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.
91 Sailing vacations found
Sailing in Croatia
A multi-activity adventure sailing cruise in Croatia
From €580 to €790 4 days ex flights
Small group travel:
2024: 20 Apr, 21 Apr, 22 Apr, 23 Apr, 24 Apr, 25 Apr, 27 Apr, 28 Apr, 29 Apr, 30 Apr, 1 May, 2 May, 4 May, 5 May, 6 May, 7 May, 8 May, 9 May, 11 May, 12 May, 13 May, 14 May, 15 May, 16 May, 18 May, 19 May, 20 May, 21 May, 22 May, 23 May, 25 May, 26 May, 27 May, 28 May, 29 May, 30 May, 1 Jun, 2 Jun, 3 Jun, 4 Jun, 5 Jun, 6 Jun, 8 Jun, 9 Jun, 10 Jun, 11 Jun, 12 Jun, 13 Jun, 15 Jun, 16 Jun, 17 Jun, 18 Jun, 19 Jun, 20 Jun, 22 Jun, 23 Jun ...
Greece sailing holiday for families
Sailing trip for families/friends in Greek islands
From £585 to £733 8 days ex flights
Small group travel:
2024: 26 May, 2 Jun, 16 Jun, 30 Jun, 14 Jul, 4 Aug, 11 Aug, 1 Sep, 15 Sep, 22 Sep
Arctic sailing voyages, North Spitsbergen
Spitsbergen tall-ship wildlife and natural history sailing
From €3,045 8 days ex flights
Small group travel:
2024: 15 May, 22 May, 26 May, 2 Jun, 8 Jun, 9 Jun, 18 Jun, 28 Jun, 8 Jul, 30 Aug
2025: 8 Jun, 18 Jun, 28 Jun
2025: 8 Jun, 18 Jun, 28 Jun
Turquoise Coast luxury gulet cruise, Turkey
Luxury gulet cruise along Turkey's southern coast,Bodrum to Gocek
From £1,189 to £1,625 8 days ex flights
Small group travel:
2024: 11 May, 25 May, 1 Jun, 7 Sep, 21 Sep
Contact Us
Call us for a chat about our vacations. We are happy to discuss your vacation and help in any way we can. No bots, queues or awful hold music.
1-866-821-6866
Call toll free
Calling from outside the USA
rosy@responsibletravel.com
Skye and the Small Isles sailing vacation
Sail Scotland's Small Isles and visit spectacular Skye
From £1,520 to £2,880 9 days ex flights
Small group travel:
2024: 16 Apr, 10 May, 14 May, 3 Aug, 7 Sep, 9 Sep
2025: 30 Apr, 4 May, 10 May, 20 May, 15 Jun, 31 Jul, 18 Aug, 19 Aug, 22 Aug, 5 Sep, 7 Sep, 9 Sep
2025: 30 Apr, 4 May, 10 May, 20 May, 15 Jun, 31 Jul, 18 Aug, 19 Aug, 22 Aug, 5 Sep, 7 Sep, 9 Sep
10% discount on all of our scottish wild isles cruises departing in april and may 2024. simply quote sprt24 when booking.
Wildlife sailing holiday in Scotland
Extraordinary wildlife above and below the waves
From £950 to £3,600 6 days ex flights
Small group travel:
2024: 14 Apr, 18 Apr, 30 Apr, 10 May, 5 Jun, 17 Jun, 7 Jul, 15 Jul, 27 Jul, 10 Aug, 18 Aug, 22 Aug, 30 Aug, 1 Sep, 19 Sep, 25 Sep, 27 Sep, 28 Sep, 3 Oct
10% discount on all of our scottish wild isles cruises departing in april and may 2024. simply quote sprt24 when booking.
Liveaboard diving and sailing vacation in Greece
Combine a sailing and diving adventure in the Greek islands
From £805 to £892 7 days ex flights
Small group travel:
2024: 4 May, 11 May, 18 May, 25 May, 1 Jun, 8 Jun, 15 Jun, 22 Jun, 29 Jun, 6 Jul, 13 Jul, 20 Jul, 27 Jul, 3 Aug, 10 Aug, 17 Aug, 24 Aug, 31 Aug, 7 Sep, 14 Sep, 21 Sep, 28 Sep, 5 Oct, 12 Oct, 19 Oct, 26 Oct
Dubrovnik to Hvar sailing vacation
Active sailing adventure around Croatian Islands
From €920 to €990 5 days ex flights
Small group travel:
2024: 9 Jun, 13 Jun, 10 Jul, 22 Jul, 26 Jul, 4 Aug, 8 Aug, 13 Aug, 17 Aug, 22 Aug, 26 Aug, 19 Sep
Cyclades sailing & walking vacation in Greece
Combine a sailing & hiking adventure around the Cyclades
From £785 to £872 7 days ex flights
Small group travel:
2024: 4 May, 11 May, 18 May, 25 May, 1 Jun, 8 Jun, 15 Jun, 22 Jun, 29 Jun, 6 Jul, 13 Jul, 20 Jul, 27 Jul, 3 Aug, 10 Aug, 17 Aug, 24 Aug, 31 Aug, 7 Sep, 14 Sep, 21 Sep, 28 Sep, 5 Oct, 12 Oct, 19 Oct, 26 Oct, 2 Nov
Whisky and wildlife sailing holiday in Scotland
Malt Whisky and Wildlife Cruise to Mull, Jura and Islay
From £2,060 11 days ex flights
Small group travel:
2025: 12 May
Sailing vacation in the Aegean Sea
Uninhabited islands in a 6 person boat
From £690 to £767 7 days ex flights
Small group travel:
2024: 4 May, 11 May, 18 May, 25 May, 1 Jun, 8 Jun, 15 Jun, 22 Jun, 29 Jun, 6 Jul, 13 Jul, 20 Jul, 27 Jul, 3 Aug, 10 Aug, 17 Aug, 24 Aug, 31 Aug, 7 Sep, 14 Sep, 21 Sep, 28 Sep, 5 Oct, 12 Oct, 19 Oct, 26 Oct, 2 Nov
Family yacht charter sailing vacation in Greece
Private sailing with fun games, reliving mythical tales
From €2,100 to €2,910 8 days ex flights
Tailor made:
This holiday is chartering the whole catamaran, minimum 6, maximum 10
Maldives private gulet cruise vacation
Cruise the Maldives island paradise by Turkish Gullet
From US $9,899 to US $29,000 8 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
Greece sailing vacation in Ionian Sea
Sail, explore and experience the Ionian islands in Greece
From €1,100 6 days ex flights
Small group travel:
2024: 23 Jun, 14 Jul, 28 Jul, 4 Aug, 11 Aug, 25 Aug, 8 Sep
Contact Us
Call us for a chat about our vacations. We are happy to discuss your vacation and help in any way we can. No bots, queues or awful hold music.
1-866-821-6866
Call toll free
Calling from outside the USA
rosy@responsibletravel.com
Saronic Greek Islands luxury charter cruise
Luxury sailing Greek islands, while reliving mythical tales
From €2,050 to €2,890 8 days ex flights
Tailor made:
This holiday is chartering the whole catamaran, minimum 6, maximum 10. Sailing Season is from May 28 to Oct 1
Sailing vacation in Scotland, Greater Clyde
Sailing and outdoor activities with local seafood in Argyll
From £600 6 days ex flights
Small group travel:
2024: 23 Jun, 30 Jun, 7 Jul, 18 Aug, 25 Aug, 1 Sep
Yoga and sailing retreat in Greece
-A week of relaxation and yoga while sailing the Ionian sea!
From £800 to £1,000 7 days ex flights
Small group travel:
2024: 2 Jun, 30 Jun, 14 Jul
Sailing vacation in Greece, Mykonos to Santorini
The boat, the beach and inviting Greek villages
From US $1,783 to US $2,155 8 days ex flights
Small group travel:
2024: 7 May, 11 May, 21 May, 25 May, 4 Jun, 8 Jun, 22 Jun, 2 Jul, 6 Jul, 16 Jul, 20 Jul, 30 Jul, 3 Aug, 13 Aug, 17 Aug, 27 Aug, 31 Aug, 10 Sep, 14 Sep, 24 Sep, 28 Sep
Late availability on these dates: 07 May, 11 May
Croatia sailing vacation, Dubrovnik to Split
Experience the old-world charm of Croatia
From US $2,153 to US $2,575 8 days ex flights
Small group travel:
2024: 11 May, 18 May, 25 May, 8 Jun, 15 Jun, 22 Jun, 6 Jul, 13 Jul, 20 Jul, 3 Aug, 10 Aug, 17 Aug, 31 Aug, 7 Sep, 14 Sep
Late availability on these dates: 11 May
Spain to the Canaries sailing vacation
Atlantic Sail: Spain to Canaries Expedition!
From US $3,077 12 days ex flights
Small group travel:
2024: 28 Oct
Bay of Biscay sailing vacation
For those seeking the thrill of the sea!
From US $3,208 13 days ex flights
Small group travel:
2024: 13 Oct
Iceland to Scotland sailing vacation, via Faroe Islands
Arctic Odyssey: Iceland to Scotland via Faroes
From US $3,245 12 days ex flights
Small group travel:
2024: 5 Aug, 19 Aug
Lofoten Islands sailing vacation, Norway
Jaw-dropping scenery, pristine beaches, and northern lights
From US $2,870 12 days ex flights
Small group travel:
2024: 22 Jul
Faroe Islands to Norway sailing vacation
Adventure sailing across the Arctic Circle.
From US $2,995 12 days ex flights
Small group travel:
2024: 1 Jul
Sardinia and Corsica wellness sailing vacation
Luxury wellness sailing adventure in Sardinia and Corsica
From €2,450 to €3,450 8 days ex flights
Small group travel:
2024: 1 Jun, 8 Jun, 22 Jun, 29 Jun, 6 Jul, 13 Jul, 20 Jul, 27 Jul
Traditional Dahabiya Nile cruise, Egypt
Explore the Nile's cultural gems in classic comfort
From €1,200 to €1,800 5 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
Tall ship sailing vacation in Northern Spain
Adventure sailing in Spain on a historic ship
From €740 to €980 6 days ex flights
Small group travel:
2024: 17 Mar, 24 Mar, 31 Mar, 7 Apr, 14 Apr, 21 Apr, 28 Apr, 5 May, 12 May, 19 May, 26 May, 2 Jun, 9 Jun, 16 Jun, 23 Jun, 30 Jun, 7 Jul, 14 Jul, 21 Jul, 28 Jul, 4 Aug, 11 Aug, 18 Aug, 25 Aug, 1 Sep, 8 Sep, 15 Sep, 22 Sep
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:
2024: 31 May, 7 Jun, 21 Jun, 28 Jun, 5 Jul, 12 Jul, 26 Jul, 2 Aug, 23 Aug
2 for 1 on double occupancy or no single supplement
on various dates, or 25% off, specified on request and valid for bookings made during 07 Feb to 17 Feb
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:
2024: 19 Apr, 26 Apr, 3 May, 10 May, 17 May, 24 May, 14 Jun, 21 Jun, 28 Jun, 5 Jul, 12 Jul, 19 Jul, 26 Jul, 16 Aug, 30 Aug, 6 Sep, 13 Sep, 20 Sep, 27 Sep, 4 Oct, 11 Oct, 18 Oct
2 for 1 on double occupancy or no single supplement
on various dates, or 25% off, specified on request and valid for bookings made during 07 Feb to 17 Feb
Arctic sailing voyages, around Spitsbergen
Spitsbergen tall-ship wildlife and natural history sailing
From €6,040 to €6,389 15 days ex flights
Small group travel:
2024: 30 Jun, 15 Jul, 18 Jul, 1 Aug, 15 Aug
