Small ship cruising vacations in Greece

It's the ultimate destination for very chilled-out island hopping. On small ship cruising vacations in Greece, your only concern is bagging the best anchorage on the island. Moor up alongside perky-looking fishing vessels, stop for lunch and a swim in a sparkling cove, and cruise along with an unparalleled view of soothing blue in every direction. It's no myth: Greek cruising is bliss.

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Sailing vacation in the Aegean Sea

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

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
Greece sailing vacation in Ionian Sea

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
Island hopping cruise in Greece

Island hopping cruise in Greece

Classic small ship cruise to Greek Islands & Ephesus
From £2,349 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
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Greek Islands family sailing vacation

Greek Islands family sailing vacation

Enjoy the beauty of the Greek islands
From US $1,340 to US $1,610 8 days ex flights
Small group travel: 2024: 21 Jul, 28 Jul, 4 Aug, 18 Aug
Sailing vacation in the Ionian Sea

Sailing vacation in the Ionian Sea

An unforgettable sailing adventure
From £690 to £767 7 days ex flights
Small group travel: 2024: 4 May, 18 May, 1 Jun, 15 Jun, 29 Jun, 13 Jul, 27 Jul, 10 Aug, 24 Aug, 7 Sep, 21 Sep
Greek island hiking cruise

Greek island hiking cruise

Our Hiking Cruise in Greece offers the best of two worlds.
From £1,913 to £2,913 8 days ex flights
Small group travel: 2024: 5 Apr, 25 Oct
Small ship sail powered Greek Island cruise

Small ship sail powered Greek Island cruise

-Sail on a beautiful ship around the Greek Islands
From £4,402 to £4,650 8 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
Greek Islands cruise holiday, Antiquity to Byzantium

Greek Islands cruise holiday, Antiquity to Byzantium

Cruising in the beautiful Greek Islands
From £1,435 to £2,913 8 days ex flights
Small group travel: 2024: 22 Mar, 29 Mar, 5 Apr, 12 Apr, 25 Oct, 1 Nov, 8 Nov
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
Greece wine tasting cruise

Greece wine tasting cruise

Wine tasting around the Greek islands!
From £3,783 to £5,174 8 days ex flights
Small group travel: 2024: 30 Aug
Classical Greece small ship cruise vacation

Classical Greece small ship cruise vacation

Ancient history through crystal blue waters!
From US $2,990 to US $4,690 8 days ex flights
Small group travel: 2024: 24 May, 31 May, 7 Jun, 14 Jun, 21 Jun, 28 Jun, 5 Jul, 12 Jul, 19 Jul, 26 Jul, 2 Aug, 9 Aug, 16 Aug, 23 Aug, 30 Aug, 6 Sep, 13 Sep, 20 Sep
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 Aegean Island hopping vacation

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 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
Luxury Greece yacht charter in the Aegean

Luxury Greece yacht charter in the Aegean

Luxury sailing the Aegean, while reliving mythical tales
From €2,100 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
Responsible Travel, Travel Team

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
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Greek cruise and island walking vacation

Greek cruise and island walking vacation

Explore Evia on this walking and cruise trip
From US $1,340 to US $1,520 8 days ex flights
Small group travel: 2024: 9 Jun, 8 Sep
Corfu and Ionian cruise in Greece

Corfu and Ionian cruise in Greece

Cruise the Ionian islands from Corfu on a beautiful gulet.
From £1,075 to £1,247 8 days ex flights
Small group travel: 2024: 10 Jun, 8 Jul, 15 Jul, 29 Jul
Malta, Sicily and The Aeolian Islands Cruise

Malta, Sicily and The Aeolian Islands Cruise

Cruise the amazing Sicily, Malta and Aeolian islands.
From £2,314 8 days ex flights
Small group travel
Greek Island Cruise

Greek Island Cruise

Discover Greece on this relaxing cruise around Evia
From US $1,340 to US $1,610 8 days ex flights
Small group travel: 2024: 16 Jun, 23 Jun, 30 Jun, 7 Jul, 25 Aug, 1 Sep, 15 Sep, 22 Sep
Private sailing and cycling island hopping, Greece

Private sailing and cycling island hopping, Greece

Self guided or guided (upon request) tour in the Cyclades
From €1,500 8 days ex flights
Small group travel: 2024: 1 May, 8 May, 15 May, 22 May, 29 May, 5 Jun, 12 Jun, 19 Jun, 26 Jun, 3 Jul, 10 Jul, 17 Jul, 24 Jul, 31 Jul, 7 Aug, 14 Aug, 21 Aug, 28 Aug, 4 Sep, 11 Sep, 18 Sep, 25 Sep, 2 Oct, 9 Oct, 16 Oct, 23 Oct, 30 Oct
Greece small ship cruise, ancient sites of the Peloponnese

Greece small ship cruise, ancient sites of the Peloponnese

Small ship cruise to many of Greece's top ancient sites
From £1,333 to £1,892 8 days ex flights
Small group travel: 2024: 22 Mar, 29 Mar, 5 Apr, 12 Apr, 25 Oct, 1 Nov, 8 Nov
Cyclades Islands sailing vacation, Greece

Cyclades Islands sailing vacation, Greece

Swim in turquoise seas & explore ancient towns
From US $2,533 to US $2,923 10 days ex flights
Small group travel: 2024: 4 May, 14 May, 24 May, 3 Jun, 7 Jun, 13 Jun, 17 Jun, 23 Jun, 27 Jun, 3 Jul, 7 Jul, 13 Jul, 17 Jul, 23 Jul, 27 Jul, 2 Aug, 6 Aug, 12 Aug, 16 Aug, 22 Aug, 26 Aug, 1 Sep, 5 Sep, 11 Sep, 15 Sep, 21 Sep
Late availability on these dates: 04 May, 14 May
Greek Islands bike and boat vacation

Greek Islands bike and boat vacation

Bicycle and sail around the Cyclades Greek Islands
From US $3,990 8 days ex flights
Small group travel: 2024: 19 Apr, 3 May, 7 Jun, 14 Jun, 23 Aug, 30 Aug, 6 Sep
Late availability on these dates: 19 Apr, 03 May
    Photo credits: [Page banner: Alex Antoniadis] [Cultural vacations : A.Savin] [Activities : Patrick Hendry] [On the water : pxhere] [Family vacations : Explore] [Where to go in Greece : momo]