7 Days of Eating, Exploring & Adventuring in Puerto Rico

Advisor - Jana Schmersahl
Curated By

Jana Schmersahl

Icon Share


  • International Travel

  • Domestic Travel

  • Puerto Rico

  • Adventure Travel

  • Arts & Culture

  • Beaches

  • Luxury Travel

  • Local Culture

  • Local Cuisine

  • Island-Life

Body of water next to cliff with houses during sunset
Curator’s statement

Puerto Rico will always have a special place in my heart because my now husband and I got engaged here! Whether you travel here as a couple's getaway or a family friendly adventure, there is something for everyone to enjoy. I would even venture to say that San Juan itself has more vibrancy and culture than any other island in the Caribbean.

The Fora Difference

Book with Jana to access exclusive perks and experiences on your trip.

[object Object]
Killer perks

Free upgrades, spa credits and more—we got you

[object Object]
Personalized recs

Customized travel planning for your style

[object Object]
Insider knowledge

Expert advice from people who’ve actually been there

Where to stay

Hotel El Convento

Long-time favorite in Old San Juan, with a traditional look and access to a sister beach club.

Fora Perks
  • $100 food / beverage credit.

  • Breakfast daily.

  • Upgrade & extended check-in/out whenever possible.

El Blok Hotel

Chic and alluring Vieques hotel with full-service, ethereal-style suites and incredible reef to explore nearby.

Advisor - Jana Schmersahl

Unlock perks by contacting Jana to book your trip.

Day 1: Arrive to Puerto Rico

Street lined with cars and colorful buildings during daytime

Arrive in Puerto Rico and head to Enterprise-Rent-a-Car for convenient pick-up and drop off at SJU airport.

Hotel El Convento: Free daily hospitality bar, valet parking and coin laundry.

Dinner at Raices: 315 Calle Recinto Sur, Old San Juan - Incredible local authentic Puerto Rican food, famous for their mofongo!

Cocktails at La Factoria: Despacito music video filmed in this bar!

Day 2: Coffee tasting, shopping and ATV tour

White mug filled with coffee on a wooden table

Coffee tasting at Cuatro Sombras: Discover Puerto Rico's coffee culture!

Next, go shopping on Cristo Street and Fortaleza Street, including:

Don Collins Cigar Factory.

Con Calma, an artisan bag shop.

Have lunch at La Bombonera.

Afternoon snack at Choco Bar: Famous chocolate and cheese sandwiches, cocktails and art gallery upstairs.

ATV Tour Reservation, 3pm at Campo Rico.

Dinner at La Fonda El Jibarito.

Popsicles at Senor Paleta.

Day 3: Cultural tours & trolley ride

Green bus on the street next to a yellow building during daytime

Cathedral Basilica of Saint John the Baptist: Burial site of Ponce de Leon, houses relics of Pope John Paul II, built in 1521.

Cortadito coffee on the patio at Café Berlin.

Guided Tour, 10am Museo de Arte de Puerto Rico.

Outdoor Market La Placita Mercado.

Gastronomic Park lunch at Lote 23.

Trolley Ride around Old San Juan: Board and exit trolley at Plaza Colon in front of Café Berlin; stops in 30 minute intervals and the entire route takes about 1 hour to complete.

Rum Tasting reservation, 4pm at Casa Melaza Boutique.

Dinner reservation, 7pm at Jose Enrique.

Day 4: Brunch and outdoor market

Buildings on top of grass field during daytime

Have brunch at La Casita Blanca.

Next, check out the outdoor market El Mercado Urbano.

Enjoy sunset views from Castillo San Felipe del Morro, a 16th century military fort, UNESO World Heritage Site.

Day 5: Travel to Vieques Island

Road lined with trees with blue skies during daytime

Hotel check-out and car return at San Juan airport for flight to Vieques Island.

Take the Cape Air flight from: Luis Munoz Marin International Airport to Antonio Rivera Rodriguez Airport.

Check into El Blok Hotel for a free daily continental breakfast, restaurant and rooftop bar, lounge/game room.

Dinner at hotel restaurant, Placita.

Day 6: Rum distillery tour and kayak tour

Body of water with boats next to land during daytime

On day 6, have lunch at Duffy’s.

Then, check out the rum Distillery Tour and Tasting at Crab Island Rum.

Head out for a Bio-Bay kayak tour with Taino Aqua Adventures.

Arrange a pickup at the hotel and head to dinner at Lazy Jack’s.

Day 7: Snorkel tour

Body of water during daytime

Snorkel Tour, 10am with Black Beard Sports.

For your final evening in Puerto Rico, arrange a pickup at the hotel and head to dinner at El Guayacan.

Advisor - Jana Schmersahl

Travel Advisor

Jana Schmersahl

Get in touch with Jana

Did you like this guide? Reach out to customize and book your own experience. Or, just to chat about travel in general.

You can normally expect a response from Jana within a business day or so. You’ll also be subscribed to our travel newsletter (you can unsubscribe at any time).