Whether arriving by train or plane, upon arriving in Bordeaux you’ll be taxied to your three-star hotel in Pauillac, home of three of the five first vintages of the Médoc. After settling in, the hotel staff will outfit you with bikes, maps and all other pertinent information for your tour. If needed, you can call your guide at any time. At night you’ll feast on local French cuisine while sharpening your toast-giving skills with some of the region’s famous red wines.

Pauillac is a "Bordeaux appellation" that houses some of the most prestigious chateaux in the world. En route to Moulis, you will discover estates listed in the Bordeaux Wine Official Classification of 1855 and other jewels. You’ll see the renowned Lafite Rothschild, Latour, and Mouton Rothschild, "1ers Grands Crus Classés" (their wines have been officially designated some of the world's best vintages). If that’s not enough excellent wine for you, you’ll be entranced by Chateaux Pichon Longueville (second "cru classé"), Pontet Canet, and Lynch Bages (5th "cru classé"). The villages of Pauillac, Saint-Julien, Moulis, and Margaux are all worth a visit. Be sure to stop and admire the classical façade of the entrance to Château Margaux and peek at their prestigious vines!

Today you’ll cross the Gironde Estuary via ferry into Blaye. The Citadel of Blaye, the town’s most famous architectural landmark, enjoys status as a UNESCO World Heritage Site. Perhaps equally as famous, but for different reasons, are the neighboring Côtes de Blaye vineyards. Just like yesterday, you will have plenty of chances to clink and drink. From here you’ll continue south along the Gironde, following the scenic “Route de la Corniche Fleurie” into Virsac. This timeless village, full of ancient architecture, will serve as home for the night.

You’ll exit Virsac, pedaling southeast into Fronsac, an area that’s as distinct for its hills as it is for its wines. The vineyards that terrace down Fronsac’s limestone bluffs have long produced history’s grape of choice, sating the thirsts of Charlemagne, Cardinal de Richelieu and King Louis XIV. From here you’ll bicycle into Pomerol, the Bordeaux region’s smallest wine producing area. Despite its limited size, Pomerol enjoys all-star status with wine aficionados, especially for its Château Petrus, one of the planet’s most highly regarded vintages. The day concludes in Saint-Emilion, perhaps the Bordeaux region’s most quintessential wine village. You’ll spend two nights here, giving you plenty of time to explore this UNESCO World Heritage Site.

Today’s loop will allow you to fully experience Saint-Emilion and its surrounding villages and vineyards. Most of the wine estates you’ll visit are smaller in scope, combining rural charm with pastoral elegance. Before bending back to Saint-Emilion you’ll wheel through Castillon-la-Bataille, site of the famous battle between France and England in 1453 that ended the 100 Years’ War.

The day’s short ride will give you plenty of time to wander through Saint-Emilion’s narrow cobblestone streets and fully absorb its Old World splendor. Wine shops outnumber cafés, it seems — both are excellent places to pause. Beneath Saint-Emilion lies the world’s largest monolithic cathedral, a must-see that requires you to descend underground for a visit!

Bicycle through the village of Branne before turning west along the Dordogne River and merging on to the “Roger Lapébie Bike Path.” Named after the winner of the 1937 Tour de France, this 58-kilometer green path was originally a rail line. Many of the old train buildings have since been converted into cafes, wine bars, and bike stations, making the trail a biking nirvana. After passing through the village of Créon, you’ll eventually pedal into the heart of Bordeaux, stopping at the front steps of the Place de la Bourse — one of France’s true architectural masterpieces. Your downtown hotel will allow for immediate access to Bordeaux’s many attractions.

After breakfast, you may depart on your own timetable.