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Rum, Cigars and Espadrilles in Old San Juan

Recommended by 100% of travelers
San Juan, Puerto Rico
Great choice
5+ bookings last month.
  • 3 hours (approx.)
  • Mobile ticket
  • Offered in: English

Why travelers loved this

5.0
·
· Matthew_W ·
Jan 2026
Great time with Alex. Tasted great rum (don’t miss the whiskey aged rum). Had a little walking tour and smoked some cigars. Wrapped it up with champagne and Espadrilles. Everyone enjoyed!
· Barnaby_N ·
Jun 2026
The activities were excellent! Our tour guide, Alex, has great knowledge of the history of San Juan and took us on a nice tour of Old San Juan. He ans his entire staff was friendly and courteous. Would recommend this activity for groups!

Overview

    Sample Menu

    Starter

    Cava, Cheese and Serrano Ham

    Served at the end, as a celebration party

    What's Included

    • Snacks
      Snacks and nuts
    • Alcoholic Beverages
      Rum
    • Classic Espadrilles
    • 79.90 USD/pax for a wedge upgrade

    Meeting and Pickup

    Meeting point

    • 150 C. de la Fortaleza, San Juan, 00901, Puerto Rico

      We will meet at our family-owned shop, at the HANDMADE THE BRAND® shop . We will visit traditional places that define Old San Juan culture. On each stop we will have a special surprise for our guests. PARTICIPANTS WILL NOT BE ALLOWED TO ENTER THE WORKSHOP MORE THAN 15 MINUTES AFTER THE START TIME

    End point

    This activity ends back at the meeting point.

    Start time
    .11:00 am

    Itinerary

    1

    Calle De La Fortaleza

    15 minutes • Admission Ticket Free

    2

    Calle De La Fortaleza

    30 minutes • Admission Ticket Free

    3

    Calle De La Fortaleza

    30 minutes • Admission Ticket Free

    4

    Calle De La Fortaleza

    1 hour 30 minutes • Admission Ticket Free

    Additional Info

    • Confirmation will be received at time of booking
    • Wheelchair accessible
    • Near public transportation
    • Transportation is wheelchair accessible
    • Surfaces are wheelchair accessible
    • No heart problems or other serious medical conditions
    • Most travelers can participate
    • This tour/activity will have a maximum of 17 travelers

    Cancellation Policy

    You can cancel up to 24 hours in advance of the experience for a full refund.

    Traveler Photos

    Gallery picture 1 (from a traveler's review)
    Gallery picture 2 (from a traveler's review)
    Gallery picture 3 (from a traveler's review)
    Gallery picture 4 (from a traveler's review)
    Gallery picture 5 (from a traveler's review)

    Reviews

    5.0
    based on 34 reviews
    Total reviews and rating from Viator & Tripadvisor
    Sort by: Most insightful

    A Must Do Excursion

    Karen_R, Sep 2026
    The walking tour of Old San Juan from the store to the cigar bar was fabulous. Calilia was absolutely fabulous. The cigar bar was fabulous and ending with shoe shopping my kind of trip. I’d consider this a must do excursion.

    One of our favorite outings!

    Scott_S, Jul 2026
    We had a wonderful time. The tour of the city was great. The rum and cigar tasting was excellent, and the shoe store and shopping was a lot of fun. We got to try several rums and even bought a bottle it was so good. The cigars were very smooth and I’m not a regular cigar smoker. The short tour around the city was very informative and fun. The time in the shoe store was a blast. We had bubbly and picked out some of the free shoes as well as upgrading to buying others. Our guide was awesome and the entire staff at both locations were very friendly and fun. Couldn’t recommend this experience more!

    Great Experience!

    Barnaby_N, Jun 2026
    The activities were excellent! Our tour guide, Alex, has great knowledge of the history of San Juan and took us on a nice tour of Old San Juan. He ans his entire staff was friendly and courteous. Would recommend this activity for groups!

    We had a time!!! The Vibes ❤️……….

    Shondell_G, May 2026
    As a solo traveler, you have some reservations about meeting new people! Let me tell you that this experience was the absolute best with some great vibes! I even got to meet some celebrities. FYI - you might not walk straight after the tour 🇵🇷

    Can’t go wrong with shoes, liquor and cigars!

    Heather_R, Jan 2026
    Perfect excursion for the Cigar lover who’s significant other loves shoes! Highly recommend you upgrade to the premium package. Our guide Alex was fantastic!

    Our best tour in San Jaun.

    Matthew_W, Jan 2026
    Great time with Alex. Tasted great rum (don’t miss the whiskey aged rum). Had a little walking tour and smoked some cigars. Wrapped it up with champagne and Espadrilles. Everyone enjoyed!

    Fun, informative, definitely book it!

    7g49p4x2ty, Jan 2026
    This tour is great- we will be recommending it to everyone we know traveling to PR. Alex is a very knowledgeable guide, very friendly, and professional! We had a great time, the tour is private, informative, and very worth the $. Great choice for couples in VSJ.

    Something for him and her!

    Tammy_g, Oct 2025
    I love shoes! He loves Cigars and Rum…Perfect blended experience! Recommend this tour for anyone who loves to experience the local vibes!

    Favorite Tour Ever

    Lia_M, Oct 2025
    This experience is one of my most favorite tours that I’ve ever booked. It is so fun and informative and a must-book when in San Juan. You start by walking into the beautiful Handmade Avarcas and Espadrilles shop. You are seated at the back and your tour guide comes to greet you, with a Medalla and a snack pack. Our guide was Amira, who was amazing. After a brief introduction and overview, you start the tour. We walked to a lookout and then a church and got some history of the city. The church is very pretty. From there, we continued on to Don Collins, for cigars and rum/pitorro. Smoking a cigar while sipping pitorro was a fantastic experience and so much fun. After that, it’s back to the shop for a very fun conclusion. I highly recommend you add on a pair of espadrilles. It’s a great souvenir and they are really comfortable. This tour was some of the most fun I’ve ever had and I cannot say enough good things about it. I honestly feel like I’m underselling it. If you are considering this at all, just book it, you’re going to be very happy.

    If you're headed to Old...

    Barry_L, Sep 2025
    If you're headed to Old San Juan and enjoy a good cigar, a sip of rum, and a bit of history, this excursion is for you. Alex and Jibette were outstanding guides — knowledgeable, personable, and passionate about the history of Puerto Rico. On the way to the cigar lounge, they took us through the historic streets of Old San Juan, stopping at a few key historical sites. The Don Collins Cigar Lounge stop was fun and I enjoyed the rum and cigars. Christian at the lounge provided exceptional service—attentive without hovering, and incredibly well-versed in cigar recommendations and drink pairings. The lounge had a relaxed, welcoming vibe that made you want to stay for hours. And finally you would never tell me I would consider wearing a pair of espadrilles but on our final stop I found a pair that are comfortable and fashionable and I can't wait to wear them. Great job Jibette and Alex!

    A Must Do

    Katye_M, Apr 2025
    This experience was amazing! Knowledgeable, friendly and welcoming! Great experience to explore 3 things in 1! Highly recommend if want to get a taste of PR culture! 5 Stars!

    Fabulous experience for 2 friends

    alexis_g, Feb 2025
    Was throwing a surprise bachelorette for a friend and needed to pass the time before everyone came to PR. Found this experience and it was just perfect. Alex was a total gentleman and even though the tour turned out to be just the two of us, it was perfect. I will say, I think the espadrills lean toward the cheap side but hey, they come with the experience. Definitely recommend this tour for the ladies!

    Good tour

    Robyn_R, Dec 2024
    The guide, Alex, was very informative. He was kind, humorous and generous with his conversation and teaching.

    10 stars ⭐️⭐️⭐️

    Trivina_B, Nov 2024
    Visiting PR to celebrate our Anniversary and Alex made our day of celebration a memorable one. Very knowledgeable and he went beyond and above to make sure we had everything we needed!!!

    Cigars, rum and so much more!

    Brianne_A, Oct 2024
    This was an awesome experience from start to finish. Alex was amazing and exceeded our expectations. Thanks for such a memorable day!!!

    A well worth it experience!

    Quarmia_J, Sep 2024
    Alex, Andrea and the rest of the beauties at Handmade Shop made this one of our most memorable experiences! From the time we arrived at the shop for the start of the tour, we were greeted with a welcome drink (Medellin beer) and a snack. As we started our walking tour Alex took us to some historical landmarks and explained its purpose and history. The knowledge we gained about the Puerto Rican history and culture was mind blowing yet beautiful. Alex was very knowledgeable and patient with answering any questions we had. I got distracted for a second with the sight of visitors standing in a crowd black birds, and letting them stand on their arms and head, so I might have missed something Lol! Next, we headed to Don Collin’s for some rum tasting and cigars where we had a chance to sit back for a while, sip some of Puerto Rico’s finest rum and smoke some of the smoothest sticks. After the tour we headed back to Handmand Shop where they had a birthday celebration for my significant other with champagne and his favorite music. Our parting gift was a pair of espadrilles for each of us (I wish we would have upgraded them, but we are planning to return and do the workshop). We did not have to pay for anything extra because it was all included in the price. We loved everything about this experience and recommend it 100%! Alex and the girls were so much fun, his personality sense of humor caught us from the start! We have gained some new friends in Puerto Rico for sure 🇵🇷

    Date night

    Diamond_W, Aug 2024
    We were the only ones on the tour and it was worth the price. Definitely will come back, we had a good time and got cute shoes out of it too.

    Best Tour In San Juan!

    Sarah_P, Apr 2024
    We had such a great experience on this tour with Alex! He started us off with a welcome drink (and snack) before we set off on a brief walking tour on our way to the rum + cigar shop. During the tour, he took us around a few places in Old San Juan, sharing stories about Puerto Rico’s history and culture while highlighting important points of interest. At the cigar shop and rum tasting, he helped us narrow down from all the delicious choices and then took the time to get to know each of us a bit while we imbibed. After the tasting, we walked back to the Handmade Espadrille Shop, where we had the choice to take a basic espadrille home with us or upgrade or personalize other pairs made at the store! Everyone in our group decided to upgrade, and had so much fun choosing our pairs - Alex even took the time to make sure we all knew how to properly tie them before we left! It was one of our top moments on the trip, and I’d highly recommend this tour to anyone traveling to San Juan who is looking for a unique way to experience the city!

    A time was had

    Erica_E, Apr 2024
    This Tour was everything we expected it to be plus so much more. Alex was a very knowledgeable and personable host

    More than just shoes, rum and cigars

    Dhruv_P, Dec 2023
    Alex was an awesome host giving an insider walking tour with local knowledge that my other larger walking tour did not cover. Rum, cigars and especially the espadrille shoe were great. The shoe store is beautiful and located in a central location in old San Juan

    AMAZING EXPERIENCE!!!!

    Tim_M, Nov 2023
    AMAZING EXPERIENCE!!!!! I am still in awe of this experience. Alex is incredible and his team. They went above and beyond to ensure our time was well spent. You won’t regret this, thank you for making this event so memorable for us!

    The excursion was...

    Heather_R, Aug 2023
    The excursion was excellent. We loved every part of it. Alex was awesome. He was knowledgeable and personable, which we loved. His staff were great as well. We would recommend this tour 100%!
    Member Pricing
    From

    $170.90

    per person
    Was $179.90(-5%)

    up to 24 hours before the experience starts (local time)

    Book ahead!
    On average, this is booked 34 days in advance.

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