San Juan → Simpson Bay

4 nights · San Juan → Simpson Bay

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SeaDream

SeaDream

San Juan → Simpson Bay

4 nights8 portsSan Juan → Simpson BaySeaDream I

From $6,220 per person

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The Journey

Day by Day

4 nights · 8 ports

Day 1San Juan, Puerto Rico
Day 2Cruz Bay, St. John
Day 3Road Bay, Anguilla
Day 4Gustavia, St. Barths
Day 5Philipsburg, St. Maarten
Day 6Jost Van Dyke, BVI
Day 7Virgin Gorda, BVI
Day 8San Juan, Puerto Rico
San Juan, Puerto Rico
Day 1
San Juan, Puerto Rico

Five hundred years of Spanish stone at El Morro, and blue cobblestones under cafe tables in the old city.

Embark

Cruz Bay, St. John
Day 2
Cruz Bay, St. John

Two-thirds national park, with Trunk Bay and the quiet coves the crowds never quite reach.

Ashore

Road Bay, Anguilla
Day 3
Road Bay, Anguilla

Road Bay and a dozen of the whitest beaches in the Caribbean, with beach bars worth the crossing alone.

Ashore

Gustavia, St. Barths
Day 4
Gustavia, St. Barths

The red roofs and superyachts of St. Barths, shellfish lunches above the harbour and shopping to match Paris.

Ashore

Philipsburg, St. Maarten
Day 5
Philipsburg, St. Maarten

The Dutch capital on its long crescent of sand, a duty-free town with a boardwalk built for strolling.

Ashore

Jost Van Dyke, BVI
Day 6
Jost Van Dyke, BVI

A few hundred souls, one beach bar of world renown, and the clearest anchorage in the BVI.

Ashore

Virgin Gorda, BVI
Day 7
Virgin Gorda, BVI

The Baths: granite boulders the size of houses, sea pools between them, and a ladder trail through the middle.

Ashore

San Juan, Puerto Rico
Day 8
San Juan, Puerto Rico

Five hundred years of Spanish stone at El Morro, and blue cobblestones under cafe tables in the old city.

Disembark

Scroll for the full journey

Your Ship

SeaDream I

It’s yachting, not cruising: 112 guests, toys off the stern, champagne in the surf, and harbors ships never see.

SeaDream I
SeaDream I
SeaDream · 4 Nights · San Juan → Simpson Bay

It’s yachting, not cruising: 112 guests, toys off the stern, champagne in the surf, and harbors ships never see.

  • 112 guests, 95 crew
  • Watersports marina off the stern
  • Champagne-and-caviar beach splash
  • Sleep under the stars on Balinese beds

Every Suite on This Sailing

Suite Per person
Outside$6,220
Suite$12,920

Fares are per person, double occupancy, cruise only, checked 23 July 2026. Fares shown for the 16 Jan 2027 departure; other dates price differently. Suites price and sell out independently; we verify the exact fare before anything is quoted.

Departures

16 Jan 2027 · from $6,220

Ready When You Are

Sail San Juan → Simpson Bay.

From $6,220 per person, and our planning from first question to the flight home.

Fares are per person, cruise only, as returned by our booking systems for this sailing at the time of writing (checked 23 July 2026). Airfare additional unless stated. Fares are capacity-controlled and may change or be withdrawn without notice. Elevida Luxury Journeys is an independent affiliate of Travel Planners International.