25 sailings

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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.

$952+low$1,192+typical$1,626+high

Holiday & school breaks

Caribbean

Virgin Voyages

The Caribbean loop

Aboard Valiant Lady

Round-trip from Miami

↓ $304 this month

from$952pp · cruise fare≈ $190/night pp

Fares checked nightly

Apr 2027 – Apr 2028Next 26 Apr 2027 · 17 more

Caribbean

Virgin Voyages

5 nights: Grand Cayman, the Caribbean

Aboard Valiant Lady

Round-trip from Miami

↓ $304 this month

from$952pp · cruise fare≈ $190/night pp

Fares checked nightly

May 2027 – Apr 2028Next 10 May 2027 · 15 more

Caribbean

Virgin Voyages

The Caribbean loop

Aboard Valiant Lady

Round-trip from Miami

↓ $304 this month

from$952pp · cruise fare≈ $190/night pp

Fares checked nightly

Sails monthly, Jun 2027 – Apr 2028

Caribbean

Virgin Voyages

7 nights: San Juan, the Caribbean

Aboard Valiant Lady

Round-trip from San Juan

↓ $812 this month

from$1,788pp · cruise fare≈ $255/night pp

Fares checked nightly

Sails monthly, Oct 2026 – Apr 2027

Caribbean

Virgin Voyages

7 nights: San Juan, the Caribbean

Aboard Valiant Lady

Round-trip from San Juan

↓ $812 this month

from$1,788pp · cruise fare≈ $255/night pp

Fares checked nightly

Nov 2026 – Mar 2027Next 7 Nov 2026 · 6 more

Caribbean

Virgin Voyages

The Caribbean loop

Aboard Valiant Lady

Round-trip from Miami

↓ $414 this month

from$1,192pp · cruise fare≈ $298/night pp

Fares checked nightly

Sails every two weeks, Apr 2027 – Jul 2027

Caribbean

Virgin Voyages

The Caribbean loop

Aboard Valiant Lady

Round-trip from Miami

↓ $420 this month

from$1,192pp · cruise fare≈ $238/night pp

Fares checked nightly

Sails every two weeks, Apr 2027 – Jul 2027

Caribbean

Virgin Voyages

4 nights: Nassau, the Caribbean

Aboard Valiant Lady

Round-trip from Miami

↓ $304 this month

from$952pp · cruise fare≈ $238/night pp

Fares checked nightly

Nov 2027 – Apr 2028Next 18 Nov 2027 · 3 more

Bermuda

Virgin Voyages

The Bermuda run

Aboard Valiant Lady

Round-trip from New York

↓ $484 this monthOvernight in Kings Wharf

from$1,490pp · cruise fare≈ $298/night pp

Fares checked nightly

Sails weekly, Sep 2026 – Oct 2026

Caribbean

Virgin Voyages

6 nights: San Juan, the Caribbean

Aboard Valiant Lady

Round-trip from San Juan

↓ $812 this monthRare: Basse-Terre

from$1,788pp · cruise fare≈ $298/night pp

Fares checked nightly

Nov 2026 – Mar 2027Next 14 Nov 2026 · 2 more

Americas

Virgin Voyages

5 nights: Cozumel, South America

Aboard Valiant Lady

Round-trip from Miami

↓ $304 this monthRare itinerary

from$952pp · cruise fare≈ $190/night pp

Fares checked nightly

Jun 2027 – Apr 2028Next 21 Jun 2027 · 1 more

Caribbean

Virgin Voyages

The Caribbean loop

Aboard Valiant Lady

Round-trip from New York

↓ $556 this monthOvernight in Royal Naval Dockyard

from$1,626pp · cruise fare≈ $271/night pp

Fares checked nightly

Sails weekly, Oct 2026

Caribbean

Virgin Voyages

8 nights: San Juan, the Caribbean

Aboard Valiant Lady

Round-trip from San Juan

↓ $800 this monthRare itinerary

from$1,806pp · cruise fare≈ $226/night pp

Fares checked nightly

Nov 2026 – Mar 2027Next 20 Nov 2026 · 1 more

Caribbean

Virgin Voyages

The Caribbean loop

Aboard Valiant Lady

Round-trip from Miami

↓ $318 this monthRare itinerary

from$954pp · cruise fare≈ $318/night pp

Fares checked nightly

Dec 2027Next 27 Dec 2027

Caribbean

Virgin Voyages

The Caribbean loop

Aboard Valiant Lady

Round-trip from Miami

↓ $806 this monthRare itinerary

from$1,912pp · cruise fare≈ $478/night pp

Fares checked nightly

Dec 2027Next 30 Dec 2027

Caribbean

Virgin Voyages

5 nights: San Juan, the Caribbean

Aboard Valiant Lady

San Juan → Miami

↓ $570 this monthRare itinerary

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

Fares checked nightly

Apr 2027Next 10 Apr 2027

Caribbean

Virgin Voyages

The Caribbean loop

Aboard Valiant Lady

Round-trip from Miami

↓ $454 this monthRare itinerary

from$1,290pp · cruise fare≈ $258/night pp

Fares checked nightly

Nov 2027Next 8 Nov 2027

Caribbean

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

Caribbean

Virgin Voyages

7 nights: San Juan, the Caribbean

Aboard Valiant Lady

Round-trip from San Juan

↓ $1,558 this monthRare itinerary

from$3,206pp · cruise fare≈ $458/night pp

Fares checked nightly

Dec 2026Next 26 Dec 2026

Caribbean

Virgin Voyages

7 nights: San Juan, the Caribbean

Aboard Valiant Lady

Round-trip from San Juan

↓ $1,280 this monthRare itinerary

from$2,646pp · cruise fare≈ $378/night pp

Fares checked nightly

Feb 2027Next 13 Feb 2027

Caribbean

Virgin Voyages

7 nights: Grand Cayman, the Caribbean

Aboard Valiant Lady

Round-trip from Miami

↓ $948 this monthRare itinerary

from$2,226pp · cruise fare≈ $318/night pp

Fares checked nightly

Dec 2027Next 20 Dec 2027

Caribbean

Virgin Voyages

The Caribbean loop

Aboard Valiant Lady

Round-trip from Miami

Rare itinerary

Apr 2027Next 15 Apr 2027

Caribbean

Virgin Voyages

8 nights: San Juan, the Caribbean

Aboard Valiant Lady

Round-trip from San Juan

↓ $1,546 this monthRare itinerary

from$3,184pp · cruise fare≈ $398/night pp

Fares checked nightly

Jan 2027Next 29 Jan 2027

Americas

Virgin Voyages

The Canada loop

Aboard Valiant Lady

Round-trip from New York

↓ $910 this monthRare itinerary

from$2,384pp · cruise fare≈ $298/night pp

Fares checked nightly

Sep 2026Next 19 Sep 2026

Caribbean

Virgin Voyages

12 nights: San Juan, the Caribbean

Aboard Valiant Lady

New York → San Juan

↓ $876 this monthOvernight in Royal Naval Dockyard

from$2,376pp · cruise fare≈ $198/night pp

Fares checked nightly

Oct 2026Next 19 Oct 2026