Home > Cruises > Island Hopping Cruises & Sailing Trips > October 2027

Island Hopping Cruises Starting In October 2027

Are you looking to embark on an island hopping cruise in October 2027? Choose from 144 unique cruise itineraries and 5,646 departures from the world's leading cruise lines.
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Departures (October 2027)
< September 2027 November 2027 >
Duration
4 Days
37 Days
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$400pp
$94,850pp
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144 Cruises (5,646 Cruise Departures)
14 Day Country Roads of Croatia with Insight Vacations
Tour
 (13)

14 Days Zagreb to Dubrovnik
Operated By: Insight Vacations
Departures: Apr 2026 to Oct 2027
Trip Styles: Coach, Island Hopping, Scenic
Visit: Croatia, Slovenia
Sign Up Savings
Today's Deal
Exclusive Savings
From
US$3,884
Save 864
Per Person
View Trip
9 Day Dalmatian Elegance with Insight Vacations
Cruise
 (3)

9 Days (8 Nights) Split to Split
Operated By: Insight Vacations
Departures: Apr 2026 to Oct 2027
Visit: Croatia
Today's Deal
Exclusive Savings
From
US$3,243
Save 680
Per Person
View Trip
10 Day Greek Island Hopper with Globus
Tour
 (3)

10 Days Athens to Athens
Operated By: Globus
Departures: Apr 2026 to Oct 2027
Trip Styles: Coach, Island Hopping, Scenic
Visit: Greece
Exclusive Savings
From
US$3,117
Save 289
Per Person
View Trip
30 Day Ultimate South America with Brazil's Amazon & Galapagos Cruise with Cosmos
Tour + Cruise
 (3)

30 Days Manaus to Guayaquil
Operated By: Cosmos
Departures: Jun 2026 to Nov 2027
Visit: Brazil, Argentina, Peru, Ecuador, Galapagos
Exclusive Savings
From
US$9,416
Save 351
Per Person
View Trip
9 Day Galapagos Discovery with Intrepid Travel
Tour
 (2)

9 Days Quito to Quito
Operated By: Intrepid Travel
Departures: Nov 2025 to Dec 2027
Visit: Ecuador, Galapagos
Exclusive Savings
From
US$2,318
Save 480
Per Person
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5 Day Iconic Aegean with Celestyal Cruises
Cruise
 (2)

5 Days (4 Nights) Athens to Athens
Cruise Line: Celestyal Cruises
Ship: Celestyal Discovery
Departures: Nov 2025 to Oct 2027
Visit: Greece, Turkey
Inside
$639
Oceanview
$799
Balcony
$1,269
Suite
$1,389
From
US$639
Per Person
View Trip
15 Day Classical Greece Plus Island Hopper with Globus
Tour
 (1)

15 Days Athens to Athens
Operated By: Globus
Departures: Apr 2026 to Oct 2027
Trip Styles: Coach, Island Hopping, Scenic
Visit: Greece
Exclusive Savings
From
US$4,778
Save 233
Per Person
View Trip
8 Day Croatia Sailing Adventure: Dubrovnik to Split with Intrepid Travel
Cruise
 (1)

8 Days (7 Nights) Dubrovnik to Split
Operated By: Intrepid Travel
Departures: May 2026 to Oct 2027
Visit: Croatia
Exclusive Savings
From
US$2,119
Save 69
Per Person
View Trip
14 Day Dubrovnik to Ljubljana with Intrepid Travel
Tour
 (1)

14 Days Dubrovnik to Ljubljana
Operated By: Intrepid Travel
Departures: Apr 2026 to Oct 2027
Visit: Croatia, Slovenia
Exclusive Savings
From
US$4,918
Save 169
Per Person
View Trip
9 Day Galápagos Adventure: Snorkelling & Sea Lions with G Adventures
Tour
 (1)

9 Days Quito to Quito
Operated By: G Adventures
Departures: Dec 2025 to Dec 2027
Visit: Ecuador, Galapagos
Exclusive Savings
From
US$2,065
Save 68
Per Person
View Trip
7 Day Galapagos Explorer: Southern Islands (Grand Queen Beatriz) with Intrepid Travel
Cruise
 (1)

7 Days (6 Nights) Quito to Quito
Operated By: Intrepid Travel
Departures: Nov 2025 to Dec 2027
Visit: Ecuador, Galapagos
Exclusive Savings
From
US$4,406
Save 899
Per Person
View Trip
9 Day Galápagos Island Hopping with G Adventures
Tour
 (1)

9 Days Quito to Quito
Operated By: G Adventures
Departures: Dec 2025 to Dec 2027
Visit: Ecuador, Galapagos
Exclusive Savings
From
US$3,297
Save 114
Per Person
View Trip
8 Day Greek Island Glow with Virgin Voyages
Cruise
 (5)

8 Days (7 Nights) Athens to Athens
Cruise Line: Virgin Voyages
Ship: Scarlet Lady
Departures: May 2027 to Oct 2027
Visit: Greece, Turkey
Inside
$1,557
Oceanview
$1,708
Balcony
$1,936
Suite
$4,625
From
US$1,557
Per Person
View Trip
8 Day Mediterranean Enchantment with Emerald Cruises
Cruise

8 Days (7 Nights) Dubrovnik to Athens
Cruise Line: Emerald Cruises
Ships: Emerald Azzurra, Emerald Raiya
Departures: Jul 2027 to Oct 2027
Visit: Croatia, Montenegro, Albania, Greece
Fly Free Economy
Fly Free Premium Economy
Exclusive Savings
Inside
-
Oceanview
$7,015
Balcony
-
Suite
$9,124
From
US$7,015
Save 10,882
Per Person
View Trip
14 Day Thailand Island Hopper with TruTravels
New ReleaseTour
 (1)

14 Days Bangkok to Phuket
Operated By: TruTravels
Departures: Nov 2025 to Nov 2027
Visit: Thailand
From
US$1,425
Per Person
View Trip
26 Day Ultimate South America with Galapagos Cruise with Cosmos
Tour + Cruise
 (1)

26 Days Rio de Janeiro to Guayaquil
Operated By: Cosmos
Departures: Feb 2026 to Nov 2027
Visit: Brazil, Argentina, Peru, Ecuador, Galapagos
Exclusive Savings
From
US$9,939
Save 543
Per Person
View Trip
15 Day Discover the Eastern Mediterranean with Emerald Cruises
New ReleaseCruise
 (3)

15 Days (14 Nights) Athens to Dubrovnik
Cruise Line: Emerald Cruises
Ships: Emerald Azzurra, Emerald Raiya
Departures: May 2027 to Oct 2027
Visit: Greece, Turkey, Albania, Montenegro, Croatia
Fly Free Economy
Fly Free Premium Economy
Exclusive Savings
Inside
-
Oceanview
$14,092
Balcony
-
Suite
$18,312
From
US$14,092
Save 16,210
Per Person
View Trip
8 Day Greek Island Hues & Turkish Views with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) Athens to Athens
Cruise Line: Virgin Voyages
Ship: Scarlet Lady
Departures: May 2027 to Oct 2027
Visit: Greece, Turkey
Inside
$1,631
Oceanview
$1,783
Balcony
$2,010
Suite
$4,625
From
US$1,631
Per Person
View Trip
8 Day Philippines East with TruTravels
New ReleaseTour

8 Days Cebu to Boracay
Operated By: TruTravels
Departures: Nov 2025 to Dec 2027
Visit: Philippines
From
US$1,250
Per Person
View Trip
22 Day Greek Isles With Istanbul, Rhodes & Egypt with Holland America
Cruise
 (2)

22 Days (21 Nights) Athens to Athens
Cruise Line: Holland America
Ship: Oosterdam
Departure: 02 October 2027
Visit: Greece, Turkey, Egypt, Israel, Cyprus
Book Early & Have It All Fare Option
Exclusive Savings
Inside
$3,932
Oceanview
$4,207
Balcony
$5,667
Suite
$8,117
From
US$3,932
Per Person
View Trip
17 Day Philippines Island Hopper with TruTravels
New ReleaseTour

17 Days Manila to Boracay
Operated By: TruTravels
Departures: Nov 2025 to Dec 2027
Visit: Philippines
Exclusive Savings
From
US$2,711
Save 96
Per Person
View Trip
7 Day Cycle Croatia with Intrepid Travel
Tour

7 Days Split to Dubrovnik
Operated By: Intrepid Travel
Departures: May 2026 to Oct 2027
Visit: Croatia
Exclusive Savings
From
US$3,337
Save 113
Per Person
View Trip
23 Day South American Discovery with Galápagos Cruise with Globus
Tour + Cruise

23 Days Rio de Janeiro to Guayaquil
Operated By: Globus
Departures: Mar 2026 to Nov 2027
Visit: Brazil, Argentina, Peru, Ecuador, Galapagos
Exclusive Savings
From
US$11,686
Save 869
Per Person
View Trip
8 Day San Cristóbal to San Cristóbal with Silversea
Cruise

8 Days (7 Nights) Quito to Guayaquil
Cruise Line: Silversea
Ship: Silver Origin
Departures: Dec 2025 to Mar 2028
Visit: Ecuador, Galapagos
All-Inclusive Plus Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$11,200
Suite
$17,400
From
US$11,200
Save 2,800
Per Person
View Trip
8 Day Galapagos Outer Loop Cruise with Celebrity Cruises
Cruise

8 Days (7 Nights) Baltra Island to Baltra Island
Cruise Line: Celebrity Cruises
Ship: Celebrity Flora
Departures: Jan 2026 to Dec 2027
Visit: Galapagos
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$7,609
From
US$7,609
Save 4,409
Per Person
View Trip
22 Day The Best of the Mediterranean with Princess
Cruise
 (1)

22 Days (21 Nights) Athens to Rome
Cruise Line: Princess
Ship: Enchanted Princess
Departure: 16 October 2027
Visit: Greece, Sicily, Malta, Turkey, Italy
Princess Standard
Inside
$3,490
Oceanview
-
Balcony
$3,911
Suite
$5,551
From
US$3,490
Per Person
View Trip
17 Day Active Galápagos & Machu Picchu (Machu Picchu by Train) with G Adventures
New ReleaseTour

17 Days Quito to Cusco
Operated By: G Adventures
Departures: Jan 2026 to Oct 2027
Visit: Ecuador, Peru, Galapagos
Exclusive Savings
From
US$5,334
Save 186
Per Person
View Trip
9 Day Island Hopping in the Galapagos with Exodus Adventure Travels
New ReleaseCruise

9 Days (8 Nights) Quito to Quito
Departures: Feb 2026 to Dec 2027
Visit: Ecuador, Galapagos
Sign Up Savings
Exclusive Savings
From
US$4,889
Save 1,411
Per Person
View Trip
8 Day Highlights of the Greek Islands with G Adventures
Tour

8 Days Athens to Santorini
Operated By: G Adventures
Departures: Apr 2026 to Oct 2027
Visit: Greece
Exclusive Savings
From
US$2,133
Save 73
Per Person
View Trip
10 Day Galápagos - East, Central, & West Islands aboard the Eden with G Adventures
Cruise

10 Days (9 Nights) Quito to Quito
Operated By: G Adventures
Departures: Jan 2026 to Dec 2027
Visit: Ecuador, Galapagos
Exclusive Savings
From
US$5,606
Save 187
Per Person
View Trip
Results: 1-30 of 144

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Trip Lengths

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Departure Months

October 2025 November 2025 December 2025 January 2026 February 2026 March 2026 April 2026 May 2026 June 2026 July 2026 August 2026 September 2026 October 2026 November 2026 December 2026 January 2027 February 2027 March 2027 April 2027 May 2027 June 2027 July 2027 August 2027 September 2027 October 2027 November 2027 December 2027 January 2028 February 2028 March 2028 April 2028 May 2028 August 2028 September 2028 October 2028 November 2028 December 2028

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