7 Cruiser-Friendly Towns, on the East Coast, to Escape the Winter Blues with Your Loved One.

As we sailed south, dodging Nor’easters, oak trees turned into marshes. Marshes changed into mangroves. We could not wait to reach the warm, winter destinations.

The charm, history and sunshine in these beautiful coastal towns offer an unforgettable romantic getaway aboard your boat.

1. Charleston, SC

The Holy City is voted one of America’s Most Romantic Cities, by national publications.

Every year.

Even with a bit of winter chill in the air, the warm hospitality (and an extra layer of clothes) will keep you cozy.

Highly Rated Tours in Winter

Charleston’s Old South Carriage Historic Horse & Carriage Tour – One of the best-selling and most affordable historic carriage tours. The free Downtown Shuttle will take you right from the city marina.

Bring a warm blanket. Much more authentic, than a bus tour.

Undiscovered Charleston: Half Day Food, Wine & History Tour with Cooking Class – If you have a bit more time in Charleston (as you should; take the next weather window), make it a true southern romance.

Besides, people rave about Chef Parker’s culinary talent.

Romantic Dinner

While dining with a view of the water is hard to beat, cruisers are spoiled with such on a daily basis.

Poogan’s Porch – order a classic, southern, delicious meal downtown. Try their She-Crab Soup and Pimento Cheese Fritters.

Great Marina

Safe Harbor Charleston City Marina – They have excellent facilities, free Downtown shuttle and a Publix within a walking distance (less than a mile).

The current in Charleston area is quite strong. Anchoring would not be a fun experience and dragging is quite likely. Nothing romantic about that.

2. Beaufort, SC

We love, love Beaufort. We have visited a few times and this charming small town never fails to enchant.

Highly Rated Tours in Winter

Beaufort City Minibus Tour – it is led by some of the highest-rated tour guides. As you learn both history and Hollywood stories, you will have a nice list of classics to see (or see again).

Complete History and Movie Walking Tour of Beaufort – While it might be a bit cold in February, walking is our favorite way to explore any destination. As they say, there is no such thing as poor weather, only poor clothing.

Romantic Dinner

Lost Local – A nice dining place, not pretentious, just good food in good company. Right in the spirit of Beaufort, SC.

If you have a bit more time, grab a ride to Bee-Town Mead & Cider. The flavors are amazing. We bought gifts for everyone.

Great Marina

Lady’s Island Marina is a great marina, I have yet to see a poor review for that place. It is very close to the ICW. It is only a mile from Beaufort downtown area, and they offer a loaner car and bicycles.

Safe Harbor Beaufort – This is the downtown marina and mooring field. When we visited, the staff was very friendly and helpful. Mooring balls cannot be reserved, but it is hard to beat the location, right in the middle of the cute park and downtown area.

3. Savannah, GA

What’s not to love about Savanah! We sailed there just for a bit but ended up staying a few weeks as plans changed (a constant for boaters).

Highly Rated Tours

Private Historic Savannah Tour in a Vintage Citroën – What a romantic trip and starting from a location of your own choice. As they pick you up at the marina, enjoy a cozy and warm ride in this unforgettable town.

Savannah History plus Coffee and Chocolate Walking Tour – Speaking of romantic – chocolate is a given. The history, the chocolate and the coffee are all local. And customizable, so make sure you try the dark truffles.

Romantic meal

You must walk by the river. Visit at least a couple of the art and candy shops, even if just to browse (good luck with the candy ones).

While strolling and enjoying the view, stop at Huey’s on the River southern cafe. Customers rave about their gumbo. It is a bit hard to find, but those are the best places.

Great Marinas

Reaching marinas from the ocean is a bit of a ride, but we enjoyed the scenery. For those cruising the ICW, however, both marina locations are excellent.

Thunderbolt Marina – Located on the ICW, it is a very well-maintained marina. Due to the location of Savannah, you will not be able to find a marina in town, but Uber is very convenient.

Isle of Hope Marina – Another marina right off the ICW. Very well-reviewed, in a quiet location, yet close enough for a ride to Savannah.

4. St. Augustine, FL

It is one of our favorite cruising towns with a vibrant boaters’ community. What was planned as a quick 2-week stop, turned into five months aboard, in St. Augustine.

I am not complaining.

Highly Rated Tours

St. Augustine has so much to offer that a tour is just the gateway into a visit. We walked, and walked, and walked, for five months, and still did not have enough.

Pastime private historic tours – ride in a vintage car and take plenty of photos. The weather is usually cool in the winter, but the open-car ride can be rescheduled, or cancelled, if needed. Remember all the places you drive by, because you must walk around as well.

Wine & Dine Culinary Tour (Chauffeured/Historic District) – For a true romantic flavor, sip and dine in style, along with a history tour. A nice touch are treats from local restaurants. Hidden gems that are easy to miss otherwise.

Romantic meals

For a tucked-away restaurant, right in the middle of Old Town, visit Casa Maya. It is small enough to match this jewel of a town, yet serving grand flavors.

Order their Seafood Paella (for two). Authentic Spanish flavors belong in this town, more than anywhere else in the US. And the restaurant boasts returning customers, even years later.

Great Marina

St. Augustine Municipal Marina – The marina is a bit expensive, but we liked it. However, for a true unique experience and views, reserve a mooring ball. The latest rates are $30/day (call to confirm boat length). There is a shuttle, and Old Town St. Augustine is a short walk away.

5. Titusville, FL

If you love gazing at the stars, watching a rocket launch at Titusville will make for an unforgettable memory of Titusville. That’s what we did, from the romantic setting of our own tiny boat.

Highly Rated Tours

Florida Bioluminescence Kayaking Tour – You do not need to sail to Puerto Rico to see amazing glowing plankton. But if you decide to, read this post first.

Kennedy Space Center – There is nothing like it. We loved the visit. What is more romantic than the stars and space, and rockets. For the science lovers out there – Titusville is a must-stop cruising destination.

Romantic meal

Pier 220 Seafood and Grill – A great restaurant, with amazing views. The best part – just ride your dinghy and dock it there, while dining. It is really close to the marina.

Great Marina

Titusville Marina – We have stayed both at a slip and at the mooring field. We love the place. The mooring field was excellent to watch a night rocket launch. I consider this one of the most romantic dates ever.

6. Miami, FL

Miami will not be on my list of romantic destinations, if arriving by land.

However, Miami from the water is a completely different experience. I will sail back in a heartbeat.

Highly Rated Tours

Little Havana Food, Cuban Culture & Street Art Tour – We love Little Havana. Miami is a country of its own, and there is so much more to it, than Miami Beach and the busy downtown. Just be careful, the coffee is super sweet.

Romantic Miami Private Plane Tour With Champagne – Now that you have conquered the seas, let’s look up. Because the best way to enjoy Miami is from a distance – either from the bay, or from the sky. Remember to bring your best camera.

Romantic meal

Havana Harry’s – While visiting Little Havana, it is only natural to complete the day with a great Cuban fusion meal. Of course, try their Cuban sandwiches (rivalled only by the ones in Luperon, DR, but that’s a different sailing trip.)

Great Marina

Dinner Key Marina – We spent two months at their mooring field. The marina slips are impossible to rent and very expensive.

The mooring field offers privacy and breath-taking views of the city. And lots of space and clean water for the kids to swim around.

Also, day sails are easy and pleasant, in the bay.

7. Key West, FL

Key West is a popular boating destination. You do not need to sail to the Bahamas for crystal clear water and a sunny getaway.

We loved Key West, and I think I liked it better on land, actually.

Highly Rated Tours

Guided Bicycle Tour of Old Town Key West – It covers the island and everything you need to see. A slice of Key Lime pie at the end – just to have something sweet to look forward to. Love it.

Key West Southernmost Food and Cultural Walking Tour – Is it a surprise that you will get to taste great Cuban food… and rum. And Key Lime Pie. There is much history in Key West, it is worth the walk.

Romantic meal

Latitudes – You must go there, if you wish to have an unforgettable romantic experience. It is quite expensive, but it was recommended by a local friend we trust. She loves their wagyu.

Great Marina

The Perry Hotel and Marina – It is a very highly reviewed marina and the facility is exquisite. It includes swimming pools, fitness and great customer service.

Having said that, anchoring in the Keys is also great. Just make sure your boat is in good shape, doing repairs in the Keys can be expensive.

Bonus – St. Petersburg, FL

While not technically east coast US, we love the Gulf side so much, I have to include it. Besides there is a neat boating community there, including close friends or ours.

We love Tarpon Springs and their vibrant Greek community, and food! If you have time, grab an Uber and visit, it is well worth it.

Highly Rated Tours

St Pete Awesome Mural Biking Tour – An art tour, along with the history and stories behind the murals. The meeting location is about 2 miles from the municipal marina.

Parasail Flight at Madeira Beach – A bit more thrilling experience, than a city tour, but why not? Make it a memorable time in St. Petersburg.

Romantic meal

Columbia Restaurant – Florida’s oldest restaurant might be a bit pricey, but for a romantic dinner, it is worth it. The interior itself offers a mini tour through time and cultures.

Great Marina

St. Pete’s Municipal Marina – a marina in the hearth of St. Petersburg. While some renovations are still underway, it is a great place to stop, very protected and within walking distance to attractions.

Boater’s Note

No matter where you cruise, make reservations as early as possible. Even though the cruising-south season is busier in November, marinas in the south are always full.

It is easy to call and reschedule reservations. Marina owners get it, we are much dependent on the weather.

The US East Coast is a remarkable stretch of vastly different towns and anchorages. One does not need to sail away to exotic destinations. We have it all right at home.

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