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            Cities and Culture

            We found 57 Holidays in your search for:

            Destinations (72)
            Types of Cycling / Grades (7)
            Departure Month

            2025

            2026

            2027

            Level of Support

            We found 57 Holidays in your search for:

            Select Order Order By
            Destinations (72)
            Types of Cycling / Grades (7)
            Departure Month

            2025

            2026

            2027

            Level of Support

            From the Moorish architecture of Granada and Seville to the ancient wonders of Rome, vibrant culture of Ljubljana and inspiring art in Vienna, there’s so much to experience on these incredible tours of cities and culture. We’ve curated the best itineraries that blend scenic cycling with sight-seeing and cultural experiences. Whether you’re looking for a relaxed e-bike ride or something a little more challenging, we’ve got a tour that’s just right for you.

            • All Cycling Holidays
            • Cities and Culture

            Page 3 of 6

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            Guided
            Guided
            Italy

            Tuscany - Giro della Toscana

            Guided Road Bike Tour

            Duration

            8 days

            Prices from

            $2,910 P.P.
            View Reviews
            2
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            Grade 3: Moderate
            More Info BOOK NOW

            Tuscany - Giro della Toscana

            Guided Road Bike Tour

            Start DateEnd DatePrice p.p.
            * 30/08/2025
            Fully Booked
            06/09/2025$2,910.00
            • Cycling through the historic wine regions of Tuscany, stopping off for a bit of wine tasting along the way
            • Staying in quality accommodation, with fantastically warm hospitality
            • Easing along the rolling hills of the Colli Sienesi
            • Riding the stunning UNESCO heritage region of Val d’Orcia
            • Stopping off at the lovely San Gimignano and Montalcino
            • Chilling out with a post-ride Chianti
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            Spain

            Granada to Seville

            Self-Guided Leisure Bike Tour

            Duration

            9 days

            Prices from

            $2,495 P.P.
            View Reviews
            3
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            Grade 3 : Moderate
            More Info BOOK NOW

            Granada to Seville

            Self-Guided Leisure Bike Tour

            E-Bike Hire Available

            This tour is well-suited to both regular bikes and pedal assist e-bikes, and you can choose to hire either when you book your tour with us. Confident cyclists will enjoy the boost from a battery for those cheeky climbs, and with less effort required on the bike, you’ll have more energy at the end of the day for off-the-bike activities. You may choose to hire an e-bike on a group or supported tour but bear in mind that the pace will be set to riders without an e-bike. You may choose to hire an e-bike on a group or supported tour but bear in mind that the pace will be set to riders without an e-bike.

            Start DateEnd DatePrice p.p.
            28/09/2025
            Guaranteed
            06/10/2025$2,495.00

            Daily departures available. The season prices below are per person and are applicable for all start dates between and inclusive of the stated dates.

            2025 01 Mar – 30 Nov (excluding dates from 18 Apr – 4 May and 01 Jul to 13 Sep)

            Season 1 – $2850 01 – 13 Mar / 01 – 30 Nov

            Season 2 – $3080 14 Mar – 11 Apr / 05 May – 30 Jun / 14 Sep – 31 Oct

            2026 01 Mar – 30 Nov (excluding dates from 29 Mar – 05 Apr / 11 – 18 Apr / 01 Jul to 05 Sep)

            Season 1 – $2935 01 – 28 Mar / 01 – 30 Nov

            Season 2 – $3175 06 – 10 Apr / 19 Apr – 30 Jun / 06 Sep – 31 Oct

            Alternatively for a great value holiday choose one of our scheduled departures below.

            • Cycling between 3 of the most magnificent cities in Andalucia
            • Travelling through rolling sierras and olive plantations
            • Making use of the Vias Verdes
            • Exploring the architectural wonders of Granada
            • Visiting Cordoba – the birth place of Spanish Flamenco
            • Celebrating your trip in the capital of the south, Seville
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            Portugal

            Azure Ocean Ride

            Self-Guided Leisure Bike Tour

            Duration

            8 days

            Prices from

            $2,345 P.P.
            View Reviews
            1
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            Grade 3 : Moderate
            More Info BOOK NOW

            Azure Ocean Ride

            Self-Guided Leisure Bike Tour

            E-BIKE HIRE AVAILABLE

            This tour is well-suited to both regular bikes and pedal assist e-bikes, and you can choose to hire either when you book your tour with us. Confident cyclists will enjoy the boost from a battery for those cheeky climbs, and with less effort required on the bike, you’ll have more energy at the end of the day for off-the-bike activities.

            Daily departures available. The season prices below are per person and are applicable for all start dates between and inclusive of the stated dates.

            2025 05 Jan – 13 Dec

            Season 1 – $2565 05 Jan – 29 Jun and 15 Sep – 13 Dec

            Season 2 – $3050 30 Jun – 14 Sep

            2026 05 Jan – 13 Dec (excl. Easter week between 29 Mar and 05 Apr)

            Season 1 – $2710 05 Jan – 30 Jun and 16 Sep – 13 Dec

            Season 2 – $3210 01 Jul – 15 Sep

            Worth noting We run this tour from Jan through to Dec. The summer months however (generally from 01 Jul – 15 Sep) can be really busy. More people, more cyclists, busier restaurants, busier hotels etc, so we’d recommend travelling in the Spring or Autumn if you‘re looking for a quieter getaway with less cyclists to share the route with.

            Please note We are generally not able to confirm any bookings for this tour made within 4 weeks of departure. Please contact our office if you are looking to book and begin your holiday within this period and we will do our best to accommodate your request.

            • Discovering Portugal’s most beautiful beaches
            • Cycling alongside the Ria de Aviero, a 40km stretch of blue lagoon
            • Helping the fishermen with their catch in Praia da Vieira
            • Enjoying the views of the western shoreline from the Sitio viewpoint
            • Exploring the historical, castle walled village of Óbidos
            • Visiting the lovely Vimeiro
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            Italy

            Lake Garda to Venice

            Self-Guided Leisure Bike Tour

            Duration

            8 days

            Prices from

            $2,535 P.P.
            View Reviews
            4
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            Grade 2 : Gentle
            More Info BOOK NOW

            Lake Garda to Venice

            Self-Guided Leisure Bike Tour

            E-BIKE HIRE AVAILABLE

            This tour is well-suited to both regular bikes and pedal assist e-bikes, and you can choose to hire either when you book your tour with us. Confident cyclists will enjoy the boost from a battery for those cheeky climbs, and with less effort required on the bike, you’ll have more energy at the end of the day for off-the-bike activities.

            Daily departures available. The season prices below are per person and are applicable for all start dates between and inclusive of the stated dates.

            2025 21 Apr – 29 Oct (excluding dates throughout July and August)

            Season 1 – $2535 21 Apr – 16 Jun and 03 Sep – 29 Oct

            Season 2 – $2850 17 Jun – 30 Jun and 01 – 02 Sep

            2026 18 Apr – 26 Oct (excluding dates throughout July and August)

            Season 1 – $2665 18 Apr – 14 Jun and 09 Sep – 26 Oct

            Season 2 – $2995 15 Jun – 30 Jun and 01 – 08 Sep

            If you‘re looking for a longer holiday, our Via Claudia route links into this tour perfectly; two self-guided tours of a similar grade that you‘re able to do back to back. Contact us if you’d like more info on this!

            To ensure you have the best experience possible, we’d recommend travelling in the Spring or in the Autumn. We don’t as standard offer this tour in the hotter, more humid, busier summer months of July and August. If however your dates are set in July or August, please call us for a chat and we’ll do what we can to accommodate you.

            • Enjoying a swim in Lake Garda
            • Cycling along Pellestrina Island surrounded by Venetian lagoons and fishing boats
            • Absorbing the hidden Rennaisance gems of the ‘belpaese’
            • Exploring Verona – a piece of art in itself
            • Discovering the medieval fortification of Montagnana
            • Taking a gondola ride along the canals of Venice
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            Italy

            Lake Garda to Venice

            Self-Guided Family Bike Tour

            Duration

            8 days

            Prices from

            $2,535 P.P.
            1
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            Grade 2 : Gentle
            More Info BOOK NOW

            Lake Garda to Venice

            Self-Guided Family Bike Tour

            Child Discounts

            Daily departures available. The season prices below are per person and are applicable for all start dates between and inclusive of the stated dates.

            2025 21 Apr – 29 Oct (excluding dates throughout July and August)

            Season 1 – $2535 21 Apr – 16 Jun and 03 Sep – 29 Oct

            Season 2 – $2850 17 Jun – 30 Jun and 01 – 02 Sep

            2026 18 Apr – 26 Oct (excluding dates throughout July and August)

            Season 1 – $2665 18 Apr – 14 Jun and 09 Sep – 26 Oct

            Season 2 – $2995 15 Jun – 30 Jun and 01 – 08 Sep

            We can offer the following discounts for children under 18:

            We can offer a 20% discount for any child under 18 travelling with 2 fully-paying passengers. If you’re happy to share a family room (where available) we can often offer an additional 10% – please chat to our team about your preferred rooming arrangements.

            To ensure you have the best experience possible, we’d recommend travelling in the Spring or in the Autumn. We don’t as standard offer this tour in the hotter, more humid, busier summer months of July and August. If however your dates are set in July or August, please call us for a chat and we’ll do what we can to accommodate you.

            • Enjoying a swim in Lake Garda
            • Cycling along Pellestrina Island surrounded by Venetian lagoons and fishing boats
            • Absorbing the hidden Rennaisance gems of the ‘belpaese’
            • Exploring Verona – a piece of art in itself
            • Discovering the medieval fortification of Montagnana
            • Taking a gondola ride along the canals of Venice
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            Italy

            Tuscany - Sacred Routes

            Self-Guided Mountain Bike Tour

            Duration

            8 days

            Prices from

            $2,425 P.P.
            View Reviews
            4
            1
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            3
            4
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            Grade 3 - 4: Moderate/ Challenging
            More Info BOOK NOW

            Tuscany - Sacred Routes

            Self-Guided Mountain Bike Tour

            Daily departures available. The season prices below are per person and are applicable for all start dates between and inclusive of the stated dates.

            2025 24 Mar – 29 Oct (excluding dates throughout July and August)

            Season 1 – $2425 24 Mar – 16 Jun and 03 Sep – 29 Oct

            Season 2 – $2665 17 Jun – 30 Jun and 01 – 02 Sept

            2026 29 Mar – 26 Oct (excluding dates throughout July and August)

            Season 1 – $2550 29 Mar – 14 Jun and 09 Sep – 26 Oct

            Season 2 – $2810 15 Jun – 30 Jun and 01 – 08 Sep

            To ensure you have the best experience possible, we’d recommend travelling in the Spring or in the Autumn. We don’t as standard offer this tour in the hotter, more humid, busier summer months of July and August. If however your dates are set in July or August, please call us for a chat and we’ll do what we can to accommodate you.

            • Staying in lovely Tuscan accommodation overlooking stunning landscapes
            • Riding the Montagnola trails, the location of a well-known Sienese MTB race
            • Sampling the best wines of Chianti, Montepulciano and Montalcino
            • Riding down the “Crete Senesi” on a roller coaster ridge ride
            • Enjoying the journey across Tuscany on a variety of terrain
            • Visiting the famous hilltop towns of San Gimignano, Monteriggioni, San Quirico d‘Orcia and Pienza
            Photo Highlights Dates
            Guided
            Guided
            Italy

            Tuscany to Rome

            Guided Electric Bike Tour

            Duration

            8 days

            Prices from

            $3,225 P.P.
            View Reviews
            6
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            3
            4
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            Grade 3 : Moderate
            More Info BOOK NOW

            Tuscany to Rome

            Guided Electric Bike Tour

            E-BIKE TOUR

            This holiday has been designed as an e-bike tour allowing you to experience more on two wheels whilst riding with like-minded Skedaddlers. Confident cyclists will enjoy the boost from a battery for those cheeky climbs and longer distances. With less effort required on the bike, you’ll have more energy at the end of the day for off-the-bike activities. Remember to select your e-bike hire when you book your holiday with us.

            Start DateEnd DatePrice p.p.
            13/09/2025
            Fully Booked
            20/09/2025$3,225.00
            • Staying in Tuscan accommodation overlooking stunning landscapes
            • Discovering the amazing towns of Siena, San Quirico and Pienza
            • Sampling the best wines of Chianti, Montepulciano and Montalcino
            • Enjoying the journey from Tuscany to Rome on a variety of terrain, including ancient Roman roads
            • Exploring the lesser-known historical towns of Lazio, such as Sutri with it’s Roman amphitheatre
            • The sense of achievement riding into St Peter’s Square in Rome
            Photo Highlights Dates
            Bike and Boat
            Bike and Boat
            Italy

            Venetian Waterways (Mantova to Venice)

            Bike and Barge Tour

            Duration

            8 days

            Prices from

            $1,665 P.P.
            View Reviews
            5
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            3
            4
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            Grade 1-2 : Easy/Gentle
            More Info BOOK NOW

            Venetian Waterways (Mantova to Venice)

            Bike and Barge Tour

            E-BIKE HIRE AVAILABLE

            This tour is well-suited to both regular bikes and pedal assist e-bikes, and you can choose to hire either when you book your tour with us. Confident cyclists will enjoy the boost from a battery for those cheeky climbs, and with less effort required on the bike, you’ll have more energy at the end of the day for off-the-bike activities.

            Start DateEnd DatePrice p.p.
            05/07/2025 Vita Pugna
            Contact Us
            12/07/2025$2,325.00
            12/07/2025 Ave Maria
            Fully Booked
            19/07/2025$2,895.00
            19/07/2025 Vita Pugna
            Contact Us
            26/07/2025$2,325.00
            26/07/2025 Ave Maria
            Contact Us
            02/08/2025$2,895.00
            02/08/2025 Vita Pugna
            Fully Booked
            09/08/2025$2,325.00
            09/08/2025 Ave Maria
            Fully Booked
            16/08/2025$2,895.00
            16/08/2025 Vita Pugna
            Fully Booked
            23/08/2025$2,325.00
            23/08/2025 Ave Maria30/08/2025$3,465.00
            30/08/2025 Vita Pugna
            Fully Booked
            06/09/2025$2,695.00
            06/09/2025 Ave Maria
            Fully Booked
            13/09/2025$3,465.00
            13/09/2025 Vita Pugna
            Fully Booked
            20/09/2025$2,695.00
            20/09/2025 Ave Maria
            Fully Booked
            27/09/2025$3,465.00
            27/09/2025 Vita Pugna
            Fully Booked
            04/10/2025$2,695.00
            04/10/2025 Ave Maria11/10/2025$3,465.00
            11/10/2025 Vita Pugna
            Fully Booked
            18/10/2025$2,695.00
            18/10/2025 Ave Maria25/10/2025$3,180.00
            21/03/2026 Ave Maria28/03/2026$1,995.00
            28/03/2026 Vita Pugna04/04/2026$1,665.00
            04/04/2026 Ave Maria11/04/2026$3,180.00
            11/04/2026 Vita Pugna18/04/2026$2,510.00
            18/04/2026 Ave Maria25/04/2026$3,180.00
            25/04/2026 Vita Pugna02/05/2026$2,510.00
            02/05/2026 Ave Maria09/05/2026$3,510.00
            09/05/2026 Vita Pugna16/05/2026$2,695.00
            16/05/2026 Ave Maria23/05/2026$3,510.00
            23/05/2026 Vita Pugna30/05/2026$2,695.00
            30/05/2026 Ave Maria06/06/2026$3,180.00
            06/06/2026 Vita Pugna13/06/2026$2,510.00
            13/06/2026 Ave Maria20/06/2026$3,180.00
            20/06/2026 Vita Pugna27/06/2026$2,510.00
            27/06/2026 Ave Maria04/07/2026$2,650.00
            04/07/2026 Vita Pugna11/07/2026$2,335.00
            11/07/2026 Ave Maria18/07/2026$2,650.00
            18/07/2026 Vita Pugna25/07/2026$2,335.00
            25/07/2026 Ave Maria01/08/2026$2,650.00
            01/08/2026 Vita Pugna08/08/2026$2,335.00
            08/08/2026 Ave Maria15/08/2026$2,650.00
            15/08/2026 Vita Pugna22/08/2026$2,335.00
            22/08/2026 Ave Maria29/08/2026$2,650.00
            29/08/2026 Vita Pugna05/09/2026$2,850.00
            05/09/2026 Ave Maria12/09/2026$3,710.00
            12/09/2026 Vita Pugna19/09/2026$2,850.00
            19/09/2026 Ave Maria26/09/2026$3,710.00
            26/09/2026 Vita Pugna03/10/2026$2,850.00
            03/10/2026 Ave Maria10/10/2026$3,710.00
            10/10/2026 Vita Pugna17/10/2026$2,850.00
            17/10/2026 Ave Maria24/10/2026$3,180.00
            • Cycling through some of Northern Italy’s most enticing cities
            • Staying on board the modern, bright and spacious Ave Maria or the traditional Vita Pugna
            • Spending the day discovering Mantova
            • Riding alongside the River Po, the longest river in Italy
            • Experiencing the Po Delta, one of Europe’s largest wetlands
            • Finishing your trip in beautiful Venice
            Photo Highlights Dates
            Self-Guided
            Self-Guided
            Spain

            Bilbao to Santiago

            Self-Guided Road Bike Tour

            Duration

            10 days

            Prices from

            $2,850 P.P.
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            Grade 3: Moderate
            More Info BOOK NOW

            Bilbao to Santiago

            Self-Guided Road Bike Tour

            Daily departures available. The season prices below are per person and are applicable for all start dates between and inclusive of the stated dates.

            2025 01 Apr – 31 Oct

            Season 1 – $2850 01 – 10 Apr / 05 – 31 May / 29 Sep – 31 Oct

            Season 2 – $3135 01 Jun – 31 Jul / 01 – 28 Sep

            Season 3 – $3535 20 – 30 Apr / 01 – 31 Aug

            2026 05 Apr – 31 Oct

            Season 1 – $2935 03 – 31 May / 29 Sep – 31 Oct

            Season 2 – $3235 01 Jun – 31 Jul / 01 – 28 Sep

            Season 3 – $3650 05 – 30 Apr / 01 – 31 Aug

            • Riding along the stunning and dramatic Cantabrian coastline
            • A stunning start in the Basque city of Bilbao
            • Enjoying a fabulous seafood platter in San Vicente de Barquera
            • Pouring cider in the old town of Oviedo
            • Arriving at the roof of the ‘Camino Primitivo‘, Puerto Palo
            • Cycling through beautiful, rural, enchanting Galicia to arrive in historical Santiago to collect a pilgrims’ certificate
            Photo Highlights Dates
            Bike and Boat
            Bike and Boat
            Italy

            Venetian Waterways (Venice to Mantova)

            Bike and Barge Tour

            Duration

            8 days

            Prices from

            $1,995 P.P.
            View Reviews
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            Grade 1-2 : Easy/Gentle
            More Info BOOK NOW

            Venetian Waterways (Venice to Mantova)

            Bike and Barge Tour

            E-BIKE HIRE AVAILABLE

            This tour is well-suited to both regular bikes and pedal assist e-bikes, and you can choose to hire either when you book your tour with us. Confident cyclists will enjoy the boost from a battery for those cheeky climbs, and with less effort required on the bike, you’ll have more energy at the end of the day for off-the-bike activities.

            Start DateEnd DatePrice p.p.
            05/07/2025 Ave Maria
            Contact Us
            12/07/2025$2,895.00
            12/07/2025 Vita Pugna
            Fully Booked
            19/07/2025$2,325.00
            19/07/2025 Ave Maria
            Guaranteed
            26/07/2025$2,895.00
            26/07/2025 Vita Pugna
            Fully Booked
            02/08/2025$2,325.00
            02/08/2025 Ave Maria
            Fully Booked
            09/08/2025$2,895.00
            09/08/2025 Vita Pugna
            Fully Booked
            16/08/2025$2,325.00
            16/08/2025 Ave Maria23/08/2025$2,895.00
            23/08/2025 Vita Pugna
            Fully Booked
            30/08/2025$2,695.00
            30/08/2025 Ave Maria06/09/2025$3,465.00
            06/09/2025 Vita Pugna
            Fully Booked
            13/09/2025$2,695.00
            13/09/2025 Ave Maria
            Fully Booked
            20/09/2025$3,465.00
            20/09/2025 Vita Pugna
            Fully Booked
            27/09/2025$2,695.00
            27/09/2025 Ave Maria
            Fully Booked
            04/10/2025$3,465.00
            04/10/2025 Vita Pugna
            Fully Booked
            11/10/2025$2,695.00
            11/10/2025 Ave Maria18/10/2025$3,465.00
            18/10/2025 Vita Pugna25/10/2025$2,495.00
            25/10/2025 Ave Maria01/11/2025$3,180.00
            28/03/2026 Ave Maria04/04/2026$1,995.00
            04/04/2026 Vita Pugna11/04/2026$2,510.00
            11/04/2026 Ave Maria18/04/2026$3,180.00
            18/04/2026 Vita Pugna25/04/2026$2,510.00
            25/04/2026 Ave Maria02/05/2026$3,180.00
            02/05/2026 Vita Pugna09/05/2026$2,695.00
            09/05/2026 Ave Maria16/05/2026$3,510.00
            16/05/2026 Vita Pugna23/05/2026$2,695.00
            23/05/2026 Ave Maria30/05/2026$3,510.00
            30/05/2026 Vita Pugna06/06/2026$2,510.00
            06/06/2026 Ave Maria13/06/2026$3,180.00
            13/06/2026 Vita Pugna20/06/2026$2,510.00
            20/06/2026 Ave Maria27/06/2026$3,180.00
            27/06/2026 Vita Pugna04/07/2026$2,335.00
            04/07/2026 Ave Maria11/07/2026$2,650.00
            11/07/2026 Vita Pugna18/07/2026$2,335.00
            18/07/2026 Ave Maria25/07/2026$2,650.00
            25/07/2026 Vita Pugna01/08/2026$2,335.00
            01/08/2026 Ave Maria08/08/2026$2,650.00
            08/08/2026 Vita Pugna15/08/2026$2,335.00
            15/08/2026 Ave Maria22/08/2026$2,650.00
            22/08/2026 Vita Pugna29/08/2026$2,335.00
            29/08/2026 Ave Maria05/09/2026$3,710.00
            05/09/2026 Vita Pugna12/09/2026$2,850.00
            12/09/2026 Ave Maria19/09/2026$3,710.00
            19/09/2026 Vita Pugna26/09/2026$2,850.00
            26/09/2026 Ave Maria03/10/2026$3,710.00
            03/10/2026 Vita Pugna10/10/2026$2,850.00
            10/10/2026 Ave Maria17/10/2026$3,710.00
            17/10/2026 Vita Pugna24/10/2026$2,510.00
            24/10/2026 Ave Maria31/10/2026$3,180.00
            • Cycling through some of Northern Italy’s most enticing cities
            • Staying on board the modern, bright and spacious Ave Maria or the traditional Vita Pugna
            • Exploring the beautiful city of Venice
            • Riding alongside the River Po, the longest river in Italy
            • Experiencing the Po Delta, one of Europe’s largest wetlands
            • Spending the day discovering Mantova
            Photo Highlights Dates
            • Previous page
            • 1
            • 2
            • 3
            • 4
            • 5
            • 6
            • Next page

            Not sure which trip's right for you? Just ask!

            Get in touch and we'll help you find your perfect trip.

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