A Romantic Flight Hop Through Eight Iconic Cities

This trip is designed for couples who want a high energy romantic adventure that spans multiple continents. Over 14 days, you will move from the red rocks of Arizona to the historic streets of Europe. It is a fast paced route that balances quick city hops with longer stays in romantic hubs like Paris and Venice.

Sedona

Day 1 Leg: Start of trip

You'll want to begin your journey in Sedona, a town defined by red sandstone cliffs. You can spend your first day exploring the different areas of town. Start in Uptown Sedona, where you will find a cluster of cafés and galleries. If you prefer a quieter atmosphere with easier access to trails, head to West Sedona. For those who enjoy riverside walks, the Oak Creek valley to the south is the place to be. You should visit the Visitor Center on Forest Road to buy Red Rock Passes and talk to a ranger who can point you toward the best hikes. If you happen to visit in February, you can attend the Sedona International Film Festival or the Jazz Festival.

Where to eat: Canyon Breeze Where to sleep: Sky Rock Sedona, A Tribute Portfolio Hotel

St. Augustine

Day 2 Leg from Sedona: ~2900 km (flight required)

Next, you'll fly to St. Augustine. This city feels like a living museum. You'll want to walk through the downtown area to see Spanish style architecture and 19th century brick streets. The colonial lanes are narrow and lined with locally owned shops and restaurants that spill onto terraces overlooking the water. You should wander past the Castillo de San Marcos, a fort that has never been captured. You can also visit one of the grand hotel buildings built by Henry Flagler, which now houses a small liberal arts college.

Where to eat: The Conch House Lounge Where to sleep: Marion Motor Lodge

Charleston

Day 3 Leg from St. Augustine: ~346 km (flight required)

Your next stop is Charleston, South Carolina. You'll find a town that feels like a well preserved 19th century settlement. You'll want to walk past the pastel houses and see Spanish moss hanging from live oaks. The harbor provides great views of historic forts. To make the most of your day, stay in the historic peninsula. This allows you to walk easily to the Battery and Rainbow Row. You should also visit the French Quarter near King Street for art galleries and boutique shops, or head to South of Broad for a quieter experience.

Where to eat: East Bay Deli Where to sleep: Kings Courtyard Inn

Key West

Day 4 Leg from Charleston: ~932 km (flight required)

Fly south to Key West, a small island town where the past and present exist together. You'll want to spend your time in the Old Town area around Duval Street. This is the most walkable part of the island, featuring narrow lanes and pastel houses that lead directly to the water. You should also take a short walk south to Bahama Village. This neighborhood carries the rhythm of the Bahamian immigrants who helped build the early culture of the island.

Where to eat: Kennedy Cafe or Riviera Coffee & Sandwich Shop Where to sleep: Santa Clara Condominiums

Newport

Day 5 Leg from Key West: ~2117 km (flight required)

You'll then head to Newport, Rhode Island. This New England town offers a refined coastal experience. You'll want to explore the well preserved 19th century mansions and learn about the city's sailing heritage. The downtown area is a mix of waterfront cafés and boutique shops. You should spend some time in The Point district, which is known for its narrow streets and historic character.

Where to eat: Waterfront cafés in the downtown area Where to sleep: Carey School

Quebec City

Days 6 to 8 Leg from Newport: ~592 km (flight required)

You'll spend three days in Quebec City. You'll feel as though you have stepped into a postcard. Start in the fortified core of Old Quebec to see the stone walls and the looming Château Frontenac. You'll want to walk through the narrow Rue du Petit-Champlain. In the morning, visit the Petit-Champlain district. You can hear the clink of coffee cups at Café du Clocher Penché and watch street artists set up near the Terrasse Dufferin. You will also notice the scent of fresh baguettes drifting through the air.

Where to eat: Quoi? Where to sleep: Hôtel Château Laurier Quebec

Paris

Days 9 to 11 Leg from Quebec City: ~5274 km (flight required)

Your journey continues to Paris for three days. This is a city you can walk through while still finding something new around every corner. You'll want to visit Saint-Germain-des-Prés to sip a café au lait at a café while watching the world go by. Take a short walk to the 5th arrondissement to find quiet, tree lined lanes and boulangeries that have been baking for generations. At night, you can watch the Seine glow under the bridges or view the Eiffel Tower light show.

Where to eat: Uno Where to sleep: Ibis

Venice

Days 12 to 14 Leg from Paris: ~843 km (flight required)

The final stop is Venice, a city that exists on water and time. You'll want to move slowly here to notice the details. Start by wandering through Cannaregio. The narrow canals and quiet backstreets offer a glimpse of daily Venetian life away from the crowds of San Marco. You should stop at a tiny bar on Fondamenta della Misericordia for a cicchetto of sarde in saor while the sunset paints the palazzetti pink. For art lovers, the Gallerie dell’Accademia is a priority.

Where to eat: Gam Gam Where to sleep: Albergo Locanda Silva

Route Summary

How to adapt this trip

If you only have 10 days, you should cut the shorter one day stops. Removing Newport and Charleston will allow you to keep the longer stays in Europe and Canada without feeling too rushed.

If you have 21 days, you can add more time to the final three stops. Adding two extra nights each to Quebec City, Paris, and Venice will allow you to move at a slower pace and explore the neighborhoods like Cannaregio or Saint-Germain-des-Prés more thoroughly.