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Voyages · Caribbean & Central America

Explora Caribbean & Central America voyages

Explora's Caribbean is not the mega-ship Caribbean. On a ship this size, calling at the smaller yacht-oriented harbors rather than the big cruise terminals, a Caribbean week feels closer to a private charter than a cruise. The winter season is prime, and the right itinerary, weighted toward the quieter islands, is one of the easiest ways to convert a hotel-luxury traveler who swore cruising wasn't for them.

107 sailings · 4 ships · from $3,000 per guest, double occupancy · pricing as of July 12, 2026

When's the best time to sail Caribbean? Prices by month →

Reading before you book: Quiet Caribbean

How to read the fare status
Tracked low
The cheapest I have recorded this exact sailing since I began tracking it daily.
Good price
Priced below comparable Explora sailings of the same region and length.
Holding steady
Little movement since I started tracking it; nothing to chase right now.
Best available
The best currently bookable fare across every promotional code.

Every fare shown is the best currently bookable double-occupancy rate across all Explora promotions. The status is my read on top of that: whether it is a tracked low for this exact sailing, cheaper than comparable Explora voyages, or simply holding steady.

October 2026

  • EXPLORA III Miami to San Juan Oct 25 · 6 nights Miami · Cruz Bay (Saint John) · St. John's (Antigua) · Terre-de-Haut (Îles des Saintes) · Philipsburg + 1 more
    from $5,185 Tracked low Explora's page →
  • EXPLORA III Miami to Miami Oct 25 · 13 nights Miami · Cruz Bay (Saint John) · St. John's (Antigua) · Terre-de-Haut (Îles des Saintes) · Philipsburg + 5 more
    from $10,795 Best available Explora's page →

November 2026

December 2026

  • EXPLORA I Miami to San Juan Dec 5 · 14 nights Miami · Cozumel · Costa Maya · Santo Tomás de Castilla · Belize City + 6 more
    from $8,760 Good price Explora's page →
  • EXPLORA I Miami to Miami Dec 5 · 7 nights Miami · Cozumel · Costa Maya · Santo Tomás de Castilla · Belize City + 1 more
    from $5,320 Tracked low Explora's page →
  • EXPLORA III Miami to San Juan Dec 6 · 6 nights Miami · Cruz Bay (Saint John) · St. John's (Antigua) · Terre-de-Haut (Îles des Saintes) · Gustavia + 1 more
    from $4,880 Tracked low Explora's page →
  • EXPLORA III Miami to Miami Dec 6 · 13 nights Miami · Cruz Bay (Saint John) · St. John's (Antigua) · Terre-de-Haut (Îles des Saintes) · Gustavia + 4 more
    from $9,040 Good price Explora's page →
  • EXPLORA I Miami to San Juan Dec 13 · 6 nights Miami · Cruz Bay (Saint John) · St. John's (Antigua) · Terre-de-Haut (Îles des Saintes) · Philipsburg + 1 more
    from $4,280 Best available Explora's page →
  • EXPLORA III San Juan to San Juan Dec 13 · 14 nights San Juan · Road Bay · St. John's (Antigua) · Basseterre · Grand Turk + 6 more
    from $11,160 Best available Explora's page →
  • EXPLORA III San Juan to Miami Dec 13 · 6 nights San Juan · Road Bay · St. John's (Antigua) · Basseterre · Grand Turk + 1 more
    from $4,880 Tracked low Explora's page →
  • EXPLORA I Miami to Miami Dec 13 · 13 nights Miami · Cruz Bay (Saint John) · St. John's (Antigua) · Terre-de-Haut (Îles des Saintes) · Philipsburg + 5 more
    from $9,480 Tracked low Explora's page →
  • EXPLORA III Miami to Miami Dec 20 · 15 nights Miami · Ocho Rios · Catalina Island · Jost Van Dyke · Philipsburg + 8 more
    from $13,360 Best available Explora's page →
  • EXPLORA I San Juan to Miami Dec 20 · 6 nights San Juan · Basseterre · Road Town (Tortola) · Gustavia · Road Bay + 1 more
    from $6,650 Holding steady Explora's page →
  • EXPLORA I San Juan to San Juan Dec 20 · 14 nights San Juan · Basseterre · Road Town (Tortola) · Gustavia · Road Bay + 7 more
    from $13,095 Tracked low Explora's page →
  • EXPLORA III Miami to San Juan Dec 20 · 7 nights Miami · Ocho Rios · Catalina Island · Jost Van Dyke · Philipsburg + 2 more
    from $5,240 Best available Explora's page →
  • EXPLORA I Miami to San Juan Dec 27 · 7 nights Miami · Puerto Plata · Catalina Island · Cruz Bay (Saint John) · At Sea - Fireworks + 4 more
    from $7,515 Tracked low Explora's page →
  • EXPLORA I Miami to Miami Dec 27 · 14 nights Miami · Puerto Plata · Catalina Island · Cruz Bay (Saint John) · At Sea - Fireworks + 8 more
    from $10,535 Tracked low Explora's page →
  • EXPLORA III San Juan to Miami Dec 28 · 7 nights San Juan · St. John's (Antigua) · Pointe-à-Pitre · At Sea - Fireworks · Cruz Bay (Saint John) + 3 more
    from $6,400 Best available Explora's page →
  • EXPLORA III San Juan to San Juan Dec 28 · 15 nights San Juan · St. John's (Antigua) · Pointe-à-Pitre · At Sea - Fireworks · Cruz Bay (Saint John) + 6 more
    from $14,000 Holding steady Explora's page →

January 2027

  • EXPLORA I San Juan to Miami Jan 4 · 6 nights San Juan · Philipsburg · St. John's (Antigua) · Little Bay · Road Town (Tortola) + 1 more
    from $4,200 Best available Explora's page →
  • EXPLORA I San Juan to Miami Jan 4 · 15 nights San Juan · Philipsburg · St. John's (Antigua) · Little Bay · Road Town (Tortola) + 5 more
    from $8,960 Good price Explora's page →
  • EXPLORA III Miami to Miami Jan 5 · 15 nights Miami · Cruz Bay (Saint John) · Gustavia · St. John's (Antigua) · Road Town (Tortola) + 7 more
    from $12,410 Best available Explora's page →
  • EXPLORA III Miami to San Juan Jan 5 · 7 nights Miami · Cruz Bay (Saint John) · Gustavia · St. John's (Antigua) · Road Town (Tortola) + 2 more
    from $6,290 Tracked low Explora's page →
  • EXPLORA I Miami to Miami Jan 11 · 17 nights Miami · Puerto Plata · Cayo Levantado (Samaná Bay) · San Juan · Charlotte Amalie (Saint Thomas) + 6 more
    from $10,400 Good price Explora's page →
  • EXPLORA I Miami to Miami Jan 11 · 8 nights Miami · Puerto Plata · Cayo Levantado (Samaná Bay) · San Juan · Charlotte Amalie (Saint Thomas) + 1 more
    from $5,920 Tracked low Explora's page →
  • EXPLORA III San Juan to Miami Jan 13 · 7 nights San Juan · Philipsburg · Terre-de-Haut (Îles des Saintes) · St. George's (Grenada) · Castries + 2 more
    from $6,290 Tracked low Explora's page →
  • EXPLORA III San Juan to San Juan Jan 13 · 15 nights San Juan · Philipsburg · Terre-de-Haut (Îles des Saintes) · St. George's (Grenada) · Castries + 6 more
    from $12,620 Best available Explora's page →
  • EXPLORA I Miami to San Juan Jan 20 · 15 nights Miami · Ocho Rios · Santo Tomás de Castilla · Roatán · Belize City + 6 more
    from $9,680 Good price Explora's page →
  • EXPLORA I Miami to Miami Jan 20 · 8 nights Miami · Ocho Rios · Santo Tomás de Castilla · Roatán · Belize City + 1 more
    from $5,920 Tracked low Explora's page →
  • EXPLORA III Miami to Miami Jan 21 · 14 nights Miami · Charlotte Amalie (Saint Thomas) · Road Bay · Saint-Pierre · Basseterre + 6 more
    from $11,515 Best available Explora's page →
  • EXPLORA III Miami to San Juan Jan 21 · 7 nights Miami · Charlotte Amalie (Saint Thomas) · Road Bay · Saint-Pierre · Basseterre + 2 more
    from $6,330 Tracked low Explora's page →
  • EXPLORA I Miami to San Juan Jan 29 · 6 nights Miami · Puerto Plata · Philipsburg · Terre-de-Haut (Îles des Saintes) · Basseterre + 1 more
    from $4,600 Tracked low Explora's page →
  • EXPLORA III San Juan to Miami Jan 29 · 6 nights San Juan · Road Town (Tortola) · St. John's (Antigua) · Providenciales · Key West + 1 more
    from $5,565 Tracked low Explora's page →
  • EXPLORA III San Juan to San Juan Jan 29 · 13 nights San Juan · Road Town (Tortola) · St. John's (Antigua) · Providenciales · Key West + 5 more
    from $11,475 Best available Explora's page →

February 2027

  • EXPLORA III Miami to Miami Feb 5 · 13 nights Miami · Philipsburg · Gustavia · Basseterre · Cruz Bay (Saint John) + 5 more
    from $9,900 Best available Explora's page →
  • EXPLORA III Miami to San Juan Feb 5 · 6 nights Miami · Philipsburg · Gustavia · Basseterre · Cruz Bay (Saint John) + 1 more
    from $5,270 Tracked low Explora's page →
  • EXPLORA III San Juan to Miami Feb 12 · 6 nights San Juan · Charlotte Amalie (Saint Thomas) · St. John's (Antigua) · Terre-de-Haut (Îles des Saintes) · Puerto Plata + 1 more
    from $5,270 Tracked low Explora's page →
  • EXPLORA III San Juan to Miami Feb 12 · 15 nights San Juan · Charlotte Amalie (Saint Thomas) · St. John's (Antigua) · Terre-de-Haut (Îles des Saintes) · Puerto Plata + 4 more
    from $9,800 Tracked low Explora's page →
  • EXPLORA III Miami to Miami Feb 19 · 8 nights Miami · Puerto Plata · Cayo Levantado (Samaná Bay) · San Juan · Spanish Town (Virgin Gorda) + 1 more
    from $6,040 Tracked low Explora's page →
  • EXPLORA III Miami to San Juan Feb 19 · 15 nights Miami · Puerto Plata · Cayo Levantado (Samaná Bay) · San Juan · Spanish Town (Virgin Gorda) + 5 more
    from $9,560 Good price Explora's page →
  • EXPLORA III Miami to San Juan Feb 28 · 6 nights Miami · Cruz Bay (Saint John) · St. John's (Antigua) · Terre-de-Haut (Îles des Saintes) · Charlotte Amalie (Saint Thomas) + 1 more
    from $4,960 Tracked low Explora's page →
  • EXPLORA III Miami to Miami Feb 28 · 13 nights Miami · Cruz Bay (Saint John) · St. John's (Antigua) · Terre-de-Haut (Îles des Saintes) · Charlotte Amalie (Saint Thomas) + 5 more
    from $9,120 Best available Explora's page →

March 2027

  • EXPLORA I San Juan to Miami Mar 1 · 6 nights San Juan · St. John's (Antigua) · Road Bay · Spanish Town (Virgin Gorda) · Grand Turk + 1 more
    from $4,875 Best available Explora's page →
  • EXPLORA III San Juan to Miami Mar 7 · 6 nights San Juan · Philipsburg · Gustavia · Basseterre · Grand Turk + 1 more
    from $5,720 Best available Explora's page →
  • EXPLORA III San Juan to Bridgetown Mar 7 · 13 nights San Juan · Philipsburg · Gustavia · Basseterre · Grand Turk + 6 more
    from $8,810 Good price Explora's page →
  • EXPLORA III Miami to Bridgetown Mar 14 · 6 nights Miami · Providenciales · St. John's (Antigua) · Roseau · Bequia + 1 more
    from $4,650 Tracked low Explora's page →
  • EXPLORA III Miami to Miami Mar 14 · 14 nights Miami · Providenciales · St. John's (Antigua) · Roseau · Bequia + 6 more
    from $10,910 Best available Explora's page →
  • EXPLORA III Bridgetown to Miami Mar 21 · 7 nights Bridgetown · St. George's (Grenada) · Castries · Fort-de-France · Gustavia + 2 more
    from $6,880 Best available Explora's page →
  • EXPLORA III Bridgetown to San Juan Mar 21 · 14 nights Bridgetown · St. George's (Grenada) · Castries · Fort-de-France · Gustavia + 7 more
    from $11,475 Best available Explora's page →
  • EXPLORA III Miami to San Juan Mar 29 · 6 nights Miami · Cruz Bay (Saint John) · St. John's (Antigua) · Terre-de-Haut (Îles des Saintes) · Road Town (Tortola) + 1 more
    from $4,650 Tracked low Explora's page →
  • EXPLORA III Miami to Miami Mar 29 · 13 nights Miami · Cruz Bay (Saint John) · St. John's (Antigua) · Terre-de-Haut (Îles des Saintes) · Road Town (Tortola) + 5 more
    from $9,225 Best available Explora's page →

April 2027

November 2027

  • EXPLORA IV Miami to San Juan Nov 5 · 7 nights Miami · Providenciales · Gustavia · Pointe-à-Pitre · Basseterre + 2 more
    from $4,835 Holding steady Explora's page →
  • EXPLORA IV San Juan to Miami Nov 13 · 6 nights San Juan · Charlotte Amalie (Saint Thomas) · Catalina Island · Puerto Plata · Key West + 2 more
    from $4,020 Tracked low Explora's page →
  • EXPLORA IV Miami to San Juan Nov 20 · 6 nights Miami · Cruz Bay (Saint John) · St. John's (Antigua) · Pointe-à-Pitre · Basseterre + 1 more
    from $4,020 Good price Explora's page →
  • EXPLORA II Miami to Miami Nov 22 · 9 nights Miami · Willemstad · Oranjestad · Santa Marta · Cartagena + 1 more
    from $6,015 Good price Explora's page →
  • EXPLORA IV San Juan to Miami Nov 27 · 6 nights San Juan · Gustavia · Spanish Town (Virgin Gorda) · Charlotte Amalie (Saint Thomas) · Cayo Levantado (Samaná Bay) + 2 more
    from $4,200 Best available Explora's page →

December 2027

  • EXPLORA II Miami to Miami Dec 2 · 9 nights Miami · Port Antonio · Colón · Bocas del Toro · Puerto Limon + 1 more
    from $5,730 Good price Explora's page →
  • EXPLORA IV Miami to Miami Dec 4 · 8 nights Miami · Puerto Plata · San Juan · Cruz Bay (Saint John) · Gustavia + 1 more
    from $5,415 Holding steady Explora's page →
  • EXPLORA II Miami to San Juan Dec 12 · 6 nights Miami · Puerto Plata · Catalina Island · Charlotte Amalie (Saint Thomas) · St. John's (Antigua) + 2 more
    from $4,020 Good price Explora's page →
  • EXPLORA IV Miami to Miami Dec 13 · 9 nights Miami · Ocho Rios · Kralendijk · Willemstad · Oranjestad + 1 more
    from $5,730 Good price Explora's page →
  • EXPLORA II San Juan to Miami Dec 19 · 6 nights San Juan · Road Town (Tortola) · Pointe-à-Pitre · Gustavia · Cruz Bay (Saint John) + 1 more
    from $5,160 Holding steady Explora's page →
  • EXPLORA IV Miami to San Juan Dec 23 · 6 nights Miami · Charlotte Amalie (Saint Thomas) · St. John's (Antigua) · Road Town (Tortola) · Basseterre + 1 more
    from $4,900 Holding steady Explora's page →
  • EXPLORA II Miami to San Juan Dec 26 · 6 nights Miami · Puerto Plata · Catalina Island · Frederiksted (Saint Croix) · Charlotte Amalie (Saint Thomas) + 3 more
    from $5,730 Holding steady Explora's page →
  • EXPLORA IV San Juan to Miami Dec 30 · 6 nights San Juan · Cruz Bay (Saint John) · At Sea - Fireworks · Cayo Levantado (Samaná Bay) · Puerto Plata + 2 more
    from $5,505 Holding steady Explora's page →

January 2028

  • EXPLORA II San Juan to Miami Jan 2 · 6 nights San Juan · Road Town (Tortola) · Pointe-à-Pitre · Gustavia · Ocean Cay + 1 more
    from $4,020 Good price Explora's page →
  • EXPLORA IV Miami to Miami Jan 6 · 8 nights Miami · Cozumel · Costa Maya · Santo Tomás de Castilla · Belize City + 2 more
    from $5,160 Tracked low Explora's page →
  • EXPLORA II Miami to San Juan Jan 9 · 6 nights Miami · Puerto Plata · Catalina Island · Charlotte Amalie (Saint Thomas) · Marigot + 2 more
    from $4,020 Good price Explora's page →
  • EXPLORA IV Miami to San Juan Jan 15 · 6 nights Miami · Cruz Bay (Saint John) · St. John's (Antigua) · Pointe-à-Pitre · Basseterre + 1 more
    from $4,020 Good price Explora's page →
  • EXPLORA II San Juan to San Juan Jan 16 · 6 nights San Juan · Bequia · Castries · Bridgetown · St. John's (Antigua) + 1 more
    from $4,020 Good price Explora's page →
  • EXPLORA IV San Juan to Miami Jan 22 · 6 nights San Juan · Gustavia · Charlotte Amalie (Saint Thomas) · Cayo Levantado (Samaná Bay) · Puerto Plata + 2 more
    from $4,020 Good price Explora's page →
  • EXPLORA II San Juan to Miami Jan 23 · 6 nights San Juan · Road Town (Tortola) · Pointe-à-Pitre · Gustavia · Ocean Cay + 1 more
    from $4,020 Good price Explora's page →
  • EXPLORA IV Miami to San Juan Jan 29 · 6 nights Miami · Cruz Bay (Saint John) · St. John's (Antigua) · Terre-de-Haut (Îles des Saintes) · Basseterre + 1 more
    from $4,020 Good price Explora's page →
  • EXPLORA II Miami to San Juan Jan 30 · 6 nights Miami · Puerto Plata · Catalina Island · Charlotte Amalie (Saint Thomas) · Road Bay + 2 more
    from $4,020 Good price Explora's page →

February 2028

  • EXPLORA IV San Juan to Miami Feb 5 · 6 nights San Juan · Gustavia · Charlotte Amalie (Saint Thomas) · Spanish Town (Virgin Gorda) · Ocean Cay + 1 more
    from $4,020 Good price Explora's page →
  • EXPLORA IV Miami to San Juan Feb 12 · 6 nights Miami · Cruz Bay (Saint John) · St. John's (Antigua) · Pointe-à-Pitre · Basseterre + 1 more
    from $4,200 Best available Explora's page →
  • EXPLORA IV San Juan to Miami Feb 19 · 6 nights San Juan · Philipsburg · Terre-de-Haut (Îles des Saintes) · Road Bay · Ocean Cay + 1 more
    from $4,020 Tracked low Explora's page →
  • EXPLORA IV Miami to San Juan Feb 26 · 6 nights Miami · Providenciales · Gustavia · St. John's (Antigua) · Basseterre + 1 more
    from $4,020 Good price Explora's page →
  • EXPLORA II San Juan to Miami Feb 27 · 6 nights San Juan · Gustavia · St. John's (Antigua) · Basseterre · Ocean Cay + 1 more
    from $4,020 Good price Explora's page →

March 2028

  • EXPLORA IV San Juan to Miami Mar 4 · 6 nights San Juan · Charlotte Amalie (Saint Thomas) · Cayo Levantado (Samaná Bay) · Puerto Plata · Key West + 2 more
    from $4,020 Good price Explora's page →
  • EXPLORA II Miami to San Juan Mar 5 · 6 nights Miami · Road Bay · Charlotte Amalie (Saint Thomas) · St. John's (Antigua) · Cruz Bay (Saint John) + 1 more
    from $4,020 Good price Explora's page →
  • EXPLORA IV Miami to San Juan Mar 11 · 6 nights Miami · Providenciales · Gustavia · St. John's (Antigua) · Road Bay + 1 more
    from $4,020 Good price Explora's page →
  • EXPLORA II San Juan to Miami Mar 12 · 6 nights San Juan · Road Town (Tortola) · Gustavia · Frederiksted (Saint Croix) · Ocean Cay + 1 more
    from $4,020 Good price Explora's page →
  • EXPLORA IV San Juan to Miami Mar 18 · 6 nights San Juan · Cruz Bay (Saint John) · Pointe-à-Pitre · Marigot · Ocean Cay + 1 more
    from $4,020 Good price Explora's page →
  • EXPLORA IV Miami to San Juan Mar 25 · 6 nights Miami · Providenciales · Gustavia · St. John's (Antigua) · Basseterre + 1 more
    from $4,020 Good price Explora's page →

April 2028

  • EXPLORA IV San Juan to Miami Apr 1 · 6 nights San Juan · Charlotte Amalie (Saint Thomas) · Cayo Levantado (Samaná Bay) · Puerto Plata · Key West + 2 more
    from $4,020 Tracked low Explora's page →
  • EXPLORA IV Miami to San Juan Apr 8 · 6 nights Miami · Providenciales · Gustavia · St. John's (Antigua) · Road Bay + 1 more
    from $4,020 Good price Explora's page →
  • EXPLORA IV San Juan to Miami Apr 15 · 6 nights San Juan · Cruz Bay (Saint John) · Pointe-à-Pitre · Marigot · Ocean Cay + 1 more
    from $4,020 Good price Explora's page →
  • EXPLORA IV Miami to San Juan Apr 22 · 6 nights Miami · Providenciales · Gustavia · St. John's (Antigua) · Road Bay + 1 more
    from $4,020 Good price Explora's page →
  • EXPLORA IV San Juan to Miami Apr 29 · 6 nights San Juan · Cruz Bay (Saint John) · Pointe-à-Pitre · Basseterre · Marigot + 1 more
    from $4,020 Good price Explora's page →

Pricing sourced from explorajourneys.com /us/en, refreshed daily. The figures are the lowest currently bookable double-occupancy fare per voyage. Verify your final fare with me or with Explora before booking.

Want the right Caribbean voyage for you?

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