Margaritaville at Sea Islander Cruise Schedule & Sailing Calendar

View the full Margaritaville at Sea Islander sailing calendar month by month, including departure timing, itinerary spans, port activity, and current price snapshots.

January 2026
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Sailing
Port call

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Sun
Mon
Tue
Wed
Thu
Fri
Sat
28
29
30
Tampa
31
Key West
1
2
Cozumel
3
Progreso
Western Caribbean Loop via Key West & Cozumel (Rare Variant) • ☾ 6
4
5
Tampa
6
7
Progreso
8
9
Tampa
10
Western Caribbean Loop via Key West & Cozumel (Rare Variant) • ☾ 6 Western Caribbean Loop via Cozumel & Progreso (Best Balance) • ☾ 5
Western Caribbean Loop via Progreso (Best Balance) • ☾ 4
11
Cozumel
12
Progreso
13
14
Tampa
15
16
Progreso
17
Cozumel
Western Caribbean Loop via Cozumel & Progreso (Best Balance) • ☾ 5
Western Caribbean Loop via Progreso & Cozumel (Best Balance) • ☾ 5
18
19
Tampa
20
21
Progreso
22
23
Tampa
24
Western Caribbean Loop via Progreso & Cozumel (Best Balance) • ☾ 5 Western Caribbean Loop via Cozumel & Montego Bay (Best Balance) • ☾ 7
Western Caribbean Loop via Progreso (Best Balance) • ☾ 4
25
Cozumel
26
27
Montego Bay
28
Georgetown, Grand Cayman
29
30
Tampa
31
Western Caribbean Loop via Cozumel & Montego Bay (Best Balance) • ☾ 7
Western Caribbean Loop via Cozumel & Belize City (Rare Variant) • ☾ 7