1. Home
  2. Find a cruise
  3. ROAD BAY, ANGUILLA cruises

ROAD BAY, ANGUILLA cruises 77 ROAD BAY, ANGUILLA cruises

Your search Clear selections

Any Destination
All Sail Months
Any Length
ROAD BAY, ANGUILLA
Any Cruise Line
Any Ship

Close

77 cruises found

Filters Save search

Sort by

Filter by

Save search

Ports

  • San Juan, Puerto Rico
  • Cruz Bay, St. John, U.S.V.I.
  • WHITE BAY, JOST VAN DYKE, B.V.I.
  • ROAD BAY, ANGUILLA
  • Gustavia, St. Barthelemy
  • LOVANGO CAY, ST. JOHN, U.S.V.I.
  • Charlotte Amalie, St. Thomas
View more ports

Ports

San Juan, Puerto Rico - Cruz Bay, St. John, U.S.V.I. - WHITE BAY, JOST VAN DYKE, B.V.I. - ROAD BAY, ANGUILLA - Gustavia, St. Barthelemy - LOVANGO CAY, ST. JOHN, U.S.V.I. - Charlotte Amalie, St. Thomas - View more ports

SeaDream I S

4.9
(3 Reviews)

2025 sail dates:

$3999*
$571/night*
Oceanview
View Deal
$3999* luxuryonly.com $3999* cruisesonly.com $3999* cruises.com $3999* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Read all 3 SeaDream I reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
See Offers

N/A

$3999*

N/A

$7999*

See Offers

N/A

$3999*

N/A

$7999*

See Offers

N/A

$3999*

N/A

$7999*

 

N/A

$3999*

N/A

$7999*

Ports

  • Charlotte Amalie, St. Thomas
  • Cruz Bay, St. John, U.S.V.I.
  • WHITE BAY, JOST VAN DYKE, B.V.I.
  • ROAD BAY, ANGUILLA
  • Gustavia, St. Barthelemy
  • SOUTH FRIARS BAY, ST. KITTS
  • Philipsburg, St. Maarten
View more ports

Ports

Charlotte Amalie, St. Thomas - Cruz Bay, St. John, U.S.V.I. - WHITE BAY, JOST VAN DYKE, B.V.I. - ROAD BAY, ANGUILLA - Gustavia, St. Barthelemy - SOUTH FRIARS BAY, ST. KITTS - Philipsburg, St. Maarten - View more ports

SeaDream I S

4.9
(3 Reviews)

2025 sail dates:

$3999*
$571/night*
Oceanview
View Deal
$3999* luxuryonly.com $3999* cruisesonly.com $3999* cruises.com $3999* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Read all 3 SeaDream I reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
See Offers

N/A

$3999*

N/A

$7999*

See Offers

N/A

$3999*

N/A

$7999*

See Offers

N/A

$3999*

N/A

$7999*

 

N/A

$3999*

N/A

$7999*

Ports

  • San Juan, Puerto Rico
  • Culebra, Puerto Rico
  • Vieques, Puerto Rico
  • Prickly Pear Island, B.V.I.
  • Gustavia, St. Barthelemy
  • ROAD BAY, ANGUILLA
  • SOUTH FRIARS BAY, ST. KITTS
  • St. Eustatius, Netherlands Special Municipality
  • Falmouth Harbour,Antigua
  • Philipsburg, St. Maarten
View more ports

Ports

San Juan, Puerto Rico - Culebra, Puerto Rico - Vieques, Puerto Rico - Prickly Pear Island, B.V.I. - Gustavia, St. Barthelemy - ROAD BAY, ANGUILLA - SOUTH FRIARS BAY, ST. KITTS - St. Eustatius, Netherlands Special Municipality - Falmouth Harbour,Antigua - Philipsburg, St. Maarten - View more ports

SeaDream I S

4.9
(3 Reviews)

2025 sail dates:

$3999*
$571/night*
Oceanview
View Deal
$3999* luxuryonly.com $3999* cruisesonly.com $3999* cruises.com $3999* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Read all 3 SeaDream I reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
See Offers

N/A

$3999*

N/A

$7999*

See Offers

N/A

$3999*

N/A

$7999*

See Offers

N/A

$3999*

N/A

$7999*

 

N/A

$3999*

N/A

$7999*

Ports

  • Philipsburg, St. Maarten
  • ROAD BAY, ANGUILLA
  • SOUTH FRIARS BAY, ST. KITTS
  • Charlestown, Nevis
  • Gustavia, St. Barthelemy
  • Prickly Pear Island, B.V.I.
  • LOVANGO CAY, ST. JOHN, U.S.V.I.
  • San Juan, Puerto Rico
View more ports

Ports

Philipsburg, St. Maarten - ROAD BAY, ANGUILLA - SOUTH FRIARS BAY, ST. KITTS - Charlestown, Nevis - Gustavia, St. Barthelemy - Prickly Pear Island, B.V.I. - LOVANGO CAY, ST. JOHN, U.S.V.I. - San Juan, Puerto Rico - View more ports

SeaDream I S

4.9
(3 Reviews)

2025 sail dates:

$3999*
$571/night*
Oceanview
View Deal
$3999* luxuryonly.com $3999* cruisesonly.com $3999* cruises.com $3999* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Read all 3 SeaDream I reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
See Offers

N/A

$3999*

N/A

$7999*

See Offers

N/A

$3999*

N/A

$7999*

See Offers

N/A

$3999*

N/A

$7999*

 

N/A

$3999*

N/A

$7999*

Ports

  • Charlotte Amalie, St. Thomas
  • LOVANGO CAY, ST. JOHN, U.S.V.I.
  • Prickly Pear Island, B.V.I.
  • Gustavia, St. Barthelemy
  • ROAD BAY, ANGUILLA
  • Charlestown, Nevis
  • Norman Island, B.V.I.
  • Spanish Town, Virgin Gorda, B.V.I.
  • San Juan, Puerto Rico
View more ports

Ports

Charlotte Amalie, St. Thomas - LOVANGO CAY, ST. JOHN, U.S.V.I. - Prickly Pear Island, B.V.I. - Gustavia, St. Barthelemy - ROAD BAY, ANGUILLA - Charlestown, Nevis - Norman Island, B.V.I. - Spanish Town, Virgin Gorda, B.V.I. - San Juan, Puerto Rico - View more ports

SeaDream I S

4.9
(3 Reviews)

2026 sail dates:

$3999*
$571/night*
Oceanview
View Deal
$3999* luxuryonly.com $3999* cruisesonly.com $3999* cruises.com $3999* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Read all 3 SeaDream I reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
See Offers

N/A

$3999*

N/A

$7999*

See Offers

N/A

$3999*

N/A

$7999*

See Offers

N/A

$3999*

N/A

$7999*

 

N/A

$3999*

N/A

$7999*

Ports

  • Pointe-A-Pitre, Guadeloupe
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Falmouth Harbour,Antigua
  • Barbuda, Barbuda
  • Charlestown, Nevis
  • Gustavia, St. Barthelemy
  • ROAD BAY, ANGUILLA
  • Prickly Pear Island, B.V.I.
  • Marigot, Saint Martin
View more ports

Ports

Pointe-A-Pitre, Guadeloupe - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Falmouth Harbour,Antigua - Barbuda, Barbuda - Charlestown, Nevis - Gustavia, St. Barthelemy - ROAD BAY, ANGUILLA - Prickly Pear Island, B.V.I. - Marigot, Saint Martin - View more ports

Le Ponant S

2026 sail dates: Feb 07, Mar 07, Apr 04 More

$7460*
$1066/night*
Oceanview
View Deal
$7460* luxuryonly.com $7460* cruisesonly.com $7460* cruises.com $7460* americandiscountcruises.com $7460* dreamvacations.com $7460* americandiscountvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Ports

  • San Juan, Puerto Rico
  • LOVANGO CAY, ST. JOHN, U.S.V.I.
  • Prickly Pear Island, B.V.I.
  • Gustavia, St. Barthelemy
  • ROAD BAY, ANGUILLA
  • Charlestown, Nevis
  • SOUTH FRIARS BAY, ST. KITTS
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Port Elizabeth, Bequia, Grenadines
  • Tobago Cays, Grenadines
  • Bridgetown, Barbados
View more ports

Ports

San Juan, Puerto Rico - LOVANGO CAY, ST. JOHN, U.S.V.I. - Prickly Pear Island, B.V.I. - Gustavia, St. Barthelemy - ROAD BAY, ANGUILLA - Charlestown, Nevis - SOUTH FRIARS BAY, ST. KITTS - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Port Elizabeth, Bequia, Grenadines - Tobago Cays, Grenadines - Bridgetown, Barbados - View more ports

SeaDream I S

4.9
(3 Reviews)

2026 sail dates:

$5699*
$570/night*
Oceanview
View Deal
$5699* luxuryonly.com $5699* cruisesonly.com $5699* cruises.com $5699* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Read all 3 SeaDream I reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
See Offers

N/A

$5699*

N/A

$11399*

See Offers

N/A

$5699*

N/A

$11399*

See Offers

N/A

$5699*

N/A

$11399*

 

N/A

$5699*

N/A

$11399*

Ports

  • Charlotte Amalie, St. Thomas
  • Cruz Bay, St. John, U.S.V.I.
  • Prickly Pear Island, B.V.I.
  • ROAD BAY, ANGUILLA
  • Gustavia, St. Barthelemy
  • Charlestown, Nevis
  • SOUTH FRIARS BAY, ST. KITTS
  • Falmouth Harbour,Antigua
  • Philipsburg, St. Maarten
View more ports

Ports

Charlotte Amalie, St. Thomas - Cruz Bay, St. John, U.S.V.I. - Prickly Pear Island, B.V.I. - ROAD BAY, ANGUILLA - Gustavia, St. Barthelemy - Charlestown, Nevis - SOUTH FRIARS BAY, ST. KITTS - Falmouth Harbour,Antigua - Philipsburg, St. Maarten - View more ports

SeaDream II S

4.3
(7 Reviews)

2026 sail dates:

$3999*
$571/night*
Oceanview
View Deal
$3999* luxuryonly.com $3999* cruisesonly.com $3999* cruises.com $3999* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Read all 7 SeaDream II reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
See Offers

N/A

$3999*

N/A

$7999*

See Offers

N/A

$3999*

N/A

$7999*

See Offers

N/A

$3999*

N/A

$7999*

 

N/A

$3999*

N/A

$7999*

Ports

  • Philipsburg, St. Maarten
  • Little Bay, Montserrat
  • Roseau, Dominica
  • Castries, St. Lucia
  • Mayreau, Grenadines
  • St. George's, Grenada
  • Bequia, Grenadines
  • Anse Mitan, Martinique
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Gustavia, St. Barthelemy
  • Jost Van Dyke, B.V.I.
  • Soper's Hole, Tortola, B.V.I.
  • Spanish Town, Virgin Gorda, B.V.I.
  • ROAD BAY, ANGUILLA
  • Falmouth Harbour,Antigua
View more ports

Ports

Philipsburg, St. Maarten - Little Bay, Montserrat - Roseau, Dominica - Castries, St. Lucia - Mayreau, Grenadines - St. George's, Grenada - Bequia, Grenadines - Anse Mitan, Martinique - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Gustavia, St. Barthelemy - Jost Van Dyke, B.V.I. - Soper's Hole, Tortola, B.V.I. - Spanish Town, Virgin Gorda, B.V.I. - ROAD BAY, ANGUILLA - Falmouth Harbour,Antigua - View more ports

Wind Spirit S

4.5
(20 Reviews)

2026 sail dates:

$4799*
$282/night*
Oceanview
View Deal
$4799* luxuryonly.com $4799* cruisesonly.com $4799* cruises.com $4799* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Read all 20 Wind Spirit reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
See Offers

N/A

$4799*

N/A

$11699*

See Offers

N/A

$4799*

N/A

$11699*

See Offers

N/A

$4799*

N/A

$11699*

 

N/A

$4799*

N/A

$11699*

Ports

  • Philipsburg, St. Maarten
  • Soper's Hole, Tortola, B.V.I.
  • Jost Van Dyke, B.V.I.
  • Spanish Town, Virgin Gorda, B.V.I.
  • Gustavia, St. Barthelemy
  • ROAD BAY, ANGUILLA
  • Falmouth Harbour,Antigua
View more ports

Ports

Philipsburg, St. Maarten - Soper's Hole, Tortola, B.V.I. - Jost Van Dyke, B.V.I. - Spanish Town, Virgin Gorda, B.V.I. - Gustavia, St. Barthelemy - ROAD BAY, ANGUILLA - Falmouth Harbour,Antigua - View more ports

Wind Spirit S

4.5
(20 Reviews)

2026 sail dates: Jan 24, Feb 14

$2499*
$357/night*
Oceanview
View Deal
$2499* luxuryonly.com $2499* cruisesonly.com $2499* cruises.com $2499* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Read all 20 Wind Spirit reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
See Offers

N/A

$2499*

N/A

$5999*

See Offers

N/A

$2499*

N/A

$5999*

See Offers

N/A

$2499*

N/A

$5999*

 

N/A

$2499*

N/A

$5999*

See Offers

N/A

$2499*

N/A

$5999*

See Offers

N/A

$2499*

N/A

$5999*

See Offers

N/A

$2499*

N/A

$5999*

 

N/A

$2499*

N/A

$5999*

See Offers

N/A

$2599*

N/A

$6099*

See Offers

N/A

$2599*

N/A

$6099*

See Offers

N/A

$2599*

N/A

$6099*

 

N/A

$2599*

N/A

$6099*

41 - 50 of 77

All prices are per person based on double occupancy and do not include port/government fees and gratuities.