The Perfect San Juan Beginner Day Trip - Family Sailing (2023)

Are you looking for the best way to spend a day in San Juan? Whether you're planning a stopover in Puerto Rico on a longer itinerary or visiting Puerto Rico on a cruise, the good news is that you can get the most out of the city, even for a short period of time.

This quick guide will help you make the most of your day in San Juan, Puerto Rico!

San Juan Day Itinerary

morning in san juan

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Excellent way to start the dayOld San Juan Walking Tour and Tastingfrom the spoon. You'll spend three hours with a local guide, gaining an insider's perspective on all things Puerto Rico, from the food to the history and current challenges.

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This is one of the best trips I've ever taken and the food is incredible. You'll start at the totem pole in the heart of Old San Juan, then explore the heart of the city stopping at four or five food spots along the way. hungry! We ate the equivalent of two very substantial meals and had a few cocktails.

Be sure to check the start time - it varies between 10am and 11am depending on the day. If your tour starts later, you can always change the order of the next activity!


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After your tour, take some time to wander the charming streets of Old San Juan. There are many great stores to visit such as The Artisans Corner and Handmade Avarcas & Espadrilles. Be sure to keep an eye out for local gems as you stroll! You can also walk inside the Church of San Jose and admire the newly restored fresco of the mermaid.

late in san juan

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Finally, you'll want to head to the San Juan National Historic Site to visit the Castillo San Felipe del Morro, often referred to simply as "El Morro." The oldest part of this Spanish colonial fortress is nearly 500 years old, but today it's a UNESCO World Heritage Site, where you can learn some of the island's intricate history.

Most people choose the El Morro self-guided tour, which costs just $10 per adult. Children under 15 years old do not pay, they will love the fort! Speaking of kids, it's worth taking them to the store to buy a kite (comet) they can fly on the huge lawn in front of the entrance with all the local children.

In total we spent about two hours visiting El MorroPuerto Rico with kids.Offers fascinating insight into history and breathtaking views of the coast. This is one of the best things to do in San Juan and should be on every itinerary because it's one of a kind.

Saint John at night

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The last activity on this San Juan day tour is taking pictures! The city's colorfully restored buildings and historic fortifications provide the perfect backdrop for photos.

On my most recent visit, I made a bigflight photographerMeet Karlota, a professional photographer in San Juan. like a lifePuerto rican, she knows all the best spots and took our group to beautiful places we would never find ourselves. Professional San Juan photos are the perfect souvenirs to look back on a memorable day in Old San Juan.

Save $25 on San Juan Photos

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dinner, go toPrincesa– This is one of the hottest restaurants in Old San Juan, so I recommend making reservations in advance. Unfortunately, I waited too long to get in the night I was free, so this will be a culinary adventure for my next trip to Puerto Rico.

The reviews are excellent, and the concept is unique: the recipes are so traditional, they're lifted from 19th and early 20th century Puerto Rican cookbooks. The aesthetic is also extremely unique, with the interior and exterior integrated into one.

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If you still have the time and energy, La Factoria is a world-renowned bar with several different spaces, live salsa music and some of the best cocktails in the Caribbean several times a week. Even if that's not your cup of tea, an evening walk through Old San Juan is the perfect way to end the day.

How to get to Old San Juan from the port

If you're visiting San Juan on a cruise, you'll definitely want to spend the day following the San Juan day itinerary I outlined above. You will need to find out which port the cruise ships use, as there are two: Old San Juan and Pan Am.

The Old Port of San Juan is right in Viejo San Juan, so you can explore everything on foot! Keep in mind that you'll be walking uphill as you head north to visit San Juan's best attractions. It takes about 15-20 minutes to the square where the food tour starts. A taxi or Uber ride takes just 5-10 minutes and shouldn't cost more than $5.

The Pan Am Pier is close by, but takes over an hour to walk - not a great way to use your limited time in port! Instead, take a 15-minute cab ride or Uber. Fare must not exceed USD 10 each way.

Where to stay in Puerto Rico

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On my most recent visit to Puerto Rico, I spent 5 days in beautiful San JuanHilton Caribbean Hotels.It is a beautiful hotel with its own calm beach and several restaurants on site to relax. There are even great outdoor games like chess and corn hole.

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The downside to the Caribe Hilton is that it's not very close to Old San Juan -- a 10-minute Uber ride or a 45-minute walk (though it's a nice, easy walk). If you're looking for a relaxing resort-style getaway with island flair, this could be an ideal choice.

If you want to sneak out and stay in Old San Juan, there are plenty ofbeautiful vacation homeIn the city center. Keep in mind that Calle San Sebastian is Old San Juan's "bar street" so it can be noisy any day of the week. For some visitors this is an advantage and for others it is a disadvantage. Fortunately, even a block or two away, it's much quieter.

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For trips to Puerto Rico that include lots of adventures and excursions, like boating and kayaking or trips to El Yunque National Forest, we have aLuquillo.It offers a beautiful family beach and is closer to the east side of the island. We were there for a week on our first trip to Puerto Rico and then took a day trip to San Juan - it was the perfect balance! Don't lose your pose while you're thereLuquillo Kiosk.

San Juan Day Tours FAQ

How long should you stay in San Juan?

It really depends on your priorities, but you could spend a day in San Juan or spend an entire week in San Juan. If you love cities and want to immerse yourself in them, consider spending 3 or 4 days in San Juan and then spending the rest of your time inLuquilloon the east side of the island or maybeCorner(2 hours west).

Is Old San Juan walkable?

Old San Juan is very walkable! That said, the town is built on a pretty steep slope, so people with mobility issues might need extra help or an Uber/taxi. Fortunately, getting a ride is easy and very affordable.

(Video) Ocracoke to Swan Quarter on a San Juan 21 MKII

Is Puerto Rico expensive?

While Puerto Rico isn't as expensive as some of the Caribbean islands, it certainly isn't cheap. In San Juan, you can expect prices similar to other US cities.

Do I need a passport to visit Puerto Rico?

Americans do not need a passport to visit Puerto Rico because it is a US territory. Visitors from other countries need a passport (and possibly a visa, depending on nationality).

Can I pay by credit card in Puerto Rico?

Credit cards are accepted almost everywhere in Puerto Rico. In fact, I can use Apple Pay on my watch at most establishments in San Juan! Just bring some cash to tip your guides and photographers.

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How do you spend a day on San Juan Island? ›

The Best Things to Do on San Juan Island
  1. Get Out on the Water in a Kayak.
  2. Go on a Whale Watching Tour.
  3. Whale Watching from the Land at Lime Kiln Point State Park.
  4. Explore American Camp.
  5. Explore English Camp.
  6. Explore Friday Harbor.
  7. Pelindaba Lavender Farm.
  8. Even More Things to Do on the Island.

How many days do you need in the San Juan Islands? ›

Stay for two days to enjoy the full breadth of island life with morning mist rolling through the farmlands and fiery sunsets over the water. Consider visiting during the week to avoid larger weekend crowds and spend time island-hopping between activities on San Juan, Orcas, and Lopez Island.

What do you wear to sail in the San Juan Islands? ›

Layered clothing (long and short sleeved shirts, long pant, shorts, base layer (merino, poly, silk, etc). The key is clothing layers that can be added/removed depending on weather. Fleece top and pants. Warm cap/hat, or sun hat, depending on season.

Is it worth it to go to San Juan Islands? ›

The San Juan Islands are located off the coast of Washington State, bordering Vancouver and Victoria BC islands. These islands are one of the true natural wonders of the world and definitely worth a visit, especially if you love the outdoors.

How much money should I take to San Juan? ›

How much should I budget for a trip to Puerto Rico? A week's expenses in Puerto Rico for two people can range between $1,200 and $2,300. Visitors should always budget $200 or $300 more in case of any emergency.

Does Bill Gates live on San Juan Island? ›

"Top Gun" actor Tom Skerritt has a home on Lopez Island, while Bill Gates has one on Shaw Island and musician Steve Miller is selling his mansion on namesake San Juan Island for $16.8 million.

What is the best time of year to visit the San Juan Islands? ›

This probably doesn't come as much of a surprise, but the summer and early fall are undoubtedly the best time to visit the San Juans. The travel season to the San Juan Islands typically begins in April and continues through October, with July and August being the peak of the tourist season.

Can you see the Northern Lights from the San Juan Islands? ›

With over 247 clear days (and nights) per year and low light pollution, San Juan Island is uniquely (and stunningly) suited to observing the beautiful needle pricks in the cloak of night. At times you can see meteor showers, the northern lights and the most spectacular full moons shining on the glistening Salish Sea.

Can you go to San Juan Islands for a day? ›

For now, we're taking you to San Juan Island for the day by ferry. The ferry provides beautiful views and ample time for gazing. As we mentioned, you'll want to grab one of the earliest options for a day trip to be worth your while.

Can I wear jeans sailing? ›

For casual sailing, however, you can wear anything from shorts, to yoga pants, to hiking pants, to jeans. Whatever makes sense for the day and weather. Keep in mind that jeans will be very cold and ikcy when wet, so only wear those if you don't think there will be much spray on the sailboat.

What do you wear on your feet when sailing? ›

The soles of sailing shoes should be white to avoid stains on deck. If your footwear is not waterproof, then it is advisable that it is designed to be quick drying. The sole will usually be designed with channels that evacuate water (like the grooves in car tyres) to prevent slipping in the case of very wet decks.

Do I need to swim to sail? ›

No, if you are interested in sailing then start learning now…just be sure to wear your life-jacket and pay close attention to all safety instructions. I would also make an effort to learn to swim. It's a useful skill to have and it is fun. On a calm day you can swim off the side of the boat.

Can you swim in the water at the San Juan Islands? ›

That doesn't mean you'll have to go without when vacationing on gorgeous San Juan Island. There are breathtaking lakes to explore, indoor and outdoor swimming pools and a few sheltered coves, where the salty sea does warm up enough for a refreshing dip. Find the 5 Best Places to go Swimming on San Juan Island here.

Do you need a car when visiting San Juan? ›

If you're staying close to San Juan, then transportation might be relatively simple. You'll have access to a variety of options. In many instances, guests won't need a car (taxis and Uber are convenient options in town) unless they want to extend their visit beyond the city for an adventure.

Can you island hop the San Juan Islands? ›

Each of the islands is unique, and they offer plenty of scenery and opportunities for recreation, dining, and amusement. If for no other reason, island hopping from one destination to the next on the San Juan Island ferry is an absolutely beautiful journey.

Should I carry cash in Puerto Rico? ›

If you go to the mountains of the island as a tourist, you should carry cash, just in case. To withdraw cash from an ATM, the banks from Puerto Rico will charge you a fee for each transaction and remember if you travel on an international flight, inform your credit card provider that you will be in Puerto Rico.

Does San Juan accept US dollars? ›

Since Puerto Rico is a territory of the United States, locals are American citizens, and American travelers can enter the Island without carrying a passport. Nor do U.S. travelers require international calling plans for their phones. The currency used in Puerto Rico is the U.S. dollar.

Should I bring cash to San Juan? ›

You can use your U.S. dollars.

This makes spending money a breeze for U.S. tourists, who will also have access to American banks and ATMs. Credit cards are widely accepted, but it's smart to bring cash and smaller bills for tips and restaurants outside of San Juan.

What celebrities live on San Juan Island? ›

Bill Gates, Paul Allen and Anna Faris are among many other recognizable names who have low-key places somewhere in the San Juan Island chain.

What celebrity owns property on Orcas Island? ›

Reports indicate that Oprah Winfrey has purchased a 43-acre estate on Orcas Island for $8.275 million. Part of the estate includes a 10,000-square-foot, four bedroom, 3.75 bathroom house that features Sound and mountain views. Take a look at a photo gallery of the house below.

What country owns San Juan? ›

San Juan, capital and largest city of Puerto Rico, located on the northern coast of the island, on the Atlantic Ocean. A major port and tourist resort of the West Indies, it is the oldest city now under U.S. jurisdiction.

What are the rainiest months in San Juan Puerto Rico? ›

When is Rainy Season? Puerto Rico's rainy season bridges spring through fall, lasting from April through November. August is typically the wettest month, averaging seven inches (178 mm) of rain. The island's north experiences more rainfall than the south.

What is the hottest month in San Juan? ›

June is the hottest month in San Juan with an average temperature of 28°C (82°F) and the coldest is January at 25°C (77°F) with the most daily sunshine hours at 9 in October. The wettest month is November with an average of 157mm of rain.

What is hurricane season in San Juan? ›

While Puerto Rico enjoys warm weather year-round, like the majority of tropical Caribbean destinations, it's very much affected by hurricane season, which runs from June to November, with the greatest risk in August and September.

What month is best to see the northern lights? ›

November through to February offer the darkest skies and longer evenings for maximum sky-gazing. The strongest lights tend to appear between 9pm and 2am, though the best sightings often occur between 11pm and midnight.

When can you see whales in the San Juan Islands? ›

Peak season is considered the summer months of mid-June through early September. During this time, we see whales (orcas, humpbacks, greys and/or minkes) on over 90% of our tours. There are whales here year round, but much less predictably outside of those summer months.

Do you need a tour for northern lights? ›

So if the weather and aurora forecast are good, you might not need to take a tour to see the northern lights. But it's still a very good idea to sign up for a northern lights tour. Look for a northern lights tour where the guides will do everything in their ability to help you get a glimpse of the aurora.

How long is boat ride to San Juan Islands? ›

How long is the ferry ride to the San Juan Islands? The direct passage from Anacortes to the westernmost island, San Juan Island, takes 1 hour and 5 min. Lopez, Orcas, and Shaw are all about 50-55 min direct passage from Anacortes. Routes with stops prior to your desired destination will, or course, take longer.

How long is the loop around San Juan Island? ›

San Juan Island

This island offers a great 35-mile loop so you can explore without repeating your routes. Head out of Friday Harbor on Roche Harbor Road, and enjoy a ride to San Juan Vineyards, where you can take a break for a picnic and sample the winery's wares or buy them by the glass.

Can you drink the water on San Juan Island? ›

San Juan water meets or exceeds all federal and state drinking water standards. We continuously monitor and test your water to ensure quality.

Can you wear sneakers for sailing? ›

The short answer is yes technically you can. Some tennis shoes, sneakers and moccasins are great for fine weather sailing, where there's little chance of your feet getting wet.

Do you wear shoes when sailing? ›

You may be wondering if wearing shoes on a boat is really necessary. With so much water flying around, going barefoot could be seen as a better way to go! But in reality, there are certainly plenty of reasons to consider wearing waterproof sailing shoes while on deck. The first reason is to protect your feet.

Do you wear swimsuit sailing? ›

Yes, the choice is yours. Wetsuits can create friction on the skin, so wearing a swimsuit can reduce the discomfort. Also, if you plan to remove your wetsuit once you reach your destination, wearing a swimsuit may be a good idea if you want to be able to remove your wetsuit without discomfort.

Do you wear socks with sailing shoes? ›

Do you wear socks with boat shoes? Boat shoes are designed to be comfy and airy without socks, and most people keep their ankles bare for the classic maritime look – preferably with no-show socks. If you're going for an 80s preppy look, however, socks and boat shoes are definitely part of the uniform.

Can I wear sneakers on a boat? ›

You want shoes with non-slip, non-marking soles. Most non-marking soles are made of rubber. Leather soles will generally leave marks on the deck. Deck shoes are generally a safe choice, but if you don't have these, you could also use sneakers with light rubber soles.

Can you walk in boat shoes? ›

You Plan on Hiking - Boat shoes are just fine for walking the piers and streets of town. Or the back yard or office for that matter. But under no circumstances should these shoes be used for hiking out in the woods or in rocky terrain. While boat shoes have ok traction, the traction isnn't ideal for hiking.

When should you not sail? ›

Storms or Squall Winds

With the wind speed going above 48 knots, storms are dangerous situations and the seas may have huge waves going over 8 meters. These conditions are not ideal for sailing whatsoever and you should stay at home if possible.

Can you legally sail across the ocean? ›

Yes, you can legally sail around the world. However, some jurisdictions require legal documentation, such as proof of boat ownership and a visa when entering another country's port. You'll also want to make sure you're in the appropriate type of boat.

Is it expensive to get into sailing? ›

You will need to set aside money for extra sails, motors and other parts to have on hand for repairs. Recurring cost for maintenance and sailing clubs fees will average around $2,000 annually.

Can you drink alcohol on beach San Juan? ›

Imported beers tend to follow the traditional US school of light, Budweiser-type brews, and it's hard to find a wider selection of real ales and microbrews, even in San Juan. Note that the legal drinking age in Puerto Rico is 18, but it is strictly forbidden to drink on the streets (the beach is fine).

What is the least crowded beach in San Juan? ›

Piñones Beach

If you want to stay close to San Juan, this quiet beach is just 2 miles away. It's usually only frequented by locals, so you won't find any crowds.

What beach is less crowded in San Juan? ›

If you're looking for a beach in San Juan that's less crowded than Isla Verde, drive a little farther to Ocean Park Beach. Even if Ocean Park Beach is small and doesn't have any facilities, this public beach sports a Miami Beach-style vibe and it offers adventurers sports like kite surfing and beach volleyball.

Do I need a Covid test to enter San Juan Puerto Rico? ›

Anyone arriving to Puerto Rico will be required to present negative PCR test results, no older than 1 day. Arrivals from the US are exempt.

What food is Puerto Rico known for? ›

The vibrancy of Puerto Rican culture comes alive in its dishes, a celebration of flavors that visitors have the opportunity to indulge in. Some of the favorites are mofongo, tostones, pasteles, arroz con gandules, tembleque, and coquito.

Do you need a passport to sail out of San Juan? ›

Western Caribbean cruises: Which itinerary will I like more? The rules also apply to Caribbean islands that are U.S. territories. For instance, you won't need a passport to fly to and cruise out of San Juan, Puerto Rico, or St. Thomas in the U.S. Virgin Islands.

How much does the ferry to the San Juan Islands cost? ›

The fare for a vehicle and driver on all westbound interisland ferries is $17 to $21; walk-on passengers and passengers in cars ride free. Except for service from Sidney, fares are not collected on eastbound ferries, nor are walk-on passengers charged for inter-island ferry service.

Can you do a day trip to San Juan Island? ›

The San Juan Islands are a small grouping of islands that all make for a great day trip from Seattle Southside. To get there, head north on I-5 for about an hour and a half until you reach Anacortes. From there, you'll have a chance to ride the ferry to my favorite island.

How long does it take to drive around San Juan Island? ›

The full mileage of the trip is 41 miles and takes about 1.5hrs. However it is best enjoyed with frequent stops at the many parks and viewpoints along the way. It would be a great afternoon or morning drive with either lunch or dinner in Friday Harbor or at Roche Harbor Resort.

How do you see all the San Juan Islands? ›

Ferry is by far the most popular method, and the journey from the port of Anacortes – a 90-minute drive north of Seattle – is beautiful. There are more than 170 islands in the archipelago, and regular car ferries serve the largest four: Lopez, Shaw, Orcas and San Juan Island.

Can you get around San Juan without a car? ›

If you're staying close to San Juan, then transportation might be relatively simple. You'll have access to a variety of options. In many instances, guests won't need a car (taxis and Uber are convenient options in town) unless they want to extend their visit beyond the city for an adventure.

What can you do in San Juan without a car? ›

5 Things to do on San Juan Island Without a Car
  • 1.Go for a hike. Looking up at the island from sea level is spectacular, and so is gazing out at the land and ocean from above while on San Juan Island's many hiking adventures. ...
  • 2.Ride a bike. ...
  • 3.Look to the sea. ...
  • 4.Visit the farmers' market. ...
  • 5.Spa day.
Jun 7, 2017

Is it easy to travel between the San Juan Islands? ›

The islands are accessible by ferry, plane, private boat and charters. You can either take your car on the ferry or park it at the ferry terminal and walk aboard, thus avoiding ferry lines. However, you need a vehicle to explore each island (exception, see San Juan Island topic, below).

Is it easy to get around in San Juan Puerto Rico? ›

In reality, though, Puerto Rico's capital is a vast metropolitan area that can be difficult to navigate for first-time visitors, with more than a dozen distinct neighborhoods and regions spanning more than 1900 sq miles. Here's everything you need to know about getting around in San Juan, Puerto Rico.

How deep is the water around the San Juan Islands? ›

The average depth is about 350 feet, but near its northern end it is more than 600 feet deep. Upright Channel branches off to the northeastward from San Juan Channel and separates Lopez Island from Shaw Island.

Can you see the northern lights from the San Juan Islands? ›

With over 247 clear days (and nights) per year and low light pollution, San Juan Island is uniquely (and stunningly) suited to observing the beautiful needle pricks in the cloak of night. At times you can see meteor showers, the northern lights and the most spectacular full moons shining on the glistening Salish Sea.

Can you see whales from shore in the San Juan Islands? ›

Seeing whales from shore is a possibility at Lime Kiln Point State Park, also known as Whale Watch Park, on San Juan Island's west side. Besides orcas, there's the potential for spotting humpbacks and minke whales from the park. Keep an eye out for porpoises, seals, sea lions and bald eagles there as well.

Can you see whales in the San Juan Islands? ›

Magnificent orca (or killer) whales live in the San Juan Islands year-round, and this is the best place in the world to see them in the wild. You can also spot humpbacks, minkes, gray whales, Steller sea lions, and many other species of wildlife.


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