Have questions? We're here.
San Juan, Puerto Rico

San Juan Small Ship Cruises & Tours

Travel made your way
Talk with an expert
Build your ideal Caribbean trip. Call 1.406.541.2677
Start Planning My Trip
Visit the remarkable capital and largest city of Puerto Rico, with a population of nearly 400,000 inhabitants: San Juan. Take a long walk in the downtown section of "Old San Juan" and take a sample of the original Piña Colada or visit the Paseo de la Princesa. Tour the well-known castles of San Felipe del Morro and San Cristobal, both with great coastal views of the crystal clear the Caribbean Sea. Travel on a small ship cruise that allows access to smaller coves, reefs, and ports to improve your Caribbean experience. Or combine your trip to San Juan with a trip to other Caribbean islandsContact Adventure Life's travel experts now to begin planning your personalized trip today!
All San Juan Small Ship Cruises

Top 9 San Juan Small Ship Cruises & Tours for 2025-2026

All San Juan Small Ship Cruises

Top 8 San Juan Small Ship Cruise Deals for 2025-2026

Trip Name From Days Summary
Quintessential Caribbean $7,990 8 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.
0
Caribbean Yachting Hideaways $8,390 8 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.
0
Caribbean Yachting Discovery $7,990 8 Set sail on an 8-day cruise aboard the Emerald Azzurra, uncovering pristine beaches and vibrant coral reefs while island-hopping through a tapestry of diverse cultures. Let the genuine warmth of the locals add a personal touch to your luxurious yacht adventure.
0
Caribbean Escapade $7,590 8 Set sail on an 8-day Caribbean cruise aboard the Emerald Sakara. Explore Grand Turk's pristine beaches and historic landmarks, discover Long Island's tranquil Gordon's Beach, and dive into San Salvador's vibrant coral reefs and historic sites.
0
Splendours of the Caribbean $9,190 7 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.
0
Quintessential Caribbean $9,990 8 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.
0
Discover the Yachting Islands of the Caribbean $21,180 15 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.
0
Discover the Yachting Islands of the Caribbean $21,980 15 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.
0
All Caribbean Articles

San Juan Travel Guide

The Best Time to Visit San Juan

Between mid-December and June is the best time to visit San Juan. This is the high season, so lodging will be more expensive and there will be larger crowds throughout the popular destinations in the city, but the temperature is extremely comfortable and there's the most to do in the city during these months. As the season wanes on toward April and June, lodging prices will begin to drop as crowds begin to dwindle - and these months are considered the absolute best time to visit San Juan.

Between July and September is the worst time to visit San Juan. Prices and crowds will be at their lowest, but quite a few hotels will be closed due to the upcoming hurricane season. Additionally, it will be warm and humid and you should expect rain, especially going into August. 

Between October and mid-December is an excellent time to visit San Juan. The prices on hotels and airfare are down and crowds haven't begun getting too big yet. The temperature is extremely comfortable and there will be little-to-no-rain. The only downside is some restaurants and hotels may not be done getting remodeled after the extended off-season.

Best San Juan, Puerto Rico Small Ship Cruise Line for 2025-2026
 

  • Emerald Cruises - offers luxury yacht voyages through the Caribbean, visiting Puerto Rico, the Virgin Islands, and St. Lucia, with San Juan as a highlight for its historic charm and one of the region’s finest natural harbors. Aboard the Emerald Sakara, a 110-meter superyacht for just 100 guests, travelers enjoy spacious lounges, intimate gathering spaces, and locally inspired cuisine with complimentary wines and drinks for an exceptional small-ship cruising experience.


 

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