Chicago

Route 66 Ultimate Road Trip and Mexican Riviera Taster Cruise - 20 Nights

Follow the legend of Route 66 from Chicago to the Pacific Ocean before adding a relaxing cruise escape on this exciting 20-night USA holiday. Including return UK flights, a full-size hire car with insurance, taxes and one-way drop fees covered, this adventure combines the freedom of the open road with an exciting full-board cruise. Begin with two nights in Chicago before travelling through St Louis, Springfield, Oklahoma City and Amarillo, discovering classic diners and historic attractions.

Along the way, enjoy a St Louis walking tour and a sip and savour food tour in Santa fe New Mexico. The journey continues through the striking landscapes of New Mexico and Arizona. Spend time exploring the creative atmosphere of Santa Fe, the rich heritage of Gallup and the iconic scenery surrounding Monument Valley.

Your included Arizona self-guided driving commentary enhances every mile, while opportunities to visit the West Rim of the Grand Canyon, explore historic ghost towns and enjoy two nights on the famous Las Vegas Strip add even more variety to this epic road trip. Arriving in Santa Monica, stand at the official end of Route 66 where the highway meets the Pacific Ocean. From Los Angeles, board Royal Caribbean's Ovation of the Seas for a 4-night full-board Mexican Riviera taster cruise.

Visit the beautiful island setting of Catalina Island and the colourful coastal city of Ensenada before returning to Los Angeles. This unique holiday combines America's most celebrated road trip with a taste of cruising, offering outstanding value and an incredible range of experiences in one seamless itinerary.

What’s included

  • Return flights from the UK
  • 15 days hire car with tax , insurance, unlimited mileage and one-way drop off fee included
  • Two nights' four-star room-only accommodation in Chicago (in hotel featured or similar)
  • One night's three-star bed-and-breakfast accommodation in St Louis Missouri (in hotel featured or similar)
  • Small group private walking tour of St Louis.
  • One night's four-star room-only accommodation in Springfield Missouri (in hotel featured or similar)
  • One night's three-star bed-and-breakfast accommodation in Oklahoma City (in hotel featured or similar)
  • One night's four-star bed-and-breakfast accommodation in Amarillo Texas (in hotel featured or similar)
  • Two nights' three-star bed-and-breakfast accommodation in Santa Fe New Mexico (in hotel featured or similar)
  • Santa Fe Sip and Savour Plaza Tour
  • One night's three-star bed-and-breakfast accommodation in Gallup New Mexico (in hotel featured or similar)
  • One night's three-star bed-and-breakfast accommodation in Kayenta - Monument Valley on the Navajo Reservation (in hotel featured or similar)
  • One night's four-star bed-and-breakfast accommodation in Flagstaff Arizona (in hotel featured or similar)
  • Arizona Route 66 Self Guided Driving tour commentary
  • One night's four-star bed-and-breakfast accommodation in Kingman Arizona (in hotel featured or similar)
  • Two nights' four-star room-only accommodation on the Las Vegas Strip (in hotel featured or similar)
  • Arizona Ghost Towns and Wild-West Day Trip from Las Vegas with lunch
  • Two nights' four-star bed-and-breakfast accommodation in Santa Monica L.A. near Venice Beach (in hotel featured or similar)
  • Four nights' full-board cruise accommodation on board Royal Caribbean Ovation of the Seas
  • NB: Please note that hotel taxes and resort fees may be collected at check in at each hotel - Please call for details

Ship

Ovation of the Seas

Royal Caribbean

Royal Caribbean's Ovation of the Seas, launched in 2016 is the third ship in the groundbreaking Quantum Class, following Quantum of the Seas (2014) and Anthem of the Seas (2015). Purpose‑built to deliver cutting‑edge technology, world‑class entertainment, and destination‑focused itineraries, this innovative vessel continues to be one of the fleet's most modern and activity‑packed ships. Ovation of the Seas measures 168,666 GT, stretches 1,142 ft (348 m) in length, and features 16 total decks, with 14–15 passenger‑accessible decks depending on the source. Designed to comfortably accommodate 4,180 guests (double occupancy) and around 1,300–1,500 crew, it offers a smooth passenger‑to‑space balance supported by its impressive Quantum‑Class engineering. The ship will undergo a major Royal Amplified refurbishment in April–May 2026, adding 40 new staterooms and upgrading bars, restaurants, entertainment venues, and the pool deck—introducing refreshed favourites like Giovanni's Italian Kitchen, Izumi Teppanyaki, the Pesky Parrot tiki bar, and the new late‑night Sound Cellar music venue. A floating resort with something for every kind of traveller, Ovation of the Seas boasts 18 dining and bar venues, four swimming pools (including a covered solarium pool), 10 whirlpools, and an array of signature Quantum‑Class attractions like North Star, RipCord by iFly, and the multi‑use SeaPlex, the largest indoor activity complex at sea.

Itinerary

Fly to Chicago and make your way to your hotel for an overnight hotel stay. Millennium Knickerbocker Chicago. Located just steps from Chicago's vibrant Rush Street, this luxurious hotel offers stylish accommodations with premium amenities, state-of-the-art event facilities, and exceptional dining experiences. A prime destination for shopping, dining, and business in downtown Chicago, the hotel is conveniently located near iconic attractions such as Water Tower Place, Michigan Avenue, the John Hancock Tower, and Navy Pier. World-class museums, including the Museum of Contemporary Art and the Art Institute of Chicago, are also within easy walking distance. The hotel boasts an impressive 5, 480 square meters of flexible function space, ideal for a variety of meetings and events. Its famed Crystal Ballroom, complete with a built-in illuminated dance floor and stunning crystal chandeliers, has hosted countless elegant wedding receptions. Please note, an additional fee of $20 per person applies for guests over 13 years old. Overnight stays are $76 (including tax) with unlimited in/out privileges. Shorter stay options are also available, ranging from $28 to $45 (including tax) for stays between 2 and 8 hours. Self-parking is available for $55 per night without in/out privileges.

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October 2026

MoTuWeThFrSaSu

Calendar shows the cheapest cabin that day. The table below is the full list.

OriginStart dateInteriorOceanviewBalconySuite
Heathrow31 Oct 2026Saturday£3,369£3,349£3,379£4,169
Heathrow7 Nov 2026Saturday£3,129£3,159£3,179NA
Heathrow14 Nov 2026Saturday£2,799£2,999£3,039£3,629
Heathrow28 Nov 2026Saturday£3,339£3,389£3,419£3,999
Heathrow22 Dec 2026Tuesday£3,589£3,619£3,639£4,089
Heathrow26 Dec 2026Saturday£3,529£3,559£3,579£3,999
Heathrow9 Jan 2027Saturday£3,179£3,219£3,249£3,699
Heathrow23 Jan 2027Saturday£3,139£3,169£3,189£3,649
Heathrow6 Feb 2027Saturday£3,189£3,219£3,249£3,699
Heathrow20 Feb 2027Saturday£3,319£3,349£3,369£3,839

Check availability

Adults
2
Children
0

Deck plan