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.

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Sailing in Croatia

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

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

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

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
Responsible Travel, Travel Team

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
Sailing vacation in Greece, Mykonos to Santorini

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
Up to US $130 off selected dates.
Late availability on these dates: 13 May, 16 May, 27 May, 08 Jun
Arctic sailing voyages, North Spitsbergen

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
Turkey gulet cruise, Fethiye to Demre

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

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

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

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
Up to US $80 off selected dates.
Late availability on upcoming trips
Skye and the Small Isles sailing vacation

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
Seychelles 7 day sailing cruise

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

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

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
Responsible Travel, Travel Team

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
Greek Islands sailing vacation, Santorini to Mykonos

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
Up to US $370 off selected dates.
Late availability on these dates: 06 May, 09 May, 20 May, 03 Jun, 25 Jun
Croatia sailing vacation, Dubrovnik to Split

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
Up to US $390 off selected dates.
Late availability on these dates: 13 May, 20 May, 27 May, 17 Jun, 24 Jun
Cyclades sailing & walking vacation in Greece

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

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

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

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
Spaces available for June departures
Indonesia family summer sailing vacation

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

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

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

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

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

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

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

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

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

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
Photo credits: [Page banner: Markos Mant]