Overview

Welcome to the Cotswolds, where honey-colored villages alternate with sheep pastures and stone walls line the lanes worn into the landscape over centuries. You'll meet your guides at The Store Hotel in Oxford at 11:00 AM for a private transfer to the hamlet of Shipton-under-Wychwood. Here they'll introduce you to your Trek bike with a personalized fit to ensure your comfort for the week, then cover safety tips and a route overview before you head out on your first ride. This is an introduction to the region's rhythms—gently rolling, unhurried, with the countryside opening up as you make your way north. After a light lunch at the Daylesford Farmshop organic café, you'll continue to Chipping Campden, a former wool market town whose High Street, lined with golden limestone buildings, is one of the best-preserved in the Cotswolds. Arriving at our hotel, a quiet, walled garden greets you as you settle in. We'll gather for social hour, raising a glass to the week ahead, followed by dinner together at the hotel.

Overview

Today's ride leaves Chipping Campden for Broadway Tower, an 18th-century folly standing sentinel on the Cotswolds Way, a long-distance trail popular with hikers. From its observation deck, the highest viewpoint in the Cotswolds, vistas stretch up to 62 miles in every direction, taking in the River Severn and into Wales. Back on the bike, country lanes then climb and dip toward Sudeley Castle, where there's time to explore before a relaxed lunch in the on-site café. Built in 1443, the castle has ties to several Tudor monarchs, including Catherine Parr, who is buried in its grounds. The way home completes a figure-eight back to Chipping Campden on tranquil country roads, with those who wish to ride more extending the loop through the hamlet of Lower Slaughter, with its stone footbridges over the River Eye. The rest of the afternoon and evening are free for you to relax at the hotel spa before heading into town, with your guides on hand to recommend a favorite spot for dinner.

Overview

After breakfast, you'll set off north from Chipping Campden toward Stratford-upon-Avon, the hometown of William Shakespeare and a town built almost entirely around his legacy. A short spin through Cotswold lanes to Long Marston picks up the traffic-free Stratford Greenway, a former railway line that carries you into town. You'll arrive with time to explore at your own pace: Shakespeare's birthplace, Anne Hathaway's Cottage, and the Royal Shakespeare Company's theater are all within easy reach, and lunch is yours to choose. In the afternoon, the group regathers for the ride back, loosely following the River Stour before today's challenge, a short, punchy climb out of the village of Ilmington. Riders wanting extra distance can extend the loop toward Shipston-on-Stour and Moreton-in-Marsh, while a more direct route heads back to Chipping Campden. This evening, you will dine together in an award-winning, 14th-century local pub, the Eight Bells, enjoying locally sourced, seasonal food.

Overview

Leaving Chipping Campden today, you'll head south toward Tetbury, where the Cotswolds settle into a quieter rhythm. The morning unfolds on twisting, undulating lanes, arriving around midday at Chedworth Roman Villa, the excavated remains of a Roman estate first built nearly 2,000 years ago, where your guides will prepare a signature Trek Travel picnic in the villa grounds. Afterward, there's time to explore the property, including its intricate mosaic floors and bath-house ruins. From here, you can choose to shuttle the rest of the way to our next hotel, or continue south on lanes that rise and fall through the hills. The day ends at The Hare & Hounds Hotel, a country house tucked into woodland on the outskirts of Tetbury. Once central to the Cotswold wool trade, this market town is known today for its boutique shops and royal ties, with King Charles III's private estate sitting nearby. There's time to wander the grounds of the hotel and settle in before the group gathers for a relaxed dinner this evening.

Overview

This morning, you'll pedal from Tetbury heading south toward Bath, a UNESCO World Heritage city built of curved rows of golden Georgian townhouses around Britain's only natural hot springs. The route follows the Fosse Way, a Roman road nearly two millennia old, and passes through Castle Combe, a village often called England's prettiest, before picking up a canal-side path into the city. Upon arriving in Bath, a walking tour with your guides winds through the city's Georgian streets, ending at an expert-led cheese tasting at one of the city's traditional cheesemongers that introduces the flavors of the region's local producers. From there, the afternoon is yours to wander and find lunch on your own. Bath's sweeping architecture is genuinely breathtaking, and paired with its Jane Austen connections and Roman history, it's easy to see why the city earned its UNESCO status. Those looking to extend the ride can continue back to Tetbury, while others may prefer more time in Bath before returning to the hotel by van, about 50 minutes away. This evening, the group gathers one last time at The Hare & Hounds, clinking glasses to celebrate a week of Roman ingenuity and English wit, before sitting down to a final dinner together in the Beaufort Restaurant. Enjoy the best of British cuisine with subtle continental touches, using the finest seasonal produce sourced here in the Cotswolds.

Overview

You can rise early for one more ride this morning, a short loop through the lanes around Westonbirt and Sherston that offers a final taste of the Cotswolds. Or let the morning unfold slowly, with a relaxed breakfast at The Hare & Hounds and views over the gardens to see you off. Either way, there's time to gather your belongings before departure at 11:00 AM, when a 90-minute private shuttle brings you to Oxford train station, where you can catch a train to London or spend time wandering Oxford before heading home.