Mediterranean sailing holidays
There’s nothing more memorable than a Mediterranean sailing holiday to allow sunshine and sea breeze to orchestrate a week-long trip of a lifetime. From Croatia’s islands to the Greek Cyclades, the Aegean to the Adriatic, sailing in the Mediterranean allows time to relax both on land and at sea. Experience the Med’s best beaches and exclusive anchorages without another soul in sight.
53 Mediterranean sailing holidays found
Sailing in Croatia
A multi-activity adventure sailing cruise in Croatia
From €580 to €790 4 days ex flights
Small group travel:
2022: 28 Aug, 29 Aug, 1 Sep, 3 Sep, 6 Sep, 7 Sep, 8 Sep, 11 Sep, 12 Sep, 13 Sep, 14 Sep, 15 Sep, 18 Sep, 20 Sep, 21 Sep, 22 Sep, 24 Sep, 25 Sep, 26 Sep, 27 Sep, 28 Sep, 29 Sep, 1 Oct, 2 Oct, 4 Oct, 5 Oct, 6 Oct, 8 Oct, 9 Oct, 10 Oct, 11 Oct, 12 Oct, 13 Oct, 15 Oct
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
Greek Islands sailing holiday, Santorini to Mykonos
Sapphire waters, whitewashed villages & history laden ruins
From £1,221 to £1,381 8 days ex flights
Small group travel:
2022: 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, 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, 9 Sep, 23 Sep, 26 Sep
Late availability on these dates: 10 Sep
Cyclades sailing & walking holiday in Greece
Combine a sailing & hiking adventure around the Cyclades
From £712 to £791 7 days ex flights
Small group travel:
2022: 28 Aug, 4 Sep, 11 Sep, 18 Sep, 25 Sep, 2 Oct, 9 Oct, 16 Oct, 23 Oct, 30 Oct
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.
Sailing holiday in the Aegean Sea
Unique sailing adventure off the beaten track in Greece
From £502 to £613 7 days ex flights
Small group travel:
2022: 20 Aug, 27 Aug, 3 Sep, 10 Sep, 17 Sep, 24 Sep, 1 Oct, 8 Oct, 15 Oct, 22 Oct, 29 Oct
Liveaboard diving and sailing holiday in Greece
Combine a sailing and diving adventure in the Greek islands
From £719 to £799 7 days ex flights
Small group travel:
2022: 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 £720 to £950 7 days ex flights
Small group travel:
2022: 25 Sep
2023: 28 May, 25 Jun
2023: 28 May, 25 Jun
Dubrovnik to Hvar sailing holiday
Active sailing adventure around Croatian Islands
From €920 to €990 5 days ex flights
Small group travel:
2022: 22 Aug, 10 Sep, 14 Sep
Greek Island cruising holiday
Discover a side of Greece riddled with myth and magic.
From £2,705 to £3,580£3,225 9 days ex flights
Small group travel:
2022: 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
Late availability on these dates: 08 Sep
Greek Islands bike and boat holiday
Cycle and sail around the Cyclades Greek Islands
From £2,190 8 days ex flights
Small group travel:
2023: 22 Apr, 29 Apr, 6 May, 13 May, 20 May, 27 May, 3 Jun, 10 Jun, 17 Jun, 2 Sep, 9 Sep, 17 Sep, 23 Sep, 30 Sep
Whale & dolphin research in Ligurian Sea, Italy
Whale and dolphin conservation trip
From €805 to €950 6 days ex flights
Small group travel
Sailing holiday in Greece, Mykonos to Santorini
The boat, the beach and inviting Greek villages
From £1,261 to £1,381 8 days ex flights
Small group travel:
2022: 3 Sep
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: 03 Sep
Greece sailing holiday for families
Sailing trip for families/friends in Greek islands
From €4,250 to €5,600 8 days ex flights
Small group travel:
2022: 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!
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
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.
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 holiday
Get on board and visit ten stunning Aegean islands
From €2,400 to €3,650 8 days ex flights
Small group travel:
2022: 16 Sep
Greek Cyclades island hopping cruise
Greek Island Hopping, Sandy beaches and Clear azure waters
From €2,070 to €3,450 8 days ex flights
Small group travel:
2022: 19 Aug, 26 Aug, 2 Sep, 9 Sep, 16 Sep, 23 Sep, 30 Sep, 7 Oct, 14 Oct, 21 Oct
Luxury sailing holiday in the Aegean
Luxury sailing the Aegean, while reliving mythical tales
From €2,340 to €2,940 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
Late availability for departures in September.
Saronic Greek Islands luxury cruise
Luxury sailing Greek islands, while reliving mythical tales
From €2,100 to €2,860 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
Small group sailing holiday Greece
Luxury sailing in the Greek islands with mythical adventures
From €2,740 8 days ex flights
Small group travel:
2023: 1 Jul
Family sailing holiday in Greece
Private sailing with fun games, reliving mythical tales
From €2,300 to €2,880 8 days ex flights
Tailor made:
This holiday is chartering the whole catamaran, minimum 6, maximum 10
Greek Islands sailing holiday
Luxury sailing in the Greek islands, reliving mythical tales
From €2,300 to €2,880 8 days ex flights
Tailor made:
This holiday is chartering the whole catamaran, minimum 6, maximum 10. Sailing Season is from 28th May to 1st Oct
Late availability for departures in Sept
Saronic Islands sailing holiday in Greece
Sail among the beautiful islands & ports of the Saronic Gulf
From US $2,995 7 days ex flights
Small group travel
Sardinia sailing and trekking holiday
Sail & Hike between turquoise sea & wild coast in Sardinia
From €1,380 to €1,680 8 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
Turkey gulet cruise, Fethiye to Olympos
Relax, swim and sunbathe on this four day sail
From £299 to £369 4 days ex flights
Small group travel:
2022: 3 Sep, 10 Sep, 17 Sep, 24 Sep, 1 Oct, 8 Oct, 15 Oct, 22 Oct, 29 Oct
Turkey 4 day gulet cruise, Marmaris to Fethiye
Voyage between coastal towns Marmaris and Fethiye
From £349 to £539 4 days ex flights
Small group travel:
2022: 3 Sep, 10 Sep, 17 Sep, 24 Sep, 1 Oct, 8 Oct, 15 Oct, 22 Oct, 29 Oct
Turkey gulet cruise from Marmaris
Sail along Turkey's most beautiful stretches of coastline
From £469 to £709 8 days ex flights
Small group travel:
2022: 3 Sep, 10 Sep, 17 Sep, 24 Sep, 1 Oct, 8 Oct, 15 Oct, 22 Oct, 29 Oct
Turkey gulet cruise, Fethiye and Gocek
A relaxing gulet cruise along Turkey's Turquoise Coast
From £399 to £519 8 days ex flights
Small group travel:
2022: 3 Sep, 10 Sep, 17 Sep, 24 Sep, 1 Oct, 8 Oct, 15 Oct, 22 Oct, 29 Oct
Turkey gulet cruises, Fethiye to Marmaris
5 day cruise exploring secluded islands and coves
From £349 to £499 5 days ex flights
Small group travel:
2022: 6 Sep, 13 Sep, 20 Sep, 27 Sep, 4 Oct, 11 Oct, 18 Oct, 25 Oct
Saronic Gulf small group sailing holiday in Greece
Spend a week navigating the idyllic waters of the Saronic Gulf
From £1,899 to £1,999 8 days ex flights
Small group travel:
2023: 6 May, 27 May, 9 Sep, 16 Sep
