Skip to contentAsk Jessica

Yacht charter: Chesapeake Bay and Annapolis

Boats in this US eastern coast grouping are associated with Annapolis and Chesapeake Bay.

Boats in this cruising area

Explore the fleet
Main image

SlowdownSailing yacht · Built 2019

U.S.A. · Annapolis

Dufour 430

guests
13
cabins
4
toilets
2
Length
43.4 ft / 13.24 m
  • Air condition
  • Generator

31 Oct-7 Nov 2026

From€4,512 / weekView details
Main image

Sea to SkyCatamaran · Built 2018

U.S.A. · Annapolis

Lagoon 42

guests
13
cabins
3
toilets
3
Length
42.5 ft / 12.94 m
  • Air condition
  • Generator

7-14 Nov 2026

From€6,638 / weekView details
Main image

SiaCatamaran · Built 2022

U.S.A. · Annapolis

Excess 11

guests
13
cabins
3
toilets
2
Length
37.2 ft / 11.33 m
  • Air condition
  • Generator

31 Oct-7 Nov 2026

From€6,638 / weekView details

Chesapeake Bay and Annapolis

Charter bases and sailing areas

A bay and port-city journey

Annapolis provides a specific starting point for a Chesapeake Bay trip. This is a narrower destination than the entire US eastern seaboard. Compare local bases and the setting of stops within the bay rather than inferring distant coastal offers from the broad regional name.

Before you charter

What is bareboat charter?

You charter the boat and provide your own suitably qualified skipper and crew. Qualification requirements vary by boat, operator and sailing area. We help check your documents and the charter terms for your chosen boat.

What will your charter cost?

The search price is the boat's charter price. The boat page lists known mandatory charges, optional extras and a separate security deposit. Review the complete offer for your dates; any costs still awaiting confirmation must be checked before booking.

How does a charter request work?

  1. Choose your dates, departure base and boat.
  2. Review the charter price, charges, deposit and qualification requirements.
  3. Send your request. Yachting Planet checks availability and terms before confirming the charter.