Sailing vacations
Whether you are looking to learn to sail, lie on deck and let someone do the work, or just enjoy sailing as a means of getting from one aquatically alluring A to an even more beautiful B, sailing vacations are all about going with the flow. Amalfi or Adriatic, Caribbean or Cyclades, sailing vacations take you island hopping, wildlife watching, scuba diving. Or indeed, just plain sailing.
77 Sailing vacations found
Sailing in Croatia
A multi-activity adventure sailing cruise in Croatia
From €580 to €790 4 days ex flights
Tailor made:
This can be booked daily between 10th April and 28th October
Luxury gulet cruise in the Aegean 2023
5 star services while cruising the Greek Islands in luxury
From £1,250 8 days ex flights
Small group travel:
2023: 27 May, 2 Sep
Liveaboard diving and sailing vacation in Greece
Combine a sailing and diving adventure in the Greek islands
From £719 to £799 7 days ex flights
Small group travel:
2022: 2 Jul, 9 Jul, 30 Jul, 6 Aug, 13 Aug, 20 Aug, 27 Aug, 3 Sep, 10 Sep, 17 Sep, 24 Sep, 1 Oct, 8 Oct, 15 Oct, 22 Oct, 29 Oct
Yoga and sailing retreat in Greece
-A week of relaxation and yoga while sailing the Ionian sea!
From £850 to £950 7 days ex flights
Small group travel:
2023: 28 May, 25 Jun
Travel Team
If you would like some help or advice, or just want to discuss your ideas for your next trip, do give us a call.
Dubrovnik to Hvar sailing vacation
Active sailing adventure around Croatian Islands
From €920 to €990 5 days ex flights
Small group travel:
2022: 22 Aug, 10 Sep, 14 Sep
Sailing vacation in Greece, Mykonos to Santorini
The boat, the beach and inviting Greek villages
From US $1,647 to US $1,852 8 days ex flights
Small group travel:
2022: 23 Jul, 6 Aug, 20 Aug, 1 Oct
2023: 13 May, 16 May, 27 May, 8 Jun, 10 Jun, 24 Jun, 2 Jul, 8 Jul, 22 Jul, 25 Jul, 5 Aug, 17 Aug, 19 Aug, 2 Sep, 10 Sep, 16 Sep, 30 Sep, 3 Oct
2023: 13 May, 16 May, 27 May, 8 Jun, 10 Jun, 24 Jun, 2 Jul, 8 Jul, 22 Jul, 25 Jul, 5 Aug, 17 Aug, 19 Aug, 2 Sep, 10 Sep, 16 Sep, 30 Sep, 3 Oct
Late availability on these dates: 23 Jul, 06 Aug, 20 Aug, 01 Oct
Arctic sailing voyages, North Spitsbergen
Spitsbergen tall-ship wildlife and natural history sailing
From €2,790 8 days ex flights
Small group travel:
2022: 6 Jul
2023: 15 May, 22 May, 29 May, 8 Jun, 18 Jun, 28 Jun, 8 Jul
2023: 15 May, 22 May, 29 May, 8 Jun, 18 Jun, 28 Jun, 8 Jul
Tall ship sailing holiday, Bay of Biscay
Explore bay of Biscay by tall ship
From €490 to €750 14 days ex flights
Small group travel
Sailing and biking Cyclades vacation, Greece
Self guided or guided (upon request) tour in the Cyclades
From €1,500 8 days ex flights
Small group travel:
2022: 3 Sep, 10 Sep, 17 Sep, 24 Sep, 1 Oct, 8 Oct, 15 Oct
Family sailing vacation in Turkey
Explore southern Turkey, Dalyan to Delikada Island
From US $1,170 to US $1,260 8 days ex flights
Small group travel:
2022: 23 Jul, 30 Jul, 6 Aug, 13 Aug, 20 Aug
2023: 15 Jul, 22 Jul, 29 Jul, 5 Aug, 12 Aug, 19 Aug
2023: 15 Jul, 22 Jul, 29 Jul, 5 Aug, 12 Aug, 19 Aug
Late availability on these dates: 23 Jul, 30 Jul, 06 Aug, 13 Aug, 20 Aug
Skye and the Small Isles sailing vacation
Sail Scotland's Small Isles and visit spectacular Skye
From £1,360 to £2,480 9 days ex flights
Small group travel:
2022: 21 Aug, 25 Aug, 10 Sep
2023: 8 May, 10 May, 20 Jul, 9 Aug, 16 Aug, 23 Aug, 4 Sep, 5 Sep
2024: 16 Apr, 14 May, 19 May, 17 Jun, 3 Aug, 20 Aug, 22 Aug, 7 Sep
2023: 8 May, 10 May, 20 Jul, 9 Aug, 16 Aug, 23 Aug, 4 Sep, 5 Sep
2024: 16 Apr, 14 May, 19 May, 17 Jun, 3 Aug, 20 Aug, 22 Aug, 7 Sep
Seychelles 7 day sailing cruise
Cruise the Seychelles on a beautiful wooden sailing ship
From £1,332 7 days ex flights
Small group travel
Wildlife sailing holiday in Scotland
Extraordinary wildlife above and below the waves
From £890 to £2,790 6 days ex flights
Small group travel:
2022: 30 Aug, 10 Sep, 16 Sep, 17 Sep, 19 Sep, 23 Sep, 26 Sep, 27 Sep, 1 Oct, 3 Oct, 5 Oct
2023: 13 Apr, 14 Apr, 21 Apr, 22 Apr, 30 Apr, 8 May, 10 May, 18 May, 1 Jun, 6 Jun, 13 Jun, 19 Jun, 21 Jun, 1 Jul, 3 Jul, 10 Jul, 18 Jul, 23 Jul, 28 Jul, 30 Jul, 4 Aug, 7 Aug, 9 Aug, 16 Aug, 19 Aug, 23 Aug, 26 Aug, 28 Aug, 2 Sep, 4 Sep, 5 Sep, 11 Sep, 14 Sep, 15 Sep, 19 Sep, 22 Sep, 23 Sep, 28 Sep, 30 Sep, 7 Oct, 8 Oct
2023: 13 Apr, 14 Apr, 21 Apr, 22 Apr, 30 Apr, 8 May, 10 May, 18 May, 1 Jun, 6 Jun, 13 Jun, 19 Jun, 21 Jun, 1 Jul, 3 Jul, 10 Jul, 18 Jul, 23 Jul, 28 Jul, 30 Jul, 4 Aug, 7 Aug, 9 Aug, 16 Aug, 19 Aug, 23 Aug, 26 Aug, 28 Aug, 2 Sep, 4 Sep, 5 Sep, 11 Sep, 14 Sep, 15 Sep, 19 Sep, 22 Sep, 23 Sep, 28 Sep, 30 Sep, 7 Oct, 8 Oct
Greek Island cruising vacation
Discover a side of Greece riddled with myth and magic.
From US $4,085US $3,229 to US $5,410US $4,225 9 days ex flights
Small group travel:
2022: 7 Jul, 21 Jul, 4 Aug, 11 Aug, 8 Sep
2023: 18 May, 22 Jun, 20 Jul, 3 Aug, 17 Aug, 21 Sep
2023: 18 May, 22 Jun, 20 Jul, 3 Aug, 17 Aug, 21 Sep
Up to US $850 off selected dates.
Late availability on these dates: 07 Jul, 21 Jul, 04 Aug, 11 Aug, 08 Sep
Late availability on these dates: 07 Jul, 21 Jul, 04 Aug, 11 Aug, 08 Sep
Travel Team
If you would like some help or advice, or just want to discuss your ideas for your next trip, do give us a call.
Greek Islands sailing vacation, Santorini to Mykonos
Sapphire waters, whitewashed villages & history laden ruins
From US $1,607 to US $1,852 8 days ex flights
Small group travel:
2022: 16 Jul, 30 Jul, 13 Aug, 27 Aug, 10 Sep
2023: 6 May, 9 May, 20 May, 1 Jun, 3 Jun, 17 Jun, 25 Jun, 1 Jul, 15 Jul, 18 Jul, 29 Jul, 10 Aug, 12 Aug, 26 Aug, 3 Sep, 9 Sep, 23 Sep, 26 Sep
2023: 6 May, 9 May, 20 May, 1 Jun, 3 Jun, 17 Jun, 25 Jun, 1 Jul, 15 Jul, 18 Jul, 29 Jul, 10 Aug, 12 Aug, 26 Aug, 3 Sep, 9 Sep, 23 Sep, 26 Sep
Late availability on these dates: 16 Jul, 30 Jul, 13 Aug, 27 Aug, 10 Sep
Croatia sailing vacation, Dubrovnik to Split
Experience the old-world charm of Croatia
From US $2,010US $1,514 to US $2,682 8 days ex flights
Small group travel:
2022: 9 Jul, 23 Jul, 6 Aug
2023: 13 May, 20 May, 27 May, 10 Jun, 17 Jun, 24 Jun, 8 Jul, 15 Jul, 22 Jul, 5 Aug, 12 Aug, 19 Aug, 2 Sep, 9 Sep, 16 Sep
2023: 13 May, 20 May, 27 May, 10 Jun, 17 Jun, 24 Jun, 8 Jul, 15 Jul, 22 Jul, 5 Aug, 12 Aug, 19 Aug, 2 Sep, 9 Sep, 16 Sep
Up to US $490 off selected dates.
Late availability on these dates: 09 Jul, 23 Jul, 06 Aug
Late availability on these dates: 09 Jul, 23 Jul, 06 Aug
Cyclades sailing & walking vacation in Greece
Combine a sailing & hiking adventure around the Cyclades
From £712 to £791 7 days ex flights
Small group travel:
2022: 2 Jul, 9 Jul, 16 Jul, 23 Jul, 30 Jul, 28 Aug, 4 Sep, 11 Sep, 18 Sep, 25 Sep, 2 Oct, 9 Oct, 16 Oct, 23 Oct, 30 Oct
Whisky and wildlife sailing holiday in Scotland
Malt Whisky and Wildlife Cruise to Mull, Jura and Islay
From £1,520 11 days ex flights
Small group travel:
2023: 28 Jul
2024: 29 May
2024: 29 May
Sailing vacation in the Aegean Sea
Uninhabited islands in a 6 person boat
From £502 to £613 7 days ex flights
Small group travel:
2022: 30 Jul, 20 Aug, 27 Aug, 3 Sep, 10 Sep, 17 Sep, 24 Sep, 1 Oct, 8 Oct, 15 Oct, 22 Oct, 29 Oct
Greater Clyde sailing vacation, Scotland
Sailing and outdoor activities with local seafood in Argyll
From £750 to £825 6 days ex flights
Small group travel:
2022: 17 Jul, 7 Aug, 14 Aug, 21 Aug, 4 Sep, 18 Sep, 25 Sep
Egypt cruise vacation, Aqaba to Tel Aviv
Discover Israel,Egypt and Jordan with an expert Egyptologist
From US $1,990 to US $3,190 8 days ex flights
Small group travel:
2022: 11 Dec, 25 Dec
2023: 8 Jan, 22 Jan, 5 Feb, 19 Feb, 5 Mar, 19 Mar
2023: 8 Jan, 22 Jan, 5 Feb, 19 Feb, 5 Mar, 19 Mar
Greece sailing holiday for families
Sailing trip for families/friends in Greek islands
From €4,050 to €5,600 8 days ex flights
Small group travel:
2022: 2 Jul, 9 Jul, 16 Jul, 23 Jul, 30 Jul, 6 Aug, 13 Aug, 20 Aug, 27 Aug, 3 Sep, 10 Sep, 17 Sep, 24 Sep
Enjoy a great offer -400€ for a week trip with your family/friends 25.9-1.10! This trip was originally booked and just became available!
Spain tall ship sailing holiday, Spanish speaking
Practice Spanish while sailing on a historic wooden ship
From €650 to €940 6 days ex flights
Small group travel:
2022: 24 Jul, 1 Aug, 8 Aug, 15 Aug, 22 Aug, 29 Aug, 6 Sep
Egypt, Jordan & Suez Canal small ship cruise
Gods, Kings & Pharaohs, while crossing the Suez Canal!
From US $1,990 to US $3,190 8 days ex flights
Small group travel:
2022: 18 Dec
2023: 1 Jan, 15 Jan, 29 Jan, 12 Feb, 26 Feb, 12 Mar, 26 Mar
2023: 1 Jan, 15 Jan, 29 Jan, 12 Feb, 26 Feb, 12 Mar, 26 Mar
Istria and Northern Adriatic sailing adventure, Croatia
Multi-activity sailing holiday around Croatian islands
From €1,540 5 days ex flights
Tailor made:
This trip can be booked from April to October
Small group sailing in Saronic Greek Islands
Luxury sailing in the Greek islands with mythical adventures
From €2,800 8 days ex flights
Small group travel:
2023: 8 Jul
Greek Aegean Island hopping vacation
Get on board and visit ten stunning Aegean islands
From US $2,890 to US $4,390 8 days ex flights
Small group travel:
2022: 1 Jul, 15 Jul, 16 Sep
Tall ship festival, Bilbao to San Sebastian
3 day Pasaia Maritime Festival
From €1,150 to €1,690 10 days ex flights
Small group travel
Greek Cyclades island hopping cruise
Greek Island Hopping, Sandy beaches and Clear azure waters
From US $2,790 to US $4,190 8 days ex flights
Small group travel:
2022: 1 Jul, 8 Jul, 15 Jul, 22 Jul, 29 Jul, 5 Aug, 12 Aug, 19 Aug, 26 Aug, 2 Sep, 9 Sep, 16 Sep, 23 Sep, 30 Sep, 7 Oct, 14 Oct, 21 Oct
Arctic sailing voyages, around Spitsbergen
Spitsbergen tall-ship wildlife and natural history sailing
From €5,640 15 days ex flights
Small group travel:
2023: 18 Jul
