A note from Troy
Two colonial cities, cobblestones and great food, all on foot.
This couple had their flights booked and a Virgin Islands trip planned. Here’s the part I built for them: three nights in Santo Domingo’s Zona Colonial, then two nights in Old San Juan, with a hotel in the heart of each and a private driver to and from every airport. I’ve stayed in the Zona Colonial several times, and it’s one of my favorite places in the Caribbean.
It’s the oldest European city in the Americas and a UNESCO World Heritage site: the first cathedral in the Americas, a 1500s fortress on the river, great restaurants, and live music in the square at night. Every hotel below puts all of it within a short walk. Then you trade it for Old San Juan: blue cobblestones, pastel streets and two giant Spanish forts on the sea.
Plans change, and that’s OK
This trip started as three nights in Santo Domingo.
Partway through planning, this couple decided to add two nights in San Juan before their Virgin Islands trip. So I priced four more hotels, added drivers at both airports, and built a guide to Old San Juan, the same day. Changing your mind is part of planning a trip. That’s what I’m here for.
Part 1 · Santo Domingo · Tue, Mar 2 – Fri, Mar 5 · 3 nights
Where you’ll stay in Santo Domingo
My pick
Kimpton Las Mercedes
Modern boutique · IHG · Zona Colonial
9.6 out of 10 on Expedia · 257 reviews
$947 for two
about $474 per person
Modern, polished and quiet, built around a colonial courtyard, with an excellent Italian restaurant inside. The best-rated hotel of the three.
Historic luxury
Billini Hotel
Historic boutique hotel · Zona Colonial
9.2 out of 10 on Expedia · 870 reviews
$768 for two
about $384 per person
Historic luxury with a rooftop terrace and one of the best restaurants in the old city. Fully refundable rate.
Best value
Gran Hotel Europa
Trademark by Wyndham · Zona Colonial
8.8 out of 10 on Expedia · 1,149 reviews
$477 for two
about $239 per person
A classic hotel in a historic building right in the middle of the old city. Great location and price, but the rooms are small.
Included with every hotel
A private driver, both ways.
A private car meets you at Las Américas International Airport (SDQ) when you land on March 2 and takes you straight to your hotel, about 30 to 40 minutes. On March 5 it picks you up at the hotel and takes you back for your flight. No taxi line, no haggling.
All within a short walk of your hotel
Things to do in the Zona Colonial
The Zona Colonial is the oldest European city in the Americas and a UNESCO World Heritage site. Here are the places I send everyone, all on foot from the hotels above.
Catedral Primada de América
The first cathedral in the Americas, built in the early 1500s from golden coral stone. Step inside for the vaulted ceilings and side chapels.
Fortaleza Ozama
A fortress from 1502 guarding the mouth of the Ozama River. Climb the tower for views over the river and the old city.
Calle Las Damas
The first paved street in the Americas, lined with 500-year-old stone buildings. A beautiful walk from the fortress to the Pantheon.
Panteón de la Patria
The national pantheon, set in an 18th-century Jesuit church on Calle Las Damas. Watch for the changing of the honor guard.
Museo de las Casas Reales
The seat of Spanish colonial government, now a museum of maps, armor and colonial life. A great first stop to understand the city.
Alcázar de Colón
The palace of Diego Columbus, son of Christopher Columbus, on the Plaza de España. Furnished rooms and river views.
After dark
Evenings in the old city
Have dinner on the Plaza de España, facing the Alcázar lit up at night. Walk Calle El Conde, the pedestrian street, for shops, cafés and the Parque Colón. On Sunday evenings, locals gather at the ruins of the San Francisco monastery to dance to live merengue and son. Ask me for my restaurant picks.
Side by side
Santo Domingo, for two
| For two, 3 nights | Kimpton Las Mercedes | Billini Hotel | Gran Hotel Europa |
|---|---|---|---|
| Hotel, taxes and fees included | $785 | $618 | $346 |
| Private airport transfers, round trip | about $100 | about $100 | about $100 |
| Travel insurance (estimated at about 7%) | about $62 | about $50 | about $31 |
| Total | about $947 | about $768 | about $477 |
| Per person | about $474 | about $384 | about $239 |
Your driver meets you at the Santo Domingo airport on March 2 and takes you back on March 5 for your flight to San Juan. Breakfast and meals aren’t included unless your rate says so. Want a guided walking tour of the Zona Colonial? I can add one.
Part 2 · San Juan, Puerto Rico · Fri, Mar 5 – Sun, Mar 7 · 2 nights
Where you’ll stay in San Juan
Two hotels inside Old San Juan’s walls, and two in Condado, the beach neighborhood next door. In the old city you walk to everything; in Condado you trade that for the beach and a short ride.
Getting around: Old San Juan’s free trolley is currently out of service, so plan on walking in the old city. From Condado, a taxi or Uber to Old San Juan takes about 10 minutes.
My pick
Hotel Rumbao
Tribute Portfolio (Marriott) · Old San Juan
9.0 out of 10 on Expedia · 1,983 reviews
$1,406 for two
about $703 per person
A stylish Marriott hotel right in Old San Juan, steps from the cruise piers, Paseo de la Princesa and the old city’s restaurants. Fully refundable rate.
Boutique luxury
Alma San Juan
Autograph Collection (Marriott) · Old San Juan
9.2 out of 10 on Expedia · 584 reviews
$1,451 for two
about $726 per person
A design-forward boutique hotel in the old city with a pool, two restaurants and room service. The quoted room has two double beds.
Beach area
HiBird Apartment & Suites
Condado · about 10 minutes from Old San Juan
9.2 out of 10 on Expedia · 599 reviews
$982 for two
about $491 per person
Apartment-style suites with ocean views in Condado, San Juan’s beach and restaurant district. A short taxi or Uber ride to the old city.
Best value
Flor De India
Condado · about 10 minutes from Old San Juan
9.6 out of 10 on Expedia · 99 reviews
$936 for two
about $468 per person
A small, highly rated stay in Condado with a pool and modern rooms. The best price, and a short taxi or Uber ride to Old San Juan. Fully refundable rate.
Included with every hotel
A private driver at both ends.
A private car meets you at San Juan’s Luis Muñoz Marín airport (SJU) on March 5 and takes you to your hotel, about 15 to 20 minutes. On March 7 it takes you back to the airport for your trip to the Virgin Islands.
Old San Juan · all on foot from the old-city hotels
Things to do in Old San Juan
Founded in 1521, Old San Juan’s forts and city walls are a UNESCO World Heritage site. Here’s how I’d spend your two days.
El Morro
The 16th-century Spanish fortress guarding the entrance to San Juan Bay. Wander six levels of walls, then join the locals flying kites on the big lawn out front.
Castillo San Cristóbal
The largest fortress Spain built in the Americas, with tunnels, sentry boxes and huge views of the Atlantic. One ticket covers both forts.
La Fortaleza
The governor’s mansion since the 1500s, the oldest in continuous use in the Americas. The blue-painted street in front, Calle Fortaleza, is lined with restaurants.
Paseo de la Princesa
A palm-lined promenade along the old city walls and the bay. Best at sunset, with street vendors and the Raíces fountain.
The walled city
Blue cobblestone streets, pastel buildings and tiny plazas. Walk Calle del Cristo and Calle San Sebastián and stop for coffee or a piña colada.
Eat like a local
Flavors of Old San Juan
Try mofongo, mashed fried plantains with garlic, and a piña colada in the city where it is said to have been born. Ask me for my restaurant picks.
After dark
Evenings in Old San Juan
Watch the sunset from Paseo de la Princesa, then have dinner on Calle Fortaleza, the old city’s restaurant row. Calle San Sebastián is where the bars and live music are, busiest on weekend nights, which is exactly when you’re there.
San Juan, for two
| For two, 2 nights | Hotel Rumbao | Alma San Juan | HiBird | Flor De India |
|---|---|---|---|---|
| Hotel, taxes and fees included | $1,224 | $1,266 | $828 | $785 |
| Private airport transfers, round trip | about $90 | about $90 | about $90 | about $90 |
| Travel insurance (estimated at about 7%) | about $92 | about $95 | about $64 | about $61 |
| Total | about $1,406 | about $1,451 | about $982 | about $936 |
| Per person | about $703 | about $726 | about $491 | about $468 |
Your whole trip
Both cities with my picks: about $2,353 for two
Kimpton Las Mercedes in Santo Domingo (about $947) plus Hotel Rumbao in San Juan (about $1,406), with every airport transfer and travel insurance. That’s about $1,177 per person for 5 nights. Mix and match any hotels you like.
Not included: your flights, including Santo Domingo to San Juan on March 5 (about a one-hour flight, and I can book it for you) and your Virgin Islands trip.
Good to know before you book
Terms and disclosures
Payment in full at booking
- Trips are paid in full when you book. I don’t take deposits or offer payment plans.
- Hotels and drivers are paid upfront the moment I book, so your full payment is what locks in your room and your price.
- Payment is taken by phone, never on the web.
Prices
- All prices are in U.S. dollars. Hotel prices include taxes and fees.
- These are today’s prices and aren’t held until the trip is paid in full.
- Transfer and insurance amounts are estimates, confirmed at booking.
Cancellations
- Each hotel’s own cancellation policy applies. Billini Hotel, Hotel Rumbao and Flor De India show fully refundable rates; I’ll confirm the other hotels’ terms before you book.
- Once the trip begins, there are no refunds for unused nights or services.
Travel protection
- I strongly recommend travel insurance, so it’s included in every total above.
- It’s bought when you book and isn’t refundable. I’ll get you an exact quote.
- Your flights were booked separately and aren’t covered unless you add them to the policy. Flights between Santo Domingo, San Juan and the Virgin Islands aren’t included in these prices.
Documents
- A valid passport is required. Names on the booking must match your passports exactly.
- Each traveler is responsible for entry requirements, including the Dominican e-Ticket. Flying from Santo Domingo to San Juan, you clear U.S. customs and immigration when you land.
Next steps
Ready when you are.
March is a popular month in both old cities, and these boutique hotels have few rooms. Pick a favorite and I’ll lock it in.
- Pick your hotelChoose the one that fits, or schedule a call and we’ll talk it through.
- Send your flight timesAll of them, so your drivers are waiting when you land in Santo Domingo on March 2 and in San Juan on March 5, and pick you up on time for each flight out.
- Pay in full and you’re bookedI call you to take full payment by phone, never on the web, and book everything right away at the confirmed price.