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Bed & Breakfasts: The Most Romantic Way to Wake Up in the Oldest City

It sure is charming, the Oldest City, the Ancient City — St. Augustine, Florida — and we here at Florida Water Tours pinch ourselves almost daily that we get to live in this magical place. Spanish and Gilded Age architecture, historic buildings lining brick streets, towering palms and swaying ancient oaks and gorgeous homes and inns that open their doors to travelers, inviting them to stay awhile: St. Augustine. It’s a treasure, and staying in a bed and breakfast makes it all the more intimate and cozy while you explore the sights and seas. With ample historic B&Bs downtown, you’ll be sure to enjoy a homemade breakfast, modern amenities and comforts and local culture no matter the place you choose. Here are some of our favorites:

Charming yellow building with outdoor seating under red umbrellas and a blue sky background.

Bayfront Marin House

Bayfront Marin House is an elegant and relaxing getaway, with structures dating back to the 1800s. The inn is situated directly across from Matanzas Bay, with views of the Bridge of Lions and St. Augustine Lighthouse. You may even see dolphins playing in the Intracoastal Waterway, right from your door! Rated #1 Waterfront Hotel in St. Augustine on Tripadvisor, the inn offers upscale, spacious rooms with private decks and cozy fireplaces, happy hour, parking, cruiser bikes and fantastic views — plus a delicious Southern-style breakfast is delivered right to your lodging every morning. Choose a room or suite, or a private apartment-style accommodation right near the inn. All have easy, walkable access to the sites around town, and dog-friendly accommodations are available as well. Call 904-824-4301 or go online to make a reservation. 

Poolside table with orange drinks, doughnuts, and sunglasses beside a swimming pool and lounge chairs.

St. Francis Inn

St. Francis Inn is located on a quiet and serene corner, just south of bustling St. George Street. It’s an old world bed and breakfast dating back to 1791 — making it St. Augustine’s oldest inn. This cozy B&B oozes the city’s history, offering endless stories of an intriguing past. Enjoy delicious gourmet breakfasts in their peaceful courtyard garden, filled with banana trees, bougainvillea and tropical flowers. Decadent homemade desserts are put out every evening for social hour, and the temperature-controlled pool offers a perfect swim any time of year. There are cozy sitting areas, rocking chairs on the balcony, off-street parking (adjacent to the inn) and a gift center in the inn’s welcome lobby, filled with local ceramics, ornaments, vases, magnets, robes, blankets and more — including packaged gourmet favorites straight from the inn’s kitchen. Book online or by calling 800-824-6062. 

Illuminated two-story bed and breakfast at dusk, with porch and garden, on a quaint street.

Carriage Way Inn

Carriage Way Inn is a multi-year award-winning bed and breakfast tucked away on a quiet street downtown, within steps of historic attractions, shops and restaurants. Built in 1883, this beautifully preserved Victorian home has welcomed generations of visitors, with highly-appointed rooms filled with dark wood accents and hardwood floors, antique clawfoot tubs and air-jet tubs and other luxurious amenities. Their front porch, stunning verandas and private courtyards are the perfect place to take refuge after a day of exploring. Enjoy chef’s hot breakfast every morning, complimentary beverages and freshly baked cookies every afternoon. They regard their concierge services as the best in the business, offering local insight to book reservations, plan surprises and set the most romantic of scenes. Call 904-829-2467 or book online

Elegant vintage-style living room with piano, floral rug, and wooden staircase.

Penny Farthing Inn

Penny Farthing Inn is St. Augustine’s British B&B, dating back to 1893. This charming Victorian takes you back to another time, of elegance and romance, on a quiet, tree-lined street. Relax on the inn’s many porches or inside in the cozy parlor. Gourmet breakfast is served in the dining room or out on the porch, and happy hour and snacks are served every afternoon. Rooms have high ceilings, stained glass windows and private balconies, porches and even a sundeck. One of the most special accommodations is The Treehouse, a secluded suite nestled in a magnificent 350-year-old cedar tree. Call 904-824-2100 to book or make a reservation online

A wooden porch with chairs, table, and an American flag, surrounded by palm trees and white railings.

44 Spanish Street Inn

44 Spanish Street Inn was built in 1920 as a boarding house, and retains so much of its original charm. Located in the heart of downtown, 44 Spanish is literal steps from all the sites and hospitality St. Augustine has to offer. Known as a cheerful, and adults-only cottage, their candlelit porches and vintage courtyards welcome guests with very affordable rates. Rooms are bright and cozy, with tributes to a bygone era offering luxury linens and beautiful antique furnishings. Take your respite right in the center of town. Book by calling 904-417-5002 or making a reservation online.  

And while you’re visiting, set sail with us at Florida Water Tours! Take our most popular ecotour experience, the Dolphin & Wildlife Adventure, where you’ll see dolphins, birds, manatees and turtles. If you’re looking for something more relaxing and luxurious, try the Sunset River Jazz Cruise, where smooth jazz sets a serene scene as golden hour settles in, or the Moonlit Mysteries Tour, which takes you on the water as night falls to hear ghostly tales of the old city. With more unique tours, and private charters available, celebrate the seven seas with Florida Water Tours. We’re located at 107 Yacht Club Dr., St. Augustine, FL 32084. We offer free parking and restrooms are on board. Email us at [email protected] to book or inquire about your next sail.

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