Downtown San Diego Guide
Credit: Triton Charters

Your 72-Hour Guide to a Waterfront Vacation in Downtown San Diego

Pack Your Trip With Great Food, Views, Shopping and More

For tourists and first-time visitors, America’s Finest City is known for a lot of things, mainly attractions like Balboa Park, Petco Park and the famous San Diego Zoo. But frequent travelers and locals both know that San Diego is so much more than that—it’s a city booming with delicious food, vibrant nightlife, exciting things to do and plenty of fun to go around. Whether you’re a sun chaser, a foodie, a thrill-seeker or a family looking for a new favorite vacation spot, downtown San Diego is the place to be, particularly if you want to fill your three-day trip with waterfront views and activities. Ready, set, pack! Here’s your complete guide to a waterfront vacation in downtown San Diego.

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2 p.m. Arrive and Set Sail With Triton Charters

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Downtown San Diego Guide
Credit: Triton Charters

There is no better way to start your weekend on the waterfront than being on the water itself. San Diego Bay is one of the most beautiful places to set sail, and Triton Charters makes it easy! Every vessel at Triton Charters comes with its own Captain, crew and bartender to make your day on the bay safe and fun. On their harbor cruises, you’ll spend a few hours navigating through waters to see all the major monuments, like the USS Midway, Coronado Bridge, Glorietta Bay and more.

Sip on some signature cocktails (we’re keen on the Port’s Mistress) while leaning back in a bean bag on the bow. Or report to the dancefloor and take the party up a notch. With Triton Charters at the helm, you get to take in all that the bay has to offer while gliding in style on a 75-foot catamaran yacht. And if you’re looking for a special way to celebrate an occasion with 99 of your closest friends, you can book a private charter, which gives you access to all the amenities plus a built-in waterslide! Listen to the siren’s call—this is how you kick off your weekend waterfront mandate.


4 p.m. Check-in at Marriott Marquis San Diego Marina 

Downtown San Diego Guide
Credit: Marriott Marquis San Diego Marina

Start off your three-day downtown San Diego vacation by checking in to the bayfront Marriott Marquis San Diego Marina, where panoramic views just don’t quit. Those seeking some adventure will love taking advantage of the Seaforth Boat Rentals to explore the bay or Wheel Fun bike rentals to tour nearby attractions like Seaport Village and the Gaslamp Quarter. Other fun on-site activities include the Topgolf Swing Suites and the two free-form pools. And those who are really in need of serious TLC will love soaking up some sun on the hotel’s poolside daybeds or treating themselves to a massage at the Hideaway Spa. But let’s not get too far ahead of ourselves!

After getting settled in your luxurious, recently redesigned room and freshening up or taking a quick dip in the pool, we recommend staying on-site for dinner so you can explore and enjoy everything this stunning waterfront hotel has to offer. You may even catch some live music at Tequila Bar (Friday and Saturday from 3-6 p.m.) or Marina Kitchen (Friday and Saturday from 7-10 p.m.). It’s safe to say this is one of the chicest and happening hotels in downtown San Diego.


6 p.m. Dinner at Marina Kitchen

Marina Kitchen
Credit: Marriott Marquis San Diego Marina

We don’t know about you, but nothing works up our appetite quite like a day of travel. Treat yourself to a delicious dinner at none other than Marriott Marquis San Diego Marina’s Marina Kitchen, which specializes in locally curated cuisine.

Some menu favorites of ours include the Brussels and burrata appetizer, the pan-seared scallops, Chef Victor’s seasonal creme brulee and, to drink, Marina Kitchen’s specialty cocktail: the barrel-aged Manhattan (batched and aged in-house) or a classic Tom Collins made with locally distilled Cutwater Spirits.



10 a.m. Brunch at Coco Maya + Explore Little Italy

Mary Carol Fitzgerald
Credit: Mary Carol Fitzgerald

Whether you plan on sleeping in or like to get an early start with a dip in the pool or a visit to the Marriott Marquis San Diego Marina’s fitness center, we recommend making your first stop of the day brunch at the beautiful Coco Maya. This rooftop hideaway in Little Italy presents a menu full of flavors and dishes inspired by the islands and Latin American regions of the Caribbean. Our must-orders include the Boriqua Bowl, the breakfast bokit and the dulce French toast. Afterward, walk off your meal by exploring Little Italy and browsing through shops like Vocabulary, Verde, India Street Antiques and Architectural Salvage.


Noon Shop at Wotown Vintage Market

@goldenwestclub Follow Wotown on Instagram @ wotownsd for updates on their vintage pop up markets 🚀 #sandiego #sd #downtownsandiego #vintage #vintagemarket ♬ Lost – Frank Ocean

If shopping locally and more sustainably are on your to-do list this vacay, be sure to stop by one of San Diego’s best-known vintage markets. Located on Market St, Wotown Vintage Market is a great place to snag vintage tees and other digs. Wotown Vintage Market is open Monday through Saturday from 11 a.m. to 7 p.m. and Sunday from noon-6 p.m.



2 p.m. Lunch + Topgolf at the Bayside Lounge

Now it’s time to head back to the Marriott Marquis, drop off your shopping haul and get ready for beautiful views of the marina and lunch at the Bayside Lounge’s Topgolf Swing Suite. Enjoy expertly crafted cocktails and tasty small bites from 19th Hole while playing with your favorite teammates in one of the state-of-the-art Topgolf Swing Suites, which offer an exciting selection of interactive games that’ll have kids and kids at heart working up an appetite. 


4 p.m. Paragliding at Torrey Pines Gliderport

Credit: Lexi Wheeler

Want to get the best views in town while crossing something off your bucket list? Get your heart pumping and take the leap at Torrey Pines Gliderport. The Gliderport hosts multiple forms of flying, including radio-controlled model aircraft, hang gliders and paragliders. For first-time or beginner flyers, we recommend booking a 20-minute tandem paragliding or hang-gliding session, where you and an expert pilot can fly around the Torrey Pines cliffs while getting an aerial view of the famous golf course and the sparkling Pacific. Be sure to keep an eye out for weekday specials for Tandem Paragliding—pay in cash on Tuesdays and Thursdays to get seven free photos added to your experience!


6 p.m. Dinner at Juniper & Ivy

Credit: Courtesy of Juniper and Ivy

After a day full of movement and adventure, freshen up and slip into something nice for a night out on the town—there’s no better way to start than at the one and only Juniper and Ivy. One of the best restaurants in downtown San Diego and known for its uniquely crafted dishes, this San Diego gem is serving up delicious food from James Beard-nominated Chef Anthony Wells, which is paired with a handcrafted bar program. The menu is constantly changing and rotating to keep true to the restaurant’s dedication to quality, seasonality and surprise, so we recommend ordering whatever catches your eye. 


7:30 p.m. See a Live Concert at The Rady Shell

After your meal, keep the party going with a live concert at the famous Rady Shell at Jacobs Park. With its waterfront backdrop, beautiful outdoor seating and state-of-the-art features, it’s easy to see why The Rady Shell has quickly become a San Diego staple since its recent opening in the summer of 2021. Whether you’re in the mood to dance, sing along or simply marvel at the on-stage talent, this venue always puts on a good show.

Local Insight: Upcoming Summer 2023 events include shows by Diana Ross, John Legend, Charlie Puth, Genesis, Gladys Knight and Patti Labelle.


10 p.m. Late-Night Drinks at The Commodores Club

Credit: Sergey Kolivayko, Kensley Barber

Food, shopping, VR gaming, paragliding and a concert—your day has certainly been full, but it doesn’t have to end just yet. Step out for a nightcap at The Commodores Club, a hidden speakeasy disguised as a non-existent boat repair shop. Now we don’t want to spoil the surprise, but we definitely recommend taking a look at the website since this spot is hidden in plain sight! Keep in mind that this is a private speakeasy, but it does take reservations after 7 p.m. on Fridays and Saturdays. There are only 20 seats, so be sure to reserve your place well in advance!



9 a.m. Brunch at Morning Glory

Zack Benson
Credit: Zack Benson

A downtown San Diego staple, Morning Glory is a must-visit breakfast spot for anyone who loves the most important meal of the day, incredible interior design, cute photo-ops and, of course, pink. With its eye-catching design and bold flavors, Morning Glory is a treat for the eyes and the taste buds thanks to dishes like the Japanese-style souffle pancakes, breakfast carbonara and breakfast dim sum. For coffee, you can’t go wrong with the Trending-Hard Latte.


10:30 a.m. Visit the Little Italy Mercato Farmers Market

Little Italy Mercato Farmers Market
Credit: Little Italy Mercato Farmers Market

We believe there’s no better way to appreciate San Diego’s fare than by visiting Little Italy Mercato’s Farmers Market! Put on every Saturday from 8 a.m. to 2 p.m. and every Wednesday from 9:30 a.m. to 1:30 p.m., this farmers market is the best place to indulge in fresh produce (perfect for healthy snacking!), non-perishable foods for souvenirs and one-of-a-kind goods from local artisans and craftsmen.



Noon Hop on the Coronado Ferry + Explore Coronado Island

Downtown San Diego Guide
Credit: Flagship Cruises & Events

Escape the bustling city and head over to Coronado Island for some quieter coastal charm. To get there, we recommend getting on the Coronado Ferry: a Flagship Ferry that makes hourly trips across San Diego Bay. Once on Coronado Island, enjoy a walk on the beach, grab an ice cream cone from MooTime Creamery and explore the famous Hotel del Coronado. Then, once you’re finished exploring this charming enclave, head back on the ferry and take in that refreshing ocean breeze.


3 p.m. Rent a Daybed at Marriott Marquis San Diego Marina

There’s something about 3 p.m. that makes for the perfect nap time, and there’s something about one of the Marriott Marquis San Diego Marina’s rentable daybeds that make that naptime all the more luxurious. Available for two people at a time, these daybeds are plush, poolside and are the ideal spot to soak up some sun and catch up on some reading (or some Zs). Plus, let’s face it–a daybed experience isn’t complete without some poolside sipping; order a tasty margarita from the hotel’s Tequila Bar & Grille!


4:30 p.m. Explore the Area’s Museums 

WNDR Museum
Credit: WNDR Museum

An important part of any visit is getting to appreciate the area’s history, and for this part of San Diego, much of that history is maritime! Head over to the USS Midway Museum for a tour of the aircraft carrier museum while taking in views of the stunning marina. For first-time visitors and history buffs, try to swing by The Kiss, a famous waterfront statue depicting the couple in Alfred Eisenstaedt’s “V-J Day in Times Square” photo. Other nearby museums worth checking out include the Museum of Contemporary Art San Diego, WNDR San Diego and the San Diego Chinese Historical Museum


7 p.m. Dinner at The Lion’s Share

There’s no better way to ease a growling belly than with dinner at The Lion’s Share! Located on Kettner Blvd, The Lion’s Share is a New American bar that features moody, eclectic design and meticulously crafted dishes and libations. For drinks, order the To Be Fair or Wrong Answers Only, and for food, try the surf-and-turf crudo with bison and blue prawn, the Tongue and Cheek “Reuben” with Wagyu cheek and corned bison tongue and pork bites with pickle ranch.


9 p.m. Drinks at Wolfie’s Carousel Bar

Wolfie’s Carousel Bar
Credit: James Tran

Get ready for a bar experience that’ll give you the spins—the good kind! Wolfie’s Carousel Bar melds Parisian glamor with French Quarter romance, and at the center of the restaurant is a 24-seat, carousel-shaped circular cocktail bar that makes a rotation every 14 minutes. Not only is this spot a feat of engineering, but it’s best known for its whimsical drinks and tasty eats, making it easy to see why it’s become such a local favorite since its opening in 2021. Want to try something different from your typical order? We recommend the Je T’Adore with gin and brut, Wolfie’s Fantasy with cognac and rose and the Petit Mort with mezcal and a port wine float.

Writer | Website | + posts

Born and raised near the Pacific Coast, Jordan Nishkian is a California girl through and through. She graduated from Cal State Long Beach with a BA in Creative Writing and a BA in Anthropology, and her favorite place to be is curled up in a comfy chair with a book in her hand and a pen in her hair.




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