Below is the list of planned trips for the 2019-20 academic year. Please note that the list of trips may change and the cost of a trip is not fixed until the letter is sent out about it. It is possible that a few trips will be added to, or removed from, the list but we hope that this list will help parents in making decisions about trips in which they would like their sons to take part.
| Date | Destination | Years | Cost | Staff |
| 6-7 Sep | KES Wildlife: Bustards | Lower School | ||
| 13-Sep | Sixths Geography Field Trip: Birmingham | Sixths | Free | JPS |
| 13-Sep | CCF Sailing, Rockley watersports | Fourths and above | inc. with CCF subs | DHR |
| 16-17 Sep | Navy Damage Control: Portsmouth | Upper School | inc. in subs | DHR |
| 20-22 Sep | Caving, Yorkshire | Rems | 140 | CDB |
| 20-21 Sep | Army Camp: Swynnerton | Army | inc. in CCF subs | CS |
| 20-21 Sep | Navy expedition: Watersports | Fourths and above | inc. in subs | DHR |
| 21-22 Sep | Leadership weekend | Divs | 85 | LMR |
| 23-Sep | London: Shell C and G | Shells | 33 | PKH |
| 27-Sep | Navy Sailing Rockley watersports | Fourths and above | inc. in subs | DHR |
| 27-Sep | Bosworth: Rem D, F and N | Rems | 20 | PWG |
| 29-Sep | GCSE Art: Birmingham Art Gallery | Fourths | Free | BMS |
| 30-Sep | London: Shell F and H | Shells | 33 | PKH |
| 4-Oct | CCF Sailing Rockley watersports | Fourths and above | inc. in CCF subs | DHR |
| 4-Oct | Bosworth: Rem S and T | Rems | 20 | PWG |
| 6-Oct | Cycling, Shustoke | Shells | Free | CDB |
| 7-Oct | London: Shell A | Shells | 33 | PKH |
| 11-Oct | Carding Mill Valley: Upper Middles B, K and R | Upper Middles | 16 | JPS |
| 13-Oct | Cycling, Wombourne | Shells | Free | CBD |
| 18-Oct | Carding Mill Valley: Upper Middles T, Z and Z | Upper Middles | 16 | JPS |
| 18-Oct | CCF Sailing Rockley watersports | Fourths and above | inc. in CCF subs | DHR |
| 18-20 Oct | Walking, canoeing and rock climbing | Fourths | 160 | IJC |
| 20-Oct | Tate Britain: GCSE Art | Fifths | 15 | BMS |
| 20-Oct | Hill walk: Church Stretton | Shells | 20 | CDB |
| 22-Oct | Jaguar Land Rover | Divs | Free | GJW |
| 23-29 Oct | Cyprus: Water Polo | Middle School | 800 | RVT |
| 24-28 Oct | Norway: Outdoor activities and cultural education | Rems to Divs | 1150 | JPS |
| 4-5 Nov | Navy Portsmouth | Middle School | DHR | |
| 8-Nov | London: MIT Better World | Middle School | 30 | RI |
| 15-Nov | Helping with homeless feed | All | 5 | MSN |
| 17-Nov | Hill walk: Stiperstones | Shells | 20 | CDB |
| 20-Nov | Physics masterclass, Birmingham university | Fourths | 0 | RJF |
| 21-Nov | Ancient Worlds, Warwick university | Upper Middles | HAF | |
| 23-Nov | MUN Conference: London | Upper School | 20 | PWG |
| 27-Nov | Physics in Action lectures, Warwick university | Divs | 30 | RJF |
| 3-Dec | Mathematics enrichment | Divs | 27 | TB |
| 31 Jan to 2 Feb | Hill walking, Lake District | Shells | 140 | CDB |
| 10-14 Feb | Writing retreat | Shells and Rems | 560 | JWB |
| 13-20 Feb | German Exchange: Hamburg | Fourths | 450 | AXH |
| 15-22 Feb | Skiing: Austria | Rems and above | 1450 | IJC |
| 15-21 Feb | Lapland | Shells to UMs | 1500 | CDB |
| 28 Feb to 1 Mar | Shells Caving 1 | Shells | 140 | CDB |
| 5-Mar | Theatre trip: A Monster Calls | Lower School | 22 | GJB |
| 13-15 Mar | Caving | Rems and UMs | 145 | CDB |
| 20-22 Mar | Shells Caving 2 | Shells | 140 | CDB |
| 28 Mar to 4 Apr | Nice: Language immersion | Divs | 850 | PJE |
| 18-Apr | Independent cyclists training day | UMs | Free | CDB |
| 26-Apr | Cycling | Shells and Rems | Free | CDB |
| Easter | Dubai: Junior Cricket | UMs and Fourths | 1800 | LMR |
| 5-8 Jun | Biology Field Course: Slapton Sands | Divs | 215 | DMW |
| 8-12 Jun | Shell form camps | Shells | 155 | CDB |
| 4-17 Jul | Cricket Tour: Barbados and St Lucia | Upper School | 2850 | LMR |
| 10-18 Jul | Ardèche: canoeing, ropes course, Roman sites | Shells | 990 | CDB |
| 16-22 Jul | Gozo: diving | Fourths and above | 1000 | DHR |
| 29 Jul – 7 Aug | Cycle Tour, Copenhagen to Berlin | All | 1475 | CDB |
| 11-14 Aug | Edinburgh Fringe Festival | Fifths and above | 500 | MJB |
| October | China | All | 1500 | DMW/DJA |
| February 2021 | Morocco | All | 900 | DMW |
| February 2021 | Lapland | Lower School | 1500 | CDB |
| 2-10 Jul 2021 | Ardeche | Shells and Rems | 1050 | CDB |
| 23 Jul – 1 Aug 2021 | Bavaria Cycle Tour (date TBA) | All | 1325 | CDB |
| 13-21 Aug 2021 | Vercors Caving: France | UMs and above | 1350 | CDB |
