Local’s Guide to Winter in San Diego: 3-Day Weekend Itinerary
San Diego is not just a sunny summer destination. In fact, in the winter, San Diego is all about taking it easy, relaxing, and enjoying the slower pace of life on the SoCAL coast. If sunny walks on the beach, cozy outdoor dining, and the thrill of coastal adventures make you want to pack a bag – prepare to experience the best San Diego attractions, coastal exploration ops, and holiday entertainment for the perfect 3-day weekend escape!
Treat yourself to a room or suite with a water, scenic, or garden view and spend an amazing long weekend in San Diego visiting the best San Diego attractions, our beautiful beaches, and lively coastal towns. And be sure to take advantage of our Stay Longer & Save promotion, which offers an opportunity to save on your stay at the Best Western Island Palms Hotel and Marina when you book 3 or more nights at our Shelter Island hotel.
Here’s the perfect 3-day itinerary for a dreamy winter escape to San Diego.
Winter in San Diego: The Perfect 3-Day Weekend Itinerary
Day 1: Do As the Locals Do
Morning
Start your San Diego winter vacation in Ocean Beach, just a few minutes from your suite at the Best Western Island Palms on Shelter Island. Ocean Beach offers an effortless laid-back vibe that makes this SoCAL beach so popular with locals and visitors.
Grab breakfast at Azucar, a Cuban-style bakery known for its strong coffee and legendary Guava Pastry (trust us on this one)! This Newport Avenue favorite offers unique desserts and pastries that combine traditional favorites with new flavors and designs. Another great breakfast option in Ocean Beach is Val’s Coffee Corner, a Brazilian coffee cart serving authentic açaí bowls and rich espresso drinks that will get your day off to a delicious start!
Next, take a stroll down Newport Avenue where you will find excellent shopping opportunities at the local surf shops, boutiques, and quirky vintage stores along the coast. If you’re into surfing, it’s a great place to hit the waves near the Ocean Beach Pier or relax on the sand and check out the local surf scene.
Afternoon
Head over to Liberty Station, a popular entertainment, shopping, and dining hub that is one of the most popular San Diego attractions near the Island Palms Hotel. You’ll also find plenty of holiday festivities and activities to keep you engaged including Salute the Season, a holiday extravaganza in San Diego everyone will enjoy with a Christmas tree, festive photo ops, and holiday cheer for all. Next, do some holiday shopping at Liberty Station and grab some unique gifts from Pigment, Sea Hive Station, or Moniker General for those on your holiday shopping list.
After working up an appetite shopping and enjoying the holiday festivities in San Diego, it’s time to refuel at the Liberty Public Market. Local favorites include Stone Brewing featuring outside seating, and fun activities like bocce ball and outdoor movies. The eclectic menu is delicious, and they have 40 taps of exceptional craft beers. Buona Forchetta is another favorite that offers award-winning Neapolitan-style pizza pies and upscale Italian entrées in a family-friendly space. There’s also a family seating area complete with a secure space for kids to romp about while parents enjoy their food.
After dinner at Liberty Public Market, stick around to play a round of mini-golf, catch a movie at The LOT, or relax on the lawn and people watch!
Evening
Wrap up your first night in Pacific Beach, where ocean views and happy hour go hand in hand. Dinner and drinks with a sunset view? Yes, please and thank you!
Grab a drink at The Beverly, Waterbar, or Pacific Beach Alehouse where you can relax beachside for cocktails with the perfect spot for sunset or sip a local craft beer while watching the surfers catch the last waves of the day.
Once the sun goes down in SoCAL, it’s time to grab dinner at one of the amazing restaurants in Pacific Beach. World Famous is one of the best San Diego attractions when it comes to dining. This iconic beachfront restaurant has been serving Pacific Beach since 1970. Enjoy classic SoCAL inspired cuisine including seafood, seasonal vegetables, and hand-carved steaks all with an ocean view! If you’re a sushi lover, Sushi Ota is where you will want to dine! This no-frills Mission Bay Drive restaurant offers authentic Japanese dishes including sushi, without the fuss, in a relaxing environment. And finally, Costa Brava, a local Spanish restaurant and tapas bar is a great option for an authentic Spanish dining experience including traditional cuisine and live flamenco music!
Day 2: The Chill Day
After a busy day at Liberty Station exploring and shopping, relax and take a slower pace today as you enjoy the sunny and warm winter weather and the best San Diego attractions near the water.
Morning
Ease into the day with a leisurely breakfast at Blue Wave Bar & Grill onsite at the Island Palms. Be sure to book our breakfast package which includes daily breakfast for two, on us! Enjoy beautiful marina and coastal views while dining outdoors at our popular onsite café with your choice of everything from Avocado Toast and Grandmas Pancakes to House Benedicts and Bloody Marys!
After a leisurely start to the day, wander along the Shelter Island waterfront looking for adventures like fishing from the pier, water sports, and relaxing on the beach. Or better yet, rent bikes onsite at the Best Western Island Plus and cruise along the bayside path to all the popular San Diego attractions near the hotel.
Afternoon
Lucky for you, it’s winter whale watching season in San Diego! You are in for quite a treat when you book a tour with Next Level Sailing, conveniently located onsite at our marina. You’ll see the majestic gray whales migrating along the California coast, which is quite an exciting experience!
If being out on the water isn’t your thing, and you’d prefer a land adventure, take a scenic winter hike at Sunset Cliffs Natural Park or Torrey Pines State Reserve instead. Located just 2.5 miles from your Island Palms Hotel suite, both San Diego attractions offer stunning ocean views and cool, breezy weather perfect for exploring.
Evening
When dining in San Diego, treating yourself to dinner and drinks on a local rooftop with a view is a must! In fact, one of the most popular things to do in San Diego is to spend some time at one of our amazing rooftop restaurants and bars. Cannonball in Mission Beach is a great choice for sushi with sunset views! If you’re into the downtown San Diego vibe, Seneca Trattoria for Italian fare is fantastic and has a chic coastal/city vibe you’ll enjoy with skyline views and scenes of local landmarks.
If your San Diego winter vacation is during the holidays, head to Liberty Station’s Rady Children’s Ice Rink or Coronado’s beachside skating rink for a quintessential "only in San Diego" winter experience. Open daily from November 20 through January 4, Ice skating on the beach is something you MUST experience this winter in San Diego! Grab your winter socks and have some fun at these popular San Diego attractions.
End the evening back at the Island Palms Hotel with a glass of wine and a relaxing evening under the stars in one of our two outdoor hot tubs by the marina! Be sure to call it an early night and get some rest since you’ll have a big last day of fun in San Diego tomorrow!
Day 3: It’s FUN Being a Tourist in San Diego – Let’s Go!
Today’s all about hitting the iconic San Diego spots—without feeling rushed. Get out and enjoy the California sunshine as you enjoy a leisurely day exploring our coastal playground and the best touristy San Diego attractions.
Morning
Start the day off in beautiful Balboa Park with a coffee at Panama 66. This popular spot is located inside the Sculpture Court at the San Diego Museum of Art and is a great first stop before your adventure. Next, spend the morning exploring the beautiful gardens and museums at Balboa Park, one of the best San Diego attractions near the Island Palms Hotel. The next adventure starts at the world-famous San Diego Zoo where you can have fun with the animal adventures and exhibitions, including the refreshed Panda Ridge Exhibit! So much to see and do at the San Diego Zoo this winter!
Afternoon
Next stop is lunch with a view. Seaport Village has a variety of great places to grab a bit to eat, including Malibu Farm for fresh SoCal-inspired dining. They also have an ice cream and espresso bar! The Embarcadero is also a fun place for lunch with a view. Enjoy Pier 23 Cafe with lunch on the patio with low key vibes by the water and delicious fresh seafood in a casual environment at the Embarcadero in San Diego.
If you’re feeling extra adventurous, hop aboard a harbor cruise for a fresh perspective of the San Diego skyline. Flagship Cruises and Events offers harbor tours that cruise past sea lions, Navy ships, and under the Coronado Bridge. See the most popular San Diego attractions from the water as an expert guide tells stories about the area. It’s the perfect way to explore the San Diego waterfront.
Take a walk along the waterfront in San Diego for a little history lesson as you see the USS Midway Museum during the 80th Birthday Celebration. Also, be sure not to miss a visit to the popular Unconditional Surrender Statue, known as the Kissing Statue, which depicts a sailor kissing a nurse in celebration of the end of World War II. You will also have the chance to shop for souvenirs at The Headquarters at Seaport where you can get a token to remember your winter vacation in San Diego at this open-air lifestyle center with an exclusive collection of specialty shops and restaurants.
Evening
Spend the last night in San Diego with a delicious dinner in Little Italy, one of San Diego’s most vibrant neighborhoods. From cozy trattorias to exciting rooftop bars, you will love the culture and ambiance in Little Italy. Our favorites are Monello for 25 different kinds of daily handcrafted pasta, Barbusa for authentic Sicilian cuisine with a modern flare, and Kettner Exchange for two levels of indoor/outdoor drinking and award-winning dining.
Since you’re in Little Italy, it is a MUST to grab dessert at Extraordinary Desserts! The name says it all at this popular San Diego dessertery! From handmade ice cream to homemade cakes, you’ll be delighted with the desserts at this San Diego fave. After treating yourself to something so sweet and delicious, take a stroll through the twinkling Piazza della Famiglia. This 10,000-square-foot European-style piazza is home to a beautiful, tiled fountain and tables to gather to take in the beautiful scene and San Diego Bay views over food or coffee. No trip to Little Italy in San Diego is complete without a visit to the Piazza della Famiglia.
Spend Winter in San Diego at the Best Western Island Palms
Now that you have the perfect 3-day weekend itinerary in San Diego, it’s time to make plans for your winter escape to Southern California.
The Best Western Island Palms is the perfect place to be to enjoy all the best San Diego attractions this winter. Enjoy resort-style amenities, a convenient location near all the most popular San Diego activities, and comfortable rooms with water and marina views on beautiful Shelter Island. Book your winter vacation now!
