park

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