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Flexible datesWhen is it cheapest?

Cheapest cruise-line fare we’ve captured per month, refreshed nightly. Tap a month to see those departures; an advisor confirms your exact price.

$1,014+low$1,272+typical$1,490+high
Holiday & school breaks
5-Night Caribbean CruiseCaribbean

Virgin Voyages

The Caribbean loop

Aboard Valiant Lady

Round-trip from Miami

↓ $346 this month

from$1,032pp · cruise fare≈ $206/night pp

Fares checked nightly

Apr 2027 – Apr 2028Next 26 Apr 2027 · 17 more
5-Night Caribbean CruiseCaribbean

Virgin Voyages

5 nights: Grand Cayman, the Caribbean

Aboard Valiant Lady

Round-trip from Miami

↓ $346 this month

from$1,032pp · cruise fare≈ $206/night pp

Fares checked nightly

May 2027 – Apr 2028Next 10 May 2027 · 15 more
5-Night Caribbean CruiseCaribbean

Virgin Voyages

The Caribbean loop

Aboard Valiant Lady

Round-trip from Miami

↓ $346 this month

from$1,032pp · cruise fare≈ $206/night pp

Fares checked nightly

Sails monthly, Jun 2027 – Apr 2028
7-Night Caribbean CruiseCaribbean

Virgin Voyages

7 nights: San Juan, the Caribbean

Aboard Valiant Lady

Round-trip from San Juan

↓ $746 this month

from$1,666pp · cruise fare≈ $238/night pp

Fares checked nightly

Dec 2026 – Apr 2027Next 5 Dec 2026 · 5 more
7-Night Caribbean CruiseCaribbean

Virgin Voyages

7 nights: San Juan, the Caribbean

Aboard Valiant Lady

Round-trip from San Juan

↓ $724 this month

from$1,666pp · cruise fare≈ $238/night pp

Fares checked nightly

Nov 2026 – Mar 2027Next 7 Nov 2026 · 6 more
Key West & Bimini Beach ClubCaribbean

Virgin Voyages

The Caribbean loop

Aboard Valiant Lady

Round-trip from Miami

↓ $456 this month

from$1,272pp · cruise fare≈ $318/night pp

Fares checked nightly

Sails every two weeks, Apr 2027 – Jul 2027
Grand Turk & Bimini Beach ClubCaribbean

Virgin Voyages

The Caribbean loop

Aboard Valiant Lady

Round-trip from Miami

↓ $510 this month

from$1,352pp · cruise fare≈ $270/night pp

Fares checked nightly

Sails every two weeks, Apr 2027 – Jul 2027
Bahamas & Bimini Beach ClubCaribbean

Virgin Voyages

4 nights: Nassau, the Caribbean

Aboard Valiant Lady

Round-trip from Miami

↓ $352 this month

from$1,014pp · cruise fare≈ $254/night pp

Fares checked nightly

Nov 2027 – Apr 2028Next 18 Nov 2027 · 3 more
Southern Caribbean CruiseCaribbean

Virgin Voyages

6 nights: San Juan, the Caribbean

Aboard Valiant Lady

Round-trip from San Juan

↓ $724 this monthRare: Basse-Terre

from$1,666pp · cruise fare≈ $278/night pp

Fares checked nightly

Nov 2026 – Mar 2027Next 14 Nov 2026 · 2 more
Mexico & Bimini Beach ClubAmericas

Virgin Voyages

5 nights: Cozumel, South America

Aboard Valiant Lady

Round-trip from Miami

↓ $346 this monthRare itinerary

from$1,032pp · cruise fare≈ $206/night pp

Fares checked nightly

Jun 2027 – Apr 2028Next 21 Jun 2027 · 1 more
Southern Caribbean CruiseCaribbean

Virgin Voyages

8 nights: San Juan, the Caribbean

Aboard Valiant Lady

Round-trip from San Juan

↓ $724 this monthRare itinerary

from$1,666pp · cruise fare≈ $208/night pp

Fares checked nightly

Nov 2026 – Mar 2027Next 20 Nov 2026 · 1 more
Bimini Beach Club CruiseCaribbean

Virgin Voyages

The Caribbean loop

Aboard Valiant Lady

Round-trip from Miami

↓ $352 this monthRare itinerary

from$1,014pp · cruise fare≈ $338/night pp

Fares checked nightly

Dec 2027Next 27 Dec 2027
4-Night Caribbean CruiseCaribbean

Virgin Voyages

The Caribbean loop

Aboard Valiant Lady

Round-trip from Miami

↓ $892 this monthRare itinerary

from$2,072pp · cruise fare≈ $518/night pp

Fares checked nightly

Dec 2027Next 30 Dec 2027
Eastern Caribbean: San Juan to MiamiCaribbean

Virgin Voyages

5 nights: San Juan, the Caribbean

Aboard Valiant Lady

San Juan → Miami

↓ $786 this monthRare itinerary

from$1,790pp · cruise fare≈ $358/night pp

Fares checked nightly

Apr 2027Next 10 Apr 2027
Red Hot Sailing Club Voyage from MiamiCaribbean

Virgin Voyages

The Caribbean loop

Aboard Valiant Lady

Round-trip from Miami

↓ $508 this monthRare itinerary

from$1,390pp · cruise fare≈ $278/night pp

Fares checked nightly

Nov 2027Next 8 Nov 2027
5-Night Caribbean CruiseCaribbean

Virgin Voyages

5 nights: Cozumel, the Caribbean

Aboard Valiant Lady

Round-trip from Miami

↓ $498 this monthRare itinerary

from$1,390pp · cruise fare≈ $278/night pp

Fares checked nightly

Oct 2027Next 30 Oct 2027
Southern Caribbean New Year's CruiseCaribbean

Virgin Voyages

7 nights: San Juan, the Caribbean

Aboard Valiant Lady

Round-trip from San Juan

↓ $1,632 this monthRare itinerary

from$3,346pp · cruise fare≈ $478/night pp

Fares checked nightly

Dec 2026Next 26 Dec 2026
Sisters at Sea: Valiant LadyCaribbean

Virgin Voyages

7 nights: San Juan, the Caribbean

Aboard Valiant Lady

Round-trip from San Juan

↓ $1,430 this monthRare itinerary

from$2,926pp · cruise fare≈ $418/night pp

Fares checked nightly

Feb 2027Next 13 Feb 2027
7-Night Caribbean CruiseCaribbean

Virgin Voyages

7 nights: Grand Cayman, the Caribbean

Aboard Valiant Lady

Round-trip from Miami

↓ $1,100 this monthRare itinerary

from$2,506pp · cruise fare≈ $358/night pp

Fares checked nightly

Dec 2027Next 20 Dec 2027
Western Caribbean & Bimini Beach ClubCaribbean

Virgin Voyages

The Caribbean loop

Aboard Valiant Lady

Round-trip from Miami

Rare itinerary
Apr 2027Next 15 Apr 2027
Southern Caribbean & Aruban NightsCaribbean

Virgin Voyages

8 nights: San Juan, the Caribbean

Aboard Valiant Lady

Round-trip from San Juan

↓ $1,460 this monthRare itinerary

from$3,024pp · cruise fare≈ $378/night pp

Fares checked nightly

Jan 2027Next 29 Jan 2027