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Discover incredible history and culture in Puerto Rico

Top Puerto Rico Trips & Tours

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Select one of the below 5 best Puerto Rico trips for 2025 and 2026. Your local English-speaking guide will lead your small group or personalized private tour on an extraordinary adventure exploring San Juan, Culebra, and Vieques. Our Puerto Rico trips for 2025 feature Small Ship Sailing, Local Market Visits, Village Visits, Archaeological Site Visits, and Hiking, and start from $5,245 for trips of 8 days. Contact Adventure Life's Puerto Rico trip planning experts to start planning your next seamless trip.
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Explore the famous rock formations of the baths
from $5,245
EXPLORE

A Colorful Caribbean Time-Out

San Juan Roundtrip - 8 Day Itinerary aboard Sea Cloud Spirit
Starts / Ends
San Juan / San Juan
Activity Level
Variable
Embark on an 8-day cruise aboard Sea Cloud Spirit sailing to explore Old San Juan's historic charm. Wander streets lined with colorful facades and salsa-filled cafes. Discover UNESCO-listed sites like La Fortaleza and Fort San Felipe del Morro, resonating with centuries of history and cultural vibrancy.
  • Explore Old San Juan's forts
  • Enjoy salsa music
  • Sail in the British Virgin Islands
  • Explore unique rock formations
Cruise Details
0
Explore beautiful Jost van Dyke
from $8,390
2for1
EXPLORE

Caribbean Yachting Hideaways

San Juan - St John's - 8 Day Itinerary aboard Emerald Azzurra
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.
  • Discover Culebra Island’s shores
  • Explore Vieques Island waterfront
  • Tour St. John’s Annaberg ruins
  • Relax on Jost Van Dyke’s White Bay
Cruise Details
0
Explore the famous rock formations of the baths
from $7,990
2for1
EXPLORE

Quintessential Caribbean

San Juan - St Thomas - 8 Day Itinerary aboard Emerald Sakara
Starts / Ends
San Juan / St. Thomas
Activities
Archaeological Site Visits
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.
  • Relax on Prickly Pear Cays' beaches
  • Visit Guadeloupe’s fishing village
  • Visit port of Falmouth Harbor
  • Wander through lively Cruz Bay
Cruise Details
0
Nassau Lighthouse
from $7,590
2for1
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Caribbean Escapade

San Juan - Miami - 8 Day Itinerary aboard Emerald Sakara
Starts / Ends
San Juan / Miami
Activities
Small Ship Sailing, Local Market Visits, Snorkeling, Kayaking
Activity Level
Variable
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.
  • Explore the pristine beaches
  • Snorkel in crystal-clear waters
  • Relax on secluded Gordon’s Beach
  • Explore Grand Turk’s beaches
Cruise Details
0
St Barts harbor view
from $7,990
2for1
EXPLORE

Caribbean Yachting Discovery

St John's - San Juan - 8 Day Itinerary aboard Emerald Azzurra
Starts / Ends
St. John's / San Juan
Activities
Village Visits, Wildlife Viewing
Activity Level
Variable
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.
  • Explore Barbuda's pink beaches
  • Discover Deshaies’ architecture
  • Visit Gustavia’s charming boutiques
  • Experience Virgin Gorda’s baths
Cruise Details
0
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