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Cruises to Charlestown

42 live cruises call at Charlestown — 7 to 21 nights, departing 10 ports, across 4 lines. A NestCruise advisor narrows them to the one that fits.

42 sailings
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Eastern Caribbean with St. BarthsCaribbean

Emerald Cruises

7 nights in the Caribbean

Aboard Emerald Azzurra

Bridgetown → Marigot

↓ $873 this monthCaribbean Sale!

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

Fares checked nightly

Sails every two weeks, Dec 2026 – Feb 2027
Eastern Caribbean with St. BarthsCaribbean

Emerald Cruises

7 nights in the Caribbean

Aboard Emerald Sakara

Bridgetown → Philipsburg

↓ $578 this monthCaribbean Sale!

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

Fares checked nightly

Nov 2027 – Feb 2028Next 13 Nov 2027 · 5 more
History and culture visiting Caribbean jewelsCaribbean

PONANT EXPLORATIONS

7 nights in the Caribbean

Aboard Le Ponant

Marigot → Pointe-à-Pitre

Ponant Bonus 10%

from$20,240pp · cruise fare≈ $2,891/night pp

Fares checked nightly

Sails every two weeks, Dec 2026 – Mar 2027
Eastern Caribbean Cruise: Saint Lucia, Dominica & Sint MaartenCaribbean

Azamara

6 nights: San Juan, the Caribbean

Aboard Azamara Journey

Bridgetown → San Juan

↓ $419 this monthRare itinerary

from$1,349pp · cruise fare≈ $225/night pp

Fares checked nightly

Sails every two weeks, Nov 2026 – Dec 2026
7-Night Caribbean CruiseCaribbean

Azamara

7 nights: San Juan, the Caribbean

Aboard Azamara Quest

Bridgetown → San Juan

Rare itinerary

from$1,939pp · cruise fare≈ $277/night pp

Fares checked nightly

Sails every two weeks, Nov 2027 – Dec 2027
Wonders of the CaribbeanCaribbean

PONANT EXPLORATIONS

The Caribbean loop

Aboard Le Champlain

Round-trip from Fort-de-France

Rare itinerary
Sails every two weeks, Dec 2027
San Juan to MiamiCaribbean

Silversea

8 nights: San Juan, the Caribbean

Aboard Silver Nova

San Juan → Miami

Rare itinerary
Dec 2026Next 29 Dec 2026
12-Night Caribbean CruiseCaribbean

PONANT EXPLORATIONS

The Caribbean loop

Aboard Le Lapérouse

Round-trip from Fort-de-France

Rare itinerary
Mar 2027Next 22 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
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
History and culture visiting Caribbean jewelsCaribbean

PONANT EXPLORATIONS

7 nights in the Caribbean

Aboard Le Ponant

Pointe-à-Pitre → Marigot

Ponant Bonus 15%Rare itinerary

from$20,800pp · cruise fare≈ $2,971/night pp

Fares checked nightly

Mar 2028Next 20 Mar 2028
Eastern Caribbean Cruise: Saint Kitts, Nevis & Saint BarthélemyCaribbean

Azamara

7 nights: San Juan, the Caribbean

Aboard Azamara Journey

Bridgetown → San Juan

↓ $419 this monthRare itinerary

from$1,349pp · cruise fare≈ $193/night pp

Fares checked nightly

Nov 2026Next 28 Nov 2026
Caribbean Combination Cruise: Dominica, Bequia & GrenadaCaribbean

Azamara

14 nights: San Juan, the Caribbean

Aboard Azamara Quest

Round-trip from Bridgetown

Rare itinerary

from$3,699pp · cruise fare≈ $264/night pp

Fares checked nightly

Sails every two weeks, Nov 2027
Discover Eastern Caribbean & GrenadinesCaribbean

Emerald Cruises

14 nights in the Caribbean

Aboard Emerald Azzurra

Bridgetown → Marigot

Overnight in Union Island

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

Fares checked nightly

Sails monthly, Nov 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
Eastern Caribbean Cruise: Barbados, Saint Lucia & British Virgin IslandsCaribbean

Azamara

7 nights: San Juan, the Caribbean

Aboard Azamara Journey

Bridgetown → San Juan

↓ $451 this monthRare itinerary

from$1,889pp · cruise fare≈ $270/night pp

Fares checked nightly

Nov 2026Next 14 Nov 2026
Caribbean Combination Cruise: Antigua, Grenada & Saint LuciaCaribbean

Azamara

14 nights: San Juan, the Caribbean

Aboard Azamara Quest

Round-trip from San Juan

Rare itinerary

from$3,699pp · cruise fare≈ $264/night pp

Fares checked nightly

Sails every two weeks, Nov 2027 – Dec 2027
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
7-Night Caribbean CruiseCaribbean

Emerald Cruises

7 nights in the Caribbean

Aboard Emerald Sakara

Philipsburg → Bridgetown

↓ $578 this monthCaribbean Sale!

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

Fares checked nightly

Dec 2027 – Apr 2028Next 4 Dec 2027 · 3 more
Caribbean New Year's Cruise: Aruba, Saint Lucia & Saint CroixCaribbean

Azamara

8 nights: San Juan, the Caribbean

Aboard Azamara Journey

Bridgetown → San Juan

↓ $616 this monthRare itinerary

from$1,929pp · cruise fare≈ $241/night pp

Fares checked nightly

Dec 2026Next 28 Dec 2026
Caribbean Combination Cruise: Dominica, Bequia & GrenadaCaribbean

Azamara

15 nights: San Juan, the Caribbean

Aboard Azamara Quest

Round-trip from Bridgetown

Rare itinerary

from$4,749pp · cruise fare≈ $317/night pp

Fares checked nightly

Dec 2027Next 12 Dec 2027
6-Night Caribbean CruiseCaribbean

Emerald Cruises

6 nights in the Caribbean

Aboard Emerald Azzurra

Marigot → Bridgetown

↓ $873 this monthCaribbean Sale!

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

Fares checked nightly

Dec 2026 – Apr 2027Next 21 Dec 2026 · 1 more
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
Eastern Caribbean: St.kitts, Antigua & MartiniqueCaribbean

Azamara

11 nights in the Caribbean

Aboard Azamara Journey

Miami → Bridgetown

Rare itinerary

from$3,819pp · cruise fare≈ $347/night pp

Fares checked nightly

Jan 2027Next 14 Jan 2027
Caribbean Combination Cruise: Antigua, Grenada & Saint LuciaCaribbean

Azamara

15 nights: San Juan, the Caribbean

Aboard Azamara Quest

Round-trip from San Juan

Rare itinerary

from$4,319pp · cruise fare≈ $288/night pp

Fares checked nightly

Nov 2027Next 6 Nov 2027
Discover Eastern Caribbean & GrenadinesCaribbean

Emerald Cruises

14 nights in the Caribbean

Aboard Emerald Sakara

Bridgetown → Philipsburg

Overnight in BridgetownRare itinerary

from$13,390pp · cruise fare≈ $956/night pp

Fares checked nightly

Sails every two weeks, Jan 2028 – Feb 2028
Caribbean Combination Cruise: San Juan, Antigua & St. LuciaCaribbean

Azamara

13 nights: San Juan, the Caribbean

Aboard Azamara Journey

Round-trip from San Juan

Rare itinerary

from$7,849pp · cruise fare≈ $604/night pp

Fares checked nightly

Dec 2026Next 5 Dec 2026
Bermuda & Caribbean Combination Cruise: Tortola, Barbados & Saint KittsCaribbean

Azamara

24 nights: San Juan, the Caribbean

Aboard Azamara Quest

New York → San Juan

Overnight in HamiltonRare itinerary

from$6,129pp · cruise fare≈ $255/night pp

Fares checked nightly

Oct 2027Next 28 Oct 2027
13-Night Caribbean CruiseCaribbean

Emerald Cruises

13 nights in the Caribbean

Aboard Emerald Sakara

Bridgetown → Philipsburg

Rare itinerary

from$13,390pp · cruise fare≈ $1,030/night pp

Fares checked nightly

Sails monthly, Jan 2028 – Feb 2028
Caribbean Combination Cruise: Barbados, St. Lucia & St. MaartenCaribbean

Azamara

14 nights: San Juan, the Caribbean

Aboard Azamara Journey

Round-trip from Bridgetown

Rare itinerary

from$5,719pp · cruise fare≈ $409/night pp

Fares checked nightly

Nov 2026Next 28 Nov 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
Caribbean Combination Cruise: Barbados, St. Lucia & St. KittsCaribbean

Azamara

14 nights: San Juan, the Caribbean

Aboard Azamara Journey

Round-trip from Bridgetown

Rare itinerary
Nov 2026Next 14 Nov 2026
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
Caribbean Combination Cruise: San Juan, Antigua & BarbadosCaribbean

Azamara

14 nights: San Juan, the Caribbean

Aboard Azamara Journey

Round-trip from San Juan

Rare itinerary

from$5,769pp · cruise fare≈ $412/night pp

Fares checked nightly

Nov 2026Next 21 Nov 2026
Caribbean Island Hopping: Sint Maarten to BarbadosCaribbean

Emerald Cruises

10 nights in the Caribbean

Aboard Emerald Sakara

Philipsburg → Bridgetown

↓ $883 this monthIncludes Preferred Savings

from$9,012pp · cruise fare≈ $901/night pp

Fares checked nightly

Jan 2028Next 12 Jan 2028
Caribbean Combination Cruise: San Juan, St. Lucia & St. KittsCaribbean

Azamara

14 nights: San Juan, the Caribbean

Aboard Azamara Journey

Round-trip from San Juan

Rare itinerary

from$4,349pp · cruise fare≈ $311/night pp

Fares checked nightly

Nov 2026Next 7 Nov 2026
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
Caribbean Combination Cruise: Barbados, St. Lucia & St. ThomasCaribbean

Azamara

16 nights: San Juan, the Caribbean

Aboard Azamara Journey

Round-trip from Bridgetown

Rare itinerary

from$7,459pp · cruise fare≈ $466/night pp

Fares checked nightly

Dec 2026Next 12 Dec 2026
Caribbean Combination Cruise: Barbados, Aruba & St. BartsCaribbean

Azamara

17 nights: San Juan, the Caribbean

Aboard Azamara Journey

Bridgetown → Miami

Rare itinerary

from$5,899pp · cruise fare≈ $347/night pp

Fares checked nightly

Dec 2026Next 28 Dec 2026
Caribbean Combination Cruise: San Juan, St. Barts & CuracaoCaribbean

Azamara

18 nights: San Juan, the Caribbean

Aboard Azamara Journey

Round-trip from San Juan

Rare itinerary

from$6,729pp · cruise fare≈ $374/night pp

Fares checked nightly

Dec 2026Next 18 Dec 2026
South America Combination Cruise: Miami, Rio De Janeiro & Buenos AiresAmericas

Azamara

34 nights: Rio de Janeiro & Buenos Aires, South America

Aboard Azamara Journey

Miami → Buenos Aires

Overnight in Rio de JaneiroRare itinerary

from$28,029pp · cruise fare≈ $824/night pp

Fares checked nightly

Jan 2027Next 14 Jan 2027
Circle South America Grand VoyageAmericas

Azamara

74 nights: Rio de Janeiro & Buenos Aires, South America

Aboard Azamara Journey

Round-trip from Miami

Overnight in Rio de JaneiroRare itinerary
Jan 2027Next 14 Jan 2027

Frequently asked

How many cruises to Charlestown does NestCruise have?
42 live sailings, 7 to 21 nights. A NestCruise advisor narrows them to the one that fits.
Which cruise lines visit Charlestown?
Azamara, Emerald Cruises, PONANT EXPLORATIONS and Silversea, among others.
How long are cruises to Charlestown?
Most run 7 to 21 nights.
How much do cruises to Charlestown 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.