Old San Juan Bike and History Tour with Bridge Jumping

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Old San Juan Bike and History Tour with Bridge Jumping

By I Work Where You Vacation

Free cancellation available

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Features

Free cancellation available
3h
Mobile voucher
Instant confirmation
Multiple languages

Overview

Experience the perfect blend of adventure, history, and island beauty on this three-hour guided bicycle tour from Condado to Old San Juan and back. Ride along the stunning coastline, where turquoise waters meet centuries-old walls, and feel the ocean breeze as you pedal through Puerto Rico’s most iconic sights.

You’ll glide past El Escambrón Beach’s golden sands, trace the stone ramparts of Castillo San Cristóbal, and enter the heart of Old San Juan, with its cobblestone streets, colourful colonial buildings, and views of La Puerta de San Juan and the legendary El Morro fortress. Along the way, take in the vibrant spirit of La Perla, where murals and music bring the seaside cliffs to life.

The tour ends with a splash—literally—as you cool off with an optional jump from Puente Dos Hermanos into the crystal-clear waters of the Condado Lagoon. It’s the perfect mix of culture, scenery, and thrill—a ride that captures the very soul of San Juan, its people and culture.

Activity location

Old San Juan
- San Juan, Caribbean

Meeting/Redemption Point

1043 Ashford Ave
- 1043 Ashford Avenue
- 00907, San Juan, San Juan, Caribbean

Check availability

Old San Juan Bike and History Tour with Bridge Jumping

3h
English

Travellers

Languages available

Starting time

Price details

NZ$115.91 x 1 AdultNZ$115.91

Total

What's included, what's not

Bottled water
Helmet
All guests will use our Mountain Bikes which will make riding in the city as easy as possible
Alcoholic Drinks
Meals

Know before you book

Public transport options are available nearby
Not recommended for travellers with spinal injuries
Not recommended for pregnant travellers
Not recommended for travellers with poor cardiovascular health
Suitable for all physical fitness levels

Activity itinerary

Castillo San Felipe del Morro (Pass by)

**San Felipe del Morro**, often called *El Morro*, is a historic fortress located in **San Juan, Puerto Rico**. Built by the Spanish between the **16th and 18th centuries**, it was designed to guard the entrance to **San Juan Bay** and protect the city from sea attacks. The fort features massive stone walls, ramparts, and sentry boxes (*garitas*) overlooking the Atlantic Ocean. Today, it’s a **UNESCO World Heritage Site** and part of the **San Juan National Historic Site**, attracting visitors for its impressive architecture, panoramic views, and deep colonial history.

Puente Dos Hermanos (Pass by)

**Puente Dos Hermanos** is a graceful bridge in **San Juan, Puerto Rico**, that beautifully links the vibrant **Condado** district with the historic charm of **Old San Juan**. Stretching across the tranquil **Condado Lagoon**, it offers stunning views of shimmering blue waters, lush mangroves, and the city’s skyline—especially breathtaking at sunrise and sunset. Historically, the bridge was named after the **Behn brothers**, two visionaries who helped develop Condado in the early 1900s, transforming it into one of San Juan’s most elegant areas. Though rebuilt over the years, Puente Dos Hermanos still preserves its classic charm, serving as both a scenic walkway and a symbol of connection between Puerto Rico’s natural beauty and its rich urban heritage.

Balneario El Escambron (Pass by)

**Balneario El Escambrón** is one of **San Juan’s most beautiful beaches**, blending golden sands, clear turquoise waters, and a backdrop of historic charm. Nestled near **Old San Juan**, it offers a peaceful escape where visitors can swim, snorkel among coral reefs, or simply relax under palm trees while enjoying views of the **Atlantic Ocean** and the city’s skyline. Historically, the area has long been a favourite local gathering spot, once part of the defensive zone surrounding **El Morro** and **San Cristóbal** forts. Over time, it evolved into a beloved public beach and marine reserve, balancing recreation with natural preservation. Today, **Balneario El Escambrón** stands out as a rare blend of **urban convenience, scenic beauty, and historic atmosphere**, making it one of San Juan’s most iconic coastal treasures.

Castillo de San Cristobal (Pass by)

**Castillo de San Cristóbal** is a magnificent fortress in **San Juan, Puerto Rico**, celebrated for both its historic power and breathtaking scenery. Sprawling across the eastern edge of **Old San Juan**, it rises above the Atlantic coastline, offering sweeping views of the ocean, the city’s colourful rooftops, and the distant **El Morro** fortress. Its massive stone walls, tunnels, and lookout points create a dramatic contrast with the surrounding sea and sky. Built by the **Spanish in the 18th century**, San Cristóbal was designed to defend San Juan from land-based attacks—making it the largest fortification ever built by Spain in the Americas. Today, this **UNESCO World Heritage Site** captivates visitors with its blend of **military grandeur and natural beauty**, standing as a powerful reminder of Puerto Rico’s colonial past and its enduring coastal splendour.

Old San Juan

1h 30m

**Old San Juan** is the vibrant heart of **Puerto Rico’s history and beauty**, a seven-block islet where **cobblestone streets**, **pastel-colored buildings**, and **flower-filled balconies** overlook the sparkling **Caribbean Sea**. Surrounded by ancient stone walls and crowned by fortresses like **El Morro** and **San Cristóbal**, the district blends colonial elegance with tropical charm, offering stunning views of the ocean at every turn. Founded in **1521**, Old San Juan is one of the oldest European settlements in the Americas and served as Spain’s key stronghold in the Caribbean. Today, it’s a living museum and a lively area, filled with art galleries, cafés, and music drifting through the streets. With its blend of **historic grandeur, vivid colours, and coastal beauty**, Old San Juan captures the timeless soul of Puerto Rico.

La Perla

**La Perla** is a colourful, seaside area nestled just outside the walls of **Old San Juan, Puerto Rico**, where vibrant street art and ocean waves come together in a striking display of authenticity and resilience. Perched along the rugged Atlantic coastline, its bright houses cascade down the hillside towards the sea, creating one of the island’s most unique and photogenic views—especially at sunset, when golden light bathes the murals and rooftops. Historically, **La Perla** was established in the 19th century as a community for workers and freed slaves who were not allowed to live within San Juan’s fortified walls. Though once overlooked, it has grown into a powerful symbol of **Puerto Rican culture, creativity, and community spirit**. Today, visitors are drawn to its **vivid scenery, rich music, and welcoming locals**, making La Perla a living expression of Puerto Rico’s beauty, strength, and soul.

La Puerta de San Juan (Pass by)

**La Puerta de San Juan** is one of the most iconic and picturesque landmarks in **Old San Juan, Puerto Rico**. Set within the city’s massive stone walls, this grand, crimson-colored gate once served as the **main entrance** to the fortified city. Passing through it feels like stepping back in time—beyond the gate, cobblestone streets lead to colonial plazas, centuries-old churches, and pastel-hued buildings, all framed by the gentle hum of the nearby sea. Built in the **16th century**, La Puerta welcomed governors, bishops, and royal visitors arriving by ship. Above its arch, an inscription still gives thanks to God, a reflection of the deep faith of the era. Today, it stands as a **symbol of history and endurance**, offering breathtaking views of the **San Juan Bay** and serving as a serene reminder of Puerto Rico’s colonial heritage and timeless coastal beauty.

Location

Activity location

Old San Juan
- San Juan, Caribbean

Meeting/Redemption Point

1043 Ashford Ave
- 1043 Ashford Avenue
- 00907, San Juan, San Juan, Caribbean

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