Top 12 Old San Juan Tours in Puerto Rico

1.Old San Juan Walking Tour

★★★★★★★★★★5.0 · 2,211 reviews · from $39Our pick

Walk Old San Juan with writer David Rodríguez, whose route covers Plaza Colón, San Cristóbal, the city walls, San Juan Gate, Fortaleza Street, the cathedral, and Plaza de Armas. Expect about 2 hours 15 minutes, roughly 3 miles, bottled water, plenty of history, and time for questions in a group of up to 20.

“This was a wonderful tour start to finish. David was very knowledgeable and friendly. It was around 2.5 hours and very easy to walk. Old San Juan is absolutely beautiful!”

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2.Old San Juan City Walking Tour

★★★★★★★★★★5.0 · 1,718 reviews · from $39

Spend about two hours walking from Plaza Colón to Paseo de la Princesa with a certified guide. Expect major landmarks, city views, Puerto Rican history, local customs, and practical advice on food and entertainment. Guides such as Carlos and Guillermo are known for friendly, lively presentations. Bring water and wear sturdy shoes.

“It was EXCELLENT! We loved learning about the history of Puerto Rico! The tour overall was amazing! Very colorful!!! I would definitely recommend doing this tour! Make sure you HYDRATE! A lot of walking!!! Guillermo was EXCELLENT!!!!!!!!”

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3.Segway PT and Segway Xafari Ebike Tours

★★★★★★★★★★4.5 · 634 reviews · from $108

Ride through Old San Juan with a guide such as Jose or Juan, learning about its Spanish colonial past, military defenses, and daily life. The two-hour tour covers more than 25 sights, including San Juan Cathedral, the city wall, Darsenas Square, and views of El Morro. Segway PT, kickscooter, and ebike options vary by departure time.

“The tour is a lot of fun and educational. Filled with beautiful architecture, rich history and valuable anecdotes.”

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4.Historic Old San Juan Sunset Walking Tour

★★★★★★★★★★5.0 · 634 reviews · from $39

Walk through Old San Juan with a certified guide such as Melanie, Antonio, or Jorge, stopping at historic plazas, churches, La Fortaleza, Ballajá, and El Morro. The two-hour route offers sunset views, colonial architecture, Puerto Rican history, and practical food and nightlife suggestions. Expect hills, steps, cobblestones, and more than a mile on foot.

“Very interesting, guide was very informative and very interesting. She was very enthusiastic about her information she gave us”

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5.Old San Juan Bar Crawl: Experience Local Hotspots

★★★★★★★★★★4.5 · 574 reviews · from $65

Start at 7:30 pm on Calle San Sebastian and spend about three hours visiting three Old San Juan bars. You get a complimentary mojito, a house shot at each stop, and an open-bar period at one venue. Guides such as Amanda and Yairo keep the group moving, while a Polaroid photo adds a fun souvenir.

“I went solo and ended up meeting other solo girls plus fun groups — the vibe was perfect. The tour guides were super energetic and made the whole night unforgettable. I definitely overdid it with the free drinks 😂 but the entire experience was amazing. Highly recommend this bar crawl, whether you’re solo or with friends. Just do it!”

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6.Savor the Sunset: Old San Juan Walking Food Tour

★★★★★★★★★★5.0 · 559 reviews · from $179

Meet your guide near central Old San Juan at 4 p.m. for a three-hour walk through colorful streets, family-run eateries, and local bars. Expect four or five stops, up to 10 tastings, mofongo, empanadas, rice and beans, flan, and two alcoholic drinks. Guides such as Pablo, Lorna, Desi, Nico, and Elliot bring food and island history together.

“This was a great tour to experience some traditional Puerto Rican food and drinks. Our tour guide, Elliot, was knowledgeable, patient and engaging. Our family really enjoyed seeing the city and the food was great. Highly recommend!”

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7.Old San Juan and El Morro Castle Walking Tour

★★★★★★★★★★5.0 · 480 reviews · from $54

Start near Pier 1 with a bilingual guide such as Maria, Melanie, or Antonio, then walk through Old San Juan to the cathedral, San Juan Gate, La Fortaleza, and El Morro. Expect about 2.5 hours in the sun, with fort admission, bottled water, history, views, and time to explore El Morro afterward.

“Great walking tour of a portion of Old San Juan. Melanie, our guide was very enthusiastic about the city and the culture.”

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8.Old San Juan Golf Cart Exploration (Est. 2023)

★★★★★★★★★★4.5 · 415 reviews · from $85

Ride through Old San Juan with guides such as Chris, Andres, Luis, Jorge, or William, stopping for photos at the forts, Capitol, cathedral, governor’s mansion, and Piña Colada birthplace. The covered golf cart saves you from steep streets and tropical heat, with morning and afternoon departures and groups capped at 15.

“This was an amazing experience with very fun and knowledgeable tour guides. It was a very hot day, so having the option to not walk in the hot sun was a plus for me. I would do this tour over and over again.”

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9.Old San Juan Historical Walk, Shopping, and Dining w/ Transport

★★★★★★★★★★4.5 · 381 reviews · from $34Best value

Start at Plaza Colón at 9 a.m. for a guided walk through Old San Juan, with views of the city walls, San Juan Bay, El Morro, mansions, churches, and the cathedral. Guides such as Michelle, Brandon, Nathan, and Michi lead the route. Air-conditioned transport is provided, while lunch and shopping are at your own cost.

“Very hard to hear. Our tour guide explained things while walking and if we weren’t next to him, we couldn’t hear him. He couldn’t find his mic and did not stop to talk to everyone. Also had some false information that I was able to catch.”

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10.3 Tours in 1 Day: Old San Juan, Rainforest, Beach with Transport

★★★★★★★★★★5.0 · 366 reviews · from $67

Spend 6 to 8 hours moving from Old San Juan landmarks to El Yunque’s rocky natural waterslides and Luquillo Beach. Guides such as Gabriel, William, Hector, and Bryant lead small groups of up to 19 people. Round-trip transport and life vests are included, but bring sturdy shoes, socks, water, and a swimsuit.

“The tour was very good; however, I wish we could have spent a little more time touring Old San Juan. The rainforest and waterfall slides were fantastic. The tour guide was good and entertaining.”

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11.Old San Juan Historical Walking Tour

★★★★★★★★★★5.0 · 331 reviews · from $46

Walk through Old San Juan with a local guide such as Danny, Carola, Gwen, or Pablo. In about two hours, you’ll see Casa Estrecha, San Juan Cathedral, Ballajá, and San José Church while learning how Puerto Rico’s capital grew over 500 years. Expect cobblestones, church dress rules, frequent stops, and a group of up to 18 people.

“The tour guide was very knowledgeable and entertaining. We enjoyed the walking historical tour of San Juan and Puerto Rico and viewed several sites.”

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12.FlyDining: Sunset & City Lights Dinner Over Old San Juan

★★★★★★★★★★4.5 · 326 reviews · from $159

FlyDining Puerto Rico serves a four-course dinner from a suspended platform at 153 Av. Manuel Fernández Juncos. Choose a 5:30 PM sunset seating or later dinner under the city lights. Soda, juice, and sparkling drinks are included, with a paid top-shelf open-bar upgrade. Arrive 30 minutes early and expect a lively, music-filled hour.

“Dinner in the sky was nice but I gave it a 4/5 because the views were nothing spectacular and the courses were not at advertised on the website. We gave our choice for the main course and dessert but we did not receive what was requested for dessert. We also got squash, which was very tasty, but not the watermelon gazpacho as listed on the website. The dessert was just a chocolate chip cookie with ice cream, not the selections we picked and as advertised on the website. It was a nice experience overall and the steak was just okay, but it was a bit pricey for the quality of…”

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