Home > Cruises > Island Hopping Cruises & Sailing Trips > May 2026

Island Hopping Cruises Starting In May 2026

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Departures (May 2026)
< April 2026 June 2026 >
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45 Days
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248 Cruises (6,952 Cruise Departures)
10 Day Galápagos - North, Central, & South Islands aboard the Eden with G Adventures
Cruise

10 Days (9 Nights) Quito to Quito
Operated By: G Adventures
Departures: Aug 2025 to Dec 2027
Countries Visited: Ecuador, Galapagos
Save
1,768
From
3,861
per person
View Trip
27 Day Paris to Athens with Greek Island Hopping with Contiki
Tour

27 Days Paris to Athens
Operated By: Contiki
Departures: Aug 2025 to Aug 2026
Trip Styles: Coach, 18-30's, Island Hopping, Scenic
Countries Visited: France, Spain, Monaco, Italy, Greece
Exclusive Savings
Save
1,385
From
4,967
per person
View Trip
8 Day Sailing Greece - Athens to Mykonos with G Adventures
Cruise

8 Days (7 Nights) Athens to Mykonos
Operated By: G Adventures
Departures: Sep 2025 to Sep 2026
Countries Visited: Greece
From
1,549
per person
View Trip
18 Day Ecuador Highlands & Galapagos with Intrepid Travel
Tour

18 Days Quito to Quito
Operated By: Intrepid Travel
Departures: Sep 2025 to Dec 2027
Trip Styles: Adventure, Coach, Small Group, Island Hopping, Walking & Hiking, Wildlife, Scenic, Inca Trail
Countries Visited: Ecuador, Galapagos
Exclusive Savings
Save
126
From
5,101
per person
View Trip
8 Day Philippines East with TruTravels
New ReleaseTour

8 Days Cebu to Boracay
Operated By: TruTravels
Departures: Sep 2025 to Dec 2026
Trip Styles: Adventure, Small Group, 18-30's, Island Hopping
Countries Visited: Philippines
From
1,250
per person
View Trip
9 Day Best Of Greece Cruise with Celebrity Cruises
Cruise
 (2)

9 Days (8 Nights) Athens to Athens
Cruise Line: Celebrity Cruises
Ship: Celebrity Infinity
Departure: 22 May 2026
Countries Visited: Greece, Turkey
Exclusive Deal
Inside
$1,529
Oceanview
$2,017
Balcony
$2,379
Suite
$4,658
Save
885
From
1,529
per person
View Trip
15 Day An Extended Journey Into Sensory Delights & Striking Nature with Explora Journeys
Cruise
 (1)

15 Days (14 Nights) Athens to Venice
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 25 May 2026
Countries Visited: Greece, Turkey, Croatia, Italy
Extended Journey SavingUnique Summer Special
Inside
-
Oceanview
-
Balcony
$9,600
Suite
$11,080
From
9,600
per person
View Trip
8 Day Sail Greece: Mykonos to Santorini with Intrepid Travel
Cruise

8 Days (7 Nights) Mykonos to Santorini
Operated By: Intrepid Travel
Departures: Aug 2025 to Oct 2026
Countries Visited: Greece
Save
402
From
1,723
per person
View Trip
7 Day Independent Galapagos Cruise Aboard the Galapagos Legend with Globus
New ReleaseTour + Cruise

7 Days Quito to Guayaquil
Operated By: Globus
Departures: Sep 2025 to Mar 2027
Trip Styles: Cruise, Island Hopping, Wildlife, Scenic
Countries Visited: Ecuador, Galapagos
Exclusive Savings
Save
164
From
5,050
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: Sep 2025 to Sep 2026
Countries Visited: Montenegro, Croatia
Save
1,086
From
3,013
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: Sep 2025 to Sep 2027
Trip Styles: Adventure, Small Group, 18-30's, Island Hopping
Countries Visited: Greece
From
1,505
per person
View Trip
8 Day Sailing Croatia with G Adventures
Cruise

8 Days (7 Nights) Dubrovnik to Split
Operated By: G Adventures
Departures: Aug 2025 to Oct 2026
Countries Visited: Croatia
Save
840
From
1,259
per person
View Trip
11 Day The Greek Islands, Adriatic & Corinth Canal with Emerald Cruises
New ReleaseCruise

11 Days (10 Nights) Athens to Dubrovnik
Cruise Line: Emerald Cruises
Ships: Emerald Kaia, Emerald Azzurra
Departures: May 2026 to Sep 2027
Countries Visited: Croatia, Montenegro, Albania, Greece
Mutiple Deals Available
Inside
-
Oceanview
$9,106
Balcony
-
Suite
$12,175
Save
12,405
From
9,106
per person
View Trip
15 Day Best of Greece with G Adventures
Tour

15 Days Athens to Santorini
Operated By: G Adventures
Departures: Aug 2025 to Oct 2026
Trip Styles: Adventure, Small Group, Island Hopping
Countries Visited: Greece
Save
1,139
From
3,160
per person
View Trip
7 Day Maldives Dhoni Cruise with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operated By: G Adventures
Departures: Sep 2025 to Jan 2027
Countries Visited: Maldives
Save
600
From
1,399
per person
View Trip
22 Day The Best of the Mediterranean with Princess
Cruise
 (6)

22 Days (21 Nights) Rome to Rome
Cruise Line: Princess
Ship: Sun Princess
Departures: Apr 2026 to Oct 2027
Countries Visited: Italy, Greece, Turkey, Montenegro (+4 more), Sicily, Spain, Gibraltar, France
Mutiple Deals Available
Inside
$3,288
Oceanview
$4,089
Balcony
$4,837
Suite
$5,664
From
3,288
per person
View Trip
7 Day Galapagos Adventure: Northern Islands (Grand Daphne) with Intrepid Travel
Cruise

7 Days (6 Nights) Quito to Quito
Operated By: Intrepid Travel
Departures: Aug 2025 to Dec 2026
Countries Visited: Ecuador, Galapagos
Save
1,282
From
3,758
per person
View Trip
24 Day London to Santorini (Plus) with Contiki
New ReleaseTour

24 Days London to Santorini
Operated By: Contiki
Departures: Aug 2025 to Aug 2026
Trip Styles: Coach, 18-30's, Island Hopping, Scenic
Countries Visited: England, France, Spain, Monaco, Italy, Greece
Exclusive Savings
Save
1,551
From
5,612
per person
View Trip
10 Day Classic Galapagos: Central Eastern Islands (Grand Queen Beatriz) with Intrepid Travel
Cruise

10 Days (9 Nights) Quito to Quito
Operated By: Intrepid Travel
Departures: Dec 2025 to Dec 2026
Countries Visited: Ecuador, Galapagos
Exclusive Savings
Save
172
From
8,041
per person
View Trip
20 Day Majestic Peru & Galapagos Cruise (Grand Queen Beatriz) with Intrepid Travel
Tour

20 Days Lima to Quito
Operated By: Intrepid Travel
Departure: 11 October 2025
Trip Styles: Adventure, Small Group, Island Hopping, Wildlife
Countries Visited: Ecuador, Galapagos, Peru
Exclusive Savings
Save
193
From
9,432
per person
View Trip
10 Day Galápagos – Central and East Islands aboard the Reina Silvia Voyager with G Adventures
Cruise

10 Days (9 Nights) Quito to Quito
Operated By: G Adventures
Departures: Sep 2025 to Dec 2027
Countries Visited: Ecuador, Galapagos
Save
2,386
From
5,213
per person
View Trip
15 Day Sailing Greece - Athens to Santorini with G Adventures
Cruise

15 Days (14 Nights) Athens to Santorini
Operated By: G Adventures
Departures: May 2026 to Sep 2026
Countries Visited: Greece
Exclusive Savings
Save
71
From
3,184
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: Aug 2025 to Sep 2026
Trip Styles: Adventure, Small Group, 18-30's, Island Hopping
Countries Visited: Italy, Croatia, Montenegro, Albania, Greece
Save
765
From
1,609
per person
View Trip
8 Day Croatian Coastal Cruising: Dubrovnik to Split (Aurora) with Intrepid Travel
Cruise

8 Days (7 Nights) Dubrovnik to Split
Operated By: Intrepid Travel
Departures: Aug 2025 to Oct 2026
Countries Visited: Croatia, Bosnia Herzegovina
Save
364
From
2,720
per person
View Trip
15 Day Real Turkey with Intrepid Travel
Tour

15 Days Istanbul to Istanbul
Operated By: Intrepid Travel
Departures: Sep 2025 to Nov 2027
Trip Styles: Adventure, Small Group, 18-30's, Island Hopping
Countries Visited: Turkey
From
1,840
per person
View Trip
24 Day Galapagos & Peru Adventure with Intrepid Travel
Tour

24 Days Quito to La Paz
Operated By: Intrepid Travel
Departures: Aug 2025 to Dec 2027
Trip Styles: Adventure, Small Group, Island Hopping, Walking & Hiking, Wildlife, Inca Trail
Countries Visited: Ecuador, Galapagos, Peru, Bolivia
Exclusive Savings
Save
208
From
8,531
per person
View Trip
11 Day The Eternal Aegean with Ponant
Cruise
 (1)

11 Days (10 Nights) Valletta to Istanbul
Cruise Line: Ponant
Ship: Le Boreal
Departure: 14 May 2026
Countries Visited: Malta, Sicily, Italy, Greece, Turkey
Inside
-
Oceanview
$8,160
Balcony
$8,590
Suite
$17,790
From
8,160
per person
View Trip
8 Day Greek Isles Cruise with Royal Caribbean
Cruise

8 Days (7 Nights) Venice to Venice
Cruise Line: Royal Caribbean
Ship: Explorer of the Seas
Departures: Sep 2025 to Sep 2026
Countries Visited: Italy, Greece, Croatia
Latest Offer
Inside
$869
Oceanview
$1,131
Balcony
$1,434
Suite
$1,825
Save
757
From
869
per person
View Trip
8 Day Amalfi Coast Sailing Adventure with Intrepid Travel
Cruise

8 Days (7 Nights) Procida to Procida
Operated By: Intrepid Travel
Departures: Aug 2025 to Oct 2026
Countries Visited: Italy
Save
902
From
2,585
per person
View Trip
8 Day Croatia Island Sail with Contiki
Cruise

8 Days (7 Nights) Split to Split
Operated By: Contiki
Departures: Aug 2025 to Sep 2026
Countries Visited: Croatia
From
1,379
per person
View Trip
Results: 61-90 of 248

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