The Great American Flight Hop: Eight Cities In Fourteen Days

This trip is designed for the traveler who wants to see as much as possible in a short window, moving quickly between distinct regional cultures. You will experience everything from the slow pace of the South to the high desert of New Mexico and the urban energy of the East Coast. The total duration is 14 days, utilizing flights to bridge the gaps between these eight iconic stops.

Charleston

Day 1

You begin your journey in Charleston, South Carolina. This city feels like a walk through a well preserved 19th century town. You will find streets lined with pastel houses and Spanish moss hanging from live oaks. The harbor provides views of historic forts, making it a great spot for those who love architecture and Southern cuisine.

You should stay in the historic peninsula. This location allows for easy walking to the Battery and Rainbow Row. If you are looking for boutique shops and art galleries, head to the French Quarter near King Street. For a quieter experience, the South of Broad neighborhood is your best bet.

For a meal, you can grab a sandwich at East Bay Deli. When it is time to rest, check into the Kings Courtyard Inn.

Savannah

Day 2 Leg from Charleston: ~134 km (flight required)

Next, you fly to Savannah. This city feels like a postcard that never stops moving. You can wander through the 22 historic squares where Spanish moss hangs from live oaks. The iron work balconies of the French Quarter tell stories of the 1800s.

You will want to visit Chippewa Square to see the spot where Forrest Gump’s bench is located. After that, you can sip sweet tea at a sidewalk café on Broughton Street. A walk through Forsyth Park will lead you to the marble fountain. The city layout is convenient, allowing you to hop from one square to the next on foot.

Enjoy seafood at Belford's Savannah before spending the night at The Drayton Hotel.

Miami

Day 3 Leg from Savannah: ~708 km (flight required)

Your third stop is Miami. This leg requires a flight of approximately 708 km. Once you arrive, you can explore the city's vibrant energy.

For dinner, you should visit El Cartel Colombian Restaurant for Latin American flavors. For your stay, the Residences at Bayside (by Elite City Stays) provides a comfortable home base.

New Orleans

Day 4 Leg from Miami: ~1077 km (flight required)

From Miami, you fly roughly 1077 km to New Orleans. This is a place you step into rather than just visit. In the French Quarter, you will find narrow streets where jazz spills from clubs on Frenchmen Street. The scent of fresh beignets from Café du Monde mixes with the salty tang of the Mississippi at the riverfront.

If you want food that sticks to your ribs, line up for a po’boy at Parkway Bakery & Tavern or a bowl of gumbo at Coop’s Place. These are cheap, no frills spots that locals swear by. You might also spend some time exploring the Garden District.

For dining, you can try Torshi. Your home for the night is Hotel Peter & Paul.

Santa Fe

Day 5 Leg from New Orleans: ~1611 km (flight required)

You will then fly approximately 1611 km to Santa Fe. This high desert town feels like it never stopped dreaming. The Plaza sits at the center of a maze of adobe streets. Just a few blocks away is Canyon Road, where galleries spill out onto sidewalks and the scent of fresh baked sopapillas drifts from cafés.

If you head east to the Railyard, you will find a laid back vibe with craft breweries and a weekend market that feels more local than touristy. Notable spots include the Palace of the Governors, which is the oldest public building.

Eat at Casa Chimayo Restaurant for authentic Mexican food and stay at the Santa Fe Sage Inn.

Jackson Hole

Days 6 to 8 Leg from Santa Fe: ~960 km (flight required)

Your next stop is Jackson Hole, a flight of about 960 km. Here, the mountains have a say in everyday life. The town is compact and centered around the town square, known for its iconic elk antler arches.

The action spreads into Teton Village and the surrounding valleys. You can visit Wilson to see quiet streets lined with historic log cabins, while Teton Village offers high end boutiques and ski lift traffic. The vibe is a mix of polished resort energy and laid back rancher charm. You might start your morning with coffee at Persephone.

For dining, visit Ocean City. You will spend three nights at Amangani.

San Francisco

Days 9 to 11 Leg from Jackson Hole: ~1169 km (flight required)

Fly approximately 1169 km to San Francisco. This city feels like it is always rearranging itself. You can start your morning in the Mission neighborhood with a Mission style burrito from La Taqueria. It is a filling, slightly spicy meal that costs about $9 and is considered a rite of passage.

You should hop on a historic cable car and climb up to Twin Peaks for a 360 degree view of the city as the fog rolls in. Each neighborhood has its own personality, from the lantern lit alleys of Chinatown to the Italian influence in North Beach.

Enjoy a meal at Woods Lowside and stay at the Coast Hotel for three nights.

New York

Days 12 to 14 Leg from San Francisco: ~4129 km (flight required)

The final leg is the longest, a flight of about 4129 km to New York. The city is a patchwork of neighborhoods that each feel like a different city. You can grab a $3 slice of pizza on a corner in the East Village, then take the L train to the coffee shop scene in Williamsburg within 15 minutes.

The food options are varied. A pastrami on rye at Katz's costs about $22, while a bowl of ramen at Ippudo in Midtown is around $15. If you are flying into JFK, expect the trip to Manhattan to take roughly an hour via the AirTrain and the E subway.

For dinner, visit Whiskey Tavern for American fare. You will spend your final three nights at the Conrad.

Trip Summary

How to adapt this trip

If you only have 10 days, you should cut the stops in Miami and Savannah to save on travel time. This allows you to keep the longer stays in the West and East Coast cities.

If you have 21 days, you can add more time to New Orleans and Santa Fe. These cities have a slower pace that benefits from an extra two or three days of exploration.