This is a collection of 'best of' since I moved to the island at the beginning of 2019. Activities/sights, restaurants/bars, shopping, and places to stay in San Jan each have their own section. Other regions each get a single section that combines all of the above.
James Beard Award-winning cocktail bar with several differently-themed rooms that open as the night wears on, recommended for late night any night. Live band salsa Monday nights. Good food as well, but mostly too loud to really enjoy dinner table conversation.
2
Steinway Piano Bar at the Cannon Club
Restaurant
Bar
Parrots, pianos, and art serve as the background for classic cocktails. Through some kind of ancient magic the upstairs patio stays cool even in the height of summer. Food is fine, not exceptional; ideally come here for the vibes/music/drinks.
3
Cafe Caleta
Restaurant
New sexy intimate cafe/wine bar with local ingredient-forward food from Martin Louzao, the chef behind Cocina Abierta, in the heart of Old San Juan. No reservations but if you have to wait for your table you can enjoy a glass of natural wine in the park outside next to the second oldest cathedral in the Americas.
4
Cocina Abierta
$$$$expensive
Restaurant
Excellent food, much of it local farm to table, in a wicker-meets-art deco space. Keep an eye out for their special 'Mesa Redonda' pop up dinners in the back room with guest chefs, or their 'Oriundo' series highlighting indigenous ingredients.
5
Celeste
Restaurant
Fish-forward fine dining at reasonable prices in the up and coming neighborhood of Puerta de Tierra. You can enjoy it without the suggested wine pairings, but it would be a shame to miss them.
6
La Isla
Cafe
Coworking space
Fresh healthy local food and a zero waste shop in an airy open space. Excellent wifi makes this a great place to get work done too (daytime only, closes in the evenings).
7
La Disquera
Lounge
New club open every night with New York meets Tokyo vibes, from one of the team that created Standard Hotel Group.
8
La Garita
$$$$affordable
Restaurant
Breakfast/lunch spot in La Perla, where the most viewed music video of all time, Despacito, https://www.youtube.com/watch?v=kJQP7kiw5Fk was shot. Great views and in January/February possibility of seeing humpback whales
9
Esquina El Watusi
$$$$cheap
Bar
Legendary dive bar with tables on the street, live music every Thursday and often other days of the week.
10
Café Regina
$$$$affordable
Coffee shop
Can't go wrong at this tasty hipster cafe: favorite order is the rompe calor (mango purée with a shot of matcha) and a guineo (baby banana) toast with almond butter and puffed amaranth. You can also pick up pints of Via Lactea gourmet ice cream with flavors like guava cheese, matcha, vegan chocolate brownie.
11
Pollos Scharneco
Chicken restaurant
Bar
Elevated comfort food (grilled chicken, mac'n'cheese, etc) at great prices from parts of the dream team behind Bacoa and La Factoria.
12
La Parroquia
Restaurant
A year-old bar opened by photographer Gil Ramos that feels like a mix of Havana, Paris, and something distinctly San Juan.
13
Bacoa Finca + Fogón
$$$$affordable
Puerto Rican restaurant
~45 min drive from the metro area to this always-full farm to table restaurant next to the rainforest which led the BBC to ask 'is America's best restaurant in Puerto Rico?'. Recently named one of the top 50 restaurants in the US by the NY Times. https://www.bbc.com/travel/article/20220215-is-americas-best-restaurant-in-puerto-rico (pro tip: book an afternoon reservation to fuel up after a visit to Charco El Hippie, an epic swimming hole/hike just 10 min away)
14
Berlingeri
$$$$affordable
Vegetarian restaurant
Flavorful vegan food (lunch Monday-Friday, now open for breakfast Thursday/Friday too) served by beautiful hipsters in an airy wood paneled space.
15
La Penultima
$$$$affordable
Bar
Voted most likely to run into an off duty reggeaton star. Great cocktails, good beer garden out back if there aren't too many people smoking. The disco fries are a perfect complement to a cold beer or cocktail.
16
Cocina al Fondo
Restaurant
James Beard Award winning Chef Natalia Vallejo previously had a spot in the back of Pública gallery, but was so successful she spun it out to her own restaurant in a stately home in Miramar. Make a reservation, no walk ins.
17
El Kilómetro
Art gallery
Art studio
It's a legit art gallery in a bar! Plus craft cocktails. What abundance.
18
El Bar Bero
Cocktail bar
Barber shop
Actually a barbershop during the day, mustache-themed boutique cocktail bar at night. Irregular hours but usually open Thursday-Sunday nights. The best fish tacos on Loiza Street.
19
Tia Dora
Mediterranean restaurant
Puerto Rican restaurant
My go-to dinner out: perfect Middle Eastern food in the heart of Ocean Park by chef Raul Correa, of the famous Bacoa.
20
El Axolote
$$$$affordable
Mexican restaurant
Creative Mexican food and cocktails. Most lively on a Thursday night when the surrounding area often has gallery openings.
21
JungleBird
$$$$affordable
Cocktail bar
Restaurant
Low key amazing tiki bar that always has some characters (but has recently gotten a bit touristy).
22
Café Finca Cialitos
Coffee shop
Breakfast restaurant
Coffee roasters
Best coffee in Old San Juan.
23
Los Guapos Taquería y Mercado Mexicano
Mexican restaurant
Best Mexican food in San Juan, from Xavier Pacheco (another one of the chefs behind Bacoa).
24
Café Cuatro Sombras
$$$$affordable
Coffee shop
Recommended cafe with wifi if you need to get work done, also the meeting point for dawn runs on Wednesdays (6:30am)
25
Machete
Bar
Hip bar with great cocktails (suck down a Vampiro) and food on the up and coming Calle Cerra. Can be loud but the garden in the back is generally lower key.
26
Santaella
$$$$expensive
Puerto Rican restaurant
Excellent food, pricey. Reservations needed. Friday and Saturday nights annoyingly crowded and a glitzy see and be seen scene.
27
Bocca Osteria Romana
$$$$affordable
Italian restaurant
Excellent Italian food. The cacio e pepe and salmon are highlights.
28
O:LV HOTEL
Hotel
W-style flashy design on one of the few rooftop bars (why are there so few?). Recommend as a place to visit for food/drinks rather than stay because it's not on the beach or in Old San Juan, which are the two areas you'd want to optimize for if you're visiting.
29
El Local en Santurce
$$$$cheap
Live music bar
Dive bar with occasional events of Berlin-level partying.
30
Café Comunión
$$$$affordable
Coffee shop
Cafe
high quality local coffee and good internet for working
31
La Terraza De Bonanza
$$$$cheap
Restaurant
Bar
Monday nights 'bomba y plena' live drum music, cheap street food and atmosphere.
32
Vianda
Restaurant
Tipped as the restaurant most likely to receive a Michelin star, opened by a couple who used to cook for New York's Blue Hill. Classy and delicious.
33
La Grieta
Bar
Cool mezcal hole in the wall that occasionally hosts vibey live music. Follow @lagrietavsj to know when that's happening.
34
Carli's Fine Bistro & Piano
Restaurant
Carli played with the Beach Boys for 11 years and still plays here 1-2x/week. Every night has live jazz music. The food is mediocre for the price but the ambiance is nice and Carli is a treat.
35
La Placita
Bar
Dance club
Friday night social hub beloved by locals and tourists. Be prepared for loud, loud reggaeton, cheap cocktails in plastic cups, and dancing in the street.
36
Tresbé
$$$$affordable
Restaurant
Open air food court with refreshing cucumber margaritas, good Japanese and so-so Mexican food available. Great for people watching, usually has live music on Sunday afternoons. Free Saturday 9am yoga (mats available to rent).
37
Café con Cé
$$$$cheap
Coffee shop
Tiny coffee shop tucked in the back of Tresbe, good wifi for getting work done.
38
Lote 23
$$$$affordable
Restaurant
Funky food truck park. Chef Jose Andres has a fried chicken truck towards the front (Hen House) that might be the best fried chicken sandwich I've ever had.
39
Numero Uno Beach Hotel & Restaurant
$$$$expensive
Restaurant
Service can take a while, but it's hard to beat sitting in a bean bag chair on the beach sipping a spicy margarita. Food is so-so.
40
La Bombonera
$$$$affordable
Restaurant
Cafe
Good traditional breakfast sandwiches in the old town.
41
Yoko
Japanese restaurant
Japanese food spot with dangerously good fresh sushi and tasteful vibe. Bad Bunny really likes this place so if it's 'closed' and the blinds are down during regular hours he's probably there with his entourage.
42
Scryer Rum Barrelhouse & Rooftop
Distillery
Bar
Classy rum bar with a rooftop (for some reason rare in San Juan). Can get crowded so best to go at off peak times (also recently seems to have been invaded by cruise ship tourists when they're in town :/)
43
Pa'l West
Permanently closed
$$$$cheap
Bar
Mostly locals-only dive bar that spills onto the street and always has a great (very loud) soundtrack.
44
La Santurcina
Restaurant
Very good pizza that's getting written up everywhere, but be prepared for 90+ minute waits even on 'off' days unless you go super early or late.
45
Antillano
Bar
Vibey bar / go-to date spot.
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Shop featuring local artists and designers, jewelry, + some vintage
2
Electroshock
Clothing store
Great thrift store, super cheap.
3
Vice Versa
Consignment shop
Another vintage/thrift store, a bit higher end and with furniture.
4
La Placita
Bar
Dance club
Fresh produce market in a historic building open till 6pm.
Places to stay (San Juan)
These are top hotels, for airbnb my favorites are collected at tiny.cc/airbnbop (for Ocean Park), tiny.cc/airbnbproutsidesj (for places outside of the metro area).
1
The Dreamcatcher
Hotel
Bed & breakfast
Vegetarian restaurant
Dreamy boutique hotel that has breakfast open to anyone. Come for the vibes, stay for the wifi - good place to work within Ocean Park.
2
The Gallery Inn
Hotel
Full of parrots, pianos, and art! Some rooms are like palaces, the 'artist's rooms' are dingy and to be avoided. Either way, you'll enjoy the highest rooftop view in Old San Juan and the incredible common areas.
3
Condado Vanderbilt Hotel
Hotel
Grande dame of hotels - if you're looking for the most luxury level of service.
4
Hotel El Convento
Hotel
most historic fancy hotel in Old San Juan, lovely views from the roof
5
AC Hotel by Marriott San Juan Condado
Hotel
Meeting planning service
If you're booking on miles/points, this is a pleasant modern beachfront hotel that you can often get for cheap.
Useful/necessities (San Juan)
1
Enterprise Rent-A-Car
Car rental agency
Van rental agency
Easy place to rent a car for day trips
2
Ashford Medical Center
Medical Center
The ER will have some English speaking staff.
3
Freshmart Condado
Store
Organic food store
Whole Foods-like market
4
Costco Wholesale
$$$$affordable
Warehouse store
Department store
Oh, shiny mecca of capitalism (there are a couple locations around the city).
5
Cicla Bici Shop
Bicycle Shop
Bike rentals + repair, very reasonably priced.
6
Humidity: Athlete Recovery Day Spa
Spa
Athletic club
Chiropractor
Massage spa
Sauna
For those who like spas, this is the only real game in town - saunas, cold plunge, compression cuffs, etc. Nothing local Puerto Rican about this but worth it if you need some physical therapy.
7
Cloud Spa
Massage spa
Facial spa
High end spa with good online booking system in the Gallery Plaza on Calle Loiza.
Things to explore (San Juan)
1
Ocean Park
Neighborhoods
One of the most gorgeous beaches in the world, one of the best places in the world to kiteboard (dm me for coach references). Good pick up beach volleyball game every Saturday afternoon from around 3pm till sunset at the easy-to-find courts at the end of Calle Taft. Watch sunset from the bean bags at Numero Uno beach bar. I swim here every morning around ~7:30am. Workout bars at the end of Calle Carrion Ct are our own Muscle Beach.
2
Viejo San Juan
Historic Sites
Historic Walking Areas
Neighborhoods
A 16th century walled city in the Americas! Gorgeous streets to wander north of Calle San Francisco; south of there sadly clogged with shops selling cheap souvenirs imported from China and the cruise ship tourists who like to buy them. If you have time, book this $25 2 hour Airbnb experience with Andy, a local architect whose love for his city is infectious. https://www.airbnb.com/experiences/174126?source=p2
3
Calle Cerra
Incredible public art all up and down this street. Thursdays there are often gallery openings with open parties, go to one of the restaurants or bars on the street (Axolote & Graziani current favorites) and then follow whoever looks interesting. Or grab a drink from El Watusi, a legendary dive bar, and enjoy the street art and live music.
4
Castillo San Felipe del Morro San Juan
Castle
Sights & Landmarks
Great sunset views from this awe-inspiring 16th century fort. Castillo San Cristobal, at the other end of Old San Juan, is more interesting to explore if you have time to visit only one, but views are better from El Morro.
5
Calle Loíza
Notable street
Neighborhoods
Don't be fooled by the unlovely, potholed street - this area has a string of the best restaurants, shops, and nightclubs in town (including many detailed on this list).
6
La Perla
Colorful neighborhood guidebooks will say is dangerous but really isn't any more than the surrounding area. Police don't go here, and people do sell class A drugs out of fishing tackle boxes, but there's a real community of people who take care of each other. Setting for the 'Despacito' music video. Come for beautiful vistas, friendly locals, and to escape the tourist beat.
7
Balneario El Escambrón
Outdoor Activities
Beaches
Closest beach to Old San Juan - has showers and is an easy 10 min bike ride, 40 min walk, 5-15 minute Uber from Old San Juan. Good snorkeling on calm days near the rocks.
8
Monagas Rock Climbing (a.k.a. Nuevo Bayamón)
Rock climbing
recommended rock climbing destination (haven't been yet but Google to find guides)
9
Dorado
Rich people playground. The Ritz resort, formerly the Rockefeller resort, is stunning, and populated mostly by the uber-wealthy who relocated here for the tax advantages. If this is your jam, snag an invite from someone who lives here or book a room at the $1k+/night Ritz to be able to enjoy the property.
10
Castillo de San Cristóbal
Castle
Sights & Landmarks
The smaller of the two castles in Old San Juan, so visit the larger El Morro first, but this is beautiful too.
11
Charco Prieto
A slightly challenging hike (must have good shoes and be in good shape/comfortable with small amounts of climbing) delivers you to an awe-inspiring waterfall just ~30 min from downtown San Juan.
Northeast/Vieques/Culebra
El Yunque, the only tropical rainforest in the US forest system, is a must-do possible in a half day from San Juan. Combine with a visit to Fajardo's bioluminescent bay in the evening if you're near a new moon (otherwise it'll be too bright to enjoy the bioluminescence). The paradise islands of Vieques (with one of the brightest bio bays in the world) and Culebra are also possible as a day trip (either 1.5 hour drive + 1 hour ferry each way for $2 + rental car/uber, or 20 min flight for $85-150 each way) but well worth a day or two.
1
El Yunque National Forest
National forest
Nature & Parks
Sublimely beautiful tropical rainforest. You can visit on your own but highly recommend booking a day trip with instagram.com/pabloexplorando
2
Juan Diego Falls
Nature & Parks
Waterfalls
So many great hikes to do in El Yunque, the national forest - this is a nice picturesque one (and beyond the main waterfall there are hidden waterfalls/a canyon to hike to if you have time and appetite!)
3
Ceiba Ferry Terminal
Port authority
Departure point for ferry to Vieques/Culebra (~1.5 hour drive from San Juan)
4
Fernando Ribas Dominicci/ Isla Grande Airport
Regional airport
Airport
small airport close to old San Juan that offers flights to Vieques (if you don’t want to take the bus/ferry) for cheaper than the flights from SJU (~$80 each way rather than $130)
5
Bahía Bioluminiscente
Bay
Nature & Parks
Bodies of Water
one of the coolest things to see in Puerto Rico - go kayaking in this bioluminescent bay (ideally around the new moon)
6
Sun Bay Beach
Beach
Great campground available with showers/bathrooms
7
Mosquito Pier
recommended place to go snorkeling - frequent sea turtle sightings
8
El Blok Hotel
Hotel
Design-forward hotel near the bioluminescent bay
9
Abe's snorkeling & BioBay Tours
Tour operator
Tours
Good tour guides to take you to the bioluminescent bay
10
Finca Victoria
Retreat center
Cottage
Guest house
Boutique hotel in the hills done by the same folks behind the Dreamcatcher in San Juan. The most Tulum-like of the island's lodgings.
11
Degree 18 Juice Bar
$$$$affordable
Vegetarian restaurant
Smoothies, vegan eats, and beer in a lovely garden setting. There's some connection to Michigan which fellow Michiganders might appreciate.
12
La Estación
$$$$affordable
Puerto Rican restaurant
Barbecue restaurant
Really good steak and freshly caught fish in an unpretentious setting.
Center
1
Arecibo Observatory
Observatory
Museums
2nd biggest radio telescope in the world, easy day trip from San Juan. Sadly the telescope collapsed in 2020, but the science-museum-y visitor center is fun especially with kids.
2
Cueva del Indio
Nature & Parks
Historical landmark
Stunning coastal outcrop with mini hikes and great views.
3
Salitre Meson Costero
$$$$affordable
Seafood restaurant
Gourmet grocery store
Restaurant overlooking the Atlantic specializing in fresh seafood - great to stop by before/after Arecibo/Cueva del Indio/Cueva de la Ventana
4
Cueva Ventana
Nature & Parks
Caverns & Caves
Points of Interest & Landmarks
nice small hike to a beautiful view of the surrounding valley.
5
Cañon Blanco utuado
Gorgeous canyon with easy hiking and swimming.
6
Casa Vieja
$$$$cheap
Bar
Restaurant
Stunning views, simple food, Anthony Bourdain-approved. Live music on Sundays all summer long
Rincon/the west
1
Gozalandia Falls, Official name Robles Waterfalls.
Park
Lovely easy hike to two waterfalls, one with a rope swing.
2
Castillo Labadie (Palacete Los Moreau)
Historical landmark
Castle
Gorgeous plantation home built by a former slave who inherited her former masters' fortune.
3
Playa Jobos
Beach
Outdoor Activities
A favorite beginner surf spot
4
Royal Isabela
Resort hotel
Golf course
Eco-friendly hotel with a golf course and incredible views.
5
The Wandering Bagel
Restaurant
Bagels almost as good as NYC
6
Beach house
Apartment complex
Sunset views & good margs
7
Isla Made Local Goods + Cafe
Coffee shop
Gift shop
High end coffee & cute designer goods.
Southwest
1
Cabo Rojo Lighthouse
Lighthouse
Sights & Landmarks
Points of Interest & Landmarks
The lighthouse isn't that impressive, but the setting around it is the stuff of Instagram dreams.
2
Salinas de Cabo Rojo
On the way to the lighthouse, a small but arresting patch of pink water where salt is harvested.
3
Playa Sucia
Beach
Outdoor Activities
Some describe as their favorite beach in Puerto Rico. Low key, decent snorkeling around the rocks to the right.
4
Annie's Place
$$$$affordable
Restaurant
Cheerful restaurant built into the sea with unbeatable sunset views.
5
Pika-Pika Mexican Restaurant
$$$$affordable
Mexican restaurant
Always bustling place for excellent Mexican staples with super friendly wait staff. Get the passionfruit margarita!
South
1
Yaucromatic
Art museum
Arts organization
Epic street art in a town that otherwise has little going on - worth a stop if you're driving by (which you will on your way to most things in the south).
2
Bahía Bioluminiscente de La Parguera
Nature preserve
Boat tour agency
The third bioluminescent bay on the island and the only one that you can swim in. You'll either have to kayak about 45 min to get there or you can book a tour on a boat (go for a glass bottom one!) that will drive you there and serve as your base for swimming.
3
The Fox Hotel
Hotel
Pop art inspired hotel in the central square in Ponce.
4
Salto Santa Clara
Gorgeous gorgeous waterfall hike, about 40 min each way in/out.
5
Parque de Bombas
Museum
Attraction
From the web: This historic structure served as the island's first firehouse & was made into a museum in 1990.
6
Charco Azul
Lake
The charco (swimming hole) isn't that impressive but there's an epic hike to an infinity pool that starts from a secret location up the road - I can share the pin :)
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