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.
83 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:
2023: 15 Apr, 16 Apr, 17 Apr, 18 Apr, 19 Apr, 20 Apr, 22 Apr, 23 Apr, 24 Apr, 25 Apr, 26 Apr, 27 Apr, 29 Apr, 30 Apr, 1 May, 2 May, 3 May, 4 May, 6 May, 7 May, 8 May, 11 May, 13 May, 14 May, 15 May, 16 May, 17 May, 18 May, 20 May, 21 May, 22 May, 23 May, 24 May, 25 May, 28 May, 29 May, 1 Jun, 4 Jun, 5 Jun, 6 Jun, 13 Jun, 15 Jun, 19 Jun, 22 Jun, 23 Jun, 26 Jun, 27 Jun, 6 Jul, 11 Jul, 15 Jul, 17 Jul, 18 Jul, 20 Jul, 22 Jul, 24 Jul ...
Liveaboard diving and sailing vacation in Greece
Combine a sailing and diving adventure in the Greek islands
From £730 to £879 7 days ex flights
Small group travel:
2023: 29 Apr, 6 May, 13 May, 20 May, 27 May, 5 Aug, 12 Aug, 19 Aug, 26 Aug, 2 Sep, 9 Sep, 16 Sep, 23 Sep, 30 Sep, 7 Oct, 14 Oct, 21 Oct, 28 Oct
10% off on all May departures
Yoga and sailing retreat in Greece
-A week of relaxation and yoga while sailing the Ionian sea!
From £850 to £990 7 days ex flights
Small group travel:
2023: 28 May, 18 Jun, 25 Jun, 2 Jul, 9 Jul
Dubrovnik to Hvar sailing vacation
Active sailing adventure around Croatian Islands
From €820 to €990 5 days ex flights
Small group travel:
2023: 4 May, 8 May, 28 May, 1 Jun, 11 Jun, 15 Jun, 17 Jul, 22 Jul, 4 Aug, 8 Aug, 18 Aug, 22 Aug, 27 Aug, 31 Aug, 1 Sep, 10 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.
1-866-821-6866
Call toll free
Calling from outside the USA
rosy@responsibletravel.com
Sailing vacation in Greece, Mykonos to Santorini
The boat, the beach and inviting Greek villages
From US $1,680US $1,548 to US $2,110 8 days ex flights
Small group travel:
2023: 13 May, 16 May, 27 May, 8 Jun, 22 Jul, 5 Aug, 17 Aug, 16 Sep, 30 Sep, 3 Oct
2024: 11 May, 14 May, 25 May, 8 Jun, 22 Jun, 3 Jul, 6 Jul, 20 Jul, 28 Jul, 3 Aug, 17 Aug, 22 Aug, 31 Aug, 14 Sep, 16 Sep, 28 Sep
2024: 11 May, 14 May, 25 May, 8 Jun, 22 Jun, 3 Jul, 6 Jul, 20 Jul, 28 Jul, 3 Aug, 17 Aug, 22 Aug, 31 Aug, 14 Sep, 16 Sep, 28 Sep
Up to US $130 off selected dates.
Late availability on these dates: 13 May, 16 May, 27 May, 08 Jun
Late availability on these dates: 13 May, 16 May, 27 May, 08 Jun
Arctic sailing voyages, North Spitsbergen
Spitsbergen tall-ship wildlife and natural history sailing
From €2,790 8 days ex flights
Small group travel:
2023: 15 May, 22 May, 29 May, 8 Jun, 18 Jun, 28 Jun, 8 Jul
2024: 8 Jun, 18 Jun, 28 Jun, 8 Jul
2024: 8 Jun, 18 Jun, 28 Jun, 8 Jul
Turkey gulet cruise, Fethiye to Demre
Swim and explore on this five day Turqouise Coast gulet trip
From £599 to £969 5 days ex flights
Small group travel:
2023: 13 May, 20 May, 27 May, 3 Jun, 10 Jun, 17 Jun, 24 Jun, 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
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:
2023: 1 May, 1 Jun, 1 Jul, 1 Aug, 1 Sep
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
Family sailing vacation in Turkey
Explore southern Turkey, Dalyan to Delikada Island
From US $1,550US $1,470 to US $1,590 8 days ex flights
Small group travel:
2023: 15 Jul, 22 Jul, 29 Jul, 5 Aug, 12 Aug, 19 Aug
2024: 20 Jul, 27 Jul, 3 Aug, 10 Aug, 17 Aug
2024: 20 Jul, 27 Jul, 3 Aug, 10 Aug, 17 Aug
Up to US $80 off selected dates.
Late availability on upcoming trips
Late availability on upcoming trips
Skye and the Small Isles sailing vacation
Sail Scotland's Small Isles and visit spectacular Skye
From £1,520 to £2,480 9 days ex flights
Small group travel:
2023: 16 Aug, 4 Sep, 5 Sep
2024: 16 Apr, 10 May, 14 May, 19 May, 17 Jun, 3 Aug, 20 Aug, 22 Aug, 7 Sep, 9 Sep
2024: 16 Apr, 10 May, 14 May, 19 May, 17 Jun, 3 Aug, 20 Aug, 22 Aug, 7 Sep, 9 Sep
Seychelles 7 day sailing cruise
Cruise the Seychelles on a beautiful wooden sailing ship
From £952 to £1,348 7 days ex flights
Small group travel:
2023: 29 Apr, 6 May, 13 May, 20 May, 27 May, 3 Jun, 10 Jun, 17 Jun, 24 Jun, 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, 28 Oct
Wildlife sailing holiday in Scotland
Extraordinary wildlife above and below the waves
From £950 to £2,480 6 days ex flights
Small group travel:
2023: 13 Apr, 14 Apr, 22 Apr, 30 Apr, 18 May, 1 Jun, 6 Jun, 1 Jul, 18 Jul, 28 Jul, 30 Jul, 7 Aug, 19 Aug, 23 Aug, 26 Aug, 2 Sep, 4 Sep, 5 Sep, 11 Sep, 14 Sep, 15 Sep, 19 Sep, 22 Sep, 23 Sep, 28 Sep, 30 Sep, 1 Oct
15% discount for the 8 night cruise departing on the 30th April 2023 onboard gemini explorer. twin aft with washbasin is now £1802 per person (saving of £318 per person). double ensuite is now £2380 per person (saving of £420 per person).
Greek Island cruising vacation
Discover a side of Greece riddled with myth and magic.
From US $4,205 to US $6,115US $4,745 9 days ex flights
Small group travel:
2023: 18 May, 22 Jun, 20 Jul, 3 Aug, 17 Aug, 21 Sep
Late availability on these dates: 18 May, 22 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.
1-866-821-6866
Call toll free
Calling from outside the USA
rosy@responsibletravel.com
Greek Islands sailing vacation, Santorini to Mykonos
Sapphire waters, whitewashed villages & history laden ruins
From US $1,650US $1,275 to US $2,075 8 days ex flights
Small group travel:
2023: 6 May, 9 May, 20 May, 3 Jun, 25 Jun, 18 Jul, 29 Jul, 10 Aug, 12 Aug, 26 Aug, 23 Sep, 26 Sep
2024: 4 May, 7 May, 18 May, 1 Jun, 15 Jun, 26 Jun, 29 Jun, 13 Jul, 21 Jul, 27 Jul, 10 Aug, 15 Aug, 24 Aug, 7 Sep, 9 Sep, 21 Sep
2024: 4 May, 7 May, 18 May, 1 Jun, 15 Jun, 26 Jun, 29 Jun, 13 Jul, 21 Jul, 27 Jul, 10 Aug, 15 Aug, 24 Aug, 7 Sep, 9 Sep, 21 Sep
Up to US $370 off selected dates.
Late availability on these dates: 06 May, 09 May, 20 May, 03 Jun, 25 Jun
Late availability on these dates: 06 May, 09 May, 20 May, 03 Jun, 25 Jun
Croatia sailing vacation, Dubrovnik to Split
Experience the old-world charm of Croatia
From US $2,025US $1,639 to US $2,505 8 days ex flights
Small group travel:
2023: 13 May, 20 May, 27 May, 17 Jun, 24 Jun, 8 Jul, 15 Jul, 22 Jul, 5 Aug, 12 Aug, 2 Sep, 9 Sep, 16 Sep
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
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
Up to US $390 off selected dates.
Late availability on these dates: 13 May, 20 May, 27 May, 17 Jun, 24 Jun
Late availability on these dates: 13 May, 20 May, 27 May, 17 Jun, 24 Jun
Cyclades sailing & walking vacation in Greece
Combine a sailing & hiking adventure around the Cyclades
From £726 to £797 7 days ex flights
Small group travel:
2023: 29 Apr, 6 May, 13 May, 20 May, 27 May, 3 Jun, 10 Jun, 17 Jun, 24 Jun, 1 Jul, 26 Aug, 2 Sep, 9 Sep, 16 Sep, 23 Sep, 30 Sep, 7 Oct, 14 Oct, 21 Oct, 28 Oct, 4 Nov
10% off on all May departures
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:
2024: 29 May
Sailing vacation in the Aegean Sea
Uninhabited islands in a 6 person boat
From £572 to £697 7 days ex flights
Small group travel:
2023: 29 Apr, 6 May, 13 May, 20 May, 27 May, 3 Jun, 10 Jun, 17 Jun, 24 Jun, 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, 28 Oct, 4 Nov
10% off on all May departures
Sardinia and Corsica wellness sailing vacation
Luxury wellness sailing adventure in Sardinia and Corsica
From €2,191 8 days ex flights
Small group travel:
2023: 3 Jun, 10 Jun, 24 Jun, 1 Jul, 22 Jul, 29 Jul
2024: 1 Jun, 8 Jun, 15 Jun, 22 Jun, 29 Jun, 6 Jul, 13 Jul, 20 Jul, 27 Jul
2024: 1 Jun, 8 Jun, 15 Jun, 22 Jun, 29 Jun, 6 Jul, 13 Jul, 20 Jul, 27 Jul
Spaces available for June departures
Indonesia family summer sailing vacation
Sail past the remotes islands of Indonesia with your family!
From £4,125 13 days ex flights
Small group travel:
2023: 23 Jul, 5 Aug
Sail the Islands of Indonesia, Bali to Flores
Island-hop around Indonesia aboard a traditional penisi boat
From £4,198 13 days ex flights
Small group travel:
2023: 26 Apr, 13 May, 22 May, 30 May, 10 Jun, 19 Jun, 4 Jul, 13 Jul, 23 Jul, 27 Jul, 5 Aug, 14 Aug, 23 Aug
Cross Channel sailing vacation
Challenging cross channel sail exploring the Normandy Coast
From £935 5 days ex flights
Small group travel:
2023: 12 Apr
Bristol Channel to Essex sailing vacation
Great sailing-wonderful wildlife-the Jurassic coast & more.
From £1,950 13 days ex flights
Small group travel:
2023: 10 Sep
UK sailing vacation, Edinburgh to Belfast
Once in a lifetime experience, exhilarating Cape Wrath
From £2,254 14 days ex flights
Small group travel:
2023: 13 Aug
West Coast of Ireland sailing vacation
Exhilarating & amazing - Ocean Sailing & the Emerald Isle
From £2,254 14 days ex flights
Small group travel:
2023: 27 Aug
Cross Channel sailing vacation to Calais
Challenging and exhilarating dash across the Channel
From £749 4 days ex flights
Small group travel
English Channel sailing vacation to Netherlands
Challenging Sail to Vlissingen and stunning Middelburg
From £749 5 days ex flights
Small group travel
Cross channel sailing vacation to Ostend
Hop across the Channel - Belgium - dinner and back!
From £749 5 days ex flights
Small group travel:
2023: 6 Apr
Irish Sea sailing vacation, Rhu to Milford Haven
Sail the Irish sea visiting the Emerald Isle & Wales
From £985 7 days ex flights
Small group travel:
2023: 28 May
