The Perfect 3-Day San Diego Weekend Itinerary
New year, new energy, and the perfect excuse for a little fun and relaxation. If you have been dreaming about a coastal getaway, consider this your sign to stop dreaming and start packing. Winter is the ideal time to slow down, reset, and enjoy a beach escape in sunny San Diego.
Here at The Dana on Mission Bay, days unfold at your own pace. Peaceful waterfront views, fresh coastal air, and a laid-back tropical vibe set the tone for a stay that feels both refreshing and effortless. Whether you are lounging by the bay or simply soaking in the scenery, this is your chance to truly unwind.
Feeling spontaneous? Even better. Grab a bag and head to The Dana for a weekend filled with great food, festive moments, and classic San Diego sunshine. With our Winter Reset Offer, getting away is easier and more affordable than ever. All you have to do is arrive... we take care of the rest with this perfectly planned 3-day San Diego itinerary.
Day 1: Settle In at The Dana on Mission Bay & Stay Local
Vibe: Easy, relaxed, day in San Diego with minimal planning, hanging out at or near the hotel, and enjoying a slower SoCal pace.
Check into The Dana
Let the vacation fun begin! We invite guests to grab your complimentary welcome drink from Firefly or our Lobby Pantry and ease into your San Diego vacation. Spend some time enjoying the onsite resort-style amenities our hotel has to offer, including two outdoor swimming pools and Jacuzzis, bicycle rentals, an onsite marina, tropical pool bar, fitness center, and more! After some downtime, there are plenty of exciting things to do in San Diego, just minutes from your guestroom.
Adventure Water Sports
Rent wave runners, kayaks, a pontoon boat, stand-up paddleboards, and more right here onsite at The Dana from our friends at Adventure Water Sports. Spend the afternoon soaking up the San Diego sunshine and exploring our beautiful bay. You just may even get to say hi to some sunbathing sea lions!
Take a Waterfront Walk
One of the best ways to experience Mission Bay is by taking a walk along the waterfront loop just outside our hotel doors. This scenic path winds around calm bay waters, offering beautiful views, fresh coastal air, and an easy, peaceful way to explore the area at your own pace. Whether it’s a morning stroll or a sunset walk, the Mission Bay loop is a simple yet unforgettable part of your stay.
Grab a Sweet Treat
Treat yourself to a fresh, feel-good açaí bowl or smoothie from nearby Juice Wave in Mission Beach or Açaí Carioca in Pacific Beach. So good, you’ll be thinking about it all day.
Explore Belmont Park
Belmont Park is a classic beachfront amusement park packed with old-school charm and endless fun. Ride the historic roller coaster, play a round of mini golf, try your luck at carnival games, and explore a variety of dining, shopping, and entertainment options — all right on the sand in San Diego.
Shop ‘Till You Drop
From quirky surf shops to locally owned boutiques lining the boardwalk, shopping in San Diego is a laid-back way to slow down and enjoy the coast. Browse favorites like Jack’s Surfboards, Sun Diego, and Mission Beach Surf Shop, where beachwear, souvenirs, and local style capture the easygoing San Diego vibe.
Catch Happy Hour
Raise a glass to your San Diego vacation with happy hour at Draft, a favorite beachfront bar at Belmont Park known for its ocean views and lively atmosphere. Catch the sunset with a craft beer in hand, then keep the evening going at nearby spots like Cannonball for rooftop dining or Wonderland Ocean Pub in Ocean Beach for relaxed bites by the water. Come for the drinks, stay for the coastal vibes.
Dinner at Firefly
Enjoy a bayside dinner at our onsite restaurant, Firefly Eatery & Bar, and prepare to be wowed with your choice of creative cocktails and delicious dishes like the Baked Lobster Mac and Cheese, Petite Filet, and Pacific Seared Salmon, and don’t forget the Crème Brûlée Cheesecake!
Day 2: Explore Like a Local
Vibe: Enjoying the sunny day and fresh air while exploring San Diego neighborhoods, experiencing the amazing food, and learning about different cultures.
Morning Coffee + Brunch at a Local Favorite
Visit SuperBloom at the Mission Bay Beach Club near The Dana for a morning treat of locally roasted coffee and breakfast tacos to get the day started.
Explore a Walkable San Diego Neighborhood
Take a leisurely stroll through some of San Diego’s most beloved neighborhoods — Little Italy, North Park, or La Jolla — where sunny sidewalks lead to local boutiques, art galleries, cafés, and ocean views. Each area offers its own distinct vibe, from Little Italy’s lively piazzas and Italian eateries to North Park’s creative, craft-forward energy and La Jolla’s coastal charm. Along the way, browse unique shops for souvenirs, soak up the California sunshine, and experience the character that makes each community special.
Have Lunch at a Popular Local Restaurant
Treat yourself to a leisurely lunch in San Diego at a local fave like Coco Maya’s rooftop restaurant in Little Italy, La Jolla’s Beeside Balcony, or South Park’s The Rose.
Take an Afternoon Coastal Walk or Light Hike
San Diego is perfect for a walk along the shore or hike on a popular trail. Explore San Diego along the Pacific Beach boardwalk, Mission Bay boardwalk, and Torrey Pines Nature Reserve for unique coastal views of San Diego.
Evening of Live Music
Go with the flow and enjoy an evening of live music at our sister hotel's outdoor venue, Humphreys Concerts by the bay. See your favorite bands and performers at this popular waterfront venue in San Diego. Check out the upcoming concert schedule here — and stay tuned to their full summer lineup, dropping soon!
Movie and a Swim
End the evening back at the hotel with The Dana’s Dive-In Movie Nights by the heated Tropical Pool. The splash-worthy evening features a family-friendly flick and happens every night at sundown — weather permitting!
Day 3: Enjoy a Relaxing Morning in With a Memorable Send-Off
Vibe: Have a calm and relaxing morning at The Dana with an unhurried, reflective, and peaceful attitude.
Enjoy a Leisurely Breakfast or Brunch
Mosey over to the onsite Firefly Eatery & Bar for a yummy breakfast with a view! Enjoy the Surfer Burrito or Eggs Benedict with a Bloody Mary to get your last day in San Diego started.
Take a Stroll on the Beach
Nothing says stress-free like a walk on the beach in San Diego. Grab a coffee at the popular Olive Café, known for their viral social media posts about their AMAZING Banana Bread Lattes! Then head down to the PB or Mission Bay Boardwalk next door for a final walk to enjoy the ocean air.
Do Some Shopping in San Diego
Head to nearby Bird Rock, a local, laid-back, beachy neighborhood to check out some local shops like Bird Rock Surf Shop, a locally owned shop for cute gifts and souvenirs from San Diego.
Get in Relax Mode
End your vacation to San Diego on a peaceful and relaxing note with a massage before you head home. Book our Romance on the Bay Package that includes a massage for two for the ultimate vacation relaxation!
Head Back Home & Say Bye to the Bay
Safe travels home as you are relaxed and refreshed from your amazing experience at The Dana on Mission Bay for your San Diego escape!
Escape to the Dana on Mission Bay this Winter
Relax and get away from it all at The Dana on Mission Bay. It’s the perfect place to slow down, unwind, and rejuvenate in San Diego. Enjoy resort-style amenities, the perfect location near the best things to do in San Diego, and an attentive team that is here to help you make the most of your vacation getaway!
