Annapolis Cinco De Mayo Cruises

Gather your family and friends for a floating fiesta in the sailing capital of the US. Embark on a Cinco De Mayo cruise in Annapolis to celebrate in style on the water! Our tiki boat booze cruises offer a unique way to sip, sightsee, and celebrate on these iconic waters.

Begin your journey at Nautilus Point Marina, just 4 minutes from the heart of downtown. Cruise up Back Creek, around Horn Point, and into the Annapolis Harbor. Soak in the iconic sights and sounds as you cruise past the US Naval Academy, Ego Alley, and Eastport before cruising back around Horn Point and down Back Creek.

$45-55/person | 8-16 People | BYOB & BYOF | 1 hr 30 mins

5.0
Based on 118 reviews
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Zane Newland
03:00 28 Apr 25
Great tour. We did our own thing with absolutely no rude interruptions and the captain and deck hand were very respectful and helpful. Bathroom on board. Captain was respectful and great to talk to and ready to give a guided tour if you please. Also had different ideas for our time and weather. Must try experience. Will do again.
Kendall Wiggins
17:45 21 Apr 25
We had a great experience for my bachelorette - even on a cold day, the Captain and Carly made it a blast. We loved that we could bring drinks and play our own music. Highly recommend!
Brenna Moran
13:15 14 Apr 25
We booked the tiki boat for a bachelorette party in April. The brides one request for the weekend was to be on a boat and seeing as though the weather was less than ideal for a boat day, the company was super helpful in responding to questions about cancellation and refunds as we weighed our options. We ended up deciding to sail, bundled up of course. Captain George and Carly were great hosts and helped make a dreary day one to remember for our rowdy party! Thank you guys for a great day
Sarah Fraim
20:54 07 Oct 24
Second time as a guest of this company. Professional and nice. Would recommend
liz c
15:00 27 Sep 24
Awesome people run this excursion and make sure you have an awesome time !
Demetrius McClendon
20:28 21 Sep 24
Amazing time. Both the captain and the crew mate were engaging and provided positive vibes. Highly recommended….and will be back during spring
Beatrix Langley
13:59 17 Sep 24
We had an excellent time on the Tilk cruise. The crew was fun and engaging, the sites and scenery were amazing. I highly recommend booking this cruise for your next gathering
Kseniya Scurto
20:18 15 Sep 24
It’s was an awesome experience for my best friend’s bachelorette party! We all had a blast on the tiki boat!
Anthony Booth
18:15 13 Sep 24
Had an awesome time cruising Annapolis!
Ramona Burton
12:18 09 Sep 24
We had an amazing time celebrating on the tiki boat. The crew was so friendly and lots of fun. I love that we were able to bring our own food and drinks aboard. I highly recommend this for any celebration or just a fun night out with friends.
Kate Duncan
12:34 08 Sep 24
Captain Jen and Captain Mike are awesome and the sea cruise was perfect for a networking event. Casual, fun and so pretty! Highly recommend for many occasions!
S Calloway
22:12 07 Sep 24
EPIC…from beginning to end! Thanks for making my birthday amazing!! Everyone enjoyed the evening….we will def be back!
Mitch Lemuiex
16:15 06 Sep 24
Great time! Easy sailing, great captains!!
Joshua Mcelroy
03:59 06 Sep 24
Was a great little trip, smooth ride, decent amount of time but the people really bring it all together.
Dan Rickenbach
18:05 04 Sep 24
This was a great way for a dozen of us friends to spend an afternoon. The host team is very chill and let us just have a good time! The views all around Annapolis don’t hurt either. We all said we should do it again and often!
Nancy Jones
22:28 28 Aug 24
The crew was very accommodating and have us a wonderful trip and Annapolis. Forgot how beautiful our city is from the water. They did a fabulous job.
Sharema Williams
22:03 27 Aug 24
A time was had‼️ we will highly recommend. Mike and his co captain was amazing
Tom Dagenais
22:03 26 Aug 24
Loved our experience. 5 stars all the way. We’ll be doing this again.
Leslie Durakis
14:56 22 Aug 24
We had a great time out on the water with our customers yesterday. It was the prefect day cruising the Annapolis area. The staff was very kind, informative on landmarks, and enjoyable to be around. I highly recommend taking the trip!
Julie Cole
13:06 22 Aug 24
Girls working our boat were great! Fun and very informative, we had a great time!


Annapolis Cinco De Mayo Booze Cruises and Party Boat Rentals

Grab your crew and embark on a memorable journey along the scenic waters of Annapolis. Our private boat charters can host parties of 8 to 16, making it ideal for both intimate gatherings and full-on fiestas.

Our party boats are BYOB so pack your favorite beer, wine, champagne, and hard seltzer to sip on as you sail (we’ll provide coolers). Pair them with your favorite homemade snacks or a full feast of Mexican takeout, all cruises are also BYO Food! Picture yourself sipping on cerveza, eating chips and salsa, and dancing to your favorite playlist on our Bluetooth speakers as you cruise past historic Annapolis landmarks.

Spaces for our Cinco de Mayo cruise are limited and sell out quickly. Don’t miss out on this unforgettable celebration on the water, lock in your spot before they run out!