Little Bay, Montserrat, Caribbean cruise port
CaribbeanLeeward Islands › Montserrat

Little Bay, Montserrat, Caribbean

The Emerald Isle of the Caribbean wears its volcanic scars openly. Half of the island was buried by Soufrière Hills in 1995 — Plymouth, the former capital, is now the Caribbean's own Pompeii, and Montserrat is richer for the story.

⚓ Tender (no large pier)🕒 Typical call: 6–8 hrs💵 XCD / USD accepted🗣️ English🌋 Active volcano
Docking
Anchor & tender to Little Bay pier; small expedition ships may tie up directly
Walk to center
Immediate — Little Bay beach bars 2 min from pier; rest of island requires taxi
Best For
Volcano tours, ghost-town exploration, off-the-beaten-path Caribbean
Don't Miss
Guided Plymouth exclusion zone tour & Montserrat Volcano Observatory

Getting Ashore

Ships anchor off Little Bay and run tenders to the pier; small vessels (Windstar, Ponant) may dock directly — confirm with your ship.

Getting Ashore at Little Bay

  • 1
    Tender ashoreCollect a tender ticket on board and ride to the Little Bay landing — 5–10 minutes. Expect a short queue on busy call days.
  • 2
    Clear the dockTourist info, taxis, and tour operators are immediately outside the gate. No port shuttle — everything beyond the beach requires a taxi or booked excursion.
  • 3
    Agree on taxi fares upfrontTaxis have no meters. Agree the fare before you get in. A 3–4 hour island tour runs roughly $80–100 USD per taxi (not per person).
  • 4
    Exclusion zone accessPlymouth tours require a certified guide, police permit, and MVO radio clearance. Book in advance — access is cancelled if volcanic threat level rises.

💡 Pro move: US dollars are universally accepted. Credit cards work at larger spots; carry cash for taxis and beach bars.

Piers & Tendering by Cruise Line

Little Bay is primarily a tender port; a new commercial jetty is under construction but not yet open to large vessels.

Cruise LineTypical Berth / ArrivalDock or Tender
Most cruise linesLittle Bay anchorage📍Tendered
Small/expedition ships (Windstar, Ponant, Star Clippers)Little Bay pier📍Docked

Top Excursions

Montserrat rewards the curious — every excursion here is genuinely unique, from walking through a buried city to hiking to the Caribbean's most secluded white-sand beach.

History

Plymouth Exclusion Zone Guided Tour

Walk through Plymouth, the only volcanic-buried capital in the Americas. Three-story buildings are swallowed to their rooftops in ash and lahar. An authorized guide is mandatory — and makes the experience far richer.

⏱ 2–3 hrs🚶 Easy walking🌋 Unique worldwide📋 Permit required
Find Plymouth volcano tours →
Nature

Montserrat Volcano Observatory

The MVO in Flemmings monitors the Soufrière Hills 24/7. The viewing deck delivers dramatic sight lines over the lava dome and the Belham River Valley; the on-site documentary about the 1995–1997 eruptions is gripping.

⏱ 1–2 hrs🚕 Short taxi ride💲 ~$4 USD entry📷 Great views
Find MVO & volcano tours →
Relax

Rendezvous Bay Beach Day

Montserrat's only white-sand beach is reachable by a 30-min water taxi from Little Bay or a strenuous 40-min hike over the bluff. Either way, you'll likely have the beach nearly to yourself.

⏱ Half day🚤 Water taxi or hike🤿 Good snorkeling🏝️ Very secluded
Find Rendezvous Bay water taxi →
Culture

Montserrat Cultural Centre & AIR Studios History

The Cultural Centre was inspired by George Martin's legendary AIR Studios, where The Police, Paul McCartney, and Elton John recorded in the 1980s. The Hilltop Café nearby has pre-eruption photos and memorabilia from the studio era.

⏱ 1 hr🚕 Taxi ride🎵 Music history☕ Café on-site
Find cultural tours →
Adventure

Jack Boy Hill & Panoramic Volcano Views

A free public viewpoint on the island's east side with sweeping panoramas of the volcano, the buried W.H. Bramble Airport, and the Atlantic coast. Easy stop on any island taxi tour.

⏱ 30 min🆓 Free entry📷 Best photo stop🌋 Volcano views
Find island tour operators →
Wildlife

Woodlands Beach & Turtle Nesting Site

A dramatic black-sand beach on the west coast, flanked by dark cliffs and backed by forest. Sea turtles nest here; currents can be strong, so wade carefully. A 10-min taxi ride from the port.

⏱ 1–2 hrs🚕 10 min by taxi🐢 Turtle nesting🏖️ Atmospheric
Find Montserrat beach tours →

Self-Guided Walks & Hikes

Most of Montserrat's highlights require a taxi, but Little Bay itself has a pleasant waterfront stretch — and Rendezvous Bay rewards those willing to hike.

Little Bay Waterfront Stroll

20 min · Flat · No hills

From the pier, walk the Little Bay beach past beach bars, the Montserrat National Museum, and the Cultural Centre. Grab a cold Carib and watch the tenders come in.

  1. StartLittle Bay Pier, Montserrat
  2. StopMontserrat National Museum
  3. EndMontserrat Cultural Centre
🗺️ See full route in Maps →

Rendezvous Bay Bluff Hike

3–4 km round trip · Moderate–strenuous · 40 min each way

Head north from Little Bay pier and follow the coastal trail over the bluff to Rendezvous Bay — the island's only white-sand beach. Steep in places; wear proper shoes and bring water.

  1. StartLittle Bay Pier, Montserrat
  2. EndRendezvous Bay, Montserrat
🗺️ See full route in Maps →

Weather & Best Time to Visit

Climate normals for Little Bay, Montserrat, Caribbean (2014–2023 averages). Pack for the month you sail — highs, lows, and how many rainy days to expect.

MonthAvg HighAvg LowRainy DaysSunriseSunset
Jan78°F / 26°C76°F / 24°C126:46 AM5:56 PM
Feb78°F / 26°C75°F / 24°C106:39 AM6:13 PM
Mar78°F / 26°C76°F / 24°C76:20 AM6:21 PM
Apr79°F / 26°C76°F / 24°C115:55 AM6:28 PM
May80°F / 27°C78°F / 26°C105:39 AM6:38 PM
Jun82°F / 28°C79°F / 26°C95:36 AM6:48 PM
Jul82°F / 28°C80°F / 27°C145:45 AM6:51 PM
Aug83°F / 28°C80°F / 27°C165:54 AM6:38 PM
Sep83°F / 28°C80°F / 27°C176:00 AM6:14 PM
Oct83°F / 28°C80°F / 27°C176:06 AM5:49 PM
Nov82°F / 28°C79°F / 26°C166:18 AM5:35 PM
Dec80°F / 27°C77°F / 25°C136:36 AM5:39 PM

Source: Open-Meteo ERA5 (10-yr daily averages)

Insider Tips

  • 🌋
    Exclusion zone tours can be cancelled on short notice if the MVO raises the volcanic threat level. Book with a licensed guide and have a backup plan.
  • 🚕
    No metered taxis — agree fares before you go. A full island circuit (MVO, Jack Boy Hill, volcano views, Cultural Centre) takes 3–4 hrs and costs roughly $80–100 USD per cab.
  • 💵
    US dollars work everywhere; official currency is the Eastern Caribbean Dollar (XCD). Cards accepted at larger restaurants and the MVO — carry cash for taxis and beach bars.
  • 🍲
    Try Goat Water — Montserrat's national dish, a rich stew of goat meat, cloves, rum, and yams. Best found at People's Place near Salem or local lunch spots on a taxi tour.
  • 🍀
    Shamrock passport stamp: Montserrat is the only Caribbean island with deep Irish roots (17th-century settlers). You'll get a shamrock stamp when you clear — a genuine rarity.

Cruises Calling Here

Upcoming cruises that call at Little Bay, Montserrat, Caribbean. Dates, prices, and ports of call change — always confirm with the cruise line before booking.

Seabourn Venture
Seabourn Cruises
Halifax → Bridgetown
⚓ Calls 11 Oct 06:00 - 17:00 20268 nights5 portsDeparts 2026 Oct 05
View itinerary · 5 ports
8 days, one-way from Halifax to Bridgetown
  1. 05 Oct - 17:00Departing from Halifax, Nova Scotia Canada
  2. 10 Oct 07:00 - 18:00Saint Kitts island
  3. 11 Oct 06:00 - 17:00Montserrat Island UK, Little Bay
  4. 12 Oct 08:00 - 18:00Pigeon Island, Rodney Bay, St Lucia
  5. 13 Oct 07:00Arriving in Bridgetown, Barbados
Find this cruise to book →
Price on request
Seabourn Venture
Seabourn Cruises
Halifax → Rio de Janeiro
⚓ Calls 11 Oct 06:00 - 17:00 202624 nights13 portsDeparts 2026 Oct 05
View itinerary · 13 ports
24 days, one-way from Halifax to Rio de Janeiro
  1. 05 Oct - 17:00Departing from Halifax, Nova Scotia Canada
  2. 10 Oct 07:00 - 18:00Saint Kitts island
  3. 11 Oct 06:00 - 17:00Montserrat Island UK, Little Bay
  4. 12 Oct 08:00 - 18:00Pigeon Island, Rodney Bay, St Lucia
  5. 13 Oct 07:00 - 18:00Bridgetown, Barbados
  6. 14 Oct 09:00 - 20:00Port-of-Spain, Trinidad
  7. 17 Oct 07:00 - 19:00Ile Royale Island, Salvation Islands, French Guiana
  8. 21 Oct 07:00 - 14:00Fortaleza, Brazil
  9. 22 Oct 09:00 - 17:00Natal, Brazil
  10. 24 Oct 09:00 - 18:00Salvador de Bahia, Brazil
  11. 27 Oct 07:00 - 14:00Buzios, Brazil
  12. 28 Oct 07:00 - 17:00Paraty, Brazil
  13. 29 Oct 07:00Arriving in Rio de Janeiro, Brazil
Find this cruise to book →
Price on request
Seabourn Venture
Seabourn Cruises
Halifax → Ushuaia
⚓ Calls 11 Oct 06:00 - 17:00 202645 nights19 portsDeparts 2026 Oct 05
View itinerary · 19 ports
45 days, one-way from Halifax to Ushuaia
  1. 05 Oct - 17:00Departing from Halifax, Nova Scotia Canada
  2. 10 Oct 07:00 - 18:00Saint Kitts island
  3. 11 Oct 06:00 - 17:00Montserrat Island UK, Little Bay
  4. 12 Oct 08:00 - 18:00Pigeon Island, Rodney Bay, St Lucia
  5. 13 Oct 07:00 - 18:00Bridgetown, Barbados
  6. 14 Oct 09:00 - 20:00Port-of-Spain, Trinidad
  7. 17 Oct 07:00 - 19:00Ile Royale Island, Salvation Islands, French Guiana
  8. 21 Oct 07:00 - 14:00Fortaleza, Brazil
  9. 22 Oct 09:00 - 17:00Natal, Brazil
  10. 24 Oct 09:00 - 18:00Salvador de Bahia, Brazil
  11. 27 Oct 07:00 - 14:00Buzios, Brazil
  12. 28 Oct 07:00 - 17:00Paraty, Brazil
  13. 29 Oct 07:00 - 17:00Rio de Janeiro, Brazil
  14. 31 Oct 07:00 - 18:00Balneario Camboriu, Brazil
  15. 03 Nov 07:00 - 13:00Montevideo, Uruguay
  16. 06 Novcoastal cruising
  17. 07 Nov 07:00 - 17:00Port Stanley, East Falkland Island UK
  18. 08 Nov - 16 Novcoastal cruising
  19. 19 Nov 07:00Arriving in Ushuaia, Argentina
Find this cruise to book →
Price on request
Seabourn Venture
Seabourn Cruises
Kangerlussuaq → Ushuaia
⚓ Calls 11 Oct 06:00 - 17:00 202659 nights33 portsDeparts 2026 Sep 21
View itinerary · 33 ports
59 days, one-way from Kangerlussuaq to Ushuaia
  1. 21 Sep - 17:00Departing from Kangerlussuaq, Greenland
  2. 23 Sep 07:00 - 12:00Baffin Island, Nunavut Canada
  3. 23 Sep 14:30 - 18:00Kekerten Island Canada, Nunavut
  4. 24 Sep 08:00 - 12:00Lady Franklin Island Canada, Nunavut
  5. 24 Sep 13:00 - 18:00Monumental Island Canada, Nunavut
  6. 25 Sep 07:00 - 12:00Lower Savage Islands Canada, Nunavut
  7. 25 Sep 13:00 - 17:00Resolution Island Canada, Nunavut
  8. 26 Sepfjord cruising
  9. 27 Sepcoastal cruising
  10. 28 Sepfjord cruising
  11. 29 Sep 09:00 - 17:00Nain NL, Newfoundland-Labrador Canada
  12. 30 Sep 09:30 - 17:00Indian Harbour NS, Nova Scotia Canada
  13. 01 Oct 07:00 - 11:30Battle Harbour NL, Newfoundland-Labrador Canada
  14. 01 Oct 14:30 - 19:00L'Anse aux Meadows, Newfoundland-Labrador Canada
  15. 05 Oct 07:00 - 17:00Halifax, Nova Scotia Canada
  16. 10 Oct 07:00 - 18:00Saint Kitts island
  17. 11 Oct 06:00 - 17:00Montserrat Island UK, Little Bay
  18. 12 Oct 08:00 - 18:00Pigeon Island, Rodney Bay, St Lucia
  19. 13 Oct 07:00 - 18:00Bridgetown, Barbados
  20. 14 Oct 09:00 - 20:00Port-of-Spain, Trinidad
  21. 17 Oct 07:00 - 19:00Ile Royale Island, Salvation Islands, French Guiana
  22. 21 Oct 07:00 - 14:00Fortaleza, Brazil
  23. 22 Oct 09:00 - 17:00Natal, Brazil
  24. 24 Oct 09:00 - 18:00Salvador de Bahia, Brazil
  25. 27 Oct 07:00 - 14:00Buzios, Brazil
  26. 28 Oct 07:00 - 17:00Paraty, Brazil
  27. 29 Oct 07:00 - 17:00Rio de Janeiro, Brazil
  28. 31 Oct 07:00 - 18:00Balneario Camboriu, Brazil
  29. 03 Nov 07:00 - 13:00Montevideo, Uruguay
  30. 06 Novcoastal cruising
  31. 07 Nov 07:00 - 17:00Port Stanley, East Falkland Island UK
  32. 08 Nov - 16 Novcoastal cruising
  33. 19 Nov 07:00Arriving in Ushuaia, Argentina
Find this cruise to book →
Price on request
Seabourn Venture
Seabourn Cruises
Kangerlussuaq → Rio de Janeiro
⚓ Calls 11 Oct 06:00 - 17:00 202638 nights27 portsDeparts 2026 Sep 21
View itinerary · 27 ports
38 days, one-way from Kangerlussuaq to Rio de Janeiro
  1. 21 Sep - 17:00Departing from Kangerlussuaq, Greenland
  2. 23 Sep 07:00 - 12:00Baffin Island, Nunavut Canada
  3. 23 Sep 14:30 - 18:00Kekerten Island Canada, Nunavut
  4. 24 Sep 08:00 - 12:00Lady Franklin Island Canada, Nunavut
  5. 24 Sep 13:00 - 18:00Monumental Island Canada, Nunavut
  6. 25 Sep 07:00 - 12:00Lower Savage Islands Canada, Nunavut
  7. 25 Sep 13:00 - 17:00Resolution Island Canada, Nunavut
  8. 26 Sepfjord cruising
  9. 27 Sepcoastal cruising
  10. 28 Sepfjord cruising
  11. 29 Sep 09:00 - 17:00Nain NL, Newfoundland-Labrador Canada
  12. 30 Sep 09:30 - 17:00Indian Harbour NS, Nova Scotia Canada
  13. 01 Oct 07:00 - 11:30Battle Harbour NL, Newfoundland-Labrador Canada
  14. 01 Oct 14:30 - 19:00L'Anse aux Meadows, Newfoundland-Labrador Canada
  15. 05 Oct 07:00 - 17:00Halifax, Nova Scotia Canada
  16. 10 Oct 07:00 - 18:00Saint Kitts island
  17. 11 Oct 06:00 - 17:00Montserrat Island UK, Little Bay
  18. 12 Oct 08:00 - 18:00Pigeon Island, Rodney Bay, St Lucia
  19. 13 Oct 07:00 - 18:00Bridgetown, Barbados
  20. 14 Oct 09:00 - 20:00Port-of-Spain, Trinidad
  21. 17 Oct 07:00 - 19:00Ile Royale Island, Salvation Islands, French Guiana
  22. 21 Oct 07:00 - 14:00Fortaleza, Brazil
  23. 22 Oct 09:00 - 17:00Natal, Brazil
  24. 24 Oct 09:00 - 18:00Salvador de Bahia, Brazil
  25. 27 Oct 07:00 - 14:00Buzios, Brazil
  26. 28 Oct 07:00 - 17:00Paraty, Brazil
  27. 29 Oct 07:00Arriving in Rio de Janeiro, Brazil
Find this cruise to book →
Price on request
Seabourn Venture
Seabourn Cruises
Kangerlussuaq → Bridgetown
⚓ Calls 11 Oct 06:00 - 17:00 202622 nights19 portsDeparts 2026 Sep 21
View itinerary · 19 ports
22 days, one-way from Kangerlussuaq to Bridgetown
  1. 21 Sep - 17:00Departing from Kangerlussuaq, Greenland
  2. 23 Sep 07:00 - 12:00Baffin Island, Nunavut Canada
  3. 23 Sep 14:30 - 18:00Kekerten Island Canada, Nunavut
  4. 24 Sep 08:00 - 12:00Lady Franklin Island Canada, Nunavut
  5. 24 Sep 13:00 - 18:00Monumental Island Canada, Nunavut
  6. 25 Sep 07:00 - 12:00Lower Savage Islands Canada, Nunavut
  7. 25 Sep 13:00 - 17:00Resolution Island Canada, Nunavut
  8. 26 Sepfjord cruising
  9. 27 Sepcoastal cruising
  10. 28 Sepfjord cruising
  11. 29 Sep 09:00 - 17:00Nain NL, Newfoundland-Labrador Canada
  12. 30 Sep 09:30 - 17:00Indian Harbour NS, Nova Scotia Canada
  13. 01 Oct 07:00 - 11:30Battle Harbour NL, Newfoundland-Labrador Canada
  14. 01 Oct 14:30 - 19:00L'Anse aux Meadows, Newfoundland-Labrador Canada
  15. 05 Oct 07:00 - 17:00Halifax, Nova Scotia Canada
  16. 10 Oct 07:00 - 18:00Saint Kitts island
  17. 11 Oct 06:00 - 17:00Montserrat Island UK, Little Bay
  18. 12 Oct 08:00 - 18:00Pigeon Island, Rodney Bay, St Lucia
  19. 13 Oct 07:00Arriving in Bridgetown, Barbados
Find this cruise to book →
Price on request
Silver Shadow
Silversea Cruises
Round-trip from Miami
⚓ Calls 14 Nov 08:00 - 17:00 202611 nights8 portsDeparts 2026 Nov 07
View itinerary · 8 ports
11 days, round-trip Miami, Fl To Miami, Fl
  1. 07 Nov 18:00Departing from Miami, Florida
  2. 10 Nov 09:00 - 19:00San Juan, Puerto Rico
  3. 11 Nov 08:00 - 18:00St John Island USVI, Cruz Bay, US Virgin Islands
  4. 12 Nov 08:00 - 23:00Gustavia St Barths, Saint-Barthelemy Island France
  5. 13 Nov 08:00 - 18:00Basseterre St Kitts, Port Zante
  6. 14 Nov 08:00 - 17:00Montserrat Island UK, Little Bay
  7. 15 Nov 08:00 - 14:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  8. 18 NovArriving in Miami, Florida
Find this cruise to book →
$6300from / pp
Silver Shadow
Silversea Cruises
Montreal → Miami
⚓ Calls 14 Nov 08:00 - 17:00 202625 nights16 portsDeparts 2026 Oct 24
View itinerary · 16 ports
25 days, one-way from Montreal to Miami
  1. 24 Oct 20:00Departing from Montreal, Quebec Canada
  2. 25 Oct 08:00 - 23:00Quebec City, Canada
  3. 28 Oct 08:00 - 20:00Prince Edward Island, Charlottetown, Canada
  4. 30 Oct 08:00 - 23:00Halifax, Nova Scotia Canada
  5. 01 Nov 08:00 - 19:30Boston, Massachusetts
  6. 02 Nov 01:45 - 03:15Cape Cod Canal, Massachusetts
  7. 02 Nov 08:00 - 17:00Newport RI, Rhode Island
  8. 03 Nov 08:00 - 23:00New York, NYC Manhattan-Brooklyn
  9. 07 Nov 07:00Miami, Florida
  10. 10 Nov 09:00 - 19:00San Juan, Puerto Rico
  11. 11 Nov 08:00 - 18:00St John Island USVI, Cruz Bay, US Virgin Islands
  12. 12 Nov 08:00 - 23:00Gustavia St Barths, Saint-Barthelemy Island France
  13. 13 Nov 08:00 - 18:00Basseterre St Kitts, Port Zante
  14. 14 Nov 08:00 - 17:00Montserrat Island UK, Little Bay
  15. 15 Nov 08:00 - 14:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  16. 18 NovArriving in Miami, Florida
Find this cruise to book →
$9600from / pp
Silver Shadow
Silversea Cruises
Round-trip from Miami
⚓ Calls 25 Nov 08:00 - 18:00 202612 nights9 portsDeparts 2026 Nov 18
View itinerary · 9 ports
12 days, round-trip Miami, Fl To Miami, Fl
  1. 18 Nov 18:00Departing from Miami, Florida
  2. 21 Nov 09:00 - 19:00San Juan, Puerto Rico
  3. 22 Nov 08:00 - 18:00St John Island USVI, Cruz Bay, US Virgin Islands
  4. 23 Nov 08:00 - 23:00Gustavia St Barths, Saint-Barthelemy Island France
  5. 24 Nov 08:00 - 18:00St Johns Antigua, RCI Royal Beach Club
  6. 25 Nov 08:00 - 18:00Montserrat Island UK, Little Bay
  7. 26 Nov 08:00 - 18:00Basseterre St Kitts, Port Zante
  8. 27 Nov 08:00 - 14:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  9. 30 NovArriving in Miami, Florida
Find this cruise to book →
$6200from / pp
Seabourn Ovation
Seabourn Cruises
Miami → Philipsburg St Maarten
⚓ Calls 01 Dec 08:00 - 18:00 202615 nights13 portsDeparts 2026 Nov 20
View itinerary · 13 ports
15 days, one-way from Miami to Philipsburg St Maarten
  1. 20 Nov 16:00Departing from Miami, Florida
  2. 23 Nov 10:00 - 18:00San Juan, Puerto Rico
  3. 24 Nov 08:00 - 18:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  4. 25 Nov 08:00 - 17:00Basseterre St Kitts, Port Zante
  5. 26 Nov 08:00 - 17:00Roseau, Dominica
  6. 27 Nov 08:00 - 18:00Bequia Island, Port Elizabeth, Grenadines
  7. 28 Nov 07:00 - 21:00Bridgetown, Barbados
  8. 29 Nov 08:00 - 18:00Pigeon Island, Rodney Bay, St Lucia
  9. 01 Dec 08:00 - 18:00Montserrat Island UK, Little Bay
  10. 02 Dec 08:00 - 21:00St Johns Antigua, RCI Royal Beach Club
  11. 03 Dec 08:00 - 17:00Basseterre St Kitts, Port Zante
  12. 04 Dec 08:00 - 18:00Virgin Gorda Island BVI, Spanish Town, UK Virgin Islands
  13. 05 Dec 07:00Arriving in Philipsburg St Maarten, Netherlands Antilles
Find this cruise to book →
$7499from / pp
Seabourn Quest
Seabourn Cruises
Round-trip from Miami
⚓ Calls 01 Dec 08:00 - 18:00 202614 nights11 portsDeparts 2026 Nov 22
View itinerary · 11 ports
14 days, round-trip Leeward Island Jewels
  1. 22 Nov 16:00Departing from Miami, Florida
  2. 25 Nov 10:00 - 18:00San Juan, Puerto Rico
  3. 26 Nov 08:00 - 17:00Anguilla Island, UK, Sandy Ground
  4. 27 Nov 08:00 - 17:00Basseterre St Kitts, Port Zante
  5. 28 Nov 08:00 - 17:00Roseau, Dominica
  6. 29 Nov 08:00 - 18:00Fort-de-France, Martinique
  7. 30 Nov 08:00 - 17:00Iles des Saintes, Guadeloupe
  8. 01 Dec 08:00 - 18:00Montserrat Island UK, Little Bay
  9. 02 Dec 08:00 - 17:00Virgin Gorda Island BVI, Spanish Town, UK Virgin Islands
  10. 03 Dec 07:00 - 14:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  11. 06 Dec 07:00Arriving in Miami, Florida
Find this cruise to book →
$5999from / pp
Seabourn Ovation
Seabourn Cruises
Bridgetown → Philipsburg St Maarten
⚓ Calls 01 Dec 08:00 - 18:00 20267 nights7 portsDeparts 2026 Nov 28
View itinerary · 7 ports
7 days, one-way from Bridgetown to Philipsburg St Maarten
  1. 28 Nov 21:00Departing from Bridgetown, Barbados
  2. 29 Nov 08:00 - 18:00Pigeon Island, Rodney Bay, St Lucia
  3. 01 Dec 08:00 - 18:00Montserrat Island UK, Little Bay
  4. 02 Dec 08:00 - 21:00St Johns Antigua, RCI Royal Beach Club
  5. 03 Dec 08:00 - 17:00Basseterre St Kitts, Port Zante
  6. 04 Dec 08:00 - 18:00Virgin Gorda Island BVI, Spanish Town, UK Virgin Islands
  7. 05 Dec 07:00Arriving in Philipsburg St Maarten, Netherlands Antilles
Find this cruise to book →
$4499from / pp
Seabourn Ovation
Seabourn Cruises
Round-trip from Bridgetown
⚓ Calls 01 Dec 08:00 - 18:00 202614 nights13 portsDeparts 2026 Nov 28
View itinerary · 13 ports
14 days, round-trip Exotic Caribbean In Depth
  1. 28 Nov 21:00Departing from Bridgetown, Barbados
  2. 29 Nov 08:00 - 18:00Pigeon Island, Rodney Bay, St Lucia
  3. 01 Dec 08:00 - 18:00Montserrat Island UK, Little Bay
  4. 02 Dec 08:00 - 21:00St Johns Antigua, RCI Royal Beach Club
  5. 03 Dec 08:00 - 17:00Basseterre St Kitts, Port Zante
  6. 04 Dec 08:00 - 18:00Virgin Gorda Island BVI, Spanish Town, UK Virgin Islands
  7. 05 Dec 07:00 - 21:00Philipsburg St Maarten, Netherlands Antilles
  8. 06 Dec 08:00 - 17:00Tortola Island BVI, Road Town, UK Virgin Islands
  9. 07 Dec 08:00 - 17:00Basseterre St Kitts, Port Zante
  10. 09 Dec 08:00 - 18:00Les Anses d'Arlet, Martinique
  11. 10 Dec 08:00 - 17:00Bequia Island, Port Elizabeth, Grenadines
  12. 11 Dec 08:00 - 18:00St Georges Grenada
  13. 12 Dec 07:00Arriving in Bridgetown, Barbados
Find this cruise to book →
$7999from / pp
Seabourn Quest
Seabourn Cruises
Round-trip from Miami
⚓ Calls 15 Dec 08:00 - 18:00 202614 nights11 portsDeparts 2026 Dec 06
View itinerary · 11 ports
14 days, round-trip Leeward Island Jewels
  1. 06 Dec 16:00Departing from Miami, Florida
  2. 09 Dec 10:00 - 18:00San Juan, Puerto Rico
  3. 10 Dec 08:00 - 17:00Virgin Gorda Island BVI, Spanish Town, UK Virgin Islands
  4. 11 Dec 08:00 - 17:00Basseterre St Kitts, Port Zante
  5. 12 Dec 08:00 - 17:00Roseau, Dominica
  6. 13 Dec 08:00 - 18:00Fort-de-France, Martinique
  7. 14 Dec 08:00 - 17:00Iles des Saintes, Guadeloupe
  8. 15 Dec 08:00 - 18:00Montserrat Island UK, Little Bay
  9. 16 Dec 08:00 - 17:00Anguilla Island, UK, Sandy Ground
  10. 17 Dec 07:00 - 14:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  11. 20 Dec 07:00Arriving in Miami, Florida
Find this cruise to book →
$5999from / pp
Silver Shadow
Silversea Cruises
Miami → San Juan
⚓ Calls 18 Dec 08:00 - 17:00 202610 nights9 portsDeparts 2026 Dec 10
View itinerary · 9 ports
10 days, one-way from Miami to San Juan
  1. 10 Dec 18:00Departing from Miami, Florida
  2. 13 Dec 13:00 - 19:00St John Island USVI, Cruz Bay, US Virgin Islands
  3. 14 Dec 08:00 - 18:00Philipsburg St Maarten, Netherlands Antilles
  4. 15 Dec 08:00 - 18:00Basseterre St Kitts, Port Zante
  5. 16 Dec 08:00 - 18:00Iles des Saintes, Guadeloupe
  6. 17 Dec 08:00 - 18:00Fort-de-France, Martinique
  7. 18 Dec 08:00 - 17:00Montserrat Island UK, Little Bay
  8. 19 Dec 08:00 - 18:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  9. 20 DecArriving in San Juan, Puerto Rico
Find this cruise to book →
$5100from / pp
Seabourn Ovation
Seabourn Cruises
Bridgetown → Philipsburg St Maarten
⚓ Calls 22 Dec 08:00 - 18:00 20267 nights7 portsDeparts 2026 Dec 19
View itinerary · 7 ports
7 days, one-way from Bridgetown to Philipsburg St Maarten
  1. 19 Dec 21:00Departing from Bridgetown, Barbados
  2. 20 Dec 08:00 - 18:00Castries, St Lucia Island
  3. 22 Dec 08:00 - 18:00Montserrat Island UK, Little Bay
  4. 23 Dec 08:00 - 21:00St Johns Antigua, RCI Royal Beach Club
  5. 24 Dec 08:00 - 17:00Basseterre St Kitts, Port Zante
  6. 25 Dec 08:00 - 18:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  7. 26 Dec 07:00Arriving in Philipsburg St Maarten, Netherlands Antilles
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$5499from / pp
Seabourn Ovation
Seabourn Cruises
Round-trip from Bridgetown
⚓ Calls 22 Dec 08:00 - 18:00 202614 nights13 portsDeparts 2026 Dec 19
View itinerary · 13 ports
14 days, round-trip Exotic Caribbean In Depth
  1. 19 Dec 21:00Departing from Bridgetown, Barbados
  2. 20 Dec 08:00 - 18:00Castries, St Lucia Island
  3. 22 Dec 08:00 - 18:00Montserrat Island UK, Little Bay
  4. 23 Dec 08:00 - 21:00St Johns Antigua, RCI Royal Beach Club
  5. 24 Dec 08:00 - 17:00Basseterre St Kitts, Port Zante
  6. 25 Dec 08:00 - 18:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  7. 26 Dec 07:00 - 21:00Philipsburg St Maarten, Netherlands Antilles
  8. 27 Dec 08:00 - 17:00Tortola Island BVI, Road Town, UK Virgin Islands
  9. 28 Dec 08:00 - 17:00Basseterre St Kitts, Port Zante
  10. 30 Dec 08:00 - 18:00Les Anses d'Arlet, Martinique
  11. 31 Dec 08:00 - 17:00Bequia Island, Port Elizabeth, Grenadines
  12. 01 Jan 08:00 - 18:00St Georges Grenada
  13. 02 Jan 07:00Arriving in Bridgetown, Barbados
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$10999from / pp
Silver Shadow
Silversea Cruises
Round-trip from San Juan
⚓ Calls 22 Dec 09:00 - 18:30 20267 nights7 portsDeparts 2026 Dec 20
View itinerary · 7 ports
7 days, round-trip San Juan To San Juan
  1. 20 Dec 19:00Departing from San Juan, Puerto Rico
  2. 21 Dec 08:00 - 18:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  3. 22 Dec 09:00 - 18:30Montserrat Island UK, Little Bay
  4. 23 Dec 08:30 - 18:00Castries, St Lucia Island
  5. 24 Dec 08:00 - 18:00Fort-de-France, Martinique
  6. 26 Dec 08:00 - 18:00Tortola Island BVI, Road Town, UK Virgin Islands
  7. 27 DecArriving in San Juan, Puerto Rico
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$4800from / pp
Silver Shadow
Silversea Cruises
Round-trip from San Juan
⚓ Calls 22 Dec 09:00 - 18:30 202614 nights13 portsDeparts 2026 Dec 20
View itinerary · 13 ports
14 days, round-trip San Juan To San Juan
  1. 20 Dec 19:00Departing from San Juan, Puerto Rico
  2. 21 Dec 08:00 - 18:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  3. 22 Dec 09:00 - 18:30Montserrat Island UK, Little Bay
  4. 23 Dec 08:30 - 18:00Castries, St Lucia Island
  5. 24 Dec 08:00 - 18:00Fort-de-France, Martinique
  6. 26 Dec 08:00 - 18:00Tortola Island BVI, Road Town, UK Virgin Islands
  7. 27 Dec 07:00San Juan, Puerto Rico
  8. 28 Dec 08:00 - 18:00St John Island USVI, Cruz Bay, US Virgin Islands
  9. 29 Dec 08:00 - 18:00Basseterre St Kitts, Port Zante
  10. 30 Dec 08:00 - 17:00Iles des Saintes, Guadeloupe
  11. 31 Dec 08:00 - 18:00Bequia Island, Port Elizabeth, Grenadines
  12. 02 Jan 08:00 - 18:00St Thomas Island USVI, Charlotte Amalie, US Virgin Islands
  13. 03 JanArriving in San Juan, Puerto Rico
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$8700from / pp
Seabourn Quest
Seabourn Cruises
Round-trip from Miami
⚓ Calls 31 Dec 08:00 - 18:00 202616 nights13 portsDeparts 2026 Dec 20
View itinerary · 13 ports
16 days, round-trip Leeward Island Holiday
  1. 20 Dec 16:00Departing from Miami, Florida
  2. 23 Dec 10:00 - 18:00San Juan, Puerto Rico
  3. 24 Dec 08:00 - 17:00Anguilla Island, UK, Sandy Ground
  4. 25 Dec 08:00 - 17:00Basseterre St Kitts, Port Zante
  5. 26 Dec 08:00 - 17:00Marigot, St Martin Island France
  6. 27 Dec 08:00 - 17:00Iles des Saintes, Guadeloupe
  7. 28 Dec 08:00 - 18:00Fort-de-France, Martinique
  8. 29 Dec 08:00 - 17:00Pigeon Island, Rodney Bay, St Lucia
  9. 30 Dec 08:00 - 18:00Roseau, Dominica
  10. 31 Dec 08:00 - 18:00Montserrat Island UK, Little Bay
  11. 01 Jan 08:00 - 17:00St Johns Antigua, RCI Royal Beach Club
  12. 02 Jan 07:00 - 14:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  13. 05 Jan 07:00Arriving in Miami, Florida
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$10999from / pp
MSC Explora 1
MSC Explora Journeys Cruises
Round-trip from Miami
⚓ Calls 07 Jan 08:00 - 18:00 202715 nights13 portsDeparts 2026 Dec 27
View itinerary · 13 ports
15 days, round-trip An Extended Journey through Island Joys Volcanic Majesty
  1. 27 Dec 17:00Departing from Miami, Florida
  2. 29 Dec 08:00 - 17:00Puerto Plata-Amber Cove, Dominicana
  3. 30 Dec 08:00 - 17:00Catalina Island, Dominicana
  4. 31 Dec 09:00 - 16:00St John Island USVI, Cruz Bay, US Virgin Islands
  5. 01 Jan 12:00 - 18:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  6. 02 Jan 08:00 - 17:00Basseterre St Kitts, Port Zante
  7. 03 Jan 08:00 - 21:00St Thomas Island USVI, Charlotte Amalie, US Virgin Islands
  8. 04 Jan 08:00 - 17:00San Juan, Puerto Rico
  9. 05 Jan 08:00 - 18:00Philipsburg St Maarten, Netherlands Antilles
  10. 06 Jan 09:00 - 19:00St Johns Antigua, RCI Royal Beach Club
  11. 07 Jan 08:00 - 18:00Montserrat Island UK, Little Bay
  12. 08 Jan 08:00 - 18:00Tortola Island BVI, Road Town, UK Virgin Islands
  13. 11 Jan 08:00Arriving in Miami, Florida
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$8505from / pp
Silver Shadow
Silversea Cruises
Round-trip from San Juan
⚓ Calls 07 Jan 08:00 - 18:00 20277 nights8 portsDeparts 2027 Jan 03
View itinerary · 8 ports
7 days, round-trip San Juan To San Juan
  1. 03 Jan 19:00Departing from San Juan, Puerto Rico
  2. 04 Jan 08:00 - 18:00St John Island USVI, Cruz Bay, US Virgin Islands
  3. 05 Jan 08:00 - 23:00Gustavia St Barths, Saint-Barthelemy Island France
  4. 06 Jan 08:00 - 19:00St Johns Antigua, RCI Royal Beach Club
  5. 07 Jan 08:00 - 18:00Montserrat Island UK, Little Bay
  6. 08 Jan 08:00 - 19:00Basseterre St Kitts, Port Zante
  7. 09 Jan 08:00 - 18:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  8. 10 JanArriving in San Juan, Puerto Rico
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$4500from / pp
MSC Explora 1
MSC Explora Journeys Cruises
San Juan → Miami
⚓ Calls 07 Jan 08:00 - 18:00 20277 nights6 portsDeparts 2027 Jan 04
View itinerary · 6 ports
7 days, one-way from San Juan to Miami
  1. 04 Jan 17:00Departing from San Juan, Puerto Rico
  2. 05 Jan 08:00 - 18:00Philipsburg St Maarten, Netherlands Antilles
  3. 06 Jan 09:00 - 19:00St Johns Antigua, RCI Royal Beach Club
  4. 07 Jan 08:00 - 18:00Montserrat Island UK, Little Bay
  5. 08 Jan 08:00 - 18:00Tortola Island BVI, Road Town, UK Virgin Islands
  6. 11 Jan 08:00Arriving in Miami, Florida
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$3850from / pp
MSC Explora 1
MSC Explora Journeys Cruises
San Juan → Miami
⚓ Calls 07 Jan 08:00 - 18:00 202716 nights12 portsDeparts 2027 Jan 04
View itinerary · 12 ports
16 days, one-way from San Juan to Miami
  1. 04 Jan 17:00Departing from San Juan, Puerto Rico
  2. 05 Jan 08:00 - 18:00Philipsburg St Maarten, Netherlands Antilles
  3. 06 Jan 09:00 - 19:00St Johns Antigua, RCI Royal Beach Club
  4. 07 Jan 08:00 - 18:00Montserrat Island UK, Little Bay
  5. 08 Jan 08:00 - 18:00Tortola Island BVI, Road Town, UK Virgin Islands
  6. 11 Jan 08:00 - 17:00Miami, Florida
  7. 13 Jan 09:00 - 19:00Puerto Plata-Amber Cove, Dominicana
  8. 14 Jan 08:00 - 18:00Samana, Dominicana
  9. 15 Jan 09:00 - 23:00San Juan, Puerto Rico
  10. 16 Jan 09:00 - 20:00St Thomas Island USVI, Charlotte Amalie, US Virgin Islands
  11. 17 Jan 08:00 - 18:00Virgin Gorda Island BVI, Spanish Town, UK Virgin Islands
  12. 20 Jan 08:00Arriving in Miami, Florida
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$7385from / pp
Seabourn Ovation
Seabourn Cruises
Bridgetown → Philipsburg St Maarten
⚓ Calls 12 Jan 08:00 - 18:00 20277 nights7 portsDeparts 2027 Jan 09
View itinerary · 7 ports
7 days, one-way from Bridgetown to Philipsburg St Maarten
  1. 09 Jan 21:00Departing from Bridgetown, Barbados
  2. 10 Jan 08:00 - 18:00Castries, St Lucia Island
  3. 12 Jan 08:00 - 18:00Montserrat Island UK, Little Bay
  4. 13 Jan 08:00 - 21:00St Johns Antigua, RCI Royal Beach Club
  5. 14 Jan 08:00 - 17:00Basseterre St Kitts, Port Zante
  6. 15 Jan 08:00 - 18:00Jost Van Dyke Island BVI, Belle Vue, UK Virgin Islands
  7. 16 Jan 07:00Arriving in Philipsburg St Maarten, Netherlands Antilles
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$5299from / pp
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