Your Boston Valentine’s Day Weekend Itinerary

Valentine’s Day weekend is the perfect time to celebrate love, friendship, and new connections with a variety of exciting events. From romantic dinners and vibrant markets to lively brunches and fun-filled socials, there’s something for everyone to enjoy. Whether you’re planning a special night out with your partner, gathering with friends for a festive celebration, or looking to meet someone new, this weekend offers plenty of ways to make meaningful memories. Indulge in delicious food, explore unique gifts, and take part in interactive experiences designed to bring people together. No matter how you choose to celebrate, this Valentine’s weekend is all about love in all its forms!

Greenway Valentine’s Pop Up Market: Friday, Feb 14, 2025 11:00a - 6:00p

The Greenway Valentine’s Pop-Up Market will be held on Dewey Square from February 11th through February 14th, offering a fantastic opportunity to support local artisans. This love themed market is the perfect place to find unique gifts. Curated by UpNext, shoppers can explore handcrafted goods inside heated Flexetail retail units. Featured vendors include Creme De Liqueur, Petsi Pies, Birdie & Claire, Elizabeth Lee, Lucciano’s Bakeshop, MAKOmacarons, and More Than Words.

Link: https://www.rosekennedygreenway.org/events/greenway-valentines-pop-up-market-2025-02-11/

V-day Dinner at Baleia- Friday, Feb 14, 2025 4pm- 11:00p

Skip the trip to Porto or Lisbon and enjoy a romantic dinner at Baleia in the South End instead. This Portuguese gem is offering a special four-course meal perfect for the occasion. Indulge in dishes like duck liver mousse with quince and rye cracker, steamed clams with chouriço and refogado, and a decadent bolo de chocolate with cherries and cream. For an unforgettable dining experience, Baleia brings the flavors of Portugal right to your table this Valentine’s Day.

Link: https://www.bostonchefs.com/holiday/valentines-day-boston/boston-south-end/#baleia

Swiftie Galentine’s Day Brunch-Saturday, Feb 15, 2025 12:00p - 4:00p

Get ready to celebrate all things Taylor Swift at the Swiftie Galentine’s Day Brunch/Day Party at The Greatest Bar! Wear your glitter, Eras Tour outfit, or anything that makes you happy while enjoying a day filled with fun, food, and friendship. Tickets grant entry to all the exciting activities, while brunch will be available to order from the menu on a first-come, first-serve basis. Families are welcome, with a special floor dedicated to child-friendly activities so young Swifties can join in on the fun. Expect a Swiftie Specialist DJ, karaoke, bracelet making, glitter face tattoos, stickers, a photo station, giveaways, fun menus, specialty donuts, and even hand-painted Taylor Swift shells from Lulu Shells!

Link: https://www.thebostoncalendar.com/events/swiftie-galentine-s-day-brunch-all-ages

Boston Bridal Bash- Hilton Boston Dedham:Sunday, Feb 16, 2025 12:00p - 3:00p

Get into the spirit of love and experience the magic of Bridal Bash and start planning your dream wedding with ease! This special evening brings your wedding vision to life with the help of trusted bridal vendors from all around Boston. Explore the latest trends, enjoy live music, taste delicious cake samples, and watch a stunning fashion show. Plus, all attendees have the chance to win incredible prizes, including $7,500 in giveaways and a honeymoon! Gather your bride tribe, make unforgettable memories, and take the first step toward your perfect wedding day—get free tickets for you and your lovebird or galentines with code “vday” today!

Link:www.eventbrite.com/e/945081613547/?discount=vday

Speed Dating at Castle Island Brewing: Monday, Feb 17, 2025 6:30p - 8:30p

Tired of swiping? Join us for a fun and efficient evening of speed dating, where you'll enjoy up to 15 mini-dates with singles who are ready to meet. Kick off the night with a relaxed happy hour, grab a drink, and settle in before the dating begins. Throughout the evening, you’ll have five-minute conversations and simply check off who you'd like to connect with again—no awkward rejections, just easy matchmaking. Within 24 hours, you'll receive the contact information of your matches so you can keep the conversation going and plan your next date. Get your ticket today and meet new singles in Boston in a relaxed, no-pressure setting!

Link:https://www.eventbrite.com/e/speed-dating-ages-25-34-1-drink-included-tickets-1089935028009?aff=TBC

No matter how you choose to celebrate, this Valentine’s weekend is filled with opportunities to create unforgettable memories. Whether you’re shopping for the perfect gift, enjoying a romantic dinner, bonding with friends, or meeting someone new, these events offer something special for everyone. Take this chance to embrace love in all its forms—romantic, platonic, and even self-love. With so many exciting activities to explore, your weekend is sure to be filled with joy, connection, and celebration. So grab your loved ones, mark your calendar, and make this Valentine’s Day weekend one to remember!