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Road Bay

Anguilla

Sailings from $5,599 per person

Request a cruise here

About Road Bay

Thirty-three gorgeous white-sand beaches fringe the shores of Anguilla, a British Overseas Territory and northernmost of the Leeward Islands in the Lesser Antilles chain.

A day here

Ships usually arrive
8:00 AM
Ships usually leave
5:00 PM
Time in port
about 9 hours

Sailings that call at Road Bay

See all 10 sailings

November 2026

Seabourn · Seabourn Quest · Caribbean

14-Day Leeward Island Jewels

Nov 22, 2026 to Dec 6, 2026 · 14 nights

Round trip from Miami, Florida, US

Offers: Explore Beyond Event, The Finale Sail

Ports of call and details

From $5,599 per guest based on double occupancy

Ocean View, The Finale Sail

Taxes and fees included

Ocean View
$5,599
Veranda Suite
$6,239
Owner's Suite and Above
$19,998
Penthouse Suite
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December 2026

Seabourn · Seabourn Quest · Caribbean

14-Day Leeward Island Jewels

Dec 6, 2026 to Dec 20, 2026 · 14 nights

Round trip from Miami, Florida, US

Offers: Explore Beyond Event, The Finale Sail

Ports of call and details

From $5,599 per guest based on double occupancy

Ocean View, The Finale Sail

Taxes and fees included

Ocean View
$5,599
Veranda Suite
$6,079
Penthouse Suite
Owner's Suite and Above
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Seabourn · Seabourn Quest · Caribbean

16-Day Leeward Island Holiday

Dec 20, 2026 to Jan 5, 2027 · 16 nights

Round trip from Miami, Florida, US

Offers: Explore Beyond Event

Ports of call and details

From $10,998 per guest based on double occupancy

Ocean View, Explore Beyond Event

Taxes and fees included

Ocean View
$10,998
Veranda Suite
$11,998
Penthouse Suite
$20,998
Owner's Suite and Above
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December 2027

Seabourn · Seabourn Quest · Caribbean

14-Day Windward & Leeward Islands

Dec 4, 2027 to Dec 18, 2027 · 14 nights

Round trip from Miami, Florida, US

Offers: Explore Beyond Event

Ports of call and details

From $7,498 per guest based on double occupancy

Ocean View, Explore Beyond Event

Taxes and fees included

Ocean View
$7,498
Veranda Suite
$8,998
Penthouse Suite
$11,998
Owner's Suite and Above
$14,498
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Seabourn · Seabourn Ovation · Caribbean

17-Day Hidden Yacht Harbor Holiday

Dec 11, 2027 to Dec 28, 2027 · 17 nights

Bridgetown, Barbados to Philipsburg, Sint Maarten

Offers: Seabourn Combo Savings, Explore Beyond Event

Ports of call and details

From $11,198 per guest based on double occupancy

Veranda Suite, Seabourn Combo Savings

Taxes and fees included

Veranda Suite
$11,198
Penthouse Suite
$21,298
Penthouse Spa Suite
$23,213
Owner's Suite and Above
$25,998
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Seabourn · Seabourn Ovation · Caribbean

10-Day Caribbean Yacht Harbor Holiday

Dec 18, 2027 to Dec 28, 2027 · 10 nights

Bridgetown, Barbados to Philipsburg, Sint Maarten

Offers: Explore Beyond Event

Ports of call and details

From $7,298 per guest based on double occupancy

Veranda Suite, Explore Beyond Event

Taxes and fees included

Veranda Suite
$7,298
Penthouse Suite
$11,998
Penthouse Spa Suite
$13,078
Owner's Suite and Above
$15,698
Request this sailing

Seabourn · Seabourn Ovation · Caribbean

21-Day Bonaire, Curacao & Southern Caribbean Holiday

Dec 18, 2027 to Jan 8, 2028 · 21 nights

Round trip from Bridgetown, Barbados

Offers: Seabourn Combo Savings, Explore Beyond Event

Ports of call and details

From $14,298 per guest based on double occupancy

Veranda Suite, Seabourn Combo Savings

Taxes and fees included

Veranda Suite
$14,298
Penthouse Suite
$24,698
Owner's Suite and Above
$31,398
Penthouse Spa Suite
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Seabourn · Seabourn Quest · Caribbean

10-Day Leeward Islands Holiday

Dec 18, 2027 to Dec 28, 2027 · 10 nights

Round trip from Miami, Florida, US

Offers: Explore Beyond Event

Ports of call and details

From $7,298 per guest based on double occupancy

Ocean View, Explore Beyond Event

Taxes and fees included

Ocean View
$7,298
Veranda Suite
$7,998
Penthouse Suite
$11,298
Owner's Suite and Above
$13,298
Request this sailing

Seabourn · Seabourn Ovation · Caribbean

11-Day Yachtsman's Holiday In Aruba, Bonaire & Curacao

Dec 28, 2027 to Jan 8, 2028 · 11 nights

Philipsburg, Sint Maarten to Bridgetown, Barbados

Offers: Explore Beyond Event, Ruby Collection

Ports of call and details

From $7,698 per guest based on double occupancy

Veranda Suite, Explore Beyond Event

Taxes and fees included

Veranda Suite
$7,698
Penthouse Suite
$13,998
Penthouse Spa Suite
$15,258
Owner's Suite and Above
$17,298
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See all 10 sailings

Fares are per person, double occupancy.

Cheapest month to sail here

November 2026, from $400 a night ($5,599 for 14 nights)

  1. November 2026$400 a night
  2. December 2026$400 a night
  3. December 2027$536 a night
  4. December 2028$730 a night

Cruise lines and ships

Seabourn

Seabourn Ovation, Seabourn Quest

Seabourn sailings here

Nearby ports

All cruise ports

Cruising to Road Bay?

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