Have questions? We're here.
Relax on the pristine beaches of the Virgin Islands

Top St John Cruises & Trips

Travel made your way
Talk with an expert
Build your ideal Caribbean trip. Call 1.406.541.2677
Start Planning My Trip
Explore these 9 top St John cruises for 2026 and 2027. Some of the most popular activities on our St John trips include Archaeological Site Visits, Local Market Visits, Snorkeling, Village Visits, and Wildlife Viewing. Discover with your expert local English-speaking guides who will show you the hot spots and the off-the-beaten-path hidden gems. We work with only the best small ships that carry under 500 fortunate guests, and we can give you unbiased advice to match you with the perfect ship and perfect cruise for your next vacation. Our St John cruises start from $4,800 for cruises of 7 to 22 days. Contact one of Adventure Life's St John cruise specialists for help planning a seamless trip.
Filter (9 Results)
  • Start Date
    OR, More specific start
  • Length
    to
  • Price
    to
  • Activity Levels
  • Experiences
  • Activities
  • Ships
  • Destinations
    • St John
Explore the famous rock formations of the baths
from $9,190
OBC
EXPLORE

Splendours of the Caribbean

San Juan - St. Thomas - 7 Day Itinerary aboard Emerald Sakara
  • Tour Nelson’s Dockyard
  • Explore Nevis Island plantations
  • Walk through Gustavia
  • Swim Prickly Pear Cays
Starts / Ends
San Juan / St. Thomas
Activities
Urban Exploration
Activity Level
Variable
Sail through the Caribbean on a 7-day cruise aboard Emerald Sakara, from San Juan to Saint Thomas. Visit Saint John, Nevis, Antigua, Saint Barthelemy, and Virgin Gorda. Discover colonial towns, quiet beaches, and historic sites.
Cruise Details
0
Explore beautiful Jost van Dyke
from $8,390
OBC
EXPLORE

Caribbean Yachting Hideaways

San Juan - St John's - 8 Day Itinerary aboard Emerald Azzurra
  • Discover Culebra Island’s shores
  • Explore Vieques Island waterfront
  • Tour St. John’s Annaberg ruins
  • Relax on Jost Van Dyke’s White Bay
Starts / Ends
San Juan / St. John's
Activities
Hiking
Activity Level
Variable
Set sail on an 8-day cruise from San Juan to St. John aboard the Emerald Azzurra, exploring stunning beaches and vibrant island towns. Visit highlights like Culebra, Vieques, and Saint Barthelemy while enjoying premium comfort and seamless access to diverse ports.
Cruise Details
0
Willemstad, Curacao
from $4,800
EXPLORE

San Juan to Bridgetown

San Juan - Bridgetown - 8 Day Itinerary aboard Silver Spirit
  • Explore Historic San Juan
  • Snorkel Trunk Bay Reefs
  • Stroll Willemstad Waterfront
  • Explore Bridgetown
Starts / Ends
San Juan / Bridgetown
Activities
Local Market Visits, Archaeological Site Visits, Snorkeling, Spa Relaxation, Wildlife Viewing, Whale Watching
Activity Level
Variable
Set sail on an 8-day Silver Spirit voyage from San Juan to Bridgetown. Discover Caribbean charm in St. John’s national park, Nevis’s golden beaches, Bonaire’s vibrant reefs, and Curaçao’s colorful Dutch heritage. Enjoy time at sea before disembarking in Bridgetown, where rich culture meets island beauty.
Cruise Details
0
Visit beautiful Norman Island
from $9,990
OBC
EXPLORE

Vibes of the Virgin Islands

St Thomas Roundtrip - 8 Day Itinerary aboard Emerald Sakara
  • Explore Saint John's pristine beach
  • Stroll Philipsburg's lively markets
  • Snorkel Norman Island's caves
  • Visit 'The Baths' in Virgin Gorda
Starts / Ends
St. Thomas / St. Thomas
Activity Level
Variable
Set sail on an 8-day Caribbean cruise aboard Emerald Sakara from Saint Thomas to discover the Caribbean’s finest destinations. Explore the stunning beaches of Virgin Gorda, snorkel in Norman Island’s clear waters, and experience Anguilla’s vibrant beauty.
Cruise Details
0
The Southeast Peninsula of Saint Kitts with Nevis in the Background
from $9,990
OBC
EXPLORE

Quintessential Caribbean

St Thomas - San Juan - 8 Day Itinerary aboard Emerald Sakara
  • Explore Cruz Bay town
  • Visit Nevis plantations
  • Discover Nelson’s Dockyard
  • Swim Prickly Pear Cays
Starts / Ends
St. Thomas / San Juan
Activity Level
Variable
Explore the Caribbean on an 8-day cruise from Saint Thomas to San Juan aboard Emerald Sakara. Visit Saint John, Nevis, Guadeloupe, Antigua, Saint Barthélemy, and the British Virgin Islands. Discover UNESCO-listed landmarks, swim in clear waters, and experience regional architecture, food, and history throughout the journey.
Cruise Details
0
Islands of the Caribbean
from $7,990
OBC
EXPLORE

Quintessential Caribbean

San Juan - St Thomas - 8 Day Itinerary aboard Emerald Sakara
  • Relax on Prickly Pear Cays' beaches
  • Visit Guadeloupe’s fishing village
  • Visit port of Falmouth Harbor
  • Wander through lively Cruz Bay
Starts / Ends
San Juan / St. Thomas
Activity Level
Variable
Embark on an 8-day Caribbean cruise aboard the Emerald Sakara. Explore the vibrant culture of San Juan, the charm of Saint John, the tranquil beaches of Nevis, the picturesque village of Deshaies, the historic allure of Falmouth Harbor, the lively streets of Gustavia, and the pristine beauty of Prickly Pear Cays.
Cruise Details
0
Caribbean landscapes and harbors
from $21,980
OBC
EXPLORE

Discover the Yachting Islands of the Caribbean

Roundtrip Saint John’s - 15 Day Itinerary aboard Emerald Azzurra
  • Explore Barbuda’s iconic pink sands
  • Visit Les Saintes’ quaint towns
  • Discover Deshaies’ lush hills
  • Swim off Norman Island’s shores
Starts / Ends
St. John's / St. John's
Activity Level
Variable
Embark on a 15-day cruise with Emerald Azzurra, exploring the Caribbean from St. John’s, Antigua, with stops at stunning destinations like Barbuda, Guadeloupe, and the British Virgin Islands. Enjoy snorkeling in Culebra and the relaxed vibe of Esperanza on Vieques, all amidst beautiful beaches and vibrant island culture.
Cruise Details
0
Learn about Spanish colonial history in Old San Juan
from $21,980
OBC
EXPLORE

Discover the Yachting Islands of the Caribbean

Roundtrip San Juan - 15 Day Itinerary aboard Emerald Azzurra
  • Snorkel Culebra’s coral reefs
  • Wander Vieques’ Esperanza
  • Explore St. John’s plantation ruins
  • Stroll Philipsburg’s streets
Starts / Ends
San Juan / San Juan
Activities
Village Visits, Kayaking
Activity Level
Variable
Embark on a 15-day Caribbean cruise from San Juan aboard Emerald Azzurra, exploring serene spots like Culebra, Vieques, and St. Barts. Experience stunning beaches, rich culture, and scenic ports, all in a relaxed yacht-style setting.
Cruise Details
0
Relax on the pristine beaches of the Virgin Islands
from $11,600
EXPLORE

Bridgetown to Bridgetown

22 Day Itinerary aboard Silver Spirit
  • Explore top Caribbean islands
  • Visit Bequia and Iles des Saintes
  • Explore Gustavia’s historic harbor
  • Experience the Caribbean culture
Starts / Ends
Bridgetown / Bridgetown
Activity Level
Variable
Sail round-trip from Bridgetown aboard Silver Spirit on a 22-day Caribbean cruise. Explore top islands like St. Lucia, Martinique, and Barbados, plus hidden gems like Bequia and Iles des Saintes. Enjoy beach days, island tours, and cultural stops with long port calls.
Cruise Details
0
1-9 of 9 Results
  • 1

Caribbean Travel Guide

Favorite Caribbean Caribbean All Trips

Top Caribbean Travel Destinations

Caribbean Trips by Departure Date

Top Experiences in Caribbean

Caribbean Trips by Duration

Caribbean Trips by Activity

More Reasons

Why Travel With Adventure Life

All News

Recognized By