Every trip gives you the 'hands-on' or 'sit-back' choice!
When would you like to Go Sailing
April 2020
May 2020
June 2020
July 2020
August 2020
September 2020
October 2020
Choose from Day Sails, Overnight, Short Breaks, Festivals and Holidays
2020 Full Sailing Programme
Easter Heritage Sailing Adventure
Explore the South Devon coast and its charming ports and harbours.
Fri 10 Apr 20
4 Day
PM100420
Taster
Torbay Sailing Experience
Enjoy an afternoon of traditional sailing in the sheltered waters of Torbay in Devon
Tue 14 Apr 20
1/2 Day
PM140420
Taster
Devon Traditional Sailing Day
Enjoy a day of traditional sailing in the sheltered waters of Torbay
Wed 15 Apr 20
1 day
PM150420
Taster
B&B Traditional Sailing Weekend
Sail with us for a B&B weekend experience to remember
Sat 18 Apr 20
2 day
PM180420
Taster
Brixham Trawler Sailing Experience
Enjoy an afternoon of traditional sailing in Torbay
Tue 21 Apr 20
1/2 Day
PM210420
Taster
Devon Coast Day Sail
Enjoy a day of traditional sailing in the sheltered waters of Torbay in South Devon
Wed 22 Apr 20
1 day
PM220420
Devon Spring Sailing Weekend
Explore the South Devon coast and its charming ports and harbours.
Fri 24 Apr 20
3 day
PM240420
Taster
Pilgrim Half Day Sailing Experience
Enjoy an afternoon of traditional sailing in Devon
Mon 27 Apr 20
1/2 Day
PM270420
Taster
Torbay Day Sail
Experience a whole day of traditional sailing in the sheltered waters of Torbay
Wed 29 Apr 20
1 day
PM290420
May Sailing Weekend
Explore the South Devon coast and its charming ports and harbours. It's an 'Area of Outstanding Natural Beauty.
Sat 02 May 20
3 day
PM020520
Taster
Day Sail in the Bay
Experience a whole day of traditional sailing in the sheltered waters of Torbay
Wed 06 May 20
1 day
PM060520
May Holiday Sailing Adventure
Explore the South Devon coast and its charming ports and harbours.
Fri 08 May 20
4 Day
PM080520
Taster
Sailing Trawler Day Cruise
Experience a whole day of traditional sailing in the sheltered waters of Torbay
Wed 13 May 20
1 day
PM130520
Taster
B&B Trawler Sailing Experience
Sail with us for a B&B weekend experience to remember
Sat 16 May 20
2 day
PM160520
Taster
Pilgrim Afternoon Taster Cruise
Enjoy an afternoon of traditional sailing in Devon
Tue 19 May 20
1/2 Day
PM190520
Taster
Devon Traditional Sailing Day
Experience a whole day of traditional sailing in sheltered Torbay
Wed 20 May 20
1 day
PM200520
Festival
Heritage Regatta Sailing Celebration
Join in the Regatta and compete for the King George V Cup
Sat 23 May 20
3 day
PM230520
Festival
Old Gaffers Solent Adventure
Cruise the Jurassic Coast to the Old Gaffers Solent Rally
Wed 27 May 20
7 Day
PM270520
South West Coast and Rivers
Enjoy sailing along the delightful Devon and Cornwall coasts
Thu 4 June 20
6 day
PM040620
Festival
Falmouth Classics Sailing Celebration
Join us for the Falmouth Sea Shanty Festival and the Classics Regatta
Thu 11 Jun 20
5 day
PM110620
Scilly Isles Sailing Holiday
Sail on Pilgrim from Falmouth for our annual cruise to explore the stunning Isles of Scilly
Wed 17 Jun 20
7 Day
PM170620
Channel Coasts and Islands Adventure
Enjoy sailing the coasts of south west England and Brittany
Thu 25 Jun 20
8 Day
PM250620
Taster
Brixham B & B Sailing Taster
Sail with us for a B&B sailing experience to remember
Sat 04 Jul 20
2 day
PM040720
Festival
Brest & Douarnenez Festivals Special
Our blockbuster to Brittany for the ultimate festival experience
Tue 07 Jul 20
15 Day
PM070720
Taster
Summer B & B Sailing Weekend
Sail with us for a Summer B&B Sailing experience to remember
Fri 24 Jul 20
2 day
PM240720
Taster
Summer Holiday Sailing Experience
Enjoy a whole day of traditional sailing in sheltered Devon waters
Wed 29 Jul 20
1 day
PM290720
Summer Sailing Activities Weekend
Get out on the water and explore the South Devon coast and estuaries
Fri 31 Jul 20
3 day
PM310720
Taster
Summer Holiday Sailing Day
Enjoy a full day of traditional sailing in sheltered Devon waters
Tue 04 Aug 20
1 day
PM040820
Taster
Pilgrim Summer Sailing Sleepover
Join us for a Summer Bunk and Breakfast sleepover!
Wed 05 Aug 20
2 day
PM050820
Taster
South Devon B & B Sailing
Join us for another Pilgrim weekend summer sailing experience to remember
Sat 08 Aug 20
2 day
PM080820
Festival
British Fireworks Championship Cruise
Exceptional summer sailing and spectacular fireworks in Plymouth
Tue 11 Aug 20
6 day
PM110820
Devon Sailing Short Break
It's summer, why not explore the stunning South Devon coast and its charming ports and harbours
Tue 18 Aug 20
3 day
PM180820
Taster
Pilgrim Summer Sunset Sail
Enjoy a lovely evening of traditional sailing on the English Riviera on board Pilgrim BM45
Fri 21 Aug 20
Evening
PM210820
Taster
Late Summer Sailing Sleepover
Join us for a late Summer Bunk and Breakfast sleepover!
Sat 22 Aug 20
2 day
PM220820
Festival
Dartmouth Regatta Cruise
Explore the stunning South Devon coast and visit Dartmouth for the Regatta
Wed 26 Aug 20
3 day
PM260820
Festival
Pilgrim Mayflower Commemoration Passage
Sail from Dartmouth to Plymouth - Mayflower 400 Commemoration
Wed 09 Sep 20
3 day
PM090920
Festival
Pilgrim Mayflower Commemorative Event
Join Pilgrim in Plymouth for the Mayflower 400 Commemoration
Sun 13 Sep 20
5 day
PM130920
Devon Coast Sailing Explorer
Explore the Devon coast from Plymouth and its ports and harbours
Sat 19 Sep 20
5 day
PM190920
Taster
Autumn B & B Sailing Weekend
Join us for an autumn weekend sailing experience to remember
Sat 26 Sep 20
2 day
PM080820
Taster
Dartmouth Day Sailing Experience
Enjoy a traditional day sailing from Dartmouth
Mon 28 Sep 20
1 day
PM280920
Taster
South Devon Day Sail
Enjoy a day sailing on heritage sailing trawler Pilgrim BM45 from Dartmouth to Brixham
Tue 29 Sep 20
1 day
PM290920
Taster
Brixham Trawler Sailing Day
Enjoy a day out sailing on heritage sailing trawler Pilgrim BM45
Thu 01 Oct 20
1 day
PM011020
Devon Sailing Adventure
Explore the stunning South Devon coast and its charming ports and harbours
Sat 03 Oct 20
3 day
PM031020
Taster
Afternoon Heritage Sailing Experience
Enjoy an afternoon of traditional sailing in Devon
Wed 07 Oct 20
1/2 Day
PM071020
Taster
Morning Heritage Sailing Experience
Enjoy a morning of traditional sailing in Devon
Fri 09 Oct 20
1/2 Day
PM071020
Taster
B & B Sailing Taster Weekend
Join us for an autumn weekend sailing experience to remember
Sat 10 Oct 20
2 day
PM101020
Taster
Devon Coast Day Sail
Enjoy a day out sailing on the 125 year old heritage sailing trawler Pilgrim of Brixham BM45
Wed 14 Oct 20
1 day
PM 141020
Dartmouth Cordon Bleu Sailing
Explore the stunning South Devon coast and Dartmouth Food Festival
Fri 16 Oct 20
4 Day
PM161020
Taster
Autumn Sailing in the Bays
Enjoy a lovely Autumn day out sailing on heritage sailing trawler Pilgrim BM45
Wed 21 Oct 20
1 day
PM211020
Taster
Devon Weekend Sailing Experience
Join us for a late autumn sailing experience to remember
Fri 23 Oct 20
3 day
PM231020
Taster
Morning Sailing Trawler Trip
Enjoy a morning of traditional sailing in Devon
Tue 27 Oct 20
1/2 Day
PM271020
Taster
Sailing Trawler Day Taster
Enjoy a lovely Autumn day out sailing on heritage sailing trawler Pilgrim BM45
Thu 29 Oct 20
1 day
PM291020