Home > Cruises > Island Hopping Cruises & Sailing Trips > May

Island Hopping Cruises Starting In May 2026, 2027 and 2028

Filter Results
Departures
Duration
4 Days
45 Days
Regions
Ship Size
Trip Styles
Show More...
Budget
Start & End Cities
Operators
Show More...
Price
$400pp
$94,850pp
Countries
Show More...
Filter Results
293 Cruises (7,739 Cruise Departures)
30 Day Peru & Galapagos Explorer with Intrepid Travel
Tour

30 Days Lima to Quito
Operated By: Intrepid Travel
Departures: Mar 2026 to Dec 2027
Visit: Peru, Galapagos, Ecuador
Exclusive Savings
From
US$9,529
Save 1,361
Per Person
View Trip
14 Day The Dalmatian Coast: Croatia, Corfu & Medieval Cities with G Adventures
New ReleaseTour

14 Days Rome to Corfu
Operated By: G Adventures
Departures: May 2026 to Sep 2027
Visit: Italy, Croatia, Montenegro, Albania, Greece
Exclusive Savings
From
US$1,782
Save 667
Per Person
View Trip
15 Day Greek Isles & Ephesus with Seabourn
Cruise

15 Days (14 Nights) Athens to Athens
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departures: May 2027 to Oct 2027
Visit: Greece, Turkey
Yours to Explore
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$11,098
Suite
$26,778
From
US$11,098
Save 273
Per Person
View Trip
10 Day Galápagos – West & Central Islands aboard the Reina Silvia Voyager with G Adventures
Cruise

10 Days (9 Nights) Quito to Quito
Operated By: G Adventures
Departures: Apr 2026 to Dec 2027
Visit: Ecuador, Galapagos
Exclusive Savings
From
US$7,662
Save 258
Per Person
View Trip
8 Day One Week in the Greek Islands with Intrepid Travel
Tour

8 Days Athens to Santorini
Operated By: Intrepid Travel
Departures: May 2026 to Oct 2027
Visit: Greece
Exclusive Savings
From
US$1,530
Save 55
Per Person
View Trip
18 Day Best of Peru & Galapagos with Intrepid Travel
Tour

18 Days Lima to Quito
Operated By: Intrepid Travel
Departures: Jun 2026 to Dec 2027
Visit: Peru, Galapagos, Ecuador
Exclusive Savings
From
US$7,294
Save 283
Per Person
View Trip
8 Day Galápagos - West & Central Islands aboard the Eden with G Adventures
Cruise

8 Days (7 Nights) Quito to Quito
Operated By: G Adventures
Departures: May 2026 to Dec 2027
Visit: Ecuador, Galapagos
Exclusive Savings
From
US$3,491
Save 1,008
Per Person
View Trip
9 Day Komodo Island Hopper with TruTravels
New ReleaseTour + Cruise

9 Days Lombok to Labuan Bajo
Operated By: TruTravels
Departures: Apr 2026 to Nov 2027
Visit: Indonesia
From
US$1,250
Per Person
View Trip
10 Day Philippines West with TruTravels
New ReleaseTour

10 Days Manila to Coron
Operated By: TruTravels
Departures: Apr 2026 to Dec 2027
Visit: Philippines
Exclusive Savings
From
US$930
Save 620
Per Person
View Trip
9 Day Croatia: Walking & Island-Hopping Along the Dalmatian Coast with G Adventures
New ReleaseTour

9 Days Dubrovnik to Trogir
Operated By: G Adventures
Departures: Apr 2026 to Oct 2026
Visit: Croatia
Exclusive Savings
From
US$3,545
Save 754
Per Person
View Trip
15 Day Dalmatian Coast & Montenegro Sailing with G Adventures
Cruise

15 Days (14 Nights) Split to Dubrovnik
Operated By: G Adventures
Departures: Apr 2026 to Sep 2026
Visit: Montenegro, Croatia
Exclusive Savings
From
US$2,987
Save 862
Per Person
View Trip
8 Day Independent Galapagos at the Finch Bay Resort with Globus
New ReleaseTour

8 Days Quito to Guayaquil
Operated By: Globus
Departures: Mar 2026 to Mar 2027
Trip Styles: Island Hopping, Wildlife, Scenic
Visit: Ecuador, Galapagos
Exclusive Savings
From
US$6,104
Save 270
Per Person
View Trip
15 Day Mediterranean with Greece, Turkey, & Adriatic with Princess
Cruise
 (6)

15 Days (14 Nights) Rome to Barcelona
Cruise Line: Princess
Ship: Sun Princess
Departures: Apr 2026 to Oct 2027
Visit: Italy, Greece, Turkey, Montenegro, Sicily, Spain
Princess Standard
Sanctuary Collection
Princess Premier
Exclusive Savings
Inside
$1,956
Oceanview
$2,639
Balcony
$2,921
Suite
$3,422
From
US$1,956
Save 60
Per Person
View Trip
8 Day A Journey Of Lush Landscapes & Golden Enchantment with Explora Journeys
Cruise
 (1)

8 Days (7 Nights) Athens to Venice
Cruise Line: Explora Journeys
Ship: Explora II
Departures: May 2026 to Oct 2026
Visit: Greece, Croatia, Italy
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$5,820
From
US$5,820
Per Person
View Trip
8 Day Athens to Santorini Island Hopping (Plus) with Contiki
Tour

8 Days Athens to Santorini
Operated By: Contiki
Departures: Apr 2026 to Sep 2027
Trip Styles: 18-30's, Island Hopping, Scenic
Visit: Greece
Exclusive Savings
From
US$1,415
Save 240
Per Person
View Trip
8 Day A Journey Through Legendary Marvels & Cultural Fusion with Explora Journeys
Cruise
 (1)

8 Days (7 Nights) Athens to Athens
Cruise Line: Explora Journeys
Ship: Explora II
Departures: May 2026 to Sep 2026
Visit: Greece, Turkey
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$5,225
From
US$5,225
Per Person
View Trip
24 Day Paris to Santorini (Plus) with Contiki
New ReleaseTour

24 Days Paris to Santorini
Operated By: Contiki
Departures: May 2026 to Aug 2026
Visit: France, Spain, Monaco, Italy, Greece
Exclusive Savings
From
US$4,643
Save 120
Per Person
View Trip
8 Day Greek Isles Cruise with Royal Caribbean
Cruise

8 Days (7 Nights) Venice to Venice
Cruise Line: Royal Caribbean
Ships: Brilliance of the Seas, Explorer of the Seas
Departures: May 2026 to Oct 2027
Visit: Italy, Greece, Croatia
Bonus Onboard Credit
Exclusive Savings
Inside
$1,105
Oceanview
$1,265
Balcony
$1,534
Suite
$2,084
From
US$1,105
Save 850
Per Person
View Trip
43 Day The Best of the Mediterranean with Princess
Cruise
 (1)

43 Days (42 Nights) Rome to Rome
Cruise Line: Princess
Ship: Enchanted Princess
Departure: 01 May 2027
Visit: Italy, Corsica, Sardinia, Malta (+6 more), Montenegro, Croatia, Greece, Cyprus, Turkey, Sicily
Princess Standard
Exclusive Savings
Inside
$6,987
Oceanview
-
Balcony
$8,746
Suite
$10,721
From
US$6,987
Per Person
View Trip
24 Day Galapagos Cruise & Peru in Depth (Grand Queen Beatriz) with Intrepid Travel
Tour

24 Days Quito to Lima
Operated By: Intrepid Travel
Departures: Oct 2026 to Dec 2027
Visit: Ecuador, Galapagos, Peru
Exclusive Savings
From
US$17,072
Save 528
Per Person
View Trip
15 Day Best of Greece with G Adventures
Tour

15 Days Athens to Santorini
Operated By: G Adventures
Departures: Apr 2026 to Oct 2027
Visit: Greece
Exclusive Savings
From
US$3,243
Save 936
Per Person
View Trip
25 Day Ecuador, Galapagos & Peru Explorer with Intrepid Travel
Tour

25 Days Quito to Cusco
Operated By: Intrepid Travel
Departures: Jul 2026 to Dec 2027
Visit: Ecuador, Galapagos, Peru
Exclusive Savings
From
US$7,581
Save 267
Per Person
View Trip
8 Day A Journey from Sunlit Cyclades to Adriatic Elegance with Explora Journeys
Cruise
 (1)

8 Days (7 Nights) Athens to Venice
Cruise Line: Explora Journeys
Ship: Explora II
Departures: May 2027 to Jul 2027
Visit: Greece, Croatia, Italy
Inside
-
Oceanview
-
Balcony
-
Suite
$4,380
From
US$4,380
Per Person
View Trip
32 Day The Best of the Mediterranean with Princess
Cruise
 (1)

32 Days (31 Nights) Rome to Istanbul
Cruise Line: Princess
Ship: Enchanted Princess
Departure: 01 May 2027
Visit: Italy, Corsica, Sardinia, Malta (+6 more), Montenegro, Croatia, Greece, Cyprus, Turkey, Sicily
Princess Standard
Exclusive Savings
Inside
$5,694
Oceanview
$7,386
Balcony
$6,839
Suite
$8,467
From
US$5,694
Per Person
View Trip
8 Day Greece: Walking in the Greek Islands with G Adventures
New ReleaseTour

8 Days Athens to Santorini
Operated By: G Adventures
Departures: Apr 2026 to Oct 2026
Visit: Greece
Exclusive Savings
From
US$3,622
Save 559
Per Person
View Trip
30 Day Mediterranean Medley: Italy, Turkey, Greece & Balkans with Seabourn
Cruise

30 Days (29 Nights) Dubrovnik to Venice
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 15 May 2027
Visit: Croatia, Montenegro, Italy, Greece, Turkey, Slovenia
Yours to Explore
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$29,265
Suite
-
From
US$29,265
Save 534
Per Person
View Trip
22 Day The Best of the Mediterranean with Princess
Cruise
 (1)

22 Days (21 Nights) Trieste to Istanbul
Cruise Line: Princess
Ship: Enchanted Princess
Departures: May 2027 to Oct 2027
Visit: Italy, Croatia, Montenegro, Greece (+4 more), Cyprus, Turkey, Sicily, Malta
Princess Standard
Exclusive Savings
Inside
$3,589
Oceanview
$4,508
Balcony
$4,043
Suite
$5,098
From
US$3,589
Save 62
Per Person
View Trip
15 Day Gardens of the Italian Lakes, Slovenia & Croatian Islands Cruise with APT
Tour + Cruise

15 Days Milan to Dubrovnik
Operated By: APT
Ship: MV Lady Eleganza
Departure: 26 May 2026
Visit: Italy, Slovenia, Croatia
Exclusive Savings
Inside
-
Oceanview
$11,080
Balcony
-
Suite
-
From
US$11,080
Save 215
Per Person
View Trip
17 Day Mysteries of the Inca Empire with Galapagos Cruise with Cosmos
Tour + Cruise

17 Days Lima to Quito
Operated By: Cosmos
Departures: Dec 2026 to Nov 2027
Visit: Peru, Ecuador, Galapagos
Exclusive Savings
From
US$6,957
Save 241
Per Person
View Trip
8 Day The Galápagos: Wildlife of Santa Cruz & Isabela Islands with G Adventures
New ReleaseTour

8 Days Quito to Quito
Operated By: G Adventures
Departures: May 2026 to Dec 2027
Visit: Ecuador, Galapagos
Exclusive Savings
From
US$4,015
Save 622
Per Person
View Trip
Results: 91-120 of 293

No trips found. Try adjusting the search filters.




Cruises found! Scroll up to view.

Cruises

All Cruises Adriatic Cruises Aegean Cruises Africa Cruises Alaska Cruises Antarctic Cruises Arabian & Middle East Cruises Arctic Cruises Asia Cruises Australia Cruises Bahamas Cruises Bermuda Cruises Canada & New England Cruises Caribbean Cruises Central America Cruises China Cruises Croatia Cruises Cruises to the Falkland Islands Cruising Cape Horn Europe Cruises Hawaii Cruises Indian Ocean Cruises Japan Cruises Kimberley Tours & Cruises Mediterranean Cruises Mexico Cruises New Zealand Cruises Northern Europe & Baltic Cruises Northwest Passage Cruises Norway & Iceland Cruises Norwegian Fjords Cruises Patagonia Cruises South America Cruises South East Asia Cruises South Pacific Cruises Transatlantic Cruises UK Cruises USA Cruises Western Europe Cruises Worldwide Cruises

Trip Lengths

7 Day 10 Day 2 Week 3 Week 1 Month

Departure Months

March April May June July August September October November December January February

Cruise Themes

Adults Only Cruises Christmas & New Year Cruises Expedition Cruises Family Cruises Island Hopping Cruises Luxury Cruises Northen Lights Cruises Sailing Trips Short Cruises Last Minute Cruise Deals

© 2010-2026. Global Journeys. You're viewing our site in US dollars.

    

Global Journeys | Terms & Conditions

Global Journeys Travel Inc. is a Member of the American Society of Travel Advisors (ASTA No: 900374670), CLIA (No. 00046729) & is TICO Accredited (No. 50027921).

Travel Industry Associations