Annapolis Labor Day Weekend Boat Rentals

Celebrate the end of summer in style with a memorable Labor Day Weekend cruise on the scenic waters of Annapolis, MD! Gather your friends and family for a festive tiki boat booze cruise, offering a unique way to relax and enjoy the holiday in the sailing capital of the US.

Departing from Nautilus Point Marina, just minutes from downtown, you’ll cruise up Back Creek, around Horn Point, and into the Annapolis Harbor. Take in the iconic sights of the US Naval Academy, Ego Alley, and Eastport as you enjoy a leisurely journey before returning back to the marina.

$45-65/person | 8-16 People | BYOB & BYOF | 1 hr 30 mins

4.9
Based on 260 reviews
bill groscup profile picture
bill groscup
2 days ago
10/10. Exactly what we were looking for
Terry Highsmith profile picture
Terry Highsmith
3 days ago
Jen and Kelli are the greatest. So fun and outgoing. Never stopped moving the whole trip! So much FUN!💖💖
Arthur Morales profile picture
Arthur Morales
5 days ago
All around good time
Kerry Wixted profile picture
Kerry Wixted
6 days ago
We had a lot of fun cruising around. The boat had a speaker, coolers, and plenty of space for food. It was easy to find, and the crew were great.
Jenn Jester profile picture
Jenn Jester
2 weeks ago
Had a great time on a company team day!!!
Joe Foran profile picture
Joe Foran
2 weeks ago
We had a great time, crew was outstanding, did a great job taking care of us. We'll definitely go again! Go Red Sox!
Julleanna Seely profile picture
Julleanna Seely
2 weeks ago
We had an amazing experience on our Tiki boat today with George and Brad! We called it Tiki Tuesday and brought our team out of the office for a fun team building adventure. The weather was ideal and we so enjoyed our almost 2 hour cruise thru the marinas of Annapolis. We learned some history and interesting facts, and overall had a blast! Highly recommend.
Victoria Seoane profile picture
Victoria Seoane
2 weeks ago
Awesome sunset cruise with Captain Jen and her skipper !
Jaykay profile picture
Jaykay
3 weeks ago
What a fun girls night out. Captain and First mate was very friendly and attentive to clearing our trash to taking pictures to answering questions and even joking with us! A fun experience for all ages and groups!
Erica Neal profile picture
Erica Neal
3 weeks ago
Had a wonderful evening with Captain Jen and Kelli. The weather forecast wasn’t looking great but everyone was helpful and considerate. Ended up being a beautiful night with Jen finding us calm water. Sunset and Annapolis views were great. Parking was a breeze and having a bathroom on board was a plus. Would definitely recommend as a fun group outing
Jeff Cross profile picture
Jeff Cross
4 weeks ago
Captain and Mate were friendly and knowledgeable.
Kelli & Jen are an amazing team. They are fun dynamic while also allowing us to just have fun. They shared all the boating and safety rules in an efficient manner. They also went above and beyond for us too! This wonderful crew had motion sickness wristbands. The tiki trip was on the weekend that Oceans Calling was cancelled. So we were very concerned with the water being rough or there being too much wind. The customer service agents that respond to texts were so patient and kind. Overall, it was a fantastic tiki cruise. Kelli & Jen are fun and had an excellent playlist. We will book again!
Kimberly Morrell profile picture
Kimberly Morrell
4 weeks ago
Our soccer mom social club had such a fun evening. Capts. Jen and Kelli were top notch! We can’t wait to do it again!
Emily Fusting profile picture
Emily Fusting
1 month ago
Great group activity! They have a speaker you can connect to and a cooler for your drinks. A fun time for all!
keri mcgill profile picture
keri mcgill
1 month ago
Kelli and Jen are the absolute best!
Kelli Gilhool profile picture
Kelli Gilhool
1 month ago
Kelli and Jen are the best!!! So fun!
Gail Kovach profile picture
Gail Kovach
1 month ago
Jennifer and Kelli were amazing. The best captains by far!!!
Toni Hepburn profile picture
Toni Hepburn
1 month ago
We had the BEST time on the tiki boat! Our two amazing female captains made the experience so much fun, relaxing, and memorable. Perfect for a group of moms looking for some well-deserved time to unwind, laugh, and enjoy the water. We’ll definitely be back! 🍹☀️🛥️
P A profile picture
P A
2 months ago
We booked this for my boyfriend’s birthday and truly could not have had a better time! Our captain and first mate were so warm, friendly, and easygoing from the second we got on the boat. They had a cooler stocked with ice for us, made everything incredibly easy, and took us on such a great route around the water. We had the BEST time and everyone in our group kept saying how perfect the night was. Such a fun thing to do with a group of friends, especially for a birthday or special occasion. It was worth every penny and we would 100% do it again. 10/10 recommend!!
Carly Schreiner profile picture
Carly Schreiner
3 months ago
Macy and the Captain were wonderful and soooo kind and friendly! Length of time for boat ride was totally appropriate for location. Bathroom on the boat, reasonably priced as well! My girlfriends and I had fun!!


Annapolis Labor Day Weekend Boat Rentals and Party Cruises

Our private boat charters are perfect for groups of 8 to 16, making them ideal for both intimate outings and lively celebrations. Bring your favorite beer, wine, champagne, hard seltzer, and canned cocktails—our party boats are BYOB! We’ll provide you with complimentary coolers to keep your drinks nice and cold.

Pair your beverages with your favorite homemade snacks or takeout meals, as all cruises are also BYO Food! Imagine cruising past Annapolis’s historic landmarks, enjoying your favorite playlist on our Bluetooth speakers, and soaking up the last rays of summer with your loved ones.

Spaces for our Labor Day Weekend cruises are limited and fill up quickly. Secure your spot today and make this holiday weekend one to remember with a fun-filled celebration on the water in Annapolis!