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Cruises to Anguilla

18 live cruises call at Anguilla — 7 to 20 nights, departing 5 ports, across 3 lines. A NestCruise advisor narrows them to the one that fits.

18 sailings
7-Night Caribbean CruiseCaribbean

Emerald Cruises

The Caribbean loop

Aboard Emerald Sakara

Round-trip from Saint Thomas

↓ $729 this monthCaribbean Sale!

from$4,566pp · cruise fare≈ $652/night pp

Fares checked nightly

Sails every two weeks, Dec 2026 – Mar 2027
6-Night Caribbean CruiseCaribbean

Emerald Cruises

6 nights in the Caribbean

Aboard Emerald Azzurra

Bridgetown → Marigot

↓ $873 this monthCaribbean Sale!

from$5,322pp · cruise fare≈ $887/night pp

Fares checked nightly

Sails monthly, Dec 2026 – Mar 2027
Bridgetown to MiamiCaribbean

Silversea

12 nights in the Caribbean

Aboard Silver Ray

Bridgetown → Miami

↓ $3,720 this monthRare itinerary

from$5,580pp · cruise fare≈ $465/night pp

Fares checked nightly

Feb 2027 – Mar 2028Next 26 Feb 2027 · 1 more
14-Night Leeward Island JewelsCARIBBEAN

Seabourn

14 nights: San Juan, the Caribbean

Aboard Seabourn Quest

Round-trip from Miami

Rare itinerary

from$5,524pp · cruise fare≈ $395/night pp

Fares checked nightly

Sails every two weeks, Nov 2026 – Dec 2026
Caribbean Breeze: Miami to AntiguaCaribbean

Emerald Cruises

11 nights: Nassau & San Juan, the Caribbean

Aboard Emerald Kaia

Miami → Saint John's

↓ $1,511 this monthCaribbean Sale!

from$9,884pp · cruise fare≈ $899/night pp

Fares checked nightly

Feb 2028Next 19 Feb 2028
Cruising the Leeward IslandsCaribbean

Emerald Cruises

The Caribbean loop

Aboard Emerald Sakara

Round-trip from Philipsburg

↓ $578 this monthCaribbean Sale!

from$5,717pp · cruise fare≈ $817/night pp

Fares checked nightly

Nov 2027 – Apr 2028Next 20 Nov 2027 · 6 more
Cruising the Leeward IslandsCaribbean

Emerald Cruises

7 nights in the Caribbean

Aboard Emerald Azzurra

Marigot → Philipsburg

↓ $873 this monthCaribbean Sale!

from$5,322pp · cruise fare≈ $760/night pp

Fares checked nightly

Sails monthly, Jan 2027 – Apr 2027
16-Night Leeward Island HolidayHOLIDAY

Seabourn

16 nights: San Juan

Aboard Seabourn Quest

Round-trip from Miami

Rare itinerary

from$9,349pp · cruise fare≈ $584/night pp

Fares checked nightly

Dec 2026Next 20 Dec 2026
Discover the Pearls of the CaribbeanCaribbean

Emerald Cruises

14 nights in the Caribbean

Aboard Emerald Sakara

Bridgetown → Philipsburg

Overnight in Virgin Gorda

from$12,690pp · cruise fare≈ $906/night pp

Fares checked nightly

Nov 2027 – Mar 2028Next 13 Nov 2027 · 5 more
Discover the Pearls of the CaribbeanCaribbean

Emerald Cruises

14 nights in the Caribbean

Aboard Emerald Azzurra

Bridgetown → Marigot

Overnight in Marigot

from$12,690pp · cruise fare≈ $906/night pp

Fares checked nightly

Sails monthly, Dec 2026 – Mar 2027
14-Night Caribbean CruiseCaribbean

Emerald Cruises

14 nights in the Caribbean

Aboard Emerald Sakara

Bridgetown → Philipsburg

from$12,690pp · cruise fare≈ $906/night pp

Fares checked nightly

Nov 2027 – Apr 2028Next 13 Nov 2027 · 4 more
6-Night Caribbean CruiseCaribbean

Emerald Cruises

The Caribbean loop

Aboard Emerald Azzurra

Round-trip from Marigot

↓ $873 this monthCaribbean Sale!

from$5,322pp · cruise fare≈ $887/night pp

Fares checked nightly

Sails monthly, Feb 2027 – Apr 2027
7-Night Caribbean CruiseCaribbean

Emerald Cruises

7 nights: San Juan, the Caribbean

Aboard Emerald Sakara

Saint Thomas → San Juan

↓ $1,143 this monthCaribbean Sale!

from$5,002pp · cruise fare≈ $715/night pp

Fares checked nightly

Sails monthly, Feb 2027 – Apr 2027
Cruising the Leeward Islands with Chef Rachel HargroveCaribbean

Emerald Cruises

The Caribbean loop

Aboard Emerald Azzurra

Round-trip from Marigot

Overnight in MarigotRare itinerary

from$7,540pp · cruise fare≈ $1,077/night pp

Fares checked nightly

Dec 2026Next 13 Dec 2026
20-Night Caribbean CruiseCaribbean

Emerald Cruises

20 nights in the Caribbean

Aboard Emerald Sakara

Bridgetown → Philipsburg

Rare itinerary

from$20,135pp · cruise fare≈ $1,007/night pp

Fares checked nightly

Sails monthly, Jan 2028 – Feb 2028
Discover the Hidden Wonders of the CaribbeanCaribbean

Emerald Cruises

13 nights in the Caribbean

Aboard Emerald Azzurra

Bridgetown → Philipsburg

Overnight in MarigotRare itinerary

from$33,445pp · cruise fare≈ $2,573/night pp

Fares checked nightly

Jan 2027Next 3 Jan 2027
Epic Voyage: Barbados to Sint MaartenCaribbean

Emerald Cruises

21 nights in the Caribbean

Aboard Emerald Sakara

Bridgetown → Philipsburg

Overnight in BridgetownRare itinerary

from$20,135pp · cruise fare≈ $959/night pp

Fares checked nightly

Sails monthly, Jan 2028 – Feb 2028
Epic Voyage: Sint Maarten to BarbadosCaribbean

Emerald Cruises

21 nights in the Caribbean

Aboard Emerald Sakara

Philipsburg → Bridgetown

Overnight in Virgin GordaRare itinerary

from$20,135pp · cruise fare≈ $959/night pp

Fares checked nightly

Feb 2028Next 5 Feb 2028

Frequently asked

How many cruises to Anguilla does NestCruise have?
18 live sailings, 7 to 20 nights. A NestCruise advisor narrows them to the one that fits.
Which cruise lines visit Anguilla?
Emerald Cruises, Seabourn and Silversea, among others.
How long are cruises to Anguilla?
Most run 7 to 20 nights.
How much do cruises to Anguilla cost?
NestCruise doesn't publish fares — it's a quote-only concierge. Share your dates and party size and an advisor prices your exact sailing at no cost.