Luxury Sint Maarten, Dutch Caribbean Voyages

Ports in Sint Maarten, Dutch Caribbean

Philipsburg

Philipsburg is the main town on the Dutch side of St. Maarten. The town is situated on a narrow stretch of land between Great Bay and the Great Salt Pond. Philipsburg was founded in 1763 by John Philips, a Scottish captain in the Dutch navy. The settlement soon became a center for international trade. The main shopping district is located on Front Street and is in the heart of the city. Many consider Philipsburg to be the best shopping opportunity in the Caribbean. Depending on the traffic, SeaDream has the option to anchor or dock alongside. One of the highlight activities may be to participate in the America’s Cup 12 Metre Regatta.
Simpson Bay

The smallest island in the world is shared by two countries, the Netherlands (Sint Maarten) and France (St. Martin), giving each side of the island a distinctive culture and flair. Simpson Bay straddles the best of both worlds, delivering white-sand beaches, beautiful lagoons dotted with impressive yachts, and vibrant dining spots that take in the energy of the island.
Viewing 35 Voyages
7-Day Cruise from San Juan to Philipsburg: Spanish & British Caribbean Delight

Spanish & British Caribbean Delight Club Voyage
Puerto Rico

  Dates: December 13 - December 20, 2025

  Length: 7 Days

  From: San Juan

   To: Philipsburg

Prices From $4,419
Prices are in USD
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7-Day Luxury Voyage from San Juan to Charlotte Amalie, St. Thomas: Caribbean Islands Adventure

Caribbean Islands Adventure
Puerto Rico

  Dates: December 14 - December 21, 2025

  Length: 7 Days

  From: San Juan

   To: Charlotte Amalie, St. Thomas

Prices From $4,419
Prices are in USD
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7-Day Luxury Voyage from Philipsburg to San Juan: Leeward Islands Celebration Availability Limited

Leeward Islands Celebration
Sint Maarten, Dutch Caribbean

  Dates: December 20 - December 27, 2025

  Length: 7 Days

  From: Philipsburg

   To: San Juan

Prices From $5,719
Prices are in USD
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7-Day Luxury Cruise from Charlotte Amalie, St. Thomas to Charlotte Amalie, St. Thomas: British & French Islands Explorer

British & French Islands Explorer
U.S.V.I.

  Dates: January 04 - January 11, 2026

  Length: 7 Days

  From: Charlotte Amalie, St. Thomas

   To: Charlotte Amalie, St. Thomas

Prices From $4,919
Prices are in USD
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10-Day Luxury Voyage from San Juan to Bridgetown, Barbados: The Best of the Secluded Caribbean

The Best of the Secluded Caribbean Club Voyage
Puerto Rico

  Dates: January 10 - January 20, 2026

  Length: 10 Days

  From: San Juan

   To: Bridgetown, Barbados

Prices From $7,299
Prices are in USD
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7-Day Luxury Voyage from Charlotte Amalie, St. Thomas to Philipsburg: St. Barths & Caribbean Gems

St. Barths & Caribbean Gems
U.S.V.I.

  Dates: January 11 - January 18, 2026

  Length: 7 Days

  From: Charlotte Amalie, St. Thomas

   To: Philipsburg

Prices From $5,119
Prices are in USD
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7-Day Cruise from Philipsburg to San Juan: St. Barths & Caribbean Gems Waitlisted

St. Barths & Caribbean Gems
Sint Maarten, Dutch Caribbean

  Dates: January 18 - January 25, 2026

  Length: 7 Days

  From: Philipsburg

   To: San Juan

Prices From $5,419
Prices are in USD
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7-Day Luxury Voyage from San Juan to Charlotte Amalie, St. Thomas: Caribbean Islands Adventure

Caribbean Islands Adventure
Puerto Rico

  Dates: January 31 - February 07, 2026

  Length: 7 Days

  From: San Juan

   To: Charlotte Amalie, St. Thomas

Prices From $5,419
Prices are in USD
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10-Day Luxury Cruise from Bridgetown, Barbados to Bridgetown, Barbados: Barbados & Caribbean Gems Availability Limited

Barbados & Caribbean Gems
Barbados

  Dates: February 01 - February 11, 2026

  Length: 10 Days

  From: Bridgetown, Barbados

   To: Bridgetown, Barbados

Prices From $7,599
Prices are in USD
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11-Day Luxury Voyage from Bridgetown, Barbados to Bridgetown, Barbados: Barbados & Caribbean Gems

Barbados & Caribbean Gems
Barbados

  Dates: February 11 - February 22, 2026

  Length: 11 Days

  From: Bridgetown, Barbados

   To: Bridgetown, Barbados

Prices From $8,459
Prices are in USD
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7-Day Luxury Voyage from San Juan to Charlotte Amalie, St. Thomas: Grand Island Adventure Waitlisted

Grand Island Adventure
Puerto Rico

  Dates: February 14 - February 21, 2026

  Length: 7 Days

  From: San Juan

   To: Charlotte Amalie, St. Thomas

Prices From $5,719
Prices are in USD
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7-Day Cruise from Bridgetown, Barbados to Philipsburg: Windward Islands Explorer Availability Limited

Windward Islands Explorer Club Voyage
Barbados

  Dates: February 22 - March 01, 2026

  Length: 7 Days

  From: Bridgetown, Barbados

   To: Philipsburg

Prices From $5,419
Prices are in USD
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7-Day Luxury Voyage from Charlotte Amalie, St. Thomas to Charlotte Amalie, St. Thomas: British Islands Discovery

British Islands Discovery
U.S.V.I.

  Dates: February 28 - March 07, 2026

  Length: 7 Days

  From: Charlotte Amalie, St. Thomas

   To: Charlotte Amalie, St. Thomas

Prices From $5,019
Prices are in USD
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7-Day Luxury Cruise from Philipsburg to Charlotte Amalie, St. Thomas: Leeward Islands Discovery Availability Limited

Leeward Islands Discovery
Sint Maarten, Dutch Caribbean

  Dates: March 08 - March 15, 2026

  Length: 7 Days

  From: Philipsburg

   To: Charlotte Amalie, St. Thomas

Prices From $5,719
Prices are in USD
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7-Day Luxury Voyage from San Juan to San Juan: Leeward Islands Adventure

Leeward Islands Adventure
Puerto Rico

  Dates: March 14 - March 21, 2026

  Length: 7 Days

  From: San Juan

   To: San Juan

Prices From $5,419
Prices are in USD
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7-Day Cruise from Bridgetown, Barbados to San Juan: Windward & British Virgin Islands

Windward & British Virgin Islands
Barbados

  Dates: March 22 - March 29, 2026

  Length: 7 Days

  From: Bridgetown, Barbados

   To: San Juan

Prices From $4,819
Prices are in USD
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7-Day Luxury Voyage from Charlotte Amalie, St. Thomas to Charlotte Amalie, St. Thomas: Best of British Virgin Isles & St. Barths

Best of British Virgin Isles & St. Barths
U.S.V.I.

  Dates: March 28 - April 04, 2026

  Length: 7 Days

  From: Charlotte Amalie, St. Thomas

   To: Charlotte Amalie, St. Thomas

Prices From $5,719
Prices are in USD
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14-Day Cruise from Philipsburg to Malaga: Transatlantic Spring Voyage I

Transatlantic Spring Voyage I
Sint Maarten, Dutch Caribbean

  Dates: April 18 - May 02, 2026

  Length: 14 Days

  From: Philipsburg

   To: Malaga

Prices From $5,359
Prices are in USD
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13-Day Luxury Voyage from Malaga to Philipsburg: Transatlantic Autumn Voyage I Availability Limited

Transatlantic Autumn Voyage I
Spain

  Dates: November 01 - November 14, 2026

  Length: 13 Days

  From: Malaga

   To: Philipsburg

Prices From $5,519
Prices are in USD
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7-Day Cruise from Philipsburg to Bridgetown, Barbados: British & French Islands Discovery

British & French Islands Discovery
Sint Maarten, Dutch Caribbean

  Dates: November 14 - November 21, 2026

  Length: 7 Days

  From: Philipsburg

   To: Bridgetown, Barbados

Prices From $4,819
Prices are in USD
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8-Day Luxury Voyage from San Juan to Charlotte Amalie, St. Thomas: Best of British Virgin Islands & St. Barths

Best of British Virgin Islands & St. Barths
Puerto Rico

  Dates: November 27 - December 05, 2026

  Length: 8 Days

  From: San Juan

   To: Charlotte Amalie, St. Thomas

Prices From $5,479
Prices are in USD
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7-Day Luxury Cruise from Bridgetown, Barbados to St. John's, Antigua: West Indies Explorer

West Indies Explorer
Barbados

  Dates: November 28 - December 05, 2026

  Length: 7 Days

  From: Bridgetown, Barbados

   To: St. John's, Antigua

Prices From $4,819
Prices are in USD
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7-Day Cruise from San Juan to Charlotte Amalie, St. Thomas: Spanish & British Caribbean Delight

Spanish & British Caribbean Delight
Puerto Rico

  Dates: December 12 - December 19, 2026

  Length: 7 Days

  From: San Juan

   To: Charlotte Amalie, St. Thomas

Prices From $4,819
Prices are in USD
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7-Day Luxury Voyage from Charlotte Amalie, St. Thomas to San Juan: St. Barths & Caribbean Gems

St. Barths & Caribbean Gems
U.S.V.I.

  Dates: December 12 - December 19, 2026

  Length: 7 Days

  From: Charlotte Amalie, St. Thomas

   To: San Juan

Prices From $4,819
Prices are in USD
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7-Day Luxury Voyage from San Juan to Charlotte Amalie, St. Thomas: Tropical New Year's II

Tropical New Year's II
Puerto Rico

  Dates: December 27 - January 03, 2027

  Length: 7 Days

  From: San Juan

   To: Charlotte Amalie, St. Thomas

Prices From $10,419
Prices are in USD
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7-Day Cruise from San Juan to Philipsburg: Best of British Virgin Isles & St. Barths

Best of British Virgin Isles & St. Barths Club Voyage
Puerto Rico

  Dates: November 20 - November 27, 2027

  Length: 7 Days

  From: San Juan

   To: Philipsburg

Prices From $3,419
Prices are in USD
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7-Day Cruise from Charlotte Amalie, St. Thomas to Philipsburg: St. Barths & Caribbean Gems

St. Barths & Caribbean Gems Club Voyage
U.S.V.I.

  Dates: November 21 - November 28, 2027

  Length: 7 Days

  From: Charlotte Amalie, St. Thomas

   To: Philipsburg

Prices From $3,419
Prices are in USD
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7-Day Luxury Voyage from Philipsburg to San Juan: British & French Islands Explorer

British & French Islands Explorer
Sint Maarten, Dutch Caribbean

  Dates: November 27 - December 04, 2027

  Length: 7 Days

  From: Philipsburg

   To: San Juan

Prices From $3,419
Prices are in USD
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7-Day Luxury Voyage from Philipsburg to Bridgetown, Barbados: St. Barths & Caribbean Gems

St. Barths & Caribbean Gems
Sint Maarten, Dutch Caribbean

  Dates: November 28 - December 05, 2027

  Length: 7 Days

  From: Philipsburg

   To: Bridgetown, Barbados

Prices From $3,719
Prices are in USD
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7-Day Luxury Voyage from Charlotte Amalie, St. Thomas to Philipsburg: St. Barths & Caribbean Gems

St. Barths & Caribbean Gems
U.S.V.I.

  Dates: February 27 - March 05, 2028

  Length: 7 Days

  From: Charlotte Amalie, St. Thomas

   To: Philipsburg

Prices From $3,419
Prices are in USD
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7-Day Luxury Cruise from Philipsburg to Philipsburg: Best of British Virgin Isles & St. Barths

Best of British Virgin Isles & St. Barths
Sint Maarten, Dutch Caribbean

  Dates: March 05 - March 12, 2028

  Length: 7 Days

  From: Philipsburg

   To: Philipsburg

Prices From $3,619
Prices are in USD
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7-Day Luxury Voyage from Philipsburg to Charlotte Amalie, St. Thomas: Best of the Virgin Isles & St. Barths

Best of the Virgin Isles & St. Barths
Sint Maarten, Dutch Caribbean

  Dates: March 12 - March 19, 2028

  Length: 7 Days

  From: Philipsburg

   To: Charlotte Amalie, St. Thomas

Prices From $3,419
Prices are in USD
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7-Day Luxury Voyage from Charlotte Amalie, St. Thomas to Philipsburg: St. Barths & Caribbean Gems

St. Barths & Caribbean Gems
U.S.V.I.

  Dates: March 26 - April 02, 2028

  Length: 7 Days

  From: Charlotte Amalie, St. Thomas

   To: Philipsburg

Prices From $3,419
Prices are in USD
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6-Day Luxury Cruise from Philipsburg to Marigot: St. Barths & Caribbean Gems

St. Barths & Caribbean Gems Club Voyage
Sint Maarten, Dutch Caribbean

  Dates: April 02 - April 08, 2028

  Length: 6 Days

  From: Philipsburg

   To: Marigot

Prices From $3,559
Prices are in USD
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12-Day Luxury Voyage from Lisbon to Philipsburg: Transatlantic Autumn Voyage II

Transatlantic Autumn Voyage II
Portugal

  Dates: November 20 - December 02, 2028

  Length: 12 Days

  From: Lisbon

   To: Philipsburg

Prices From $4,479
Prices are in USD
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