Sailing Sailing Tipsy Gypsy Travels

Preparing for a Gulf Stream Crossing to the Bahamas

To assist in our planning for a trip over to the Bahamas, we’ve decided to write out the ways in which we outfit our sailboat for crossing the Gulf Stream and what we do to prepare for visiting a new country. It’s not the same for everyone but we’ve done this a time or two now to know what we need to accomplish for a successful trip and know what we want to have along for the voyage. If you still have questions about anything it takes to prepare for a trip to the Bahamas, feel free to email us any time at

Every boat is different but each are prepared similarly when making a major crossing. In the upcoming weeks, Tipsy Gypsy will make its way across the Gulf Stream for the third time. We’ve put together a two part guide to share their preparations before leaving and help others know what the check-in process looks like. Here it goes!

Navigation + Weather

Although some sailors can navigate by the stars, we prefer to have electronics charts underway and paper charts for planning and for backup. It is important to make sure your electronic charts are updated and working properly before shoving off. We prefer Navionics on our mobile devices and plotter. We also use Active Captain for any social updates throughout our travels. As for paper charts for Bahamas, we prefer Explorer Chartbooks for their large-scale maps and Waterway Guides for routes and suggestions along the way.

It is also important to wait for the right weather window for your skill level. It is crucial for you to understand weather patterns, wind direction, and ocean swell. We cross reference multiple different weather apps to help us make the right decision in crossing safely. In addition to waiting for the right weather window, we have AIS and radar to help us know whats ahead of us, whether it may be another boat or an incoming front. Be prepared how you see fit but also be confident.


Boat Maintenance & Important Gear

Maintenance is an ongoing process, especially when living aboard a sailboat. To make sure you do not get overwhelmed by all the things to do, it is important to first make a list. Start at the bow and making your way to the stern, note any of the boat maintenance you may need to take care of before heading out on a major trip. From there, do the same for the interior. You of course don’t need to worry about too many cosmetic issues, just focus on the important items that will NEED attention or may be pricey away from your familiar ports. In addition to the ins and outs, check the engine room, lazerettes, and bilge. I’ll share with you our checklist but is by no means a complete guide (every boat is different after all).

A Checklist for Boat Maintenance Tips

  • Anchor + Ground Tackle – Trust your setup or make an upgrade. Have your main anchor and a back up.
    • Bahamian Mooring – Common term for setting two anchors off the bow  
  • Dinghy + Outboard – Do NOT tow your dinghy across the Gulf Stream or while making any passage. Haul it up on the deck or davits.
  • Check all your Lighting – Navigation lights and anchor light are the most important but ALL of them should be working properly for safety.
  • Windlass + Winches – Serviced and working properly
  • Macerator – Pumpouts are not readily available in the Bahamas, prepare accordingly.
  • Solar Power/Wind Power – Solar panels should be secured properly and you may need to tie down your wind generators.
  • Sails – Free of wear and tear, rips or snags
  • Engine – Oil change, replace oil pads, fuel filters, check impeller, check belts, check raw water strainer, etc.
  • Batteries – Depends on the battery – check for any sort of corrosion
  • Bilge – Make sure the bilge is clean and dry
  • Lazerettes – Keep clean and organized for easy accessibility
  • Boat Bottom – Clean the hull, clean the prop/strut, and replace zincs
  • Deck – Secure everything down
  • Cabin – Stow anything that could become a hazard underway
  • Order Spare Parts – Patches, impellers, belts, filters, zincs, etc.

Safety First

We don’t have ALL the bells and whistles when it comes to safety gear but will have as much as we can, as we can afford it. When heading over to the Bahamas, you should at least have the minimum requirements of the United States Coast Guard (USCG). Here’s a quick checklist to make sure you’re ready to go! And another in case you want to prepare even more safely.

Minimum Requirements

  • Life Jackets – USCG approved, serviced properly, and worn while underway.
  • Visual Distress Signals
  • Fire Extinguishers
  • Backfire Flame Control
  • Sound Producing Devices
  • Navigation Lights
  • Pollution Regulations
  • Marine Sanitation Devices

If you would like more details on any of the above items, here is a PDF going into more detail:

A Boater’s Guide to The Federal Requirements for Recreational Boats

Extra Credit Safety Gear

  • Life Raft – An expensive piece of equipment that we hope no one ever has to use. Make sure you keep it serviced properly in case it’s ever needed.
  • Personal EPIRB – Wear on your life jacket for personal GPS once activated.
  • Vessel EPIRB – Mount inside your vessel to provide GPS once activated.
  • Safety Courses can help boaters be better prepared. View a list of course options, here.
  • Ditch Bag – Ours is waterproof with water and food provisions, flashlights, space blankets, first aid kit, hats, sunglasses, etc.



Last but not least is provisioning for a trip to the Bahamas. Island life will make certain things more expensive and local items more affordable, so prepare accordingly. Bring extra of the items you personally enjoy, as you may not see it for a long while, and over prepare for meats, cheeses, and beer. In the Bahamas, you will have plenty of fish and seafood readily available. Locals will trade their fresh catch for beer (a lot of times) and you should have plenty on hand if you enjoy it. Beer is typically $5 per bottle (sometimes higher) whether you’re at the store or at a restaurant and that, my friends, is for a Bud Light. If you enjoy craft beers (like us), I highly suggest coming prepared so that you don’t run out πŸ˜‰ If you want different alcohol besides beer, Rum is cheap, and other liquors are reasonable. Wine is also something you don’t need to over prepare for unless you have favorite brands or types. Fresh produce is always decently priced but not the BEST looking. Paper products, crackers, chips, and other groceries can also be pricey.

The prices are inflated but for good reason, the islands receive limited shipments and aren’t the best with restocking due to the sporadic supply chain to different islands. We highly suggest knowing the days in which deliveries are made so that you may have first pick and prepare before arrival as much as you can. It of course gets pricey to provision EVERYTHING beforehand but this strategy has saved us money in the long run. If you enjoy eating out, restaurant prices are reasonable for food, and you’ll get to enjoy all the local eats as much as possible.

To help with provisioning –

Mary + Tharon’s Provisioning Checklist

Final Thoughts

Thank you to Newport Vessels for sponsoring this blog post. Learn more about them by visiting If you’re looking for a new dinghy, use code SVTIPSYGYPSY for 10% off. 

Read next –> Checking In to the Bahamas 

More Bahamas posts –> here

Cheers and thanks for reading!

If you have additional questions about making the Gulf Stream Crossing to Bahamas, email us at

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  • Reply
    February 10, 2018 at 12:41 pm

    You guys are living my dream! We’ve always wanted to sail and live aboard, but since I don’t know how to sail, I’ll have to live vicariously through your posts. What a great way to explore, and impressive how prepared you are, as you should be!

  • Reply
    February 10, 2018 at 2:28 pm

    This sounds like an epic adventure! I would love to live onboard a boat, such freedom. I’ve never came across a post like this before, very insightful.

  • Reply
    February 10, 2018 at 6:25 pm

    what an incredible experience! I have never been on a boat like this but I imagine sunshine, gorgeous water, a little marine life, and open sea!

  • Reply
    February 10, 2018 at 6:35 pm

    What an exciting trip to take! The tips for provisions are really insightful, how do you figure out how much meat and cheese you will need? I love that you have plenty of craft beer on board for your trip.

  • Reply
    Nana - PatagoniaDreaming
    February 10, 2018 at 6:36 pm

    Coolest thing ever πŸ™‚ I will sail the world in my next life, haha πŸ˜€ Best of luck with your adventure πŸ™‚

  • Reply
    Rocio Novarino
    February 10, 2018 at 6:37 pm

    Not really expert in navigation, but trust me, just interesting post!

  • Reply
    February 10, 2018 at 6:44 pm

    Wow sounds like an epic experience to have! Must feel so free on the water with beautiful sunshine. Thanks for bringing that imagery in to my mind today. What a lovely share!

  • Reply
    February 10, 2018 at 7:16 pm

    Wow, sounds like quite an adventure πŸ™‚ I have to admit, I have never been on a sailing trip. EVER!

  • Reply
    Bruna Venturinelli
    February 11, 2018 at 8:31 am

    Wow, this is awesome! I don’t think I’d be able to do it, though. I have two left hands. Lol.
    The only time I was on a boat, it was a boat tour through Amsterdam’s canals!

  • Reply
    Kaylene Isherwood
    February 11, 2018 at 9:07 am

    Sounds like such an exciting trip! What a fun experience! I’ve only been on a sail boat once, and it was so much fun! Bon voyage!

  • Reply
    February 11, 2018 at 11:34 pm

    This is cool 😎 that you travel by boat πŸš£β€β™€οΈ I don’t know πŸ€·πŸ½β€β™€οΈ anybody that has personal boat! I went on a cruise to the Bahamas πŸ‡§πŸ‡Έ which is nothing like a personal boat! I’m thinking about the fish you mentioned, I’m sure it was tasty πŸ˜‹

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